diff --git a/headroom/dashboard/templates/dashboard.html b/headroom/dashboard/templates/dashboard.html
index 7d44b366a..97263980e 100644
--- a/headroom/dashboard/templates/dashboard.html
+++ b/headroom/dashboard/templates/dashboard.html
@@ -120,13 +120,21 @@
                 <div class="text-xs text-gray-500 uppercase tracking-wide mb-1">Token Savings</div>
                 <div class="flex items-baseline gap-2">
                     <span class="text-3xl font-light tabular-nums text-accent" x-text="formatNumber(stats.tokens?.saved || 0)"></span>
-                    <span class="text-sm text-accent" x-text="(stats.tokens?.savings_percent || 0).toFixed(1) + '%'"></span>
+                    <!-- Active compression ratio: savings as fraction of what we *attempted*
+                         to compress (extracted units + tool schema). Excludes frozen-prefix
+                         bytes (user messages, system prompt, prior turns) we never touch for
+                         prefix-cache safety. The whole-request ratio is stored as
+                         `savings_percent` and shown as a small footnote for transparency. -->
+                    <span class="text-sm text-accent" x-text="(stats.tokens?.active_savings_percent || 0).toFixed(1) + '%'" title="Of compressible tokens attempted"></span>
                 </div>
                 <div class="mt-1 text-xs text-gray-500 leading-relaxed">
                     <span x-text="'Proxy ' + formatNumber(stats.tokens?.proxy_compression_saved || 0) + ' (' + proxyShareOfTotal.toFixed(1) + '%)'"></span>
                     <span class="mx-1 text-gray-600">/</span>
                     <span x-text="'RTK ' + formatNumber(stats.tokens?.rtk_saved || 0) + ' (' + rtkShareOfTotal.toFixed(1) + '%)'"></span>
                 </div>
+                <div class="mt-1 text-xs text-gray-600 leading-relaxed">
+                    <span x-text="'Of total wire: ' + (stats.tokens?.savings_percent || 0).toFixed(2) + '%'" title="Savings as fraction of all input tokens including frozen prefix"></span>
+                </div>
                 <div class="mt-2 h-8">
                     <svg class="w-full h-full" viewBox="0 0 100 32" preserveAspectRatio="none">
                         <defs>
diff --git a/headroom/proxy/handlers/anthropic.py b/headroom/proxy/handlers/anthropic.py
index 3e06aae72..ee66dae90 100644
--- a/headroom/proxy/handlers/anthropic.py
+++ b/headroom/proxy/handlers/anthropic.py
@@ -1573,6 +1573,21 @@ class AnthropicHandlerMixin:
                         _backend_name = (
                             self.anthropic_backend.name if self.anthropic_backend else "anthropic"
                         )
+                        # Eligible-only denominator for the active
+                        # compression ratio: tokens in the live zone we
+                        # actually attempted to compress. Frozen prefix
+                        # (system + prior cached turns) is byte-identical
+                        # pre/post — counting it would dilute the metric
+                        # with content we deliberately don't touch for
+                        # prefix-cache safety. Fall back to the full
+                        # pre-comp request if the live-zone count fails
+                        # so the aggregate denominator stays coherent.
+                        try:
+                            attempted_input_tokens = tokenizer.count_messages(
+                                original_client_messages[frozen_message_count:]
+                            )
+                        except Exception:
+                            attempted_input_tokens = original_tokens
                         await self.metrics.record_request(
                             provider=_backend_name,
                             model=model,
@@ -1583,6 +1598,7 @@ class AnthropicHandlerMixin:
                             cached=False,
                             overhead_ms=optimization_latency,
                             pipeline_timing=pipeline_timing,
+                            attempted_input_tokens=attempted_input_tokens,
                         )
 
                         if self.cost_tracker:
diff --git a/headroom/proxy/handlers/gemini.py b/headroom/proxy/handlers/gemini.py
index 03bbd5208..28bbed10d 100644
--- a/headroom/proxy/handlers/gemini.py
+++ b/headroom/proxy/handlers/gemini.py
@@ -439,6 +439,13 @@ class GeminiHandlerMixin:
                         uncached_tokens=uncached_input_tokens,
                     )
 
+                # Eligible-tracking is TODO for Gemini; pass the full
+                # pre-compression request size as the fallback denominator.
+                # This makes Gemini's contribution to the aggregate
+                # active_savings_percent equal its whole-request ratio —
+                # not ideal but coherent until per-part live-zone
+                # tracking exists for this provider.
+                attempted_input_tokens = total_input_tokens + tokens_saved
                 await self.metrics.record_request(
                     provider="gemini",
                     model=model,
@@ -450,6 +457,7 @@ class GeminiHandlerMixin:
                     waste_signals=waste_signals_dict,
                     cache_read_tokens=cache_read_tokens,
                     uncached_input_tokens=uncached_input_tokens,
+                    attempted_input_tokens=attempted_input_tokens,
                 )
 
                 if tokens_saved > 0:
@@ -856,6 +864,9 @@ class GeminiHandlerMixin:
                 max(0, original_tokens - compressed_tokens) if compressed_tokens > 0 else 0
             )
 
+            # Fallback denominator (see comment on the main gemini
+            # record_request site) — pre-comp request size.
+            attempted_input_tokens = compressed_tokens + tokens_saved
             await self.metrics.record_request(
                 provider="gemini",
                 model=model,
@@ -863,6 +874,7 @@ class GeminiHandlerMixin:
                 output_tokens=0,
                 tokens_saved=tokens_saved,
                 latency_ms=total_latency,
+                attempted_input_tokens=attempted_input_tokens,
             )
 
             if tokens_saved > 0:
diff --git a/headroom/proxy/handlers/openai.py b/headroom/proxy/handlers/openai.py
index 38cd602aa..45b3cb716 100644
--- a/headroom/proxy/handlers/openai.py
+++ b/headroom/proxy/handlers/openai.py
@@ -9,6 +9,7 @@ import asyncio
 import base64
 import contextlib
 import copy
+import hashlib
 import json
 import logging
 import os
@@ -38,6 +39,220 @@ from headroom.proxy.auth_mode import classify_auth_mode
 logger = logging.getLogger("headroom.proxy")
 
 
+def _json_debug_dumps(value: Any) -> str:
+    return json.dumps(value, ensure_ascii=False, default=str, separators=(",", ":"))
+
+
+def _redacted_debug_value(value: Any) -> Any:
+    from headroom.proxy.helpers import redact_for_wire_debug
+
+    return redact_for_wire_debug(value)
+
+
+# Fields that embed full payload bodies (~tens of KB per event). At INFO
+# level these dominate log volume and obscure the summary signals; at
+# DEBUG level they remain available for deep diagnosis.
+_LOG_BLOAT_FIELDS = frozenset(
+    {
+        "payload",
+        "input_payload",
+        "output_payload",
+        "input",
+        "output",
+        "original",
+        "compressed",
+        "extraction",
+        "units",
+        "router_routing_log",
+    }
+)
+
+
+def _log_codex_compression_debug(event: str, **payload: Any) -> None:
+    """Emit Codex compression diagnostics.
+
+    INFO carries the summary fields (request_id, pass_id, savings,
+    strategy_chain, units_by_category, etc.) — the line a human log
+    reader should be able to scan to understand what happened.
+
+    DEBUG carries everything, including the full request/response
+    payload bodies and per-unit text. Enable the proxy logger at DEBUG
+    when actually diagnosing a regression; leave it at INFO for
+    steady-state ops to keep proxy.log readable.
+
+    Obvious credential keys are still redacted by key name at both levels.
+    """
+
+    payload = {"event": event, **payload}
+    # DEBUG: everything.
+    if logger.isEnabledFor(logging.DEBUG):
+        logger.debug("event=%s %s", event, _json_debug_dumps(_redacted_debug_value(payload)))
+    # INFO: stripped of body-embedding fields so summaries are scannable.
+    stripped = {k: v for k, v in payload.items() if k not in _LOG_BLOAT_FIELDS}
+    logger.info("event=%s %s", event, _json_debug_dumps(_redacted_debug_value(stripped)))
+
+
+def _json_shape(value: str) -> dict[str, Any]:
+    try:
+        parsed = json.loads(value)
+    except Exception as exc:
+        return {"is_json": False, "error": type(exc).__name__}
+    if isinstance(parsed, dict):
+        return {
+            "is_json": True,
+            "kind": "object",
+            "keys": list(parsed.keys()),
+            "length": len(parsed),
+        }
+    if isinstance(parsed, list):
+        return {"is_json": True, "kind": "array", "length": len(parsed)}
+    return {"is_json": True, "kind": type(parsed).__name__}
+
+
+def _routing_log_debug(router_result: Any) -> list[dict[str, Any]]:
+    routing_log = getattr(router_result, "routing_log", []) or []
+    rows: list[dict[str, Any]] = []
+    for idx, decision in enumerate(routing_log):
+        content_type = getattr(decision, "content_type", None)
+        strategy = getattr(decision, "strategy", None)
+        rows.append(
+            {
+                "index": idx,
+                "content_type": getattr(content_type, "value", str(content_type)),
+                "strategy": getattr(strategy, "value", str(strategy)),
+                "original_tokens": getattr(decision, "original_tokens", None),
+                "compressed_tokens": getattr(decision, "compressed_tokens", None),
+                "confidence": getattr(decision, "confidence", None),
+                "section_index": getattr(decision, "section_index", None),
+                "compression_ratio": getattr(decision, "compression_ratio", None),
+            }
+        )
+    return rows
+
+
+_OPENAI_TOOL_SCHEMA_DROP_KEYS = {
+    "$id",
+    "$schema",
+    "$comment",
+    "deprecated",
+    "examples",
+    "example",
+    "markdownDescription",
+    "readOnly",
+    "title",
+    "writeOnly",
+}
+
+
+def _json_byte_len(value: Any) -> int:
+    return len(_json_debug_dumps(value).encode("utf-8", errors="replace"))
+
+
+def _compact_openai_tool_schema_value(
+    value: Any,
+) -> Any:
+    if isinstance(value, list):
+        return [_compact_openai_tool_schema_value(item) for item in value]
+
+    if not isinstance(value, dict):
+        return value
+
+    compacted: dict[str, Any] = {}
+    for key, child in value.items():
+        if key in _OPENAI_TOOL_SCHEMA_DROP_KEYS:
+            continue
+
+        if key == "description" and isinstance(child, str):
+            compacted[key] = " ".join(child.split())
+            continue
+
+        compacted[key] = _compact_openai_tool_schema_value(child)
+
+    return compacted
+
+
+def _compact_openai_responses_tools(
+    payload: dict[str, Any],
+) -> tuple[dict[str, Any], bool, int, int]:
+    tools = payload.get("tools")
+    if not isinstance(tools, list) or not tools:
+        return payload, False, 0, 0
+
+    compacted_tools = _compact_openai_tool_schema_value(tools)
+    before = _json_byte_len(tools)
+    after = _json_byte_len(compacted_tools)
+    if after >= before:
+        return payload, False, before, after
+
+    updated = copy.deepcopy(payload)
+    updated["tools"] = compacted_tools
+    return updated, True, before, after
+
+
+def _responses_input_item_text_bytes(item: Any) -> int:
+    if not isinstance(item, dict):
+        return _json_byte_len(item)
+
+    output = item.get("output")
+    if isinstance(output, str):
+        return len(output.encode("utf-8", errors="replace"))
+
+    content = item.get("content")
+    if isinstance(content, str):
+        return len(content.encode("utf-8", errors="replace"))
+    if isinstance(content, list):
+        total = 0
+        for part in content:
+            if isinstance(part, str):
+                total += len(part.encode("utf-8", errors="replace"))
+            elif isinstance(part, dict) and isinstance(part.get("text"), str):
+                total += len(part["text"].encode("utf-8", errors="replace"))
+        return total
+
+    return _json_byte_len(item)
+
+
+def _openai_responses_context_budget(payload: dict[str, Any]) -> dict[str, Any]:
+    payload_bytes = _json_byte_len(payload)
+    buckets: dict[str, int] = {}
+    for key in ("instructions", "tools", "input", "messages", "client_metadata"):
+        if key in payload:
+            buckets[key] = _json_byte_len(payload.get(key))
+
+    other_bytes = max(payload_bytes - sum(buckets.values()), 0)
+    if other_bytes:
+        buckets["other"] = other_bytes
+
+    input_breakdown: dict[str, dict[str, int]] = {}
+    items = payload.get("input") or payload.get("messages")
+    if isinstance(items, list):
+        for item in items:
+            item_type = item.get("type", "unknown") if isinstance(item, dict) else "non_dict"
+            row = input_breakdown.setdefault(
+                str(item_type),
+                {"items": 0, "bytes": 0, "text_bytes": 0},
+            )
+            row["items"] += 1
+            row["bytes"] += _json_byte_len(item)
+            row["text_bytes"] += _responses_input_item_text_bytes(item)
+
+    return {
+        "payload_bytes": payload_bytes,
+        "buckets": {
+            key: {
+                "bytes": value,
+                "pct": (value / payload_bytes * 100.0) if payload_bytes else 0.0,
+            }
+            for key, value in sorted(
+                buckets.items(),
+                key=lambda item: item[1],
+                reverse=True,
+            )
+        },
+        "input_breakdown": input_breakdown,
+    }
+
+
 # Interactive Responses turns are latency-sensitive. Fail open quickly rather
 # than holding the session hostage on memory lookup.
 RESPONSES_CONTEXT_SEARCH_TIMEOUT_SECONDS = 2.0
@@ -150,6 +365,7 @@ class OpenAIHandlerMixin:
 
     OPENAI_RESPONSES_ROUTER_MIN_BYTES = 512
     OPENAI_RESPONSES_OUTPUT_TYPES = {
+        "custom_tool_call_output",
         "function_call_output",
         "local_shell_call_output",
         "apply_patch_call_output",
@@ -203,7 +419,8 @@ class OpenAIHandlerMixin:
         *,
         model: str,
         request_id: str,
-    ) -> tuple[dict[str, Any], bool, int, list[str]]:
+        pass_id: str | None = None,
+    ) -> tuple[dict[str, Any], bool, int, list[str], dict[str, int], list[str], int]:
         """Run ContentRouter on OpenAI Responses text units.
 
         This is the Responses provider scaffold: it extracts text-bearing
@@ -213,9 +430,36 @@ class OpenAIHandlerMixin:
         items such as reasoning, compaction, tool calls, and non-string outputs
         are intentionally not exposed as text units.
         """
-        items = payload.get("input") or payload.get("messages")
+
+        def _log(event: str, **fields: Any) -> None:
+            # All events from this single compression pass share `pass_id`,
+            # so downstream analytics can attribute each unit_result to
+            # its originating pass — without this, unit_results from
+            # multiple passes get conflated under one request_id and
+            # per-pass questions become unanswerable. Savings ARE expected
+            # to sum across passes: each pass really did avoid sending
+            # those tokens upstream, regardless of any prefix-cache the
+            # upstream may apply.
+            _log_codex_compression_debug(
+                event,
+                request_id=request_id,
+                pass_id=pass_id,
+                model=model,
+                **fields,
+            )
+
+        input_items = payload.get("input")
+        messages_items = payload.get("messages")
+        items = input_items if isinstance(input_items, list) else messages_items
         if not isinstance(items, list):
-            return payload, False, 0, []
+            _log(
+                "codex_compression_payload_skipped",
+                reason="input_or_messages_not_list",
+                input_type=type(payload.get("input")).__name__,
+                messages_type=type(payload.get("messages")).__name__,
+                payload=payload,
+            )
+            return payload, False, 0, [], {}, [], 0
         try:
             from headroom.transforms.compression_units import (
                 CompressionUnit,
@@ -229,12 +473,23 @@ class OpenAIHandlerMixin:
                 request_id,
                 exc,
             )
-            return payload, False, 0, []
+            _log(
+                "codex_compression_payload_skipped",
+                reason="compression_unit_adapter_unavailable",
+                error=repr(exc),
+                payload=payload,
+            )
+            return payload, False, 0, [], {}, [], 0
 
         router = find_content_router(self.openai_pipeline)
         if router is None:
             logger.debug("[%s] OpenAI Responses ContentRouter unavailable", request_id)
-            return payload, False, 0, []
+            _log(
+                "codex_compression_payload_skipped",
+                reason="content_router_unavailable",
+                payload=payload,
+            )
+            return payload, False, 0, [], {}, [], 0
 
         try:
             tokenizer = self.openai_provider.get_token_counter(model)
@@ -244,31 +499,25 @@ class OpenAIHandlerMixin:
                 request_id,
                 exc,
             )
-            return payload, False, 0, []
+            _log(
+                "codex_compression_payload_skipped",
+                reason="tokenizer_unavailable",
+                error=repr(exc),
+                payload=payload,
+            )
+            return payload, False, 0, [], {}, [], 0
 
         def _slot_text(item: dict[str, Any]) -> tuple[str, tuple[str, int | None]] | None:
+            # Only tool-output items are eligible for in-place compression.
+            # Message items (user/system/assistant) sit inside the request's
+            # cacheable prefix; mutating them busts prefix caching on every
+            # subsequent turn. Role-level guards in compression_units.py
+            # remain as defense-in-depth.
             type_tag = item.get("type")
             if type_tag in self.OPENAI_RESPONSES_OUTPUT_TYPES:
                 output = item.get("output")
                 if isinstance(output, str):
                     return output, ("output", None)
-                return None
-
-            if type_tag == "message":
-                content = item.get("content")
-                if isinstance(content, str):
-                    return content, ("message_string", None)
-                if isinstance(content, list):
-                    for idx, part in enumerate(content):
-                        if isinstance(part, str):
-                            return part, ("message_list_string", idx)
-                        if not isinstance(part, dict):
-                            continue
-                        if part.get("type") not in ("input_text", "text", "output_text"):
-                            continue
-                        text = part.get("text")
-                        if isinstance(text, str):
-                            return text, ("message_part", idx)
             return None
 
         def _set_slot_text(
@@ -276,21 +525,9 @@ class OpenAIHandlerMixin:
             slot: tuple[str, int | None],
             replacement: str,
         ) -> None:
-            kind, part_idx = slot
+            kind, _ = slot
             if kind == "output":
                 item["output"] = replacement
-            elif kind == "message_string":
-                item["content"] = replacement
-            elif kind == "message_part" and part_idx is not None:
-                content = item.get("content")
-                if isinstance(content, list) and part_idx < len(content):
-                    part = content[part_idx]
-                    if isinstance(part, dict):
-                        part["text"] = replacement
-            elif kind == "message_list_string" and part_idx is not None:
-                content = item.get("content")
-                if isinstance(content, list) and part_idx < len(content):
-                    content[part_idx] = replacement
 
         headroom_retrieve_call_ids: set[str] = set()
         for item in items:
@@ -307,37 +544,117 @@ class OpenAIHandlerMixin:
                     headroom_retrieve_call_ids.add(call_id)
 
         candidates: list[tuple[int, tuple[str, int | None], str]] = []
+        extraction_debug: list[dict[str, Any]] = []
         for idx, item in enumerate(items):
             if not isinstance(item, dict):
+                extraction_debug.append(
+                    {
+                        "index": idx,
+                        "eligible": False,
+                        "reason": "item_not_dict",
+                        "item_type": type(item).__name__,
+                        "item": item,
+                    }
+                )
                 continue
             item_type = item.get("type")
             if item_type in self.OPENAI_RESPONSES_OUTPUT_TYPES:
                 call_id = item.get("call_id")
                 if isinstance(call_id, str) and call_id in headroom_retrieve_call_ids:
+                    extraction_debug.append(
+                        {
+                            "index": idx,
+                            "eligible": False,
+                            "reason": "headroom_retrieve_output_protected",
+                            "item_type": item_type,
+                            "call_id": call_id,
+                            "item": item,
+                        }
+                    )
                     continue
                 slot = _slot_text(item)
                 if slot is not None:
                     text, slot_ref = slot
                     candidates.append((idx, slot_ref, text))
-            elif item_type == "message":
-                slot = _slot_text(item)
-                if slot is not None:
-                    text, slot_ref = slot
-                    candidates.append((idx, slot_ref, text))
+                    extraction_debug.append(
+                        {
+                            "index": idx,
+                            "eligible": True,
+                            "item_type": item_type,
+                            "role": item.get("role"),
+                            "slot": slot_ref,
+                            "text_chars": len(text),
+                            "text_bytes": len(text.encode("utf-8", errors="replace")),
+                            "text_json_shape": _json_shape(text),
+                            "item": item,
+                            "text": text,
+                        }
+                    )
+                else:
+                    extraction_debug.append(
+                        {
+                            "index": idx,
+                            "eligible": False,
+                            "reason": "output_type_without_text_slot",
+                            "item_type": item_type,
+                            "item": item,
+                        }
+                    )
+            else:
+                extraction_debug.append(
+                    {
+                        "index": idx,
+                        "eligible": False,
+                        "reason": "unsupported_item_type",
+                        "item_type": item_type,
+                        "role": item.get("role"),
+                        "item": item,
+                    }
+                )
 
+        _log(
+            "codex_compression_extraction",
+            item_count=len(items),
+            candidate_count=len(candidates),
+            payload=payload,
+            extraction=extraction_debug,
+        )
         if not candidates:
-            return payload, False, 0, []
+            _log(
+                "codex_compression_payload_result",
+                modified=False,
+                reason="no_candidates",
+                tokens_saved_total=0,
+                transforms=[],
+                input_payload=payload,
+                output_payload=payload,
+            )
+            return payload, False, 0, [], {}, [], 0
 
         updated = copy.deepcopy(payload)
-        updated_items = updated.get("input") or updated.get("messages")
+        updated_input_items = updated.get("input")
+        updated_messages_items = updated.get("messages")
+        updated_items = (
+            updated_input_items if isinstance(updated_input_items, list) else updated_messages_items
+        )
         if not isinstance(updated_items, list):
-            return payload, False, 0, []
+            return payload, False, 0, [], {}, [], 0
 
         modified = False
         tokens_saved_total = 0
+        # `attempted_input_tokens` is the *compressible* portion of the
+        # request — only the tokens we actually fed to the router (i.e.
+        # extracted units that passed the floor + role + cache_zone
+        # gates). It excludes user messages, system prompts, prior-turn
+        # assistant content, and other frozen prefix bytes. This is the
+        # right denominator for the dashboard savings ratio: comparing
+        # tokens_saved against tokens we ATTEMPTED to compress, not
+        # against everything in the request.
+        attempted_input_tokens = 0
         transforms: list[str] = []
         routed_units: list[RoutedCompressionUnit] = []
 
+        unit_debug: list[dict[str, Any]] = []
         for item_idx, slot_ref, original_text in candidates:
             item = items[item_idx] if item_idx < len(items) else {}
             item_type = item.get("type", "unknown") if isinstance(item, dict) else "unknown"
@@ -353,16 +670,82 @@ class OpenAIHandlerMixin:
                 min_bytes=self.OPENAI_RESPONSES_ROUTER_MIN_BYTES,
             )
             routed_units.append(RoutedCompressionUnit(unit=unit, slot=(item_idx, slot_ref)))
+            unit_debug.append(
+                {
+                    "item_index": item_idx,
+                    "slot": slot_ref,
+                    "provider": unit.provider,
+                    "endpoint": unit.endpoint,
+                    "role": unit.role,
+                    "item_type": unit.item_type,
+                    "cache_zone": unit.cache_zone,
+                    "mutable": unit.mutable,
+                    "min_bytes": unit.min_bytes,
+                    "text_chars": len(unit.text),
+                    "text_bytes": len(unit.text.encode("utf-8", errors="replace")),
+                    "text_json_shape": _json_shape(unit.text),
+                    "text": unit.text,
+                }
+            )
+
+        _log(
+            "codex_compression_units",
+            units=unit_debug,
+        )
+
+        # Tally per-category counts as units stream in so the pass_summary
+        # event below can emit a one-line breakdown — log readers shouldn't
+        # have to re-aggregate from scattered unit_result events.
+        units_by_category: dict[str, int] = {}
+        strategy_chain_union: list[str] = []
 
         for slot, result in compress_units_with_router(
             routed_units,
             router=router,
             tokenizer=tokenizer,
         ):
+            item_idx, slot_ref = slot
+            router_chain = list(result.router_result.strategy_chain) if result.router_result else []
+            for s in router_chain:
+                if s not in strategy_chain_union:
+                    strategy_chain_union.append(s)
+            cat = result.reason_category or "applied"
+            units_by_category[cat] = units_by_category.get(cat, 0) + 1
+            # A unit "reached the router" iff the result carries a
+            # router_result OR was modified — both indicate we got
+            # past the early gates. Units that were size-floored,
+            # role-protected, or in a frozen cache_zone don't count.
+            if result.router_result is not None or result.modified:
+                attempted_input_tokens += result.tokens_before
+            _log(
+                "codex_compression_unit_result",
+                item_index=item_idx,
+                slot=slot_ref,
+                modified=result.modified,
+                reason=result.reason,
+                reason_category=cat,
+                text_bytes=result.text_bytes,
+                min_bytes=result.min_bytes,
+                strategy=result.strategy,
+                strategy_chain=router_chain,
+                tokens_before=result.tokens_before,
+                tokens_after=result.tokens_after,
+                tokens_saved=result.tokens_saved,
+                transforms_applied=result.transforms_applied,
+                router_strategy=(
+                    result.router_result.strategy_used.value if result.router_result else None
+                ),
+                router_summary=result.router_result.summary() if result.router_result else None,
+                router_routing_log=_routing_log_debug(result.router_result),
+                router_cache_hit=(
+                    result.router_result.cache_hit if result.router_result else False
+                ),
+                original=result.original,
+                compressed=result.compressed,
+            )
             if not result.modified:
                 continue
 
-            item_idx, slot_ref = slot
             target_item = updated_items[item_idx]
             if not isinstance(target_item, dict):
                 continue
@@ -373,7 +756,26 @@ class OpenAIHandlerMixin:
                 if transform not in transforms:
                     transforms.append(transform)
 
-        return updated, modified, tokens_saved_total, transforms
+        _log(
+            "codex_compression_payload_result",
+            modified=modified,
+            tokens_saved_total=tokens_saved_total,
+            attempted_input_tokens=attempted_input_tokens,
+            transforms=transforms,
+            units_by_category=units_by_category,
+            strategy_chain=strategy_chain_union,
+            input_payload=payload,
+            output_payload=updated if modified else payload,
+        )
+        return (
+            updated,
+            modified,
+            tokens_saved_total,
+            transforms,
+            units_by_category,
+            strategy_chain_union,
+            attempted_input_tokens,
+        )
 
     def _compress_openai_responses_payload(
         self,
@@ -381,7 +783,7 @@ class OpenAIHandlerMixin:
         *,
         model: str,
         request_id: str,
-    ) -> tuple[dict[str, Any], bool, int, list[str], str | None, int, int]:
+    ) -> tuple[dict[str, Any], bool, int, list[str], str | None, int, int, int]:
         """Compress an OpenAI Responses payload through the shared router.
 
         Provider adapters pass only the inner Responses payload here. This
@@ -391,18 +793,77 @@ class OpenAIHandlerMixin:
         """
 
         input_bytes = json.dumps(payload).encode("utf-8")
+        # Codex/Responses requests can re-enter this method many times per
+        # request_id (one per turn over the same websocket). Tag every
+        # event in this single pass with a content-derived id so dashboards
+        # can attribute each unit_result to its originating pass.
+        # Aggregation note: per-pass `tokens_saved` SHOULD sum across
+        # passes — every pass independently avoided sending those tokens
+        # upstream, regardless of any prefix cache the upstream applies.
+        # Identical pass_ids within one request_id indicate idempotent
+        # retries on the same input bytes and are the only thing that
+        # should be deduped.
+        pass_id = hashlib.sha256(input_bytes).hexdigest()[:12]
+        input_context_budget = _openai_responses_context_budget(payload)
+        _log_codex_compression_debug(
+            "codex_compression_payload_input",
+            request_id=request_id,
+            pass_id=pass_id,
+            model=model,
+            input_bytes=len(input_bytes),
+            context_budget=input_context_budget,
+            input_top_level_keys=list(payload.keys()),
+            input_field_type=type(payload.get("input")).__name__,
+            messages_field_type=type(payload.get("messages")).__name__,
+            payload=payload,
+        )
         working = payload
         modified = False
         tokens_saved = 0
         transforms: list[str] = []
         reason: str | None = None
 
-        router_payload, router_modified, router_saved, router_transforms = (
-            self._compress_openai_responses_live_text_units_with_router(
-                working,
-                model=model,
+        compacted_payload, tools_modified, tools_before_bytes, tools_after_bytes = (
+            _compact_openai_responses_tools(working)
+        )
+        if tools_modified:
+            working = compacted_payload
+            modified = True
+            reason = None
+            transforms.append("openai:responses:tool_schema_compaction")
+            try:
+                tokenizer = self.openai_provider.get_token_counter(model)
+                tokens_saved += max(
+                    0,
+                    tokenizer.count_text(_json_debug_dumps(payload.get("tools")))
+                    - tokenizer.count_text(_json_debug_dumps(working.get("tools"))),
+                )
+            except Exception:
+                pass
+            _log_codex_compression_debug(
+                "codex_tool_schema_compaction",
                 request_id=request_id,
+                pass_id=pass_id,
+                model=model,
+                modified=True,
+                tools_bytes_before=tools_before_bytes,
+                tools_bytes_after=tools_after_bytes,
+                tools_bytes_saved=tools_before_bytes - tools_after_bytes,
             )
+
+        (
+            router_payload,
+            router_modified,
+            router_saved,
+            router_transforms,
+            units_by_category,
+            strategy_chain,
+            router_attempted_tokens,
+        ) = self._compress_openai_responses_live_text_units_with_router(
+            working,
+            model=model,
+            request_id=request_id,
+            pass_id=pass_id,
         )
         if router_modified:
             working = router_payload
@@ -410,16 +871,101 @@ class OpenAIHandlerMixin:
             reason = None
             tokens_saved += int(router_saved)
             transforms.extend(router_transforms)
-        else:
+        elif not modified:
             reason = "router_no_compression"
 
+        # Total tokens we *attempted* to compress on this pass:
+        # router-fed unit tokens + the original (pre-compaction) tool
+        # schema tokens we ran schema_compaction against. Excludes
+        # instructions, user messages, prior assistant turns, and
+        # other prefix bytes we never tried to touch — those belong
+        # to the prefix-cache denominator, not the active-compression
+        # one.
+        attempted_input_tokens = int(router_attempted_tokens)
+        if tools_modified:
+            try:
+                tokenizer = self.openai_provider.get_token_counter(model)
+                attempted_input_tokens += tokenizer.count_text(
+                    _json_debug_dumps(payload.get("tools"))
+                )
+            except Exception:
+                pass
+
         deduped: list[str] = []
         for transform in transforms:
             if transform not in deduped:
                 deduped.append(transform)
 
         output_bytes = json.dumps(working).encode("utf-8")
-        return working, modified, tokens_saved, deduped, reason, len(input_bytes), len(output_bytes)
+        output_context_budget = _openai_responses_context_budget(working)
+        # One-line summary at INFO — the single event a human reading
+        # logs should scan first to understand "what happened on this
+        # pass". All the verbose per-event debug data stays available
+        # but at DEBUG level. Contains: byte totals, savings, the
+        # strategy chain we walked, unit-outcome counts by category,
+        # and the transforms applied.
+        savings_pct = (
+            (1.0 - len(output_bytes) / len(input_bytes)) * 100.0 if len(input_bytes) else 0.0
+        )
+        # Active-compression ratio: savings as a fraction of what we
+        # *attempted* to compress, not of the whole request. The whole-
+        # request ratio is in `savings_pct`; this one is the metric the
+        # dashboard should display (otherwise frozen prefix bytes drown
+        # the wins from the compressible tail).
+        #
+        # Math note: `attempted_input_tokens` is the pre-compression
+        # size of the eligible content (sum of unit.tokens_before +
+        # original tool schema). `tokens_saved` is what we removed
+        # from it. So the savings rate is plain `saved / attempted` —
+        # NOT `saved / (attempted + saved)`, which would double-count.
+        attempted_pct = (
+            (tokens_saved / attempted_input_tokens) * 100.0 if attempted_input_tokens > 0 else 0.0
+        )
+        _log_codex_compression_debug(
+            "codex_compression_pass_summary",
+            request_id=request_id,
+            pass_id=pass_id,
+            model=model,
+            modified=modified,
+            reason=reason,
+            input_bytes=len(input_bytes),
+            output_bytes=len(output_bytes),
+            bytes_saved=len(input_bytes) - len(output_bytes),
+            savings_pct=round(savings_pct, 2),
+            tokens_saved=tokens_saved,
+            attempted_input_tokens=attempted_input_tokens,
+            attempted_pct=round(attempted_pct, 2),
+            strategy_chain=strategy_chain,
+            units_by_category=units_by_category,
+            transforms=deduped,
+        )
+        _log_codex_compression_debug(
+            "codex_compression_payload_output",
+            request_id=request_id,
+            pass_id=pass_id,
+            model=model,
+            modified=modified,
+            reason=reason,
+            tokens_saved=tokens_saved,
+            attempted_input_tokens=attempted_input_tokens,
+            transforms=deduped,
+            input_bytes=len(input_bytes),
+            output_bytes=len(output_bytes),
+            context_budget_before=input_context_budget,
+            context_budget_after=output_context_budget,
+            input_payload=payload,
+            output_payload=working,
+        )
+        return (
+            working,
+            modified,
+            tokens_saved,
+            deduped,
+            reason,
+            len(input_bytes),
+            len(output_bytes),
+            attempted_input_tokens,
+        )
 
     async def handle_openai_chat(
         self,
@@ -1094,6 +1640,14 @@ class OpenAIHandlerMixin:
                     output_tokens = usage.get("completion_tokens", 0)
                     total_input_tokens = usage.get("prompt_tokens", optimized_tokens)
 
+                    # OpenAI Chat: no per-message live-zone tracking
+                    # yet. Use full pre-comp request size as the
+                    # attempted denominator so this provider's
+                    # contribution to the aggregate active_savings ratio
+                    # equals its whole-request ratio. Per-message
+                    # eligibility (tool_result-shaped messages, current
+                    # turn vs cached) is a follow-up.
+                    attempted_input_tokens = total_input_tokens + tokens_saved
                     await self.metrics.record_request(
                         provider=self.anthropic_backend.name,
                         model=model,
@@ -1105,6 +1659,7 @@ class OpenAIHandlerMixin:
                         overhead_ms=optimization_latency,
                         pipeline_timing=pipeline_timing,
                         waste_signals=waste_signals_dict,
+                        attempted_input_tokens=attempted_input_tokens,
                     )
 
                     # Mirror the streaming path: log to RequestLogger so
@@ -1419,6 +1974,10 @@ class OpenAIHandlerMixin:
                     "endpoint": "chat_completions",
                 }
 
+                # OpenAI Chat (streaming path): fallback denominator —
+                # full pre-comp size. See note at the non-streaming
+                # path for the eligible-only follow-up.
+                attempted_input_tokens = total_input_tokens + tokens_saved
                 await self.metrics.record_request(
                     provider="openai",
                     model=model,
@@ -1432,6 +1991,7 @@ class OpenAIHandlerMixin:
                     cache_read_tokens=cache_read_tokens,
                     cache_write_tokens=cache_write_tokens,
                     uncached_input_tokens=uncached_input_tokens,
+                    attempted_input_tokens=attempted_input_tokens,
                 )
 
                 # Per-request log entry for /transformations/feed +
@@ -1705,6 +2265,11 @@ class OpenAIHandlerMixin:
         optimized_messages = messages
         optimized_tokens = original_tokens
         tokens_saved = 0
+        # Eligible-only denominator for the active compression ratio.
+        # Populated by `_compress_openai_responses_payload` if it runs;
+        # stays 0 on bypass / passthrough paths so we don't fabricate a
+        # denominator we haven't earned.
+        attempted_input_tokens = 0
         transforms_applied: list[str] = []
         optimization_latency = (time.time() - start_time) * 1000
 
@@ -1880,11 +2445,13 @@ class OpenAIHandlerMixin:
                     _reason,
                     _bytes_before,
                     _bytes_after,
+                    _attempted_tokens,
                 ) = self._compress_openai_responses_payload(
                     body,
                     model=model,
                     request_id=request_id,
                 )
+                attempted_input_tokens = int(_attempted_tokens)
                 if _modified:
                     tokens_saved = int(_tokens_saved)
                     optimized_tokens = max(0, original_tokens - tokens_saved)
@@ -2126,6 +2693,7 @@ class OpenAIHandlerMixin:
                     cache_read_tokens=cache_read_tokens,
                     cache_write_tokens=cache_write_tokens,
                     uncached_input_tokens=uncached_input_tokens,
+                    attempted_input_tokens=attempted_input_tokens,
                 )
 
                 # Per-request log entry for /transformations/feed +
@@ -2547,6 +3115,10 @@ class OpenAIHandlerMixin:
 
             body: dict[str, Any] = {}
             tokens_saved = 0
+            # Session-scoped accumulator for tokens we *attempted* to
+            # compress (extracted units + schema). Drives the active-
+            # compression ratio surfaced to the dashboard.
+            attempted_input_tokens_total = 0
             transforms_applied: list[str] = []
             ws_frames_compressed = 0
             try:
@@ -2565,6 +3137,7 @@ class OpenAIHandlerMixin:
             ws_recorded_cache_write_tokens_total = 0
             ws_recorded_uncached_input_tokens_total = 0
             ws_recorded_tokens_saved_total = 0
+            ws_recorded_attempted_input_tokens_total = 0
             ws_response_create_frames = 1
             ws_client_frames_total = 1
             ws_upstream_frames_total = 0
@@ -2779,6 +3352,7 @@ class OpenAIHandlerMixin:
                             _ws_reason,
                             _bytes_before,
                             _bytes_after,
+                            _ws_attempted_tokens,
                         ) = self._compress_openai_responses_payload(
                             _inner,
                             model=_model,
@@ -2792,6 +3366,7 @@ class OpenAIHandlerMixin:
                                     _send_body = _new_inner
                                 first_msg_raw = json.dumps(_send_body)
                                 tokens_saved += int(_ws_saved)
+                                attempted_input_tokens_total += int(_ws_attempted_tokens)
                                 for _t in _ws_transforms:
                                     if _t not in transforms_applied:
                                         transforms_applied.append(_t)
@@ -2938,7 +3513,7 @@ class OpenAIHandlerMixin:
                             log reports cumulative savings across all
                             frames in the WS session.
                             """
-                            nonlocal tokens_saved, transforms_applied
+                            nonlocal tokens_saved, transforms_applied, attempted_input_tokens_total
                             nonlocal ws_frames_compressed
                             if _ws_bypass:
                                 _log_ws_passthrough(
@@ -3001,6 +3576,7 @@ class OpenAIHandlerMixin:
                                     frame_reason,
                                     bytes_before,
                                     bytes_after,
+                                    frame_attempted_tokens,
                                 ) = self._compress_openai_responses_payload(
                                     inner_payload,
                                     model=model_for_frame,
@@ -3047,6 +3623,7 @@ class OpenAIHandlerMixin:
                             else:
                                 rewritten = json.dumps(new_inner)
                             tokens_saved += int(frame_saved)
+                            attempted_input_tokens_total += int(frame_attempted_tokens)
                             for t in frame_transforms:
                                 if t not in transforms_applied:
                                     transforms_applied.append(t)
@@ -3238,6 +3815,7 @@ class OpenAIHandlerMixin:
                                 nonlocal ws_recorded_cache_write_tokens_total
                                 nonlocal ws_recorded_uncached_input_tokens_total
                                 nonlocal ws_recorded_tokens_saved_total
+                                nonlocal ws_recorded_attempted_input_tokens_total
 
                                 input_delta = ws_input_tokens_total - ws_recorded_input_tokens_total
                                 output_delta = (
@@ -3255,6 +3833,10 @@ class OpenAIHandlerMixin:
                                     - ws_recorded_uncached_input_tokens_total
                                 )
                                 saved_delta = tokens_saved - ws_recorded_tokens_saved_total
+                                attempted_delta = (
+                                    attempted_input_tokens_total
+                                    - ws_recorded_attempted_input_tokens_total
+                                )
                                 if (
                                     input_delta <= 0
                                     and output_delta <= 0
@@ -3262,6 +3844,7 @@ class OpenAIHandlerMixin:
                                     and cache_write_delta <= 0
                                     and uncached_delta <= 0
                                     and saved_delta <= 0
+                                    and attempted_delta <= 0
                                 ):
                                     return
 
@@ -3290,6 +3873,7 @@ class OpenAIHandlerMixin:
                                     cache_read_tokens=max(0, cache_read_delta),
                                     cache_write_tokens=max(0, cache_write_delta),
                                     uncached_input_tokens=max(0, uncached_delta),
+                                    attempted_input_tokens=max(0, attempted_delta),
                                 )
 
                                 ws_recorded_input_tokens_total = ws_input_tokens_total
@@ -3300,6 +3884,9 @@ class OpenAIHandlerMixin:
                                     ws_uncached_input_tokens_total
                                 )
                                 ws_recorded_tokens_saved_total = tokens_saved
+                                ws_recorded_attempted_input_tokens_total = (
+                                    attempted_input_tokens_total
+                                )
 
                             # The retry-loop variable is safe to close over here:
                             # ``_upstream_to_client`` is defined and awaited within
@@ -3742,6 +4329,10 @@ class OpenAIHandlerMixin:
                 ws_uncached_input_tokens_total - ws_recorded_uncached_input_tokens_total,
             )
             residual_tokens_saved = max(0, tokens_saved - ws_recorded_tokens_saved_total)
+            residual_attempted_input_tokens = max(
+                0,
+                attempted_input_tokens_total - ws_recorded_attempted_input_tokens_total,
+            )
             ws_session_tags = {
                 **(ws_tags or {}),
                 "auth_mode": _final_auth_mode.value,
@@ -3770,6 +4361,7 @@ class OpenAIHandlerMixin:
                 or residual_cache_read_tokens > 0
                 or residual_cache_write_tokens > 0
                 or residual_uncached_input_tokens > 0
+                or residual_attempted_input_tokens > 0
             ):
                 if self.cost_tracker:
                     self.cost_tracker.record_tokens(
@@ -3790,6 +4382,7 @@ class OpenAIHandlerMixin:
                     cache_read_tokens=residual_cache_read_tokens,
                     cache_write_tokens=residual_cache_write_tokens,
                     uncached_input_tokens=residual_uncached_input_tokens,
+                    attempted_input_tokens=residual_attempted_input_tokens,
                 )
             if getattr(self, "logger", None) is not None:
                 from headroom.proxy.helpers import compute_turn_id
diff --git a/headroom/proxy/prometheus_metrics.py b/headroom/proxy/prometheus_metrics.py
index 549b97387..81656d15a 100644
--- a/headroom/proxy/prometheus_metrics.py
+++ b/headroom/proxy/prometheus_metrics.py
@@ -86,6 +86,14 @@ class PrometheusMetrics:
         self.tokens_input_total = 0
         self.tokens_output_total = 0
         self.tokens_saved_total = 0
+        # Sum of tokens we actually attempted to compress across the
+        # session: extracted units that passed all gates + tool-schema
+        # tokens we ran compaction against. Excludes prefix-frozen
+        # content (instructions, user/system messages, prior turns).
+        # This is the right denominator for an "active compression
+        # ratio" — what fraction of the compressible-eligible tokens
+        # did we actually save?
+        self.attempted_input_tokens_total = 0
 
         # Per-strategy compression counters. Populated lazily as we see
         # each strategy tag — no hardcoded list of strategies; the keys
@@ -219,6 +227,7 @@ class PrometheusMetrics:
             self.tokens_input_total = 0
             self.tokens_output_total = 0
             self.tokens_saved_total = 0
+            self.attempted_input_tokens_total = 0
 
             self.compressions_by_strategy.clear()
             self.tokens_saved_by_strategy.clear()
@@ -395,6 +404,7 @@ class PrometheusMetrics:
         cache_write_5m_tokens: int = 0,
         cache_write_1h_tokens: int = 0,
         uncached_input_tokens: int = 0,
+        attempted_input_tokens: int = 0,
     ):
         """Record metrics for a request."""
         async with self._lock:
@@ -408,6 +418,9 @@ class PrometheusMetrics:
             self.tokens_input_total += input_tokens
             self.tokens_output_total += output_tokens
             self.tokens_saved_total += tokens_saved
+            # See the attribute definition for why this is the right
+            # denominator for the active-compression ratio.
+            self.attempted_input_tokens_total += max(0, int(attempted_input_tokens))
 
             # Track provider-specific prefix cache metrics
             if cache_read_tokens > 0 or cache_write_tokens > 0:
diff --git a/headroom/proxy/server.py b/headroom/proxy/server.py
index 30fe69b41..2ec8f2723 100644
--- a/headroom/proxy/server.py
+++ b/headroom/proxy/server.py
@@ -1049,11 +1049,25 @@ class HeadroomProxy(
         logger.info(f"Input tokens:          {m.tokens_input_total:,}")
         logger.info(f"Output tokens:         {m.tokens_output_total:,}")
         logger.info(f"Tokens saved:          {m.tokens_saved_total:,}")
+        # Active-compression ratio: savings as a fraction of what we
+        # *attempted* to compress (extracted units + tool schema),
+        # NOT the whole request. The full-request denominator is
+        # dominated by frozen prefix bytes (instructions, user msgs,
+        # prior turns) that we never touch — including them collapses
+        # the headline number even on sessions where every attempted
+        # compression succeeded.
+        attempted = getattr(m, "attempted_input_tokens_total", 0)
+        if attempted > 0:
+            # `attempted` is pre-compression; savings rate is plain
+            # saved / attempted.
+            savings_pct = (m.tokens_saved_total / attempted) * 100
+            logger.info(f"Active compression:    {savings_pct:.1f}%")
+            logger.info(f"  (attempted tokens:   {attempted:,})")
         if m.tokens_input_total > 0:
-            savings_pct = (
+            whole_request_pct = (
                 m.tokens_saved_total / (m.tokens_input_total + m.tokens_saved_total)
             ) * 100
-            logger.info(f"Token savings:         {savings_pct:.1f}%")
+            logger.info(f"Of total wire traffic: {whole_request_pct:.2f}%")
         if m.latency_count > 0:
             avg_latency = m.latency_sum_ms / m.latency_count
             logger.info(f"Avg latency:           {avg_latency:.0f}ms")
@@ -1789,6 +1803,19 @@ def create_app(config: ProxyConfig | None = None) -> FastAPI:
         all_layers_tokens_saved = proxy_compression_tokens + cli_tokens_avoided
         total_tokens_before = m.tokens_input_total + all_layers_tokens_saved
         proxy_total_before_compression = m.tokens_input_total + proxy_compression_tokens
+        # `attempted_input_tokens` is the compressible-only denominator
+        # (extracted units + tool schema). The "active compression"
+        # ratio is what fraction of the tokens we *tried* to compress
+        # actually got compressed. Excludes prefix-frozen content
+        # (user/system messages, prior turns) we never touched —
+        # otherwise the ratio is dominated by content we deliberately
+        # avoided changing for prefix-cache safety.
+        # `attempted_input_tokens_total` is already pre-compression: it
+        # accumulates `unit.tokens_before` for each eligible unit that
+        # reached the router, plus the original (pre-compaction) tool
+        # schema size. So the savings rate is plain `saved / attempted`
+        # — adding `saved` again would double-count.
+        attempted_input_tokens = getattr(m, "attempted_input_tokens_total", 0)
 
         # Build human-readable summary
         summary = _build_session_summary(
@@ -1889,6 +1916,26 @@ def create_app(config: ProxyConfig | None = None) -> FastAPI:
                 "proxy_total_before_compression": proxy_total_before_compression,
                 "total_before_compression": total_tokens_before,
                 "all_layers_saved": all_layers_tokens_saved,
+                # Compressible-only denominator: tokens we extracted as
+                # candidates + tool-schema tokens we compacted. Excludes
+                # frozen-prefix content (user msgs, system prompt, prior
+                # turns) that we deliberately don't touch. Already
+                # pre-compression — do NOT add `tokens_saved` again.
+                "proxy_attempted_tokens": attempted_input_tokens,
+                # Active compression: savings as a fraction of what we
+                # *tried* to compress. The number the dashboard headline
+                # should show — it answers "are we doing well *when we
+                # have something to compress?*" rather than diluting the
+                # win by frozen-prefix bytes we never touched.
+                "active_savings_percent": round(
+                    (proxy_compression_tokens / attempted_input_tokens * 100)
+                    if attempted_input_tokens > 0
+                    else 0,
+                    2,
+                ),
+                # Whole-request ratio kept for transparency. Heavily
+                # diluted by frozen prefix on Codex-style requests
+                # where most input is non-compressible by design.
                 "proxy_savings_percent": round(
                     (proxy_compression_tokens / proxy_total_before_compression * 100)
                     if proxy_total_before_compression > 0
diff --git a/headroom/transforms/compression_units.py b/headroom/transforms/compression_units.py
index 7253fbcf1..ab97426eb 100644
--- a/headroom/transforms/compression_units.py
+++ b/headroom/transforms/compression_units.py
@@ -8,6 +8,7 @@ replacements back into their native request shape.
 
 from __future__ import annotations
 
+import re
 from collections.abc import Iterable
 from dataclasses import dataclass, field, replace
 from typing import Protocol
@@ -37,6 +38,42 @@ class CompressionUnit:
     metadata: dict[str, str] = field(default_factory=dict)
 
 
+# Categorical buckets for unit-level outcomes. Lets log readers filter
+# by "what kind of decision" without parsing per-event reason strings.
+# - applied:           the compressor ran and produced shorter bytes
+# - protected_role:    role guard (user/system/assistant) refused compression
+# - cache_zone:        unit lived in a non-live cache zone (e.g. prefix)
+# - size_floor:        text_bytes < min_bytes — too small to be worth it
+# - immutable:         caller marked the unit unmutable
+# - compressor_noop:   router returned identical bytes (no compression possible)
+# - already_compressed: input already carried a CCR retrieval marker
+# - rejected_not_smaller: compressor produced output >= input tokens
+# - cache_hit:         result returned from result_cache (placeholder; not
+#                      currently wired into the unit path — see follow-up)
+UNIT_REASON_CATEGORIES = {
+    None: "applied",
+    "protected_user_message": "protected_role",
+    "protected_system_message": "protected_role",
+    "protected_assistant_message": "protected_role",
+    "immutable": "immutable",
+    "below_unit_floor": "size_floor",
+    "router_no_change": "compressor_noop",
+    "already_compressed": "already_compressed",
+    "rejected_not_smaller": "rejected_not_smaller",
+}
+
+
+def _categorize_reason(reason: str | None) -> str:
+    if reason is None:
+        return "applied"
+    if reason in UNIT_REASON_CATEGORIES:
+        return UNIT_REASON_CATEGORIES[reason] or "applied"
+    # cache_zone_* uses a dynamic suffix (cache_zone_frozen, cache_zone_prefix, …)
+    if reason.startswith("cache_zone_"):
+        return "cache_zone"
+    return "other"
+
+
 @dataclass(frozen=True)
 class UnitCompressionResult:
     original: str
@@ -49,6 +86,12 @@ class UnitCompressionResult:
     strategy: str
     reason: str | None = None
     router_result: RouterCompressionResult | None = None
+    # Context for log readers: why the outcome looked the way it did.
+    # `text_bytes` + `min_bytes` together explain size_floor decisions;
+    # `reason_category` is the high-level bucket for dashboard grouping.
+    text_bytes: int = 0
+    min_bytes: int = 0
+    reason_category: str = "applied"
 
 
 @dataclass(frozen=True)
@@ -59,6 +102,11 @@ class RoutedCompressionUnit:
     slot: object
 
 
+_CCR_MARKER_RE = re.compile(
+    r"(?m)^.*(?:Retrieve more: hash=|Retrieve original: hash=|<<ccr:[^>]+>>).*$"
+)
+
+
 def find_content_router(transforms: object) -> ContentRouter | None:
     """Return the first ContentRouter in a pipeline or iterable."""
 
@@ -71,6 +119,84 @@ def find_content_router(transforms: object) -> ContentRouter | None:
     return None
 
 
+def _compress_live_text_with_markers(
+    unit: CompressionUnit,
+    *,
+    router: ContentRouter,
+) -> tuple[str, list[str], RouterCompressionResult | None]:
+    """Compress text around CCR markers while preserving marker bytes."""
+
+    parts: list[str] = []
+    transforms: list[str] = []
+    last_end = 0
+    last_router_result: RouterCompressionResult | None = None
+
+    for match in _CCR_MARKER_RE.finditer(unit.text):
+        prefix = unit.text[last_end : match.start()]
+        if prefix:
+            compressed_prefix, prefix_transforms, last_router_result = _compress_marker_free_text(
+                prefix,
+                unit=unit,
+                router=router,
+                last_router_result=last_router_result,
+            )
+            parts.append(compressed_prefix)
+            transforms.extend(prefix_transforms)
+        parts.append(match.group(0))
+        last_end = match.end()
+
+    suffix = unit.text[last_end:]
+    if suffix:
+        compressed_suffix, suffix_transforms, last_router_result = _compress_marker_free_text(
+            suffix,
+            unit=unit,
+            router=router,
+            last_router_result=last_router_result,
+        )
+        parts.append(compressed_suffix)
+        transforms.extend(suffix_transforms)
+
+    if transforms:
+        transforms.insert(0, "ccr_marker_preserving")
+
+    return "".join(parts), transforms, last_router_result
+
+
+def _compress_marker_free_text(
+    text: str,
+    *,
+    unit: CompressionUnit,
+    router: ContentRouter,
+    last_router_result: RouterCompressionResult | None,
+) -> tuple[str, list[str], RouterCompressionResult | None]:
+    boundary = re.match(r"^(\s*)(.*?)(\s*)$", text, flags=re.DOTALL)
+    if boundary is None:
+        return text, [], last_router_result
+
+    leading, core, trailing = boundary.groups()
+    if len(core) < unit.min_bytes:
+        return text, [], last_router_result
+
+    router_result = router.compress(
+        core,
+        context=unit.context,
+        question=unit.question,
+        bias=unit.bias,
+    )
+    if router_result.compressed == core:
+        return text, [], router_result
+
+    strategy = router_result.strategy_used.value
+    return (
+        f"{leading}{router_result.compressed}{trailing}",
+        [
+            f"router:{unit.provider}:{unit.endpoint}:{unit.item_type}:{strategy}",
+            strategy,
+        ],
+        router_result,
+    )
+
+
 def compress_unit_with_router(
     unit: CompressionUnit,
     *,
@@ -84,6 +210,7 @@ def compress_unit_with_router(
     """
 
     tokens_before = tokenizer.count_text(unit.text)
+    text_bytes = len(unit.text.encode("utf-8", errors="replace"))
     base = UnitCompressionResult(
         original=unit.text,
         compressed=unit.text,
@@ -94,22 +221,67 @@ def compress_unit_with_router(
         transforms_applied=[],
         strategy=CompressionStrategy.PASSTHROUGH.value,
         router_result=None,
+        text_bytes=text_bytes,
+        min_bytes=unit.min_bytes,
+        reason_category="applied",
     )
 
+    def _with_reason(**kw: object) -> UnitCompressionResult:
+        # Every early-return path goes through here so reason_category
+        # stays in sync with reason. Log readers grep by category for
+        # quick "how many units were size-floored this hour" answers.
+        reason_val = kw.get("reason")
+        if isinstance(reason_val, str) or reason_val is None:
+            kw["reason_category"] = _categorize_reason(reason_val)
+        return replace(base, **kw)  # type: ignore[arg-type]
+
     if not unit.mutable:
-        return replace(base, reason="immutable")
+        return _with_reason(reason="immutable")
     if unit.role == "user":
-        return replace(base, reason="protected_user_message")
+        return _with_reason(reason="protected_user_message")
     if unit.role in {"system", "developer"}:
-        return replace(base, reason="protected_system_message")
+        return _with_reason(reason="protected_system_message")
     if unit.role == "assistant" and unit.metadata.get("compress_assistant") != "true":
-        return replace(base, reason="protected_assistant_message")
+        return _with_reason(reason="protected_assistant_message")
     if unit.cache_zone != "live":
-        return replace(base, reason=f"cache_zone_{unit.cache_zone}")
+        return _with_reason(reason=f"cache_zone_{unit.cache_zone}")
     if len(unit.text) < unit.min_bytes:
-        return replace(base, reason="below_unit_floor")
-    if "Retrieve more: hash=" in unit.text or "Retrieve original: hash=" in unit.text:
-        return replace(base, reason="already_compressed")
+        return _with_reason(reason="below_unit_floor")
+    if _CCR_MARKER_RE.search(unit.text):
+        replacement, marker_transforms, router_result = _compress_live_text_with_markers(
+            unit,
+            router=router,
+        )
+        if replacement == unit.text:
+            return _with_reason(
+                router_result=router_result,
+                reason="already_compressed",
+            )
+
+        tokens_after = tokenizer.count_text(replacement)
+        if tokens_after >= tokens_before:
+            return _with_reason(
+                compressed=replacement,
+                tokens_after=tokens_after,
+                router_result=router_result,
+                reason="rejected_not_smaller",
+            )
+
+        return UnitCompressionResult(
+            original=unit.text,
+            compressed=replacement,
+            modified=True,
+            tokens_before=tokens_before,
+            tokens_after=tokens_after,
+            tokens_saved=tokens_before - tokens_after,
+            transforms_applied=marker_transforms,
+            strategy="ccr_marker_preserving",
+            reason=None,
+            router_result=router_result,
+            text_bytes=text_bytes,
+            min_bytes=unit.min_bytes,
+            reason_category="applied",
+        )
 
     router_result = router.compress(
         unit.text,
@@ -120,8 +292,7 @@ def compress_unit_with_router(
     replacement = router_result.compressed
     strategy = router_result.strategy_used.value
     if replacement == unit.text:
-        return replace(
-            base,
+        return _with_reason(
             strategy=strategy,
             router_result=router_result,
             reason="router_no_change",
@@ -129,8 +300,7 @@ def compress_unit_with_router(
 
     tokens_after = tokenizer.count_text(replacement)
     if tokens_after >= tokens_before:
-        return replace(
-            base,
+        return _with_reason(
             compressed=replacement,
             tokens_after=tokens_after,
             strategy=strategy,
@@ -152,6 +322,9 @@ def compress_unit_with_router(
         strategy=strategy,
         reason=None,
         router_result=router_result,
+        text_bytes=text_bytes,
+        min_bytes=unit.min_bytes,
+        reason_category="applied",
     )
 
 
diff --git a/headroom/transforms/content_router.py b/headroom/transforms/content_router.py
index ccec45590..f45273a93 100644
--- a/headroom/transforms/content_router.py
+++ b/headroom/transforms/content_router.py
@@ -35,6 +35,7 @@ Pipeline Usage:
 from __future__ import annotations
 
 import hashlib
+import json
 import logging
 import os
 import re
@@ -52,6 +53,57 @@ from .content_detector import ContentType, DetectionResult
 logger = logging.getLogger(__name__)
 
 
+def _router_debug_dumps(value: Any) -> str:
+    return json.dumps(value, ensure_ascii=False, default=str, separators=(",", ":"))
+
+
+def _log_router_debug(event: str, **payload: Any) -> None:
+    payload = {"event": event, **payload}
+    logger.info("event=%s %s", event, _router_debug_dumps(payload))
+
+
+def _json_shape(content: str) -> dict[str, Any]:
+    try:
+        parsed = json.loads(content)
+    except Exception as exc:
+        return {"is_json": False, "error": type(exc).__name__}
+    if isinstance(parsed, dict):
+        return {
+            "is_json": True,
+            "kind": "object",
+            "keys": list(parsed.keys()),
+            "length": len(parsed),
+        }
+    if isinstance(parsed, list):
+        return {"is_json": True, "kind": "array", "length": len(parsed)}
+    return {"is_json": True, "kind": type(parsed).__name__}
+
+
+def _mixed_indicators(content: str) -> dict[str, bool]:
+    return {
+        "has_code_fences": bool(_CODE_FENCE_PATTERN.search(content)),
+        "has_json_blocks": bool(_JSON_BLOCK_START.search(content)),
+        "has_prose": len(_PROSE_PATTERN.findall(content)) > 5,
+        "has_search_results": bool(_SEARCH_RESULT_PATTERN.search(content)),
+    }
+
+
+def _section_debug(section: ContentSection, index: int) -> dict[str, Any]:
+    return {
+        "index": index,
+        "content_type": section.content_type.value,
+        "language": getattr(section, "language", None),
+        "start_line": getattr(section, "start_line", None),
+        "end_line": getattr(section, "end_line", None),
+        "is_code_fence": getattr(section, "is_code_fence", False),
+        "chars": len(section.content),
+        "bytes": len(section.content.encode("utf-8", errors="replace")),
+        "tokens_estimate": len(section.content.split()),
+        "json_shape": _json_shape(section.content),
+        "content": section.content,
+    }
+
+
 def _detect_content(content: str) -> DetectionResult:
     """Detect content type via the Rust detection chain.
 
@@ -290,6 +342,16 @@ class RouterCompressionResult:
         strategy_used: Primary strategy used for compression.
         routing_log: List of routing decisions made.
         sections_processed: Number of content sections processed.
+        strategy_chain: Every strategy attempted in order. For a direct
+            hit it's a single entry; for the SMART_CRUSHER → KOMPRESS →
+            LOG fallback chain it's three. Lets log readers see *how*
+            we got to the final compressor without parsing the
+            decision_reason string.
+        cache_hit: True when this result came from the router's
+            result_cache (no fresh compression ran). Currently the
+            single-content compress() path doesn't populate the cache,
+            so this is False in practice — placeholder for the
+            cache-wire-up follow-up.
     """
 
     compressed: str
@@ -297,6 +359,8 @@ class RouterCompressionResult:
     strategy_used: CompressionStrategy
     routing_log: list[RoutingDecision] = field(default_factory=list)
     sections_processed: int = 1
+    strategy_chain: list[str] = field(default_factory=list)
+    cache_hit: bool = False
 
     @property
     def total_original_tokens(self) -> int:
@@ -773,7 +837,25 @@ class ContentRouter(Transform):
         Returns:
             RouterCompressionResult with compressed content and routing metadata.
         """
+        request_debug = {
+            "chars": len(content),
+            "bytes": len(content.encode("utf-8", errors="replace")),
+            "tokens_estimate": len(content.split()),
+            "json_shape": _json_shape(content),
+            "mixed_indicators": _mixed_indicators(content),
+            "context_chars": len(context),
+            "question": question,
+            "bias": bias,
+            "content": content,
+            "context": context,
+        }
         if not content or not content.strip():
+            _log_router_debug(
+                "content_router_input",
+                **request_debug,
+                selected_strategy=CompressionStrategy.PASSTHROUGH.value,
+                selection_reason="empty_or_whitespace",
+            )
             result = RouterCompressionResult(
                 compressed=content,
                 original=content,
@@ -782,7 +864,17 @@ class ContentRouter(Transform):
             )
         else:
             # Determine strategy from content analysis
+            mixed = is_mixed_content(content)
+            detection = _detect_content(content)
             strategy = self._determine_strategy(content)
+            _log_router_debug(
+                "content_router_input",
+                **request_debug,
+                detected_content_type=detection.content_type.value,
+                detection_confidence=detection.confidence,
+                selected_strategy=strategy.value,
+                selection_reason="mixed_content" if mixed else "content_detection",
+            )
 
             if strategy == CompressionStrategy.MIXED:
                 result = self._compress_mixed(content, context, question, bias=bias)
@@ -793,6 +885,30 @@ class ContentRouter(Transform):
         # forcing function for catching strategy-level regressions.
         # Empty routing_log (passthrough fast path) → no calls.
         self._observe(result)
+        _log_router_debug(
+            "content_router_output",
+            selected_strategy=result.strategy_used.value,
+            sections_processed=result.sections_processed,
+            total_original_tokens=result.total_original_tokens,
+            total_compressed_tokens=result.total_compressed_tokens,
+            tokens_saved=result.tokens_saved,
+            savings_percentage=result.savings_percentage,
+            compression_ratio=result.compression_ratio,
+            routing_log=[
+                {
+                    "content_type": decision.content_type.value,
+                    "strategy": decision.strategy.value,
+                    "original_tokens": decision.original_tokens,
+                    "compressed_tokens": decision.compressed_tokens,
+                    "confidence": decision.confidence,
+                    "section_index": decision.section_index,
+                    "compression_ratio": decision.compression_ratio,
+                }
+                for decision in result.routing_log
+            ],
+            original=result.original,
+            compressed=result.compressed,
+        )
         return result
 
     def _observe(self, result: RouterCompressionResult) -> None:
@@ -881,6 +997,12 @@ class ContentRouter(Transform):
             RouterCompressionResult with reassembled content.
         """
         sections = split_into_sections(content)
+        _log_router_debug(
+            "content_router_mixed_sections",
+            section_count=len(sections),
+            sections=[_section_debug(section, idx) for idx, section in enumerate(sections)],
+            content=content,
+        )
 
         if not sections:
             return RouterCompressionResult(
@@ -898,7 +1020,7 @@ class ContentRouter(Transform):
 
             # Compress section
             original_tokens = len(section.content.split())
-            compressed_content, compressed_tokens = self._apply_strategy_to_content(
+            compressed_content, compressed_tokens, _section_chain = self._apply_strategy_to_content(
                 section.content,
                 strategy,
                 context,
@@ -952,7 +1074,7 @@ class ContentRouter(Transform):
         """
         original_tokens = len(content.split())
 
-        compressed, compressed_tokens = self._apply_strategy_to_content(
+        compressed, compressed_tokens, strategy_chain = self._apply_strategy_to_content(
             content, strategy, context, question=question, bias=bias
         )
 
@@ -960,6 +1082,7 @@ class ContentRouter(Transform):
             compressed=compressed,
             original=content,
             strategy_used=strategy,
+            strategy_chain=strategy_chain,
             routing_log=[
                 RoutingDecision(
                     content_type=self._content_type_from_strategy(strategy),
@@ -978,7 +1101,7 @@ class ContentRouter(Transform):
         language: str | None = None,
         question: str | None = None,
         bias: float = 1.0,
-    ) -> tuple[str, int]:
+    ) -> tuple[str, int, list[str]]:
         """Apply a compression strategy to content.
 
         Args:
@@ -990,86 +1113,206 @@ class ContentRouter(Transform):
             bias: Compression bias multiplier (>1 = keep more, <1 = keep fewer).
 
         Returns:
-            Tuple of (compressed_content, compressed_token_count).
+            Tuple of (compressed_content, compressed_token_count,
+            strategy_chain). The chain lists every strategy attempted
+            in order — first the requested one, then any fallbacks.
+            Single-entry chain means a direct hit; multi-entry means
+            the fallback chain fired (e.g. ``[smart_crusher, kompress,
+            log]``). Log readers use this to see *how* we got to the
+            final compressor without parsing decision_reason strings.
         """
         # Track original tokens for TOIN recording
         original_tokens = len(content.split())
         compressed: str | None = None
         compressed_tokens: int | None = None
+        requested_strategy = strategy
+        actual_strategy = strategy
+        compressor_name = strategy.value
+        decision_reason = "strategy_not_enabled_or_unavailable"
+        strategy_chain: list[str] = [strategy.value]
+        error: str | None = None
 
         try:
             if strategy == CompressionStrategy.CODE_AWARE:
                 if self.config.enable_code_aware:
                     compressor = self._get_code_compressor()
                     if compressor:
+                        compressor_name = type(compressor).__name__
                         result = compressor.compress(content, language=language, context=context)
                         compressed, compressed_tokens = result.compressed, result.compressed_tokens
+                        decision_reason = "code_aware"
                 if compressed is None:
                     # Fallback to Kompress
                     compressed, compressed_tokens = self._try_ml_compressor(
                         content, context, question
                     )
                     strategy = CompressionStrategy.KOMPRESS  # Update for TOIN
+                    actual_strategy = strategy
+                    compressor_name = "KompressCompressor"
+                    decision_reason = "code_aware_unavailable_fallback_kompress"
+                    strategy_chain.append(CompressionStrategy.KOMPRESS.value)
 
             elif strategy == CompressionStrategy.SMART_CRUSHER:
                 # SmartCrusher handles its own TOIN recording
                 if self.config.enable_smart_crusher:
                     crusher = self._get_smart_crusher()
                     if crusher:
+                        compressor_name = type(crusher).__name__
                         result = crusher.crush(content, query=context, bias=bias)
-                        return result.compressed, len(result.compressed.split())
+                        compressed, compressed_tokens = (
+                            result.compressed,
+                            len(result.compressed.split()),
+                        )
+                        smart_crusher_fallback = False
+                        if result.compressed == content:
+                            strategy_chain.append(CompressionStrategy.KOMPRESS.value)
+                            fallback_compressed, fallback_tokens = self._try_ml_compressor(
+                                content, context, question
+                            )
+                            if fallback_tokens < compressed_tokens:
+                                compressed = fallback_compressed
+                                compressed_tokens = fallback_tokens
+                                actual_strategy = CompressionStrategy.KOMPRESS
+                                compressor_name = "KompressCompressor"
+                                decision_reason = "smart_crusher_fallback_kompress_after_no_savings"
+                                smart_crusher_fallback = True
+                        if not smart_crusher_fallback:
+                            decision_reason = "smart_crusher"
 
             elif strategy == CompressionStrategy.SEARCH:
                 if self.config.enable_search_compressor:
                     compressor = self._get_search_compressor()
                     if compressor:
+                        compressor_name = type(compressor).__name__
                         result = compressor.compress(content, context=context, bias=bias)
                         compressed, compressed_tokens = (
                             result.compressed,
                             len(result.compressed.split()),
                         )
+                        decision_reason = "search_compressor"
 
             elif strategy == CompressionStrategy.LOG:
                 if self.config.enable_log_compressor:
                     compressor = self._get_log_compressor()
                     if compressor:
+                        compressor_name = type(compressor).__name__
                         result = compressor.compress(content, bias=bias)
+                        # Use the same word-count metric the rest of the
+                        # router uses; `compressed_line_count` is in
+                        # lines, not tokens — recording it here made
+                        # ratios meaningless against `original_tokens`.
                         compressed, compressed_tokens = (
                             result.compressed,
-                            result.compressed_line_count,
+                            len(result.compressed.split()),
                         )
+                        decision_reason = "log_compressor"
 
             elif strategy == CompressionStrategy.DIFF:
                 compressor = self._get_diff_compressor()
                 if compressor:
+                    compressor_name = type(compressor).__name__
                     result = compressor.compress(content, context=context)
                     compressed, compressed_tokens = (
                         result.compressed,
-                        result.compressed_line_count,
+                        len(result.compressed.split()),
                     )
+                    decision_reason = "diff_compressor"
 
             elif strategy == CompressionStrategy.HTML:
                 if self.config.enable_html_extractor:
                     extractor = self._get_html_extractor()
                     if extractor:
+                        compressor_name = type(extractor).__name__
                         result = extractor.extract(content)
                         compressed = result.extracted
                         # Estimate tokens from extracted text (simple word count)
                         compressed_tokens = len(compressed.split()) if compressed else 0
+                        decision_reason = "html_extractor"
 
             elif strategy == CompressionStrategy.KOMPRESS:
                 compressed, compressed_tokens = self._try_ml_compressor(content, context, question)
+                compressor_name = "KompressCompressor"
+                decision_reason = "kompress"
 
             elif strategy == CompressionStrategy.TEXT:
                 # Prefer Kompress ML compressor for text
                 # Passes through unchanged if Kompress not available
                 compressed, compressed_tokens = self._try_ml_compressor(content, context, question)
+                compressor_name = "KompressCompressor"
+                decision_reason = "text_uses_kompress"
 
         except Exception as e:
+            error = f"{type(e).__name__}: {e}"
+            decision_reason = "compression_exception"
             logger.warning("Compression with %s failed: %s", strategy.value, e)
 
         # If compression succeeded, record to TOIN
         if compressed is not None and compressed_tokens is not None:
+            fallback_eligible_strategy = strategy in {
+                CompressionStrategy.SMART_CRUSHER,
+                CompressionStrategy.CODE_AWARE,
+                CompressionStrategy.DIFF,
+                CompressionStrategy.LOG,
+            }
+            fallback_no_savings = compressed == content or compressed_tokens >= original_tokens
+            if fallback_eligible_strategy and fallback_no_savings:
+                strategy_chain.append(CompressionStrategy.KOMPRESS.value)
+                fallback_compressed, fallback_tokens = self._try_ml_compressor(
+                    content, context, question
+                )
+                if fallback_tokens < compressed_tokens:
+                    compressed = fallback_compressed
+                    compressed_tokens = fallback_tokens
+                    actual_strategy = CompressionStrategy.KOMPRESS
+                    compressor_name = "KompressCompressor"
+                    decision_reason = f"{decision_reason}_fallback_kompress_after_no_savings"
+                else:
+                    # Last-ditch: line-structured compressors (the proxy's
+                    # own log dumps land here — repetitive JSONL that
+                    # Kompress can't shrink but the log compressor can).
+                    # Only attempted when the strategy was SMART_CRUSHER so
+                    # we don't reroute genuine code/diff content.
+                    if (
+                        strategy == CompressionStrategy.SMART_CRUSHER
+                        and self.config.enable_log_compressor
+                    ):
+                        log_compressor = self._get_log_compressor()
+                        if log_compressor is not None:
+                            strategy_chain.append(CompressionStrategy.LOG.value)
+                            try:
+                                log_result = log_compressor.compress(content, bias=bias)
+                            except Exception as exc:  # noqa: BLE001
+                                logger.debug("Log fallback failed for SMART_CRUSHER: %s", exc)
+                            else:
+                                log_compressed_tokens = len(log_result.compressed.split())
+                                if log_compressed_tokens < compressed_tokens:
+                                    compressed = log_result.compressed
+                                    compressed_tokens = log_compressed_tokens
+                                    actual_strategy = CompressionStrategy.LOG
+                                    compressor_name = type(log_compressor).__name__
+                                    decision_reason = (
+                                        f"{decision_reason}_fallback_log_after_no_savings"
+                                    )
+
+            _log_router_debug(
+                "content_router_strategy_result",
+                requested_strategy=requested_strategy.value,
+                actual_strategy=actual_strategy.value,
+                strategy_chain=strategy_chain,
+                compressor=compressor_name,
+                reason=decision_reason,
+                language=language,
+                question=question,
+                bias=bias,
+                original_tokens=original_tokens,
+                compressed_tokens=compressed_tokens,
+                tokens_saved=max(0, original_tokens - compressed_tokens),
+                compression_ratio=compressed_tokens / original_tokens if original_tokens else 1.0,
+                json_shape=_json_shape(content),
+                input=content,
+                output=compressed,
+                error=error,
+            )
             self._record_to_toin(
                 strategy=strategy,
                 content=content,
@@ -1079,10 +1322,30 @@ class ContentRouter(Transform):
                 language=language,
                 context=context,
             )
-            return compressed, compressed_tokens
+            return compressed, compressed_tokens, strategy_chain
 
         # Fallback: return unchanged
-        return content, original_tokens
+        strategy_chain.append(CompressionStrategy.PASSTHROUGH.value)
+        _log_router_debug(
+            "content_router_strategy_result",
+            requested_strategy=requested_strategy.value,
+            actual_strategy=CompressionStrategy.PASSTHROUGH.value,
+            strategy_chain=strategy_chain,
+            compressor=None,
+            reason=decision_reason,
+            language=language,
+            question=question,
+            bias=bias,
+            original_tokens=original_tokens,
+            compressed_tokens=original_tokens,
+            tokens_saved=0,
+            compression_ratio=1.0,
+            json_shape=_json_shape(content),
+            input=content,
+            output=content,
+            error=error,
+        )
+        return content, original_tokens, strategy_chain
 
     def _try_ml_compressor(
         self, content: str, context: str, question: str | None = None
diff --git a/tests/test_compression_determinism.py b/tests/test_compression_determinism.py
new file mode 100644
index 000000000..31c58eaf8
--- /dev/null
+++ b/tests/test_compression_determinism.py
@@ -0,0 +1,160 @@
+"""Determinism regression test for the compression pipeline.
+
+Prefix caching at Anthropic/OpenAI is byte-exact: turn N+2's cache hit
+requires the bytes for turn-N-and-earlier tool results to be identical
+across requests. That holds iff every compressor in the pipeline is
+deterministic — same input bytes in, same output bytes out, with no
+dependence on wall clock, RNG, or process-local state.
+
+This test pins that invariant against a small fixture of representative
+tool-output shapes. If any compressor sneaks in non-determinism (e.g. a
+timestamp, a uuid, an iteration-order dependency), this test fails
+before the change ships and silently busts cache hit rates in
+production.
+"""
+
+from __future__ import annotations
+
+import json
+
+from headroom.transforms.compression_units import (
+    CompressionUnit,
+    compress_unit_with_router,
+)
+from headroom.transforms.content_router import (
+    ContentRouter,
+    ContentRouterConfig,
+)
+
+
+class _WhitespaceTokenizer:
+    """Stand-in tokenizer — matches the production token-counter protocol
+    used by `compress_unit_with_router`. Deterministic by construction;
+    real tokenizers (tiktoken, anthropic) are also deterministic for the
+    same input + model."""
+
+    def count_text(self, text: str) -> int:
+        return len(text.split())
+
+
+_FIXTURES: dict[str, str] = {
+    "git_diff_wrapped": (
+        "Chunk ID: 904f13\n"
+        "Wall time: 0.0000 seconds\n"
+        "Process exited with code 0\n"
+        "Original token count: 1996\n"
+        "Output:\n"
+        "headroom/proxy/handlers/openai.py | 12 ++++++++++++\n"
+        " 1 file changed, 12 insertions(+)\n\n"
+        "--- Changes ---\n\n"
+        "diff --git a/headroom/proxy/handlers/openai.py b/headroom/proxy/handlers/openai.py\n"
+        "@@ -10,6 +10,18 @@\n"
+        " def handle():\n"
+        "+    # twelve lines of added context\n" * 6 + "     return None\n"
+    ),
+    "jsonl_log_lines": "\n".join(
+        json.dumps(
+            {
+                "ts": f"2026-05-10T14:13:{seconds:02d}",
+                "level": "INFO",
+                "event": "codex_compression_units",
+                "request_id": f"hr_1778447324_{seconds:06d}",
+                "model": "gpt-5.5",
+                "tokens_before": 1234 + seconds,
+                "tokens_after": 567 + seconds,
+            },
+            separators=(",", ":"),
+        )
+        for seconds in range(30)
+    ),
+    "search_results_grep": "\n".join(
+        f"src/foo/bar/{n:03d}.py:{n * 7}:    def function_{n}(self, arg):" for n in range(40)
+    ),
+    "plain_long_text": " ".join(["headroom"] * 400),
+}
+
+
+def _compress(content: str, *, router: ContentRouter) -> str:
+    """Run one canonical compression round-trip through the unit layer.
+
+    Uses a fresh router so this exercises the full detection +
+    strategy-selection path each call (no result_cache priming from a
+    prior call leaking the answer)."""
+
+    unit = CompressionUnit(
+        text=content,
+        provider="openai",
+        endpoint="responses",
+        role="tool",
+        item_type="function_call_output",
+        cache_zone="live",
+        mutable=True,
+        min_bytes=64,
+    )
+    result = compress_unit_with_router(
+        unit,
+        router=router,
+        tokenizer=_WhitespaceTokenizer(),
+    )
+    return result.compressed
+
+
+def test_compression_pipeline_is_byte_deterministic() -> None:
+    """Two independent runs of every fixture must produce identical
+    bytes. Fresh `ContentRouter` instances avoid the in-process result
+    cache short-circuiting the second call — we want the *compression*
+    to be deterministic, not just memoized."""
+
+    for name, content in _FIXTURES.items():
+        router_a = ContentRouter(ContentRouterConfig())
+        router_b = ContentRouter(ContentRouterConfig())
+
+        first = _compress(content, router=router_a)
+        second = _compress(content, router=router_b)
+
+        assert first == second, (
+            f"Non-deterministic compression for fixture {name!r}: "
+            f"len(first)={len(first)} len(second)={len(second)}"
+        )
+
+
+def test_compression_result_cache_returns_identical_bytes() -> None:
+    """Within one router, two calls on the same content must return
+    identical bytes. Catches a result-cache that stores partial state
+    or re-runs the compressor with different seeds on cache miss vs
+    cache hit."""
+
+    for name, content in _FIXTURES.items():
+        router = ContentRouter(ContentRouterConfig())
+
+        first = _compress(content, router=router)
+        second = _compress(content, router=router)
+
+        assert first == second, (
+            f"Result-cache returned different bytes for fixture {name!r}: first_hash≠second_hash"
+        )
+
+
+def test_protected_roles_pass_through_unchanged() -> None:
+    """Companion guarantee to determinism: protected roles never see
+    any compressor at all, regardless of size. If this regresses, the
+    prefix-cache invariant for user/system/assistant content is gone."""
+
+    router = ContentRouter(ContentRouterConfig())
+    payload = _FIXTURES["plain_long_text"]
+
+    for role in ("user", "system", "developer", "assistant"):
+        result = compress_unit_with_router(
+            CompressionUnit(
+                text=payload,
+                provider="openai",
+                endpoint="responses",
+                role=role,
+                item_type="message",
+                min_bytes=64,
+            ),
+            router=router,
+            tokenizer=_WhitespaceTokenizer(),
+        )
+        assert result.modified is False, f"role={role!r} was modified"
+        assert result.compressed == payload, f"role={role!r} bytes changed"
diff --git a/tests/test_compression_units.py b/tests/test_compression_units.py
index d012fce29..870f3563d 100644
--- a/tests/test_compression_units.py
+++ b/tests/test_compression_units.py
@@ -158,3 +158,52 @@ def test_compress_unit_protects_prompt_roles() -> None:
 
         assert result.modified is False
         assert result.reason == reason
+
+
+def test_live_unit_with_retrieval_marker_compresses_surrounding_text() -> None:
+    marker = "[100 items compressed to 10. Retrieve more: hash=abc123]"
+    text = f"alpha beta gamma delta epsilon\n{marker}\nzeta eta theta iota kappa"
+
+    result = compress_unit_with_router(
+        CompressionUnit(
+            text=text,
+            provider="openai",
+            endpoint="responses",
+            role="tool",
+            item_type="function_call_output",
+            min_bytes=1,
+        ),
+        router=Router("short"),
+        tokenizer=TokenCounter(),
+    )
+
+    assert result.modified is True
+    assert result.reason is None
+    assert result.strategy == "ccr_marker_preserving"
+    assert result.compressed == f"short\n{marker}\nshort"
+    assert marker in result.compressed
+    assert result.tokens_saved > 0
+    assert "ccr_marker_preserving" in result.transforms_applied
+
+
+def test_non_live_unit_with_retrieval_marker_preserves_prefix_cache() -> None:
+    marker = "[100 items compressed to 10. Retrieve more: hash=abc123]"
+    text = f"alpha beta gamma delta epsilon\n{marker}\nzeta eta theta"
+
+    result = compress_unit_with_router(
+        CompressionUnit(
+            text=text,
+            provider="openai",
+            endpoint="responses",
+            role="tool",
+            item_type="function_call_output",
+            cache_zone="prefix",
+            min_bytes=1,
+        ),
+        router=Router("short"),
+        tokenizer=TokenCounter(),
+    )
+
+    assert result.modified is False
+    assert result.reason == "cache_zone_prefix"
+    assert result.compressed == text
diff --git a/tests/test_openai_responses_compression_units.py b/tests/test_openai_responses_compression_units.py
index 7c5193c4e..654978d58 100644
--- a/tests/test_openai_responses_compression_units.py
+++ b/tests/test_openai_responses_compression_units.py
@@ -51,7 +51,7 @@ def test_openai_responses_adapter_compresses_only_live_text_slots():
         ],
     }
 
-    new_payload, modified, saved, transforms = (
+    new_payload, modified, saved, transforms, units_by_category, strategy_chain = (
         handler._compress_openai_responses_live_text_units_with_router(
             payload,
             model="gpt-5",
@@ -66,6 +66,71 @@ def test_openai_responses_adapter_compresses_only_live_text_slots():
     assert new_payload["input"][2]["output"] == "kept words"
     assert new_payload["input"][3]["content"][0]["text"] == long_text
     assert any(t.startswith("router:openai:responses:") for t in transforms)
+    assert units_by_category == {"applied": 1}
+    assert strategy_chain == []
+
+
+def test_openai_responses_adapter_compresses_custom_tool_call_output():
+    router = ContentRouter()
+
+    def compress(self, content: str, **_kwargs):
+        return RouterCompressionResult(
+            compressed="custom output summary",
+            original=content,
+            strategy_used=CompressionStrategy.KOMPRESS,
+        )
+
+    router.compress = MethodType(compress, router)
+    handler = _handler_with_router(router)
+    long_text = " ".join(f"word{i}" for i in range(180))
+    payload = {
+        "model": "gpt-5",
+        "input": [
+            {
+                "type": "custom_tool_call_output",
+                "call_id": "c1",
+                "output": long_text,
+            }
+        ],
+    }
+
+    new_payload, modified, saved, transforms, units_by_category, strategy_chain = (
+        handler._compress_openai_responses_live_text_units_with_router(
+            payload,
+            model="gpt-5",
+            request_id="req_test",
+        )
+    )
+
+    assert modified is True
+    assert saved > 0
+    assert new_payload["input"][0]["output"] == "custom output summary"
+    assert (
+        "router:openai:responses:custom_tool_call_output:kompress" in transforms
+    )
+    assert units_by_category == {"applied": 1}
+    assert strategy_chain == []
+
+
+def test_openai_responses_adapter_accepts_empty_input_list():
+    router = ContentRouter()
+    handler = _handler_with_router(router)
+    payload = {"model": "gpt-5", "input": [], "tools": []}
+
+    new_payload, modified, saved, transforms, units_by_category, strategy_chain = (
+        handler._compress_openai_responses_live_text_units_with_router(
+            payload,
+            model="gpt-5",
+            request_id="req_test",
+        )
+    )
+
+    assert new_payload == payload
+    assert modified is False
+    assert saved == 0
+    assert transforms == []
+    assert units_by_category == {}
+    assert strategy_chain == []
 
 
 def test_openai_responses_adapter_preserves_headroom_retrieve_outputs():
@@ -98,7 +163,7 @@ def test_openai_responses_adapter_preserves_headroom_retrieve_outputs():
         ],
     }
 
-    new_payload, modified, saved, transforms = (
+    new_payload, modified, saved, transforms, units_by_category, strategy_chain = (
         handler._compress_openai_responses_live_text_units_with_router(
             payload,
             model="gpt-5",
@@ -110,6 +175,8 @@ def test_openai_responses_adapter_preserves_headroom_retrieve_outputs():
     assert saved == 0
     assert transforms == []
     assert new_payload == payload
+    assert units_by_category == {}
+    assert strategy_chain == []
 
 
 def test_openai_responses_adapter_keeps_small_and_opaque_items():
@@ -132,7 +199,7 @@ def test_openai_responses_adapter_keeps_small_and_opaque_items():
         ],
     }
 
-    new_payload, modified, saved, transforms = (
+    new_payload, modified, saved, transforms, units_by_category, strategy_chain = (
         handler._compress_openai_responses_live_text_units_with_router(
             payload,
             model="gpt-5",
@@ -144,6 +211,8 @@ def test_openai_responses_adapter_keeps_small_and_opaque_items():
     assert saved == 0
     assert transforms == []
     assert new_payload == payload
+    assert units_by_category == {"size_floor": 1}
+    assert strategy_chain == []
 
 
 def test_openai_responses_payload_routes_through_content_router_without_rust(
diff --git a/tests/test_openai_responses_context_compaction.py b/tests/test_openai_responses_context_compaction.py
new file mode 100644
index 000000000..2b5c0a6c2
--- /dev/null
+++ b/tests/test_openai_responses_context_compaction.py
@@ -0,0 +1,374 @@
+from __future__ import annotations
+
+from types import SimpleNamespace
+from typing import Any
+
+from headroom.proxy.handlers.openai import (
+    OpenAIHandlerMixin,
+    _compact_openai_responses_tools,
+    _openai_responses_context_budget,
+)
+from headroom.transforms.content_router import (
+    CompressionStrategy,
+    ContentRouter,
+    ContentRouterConfig,
+)
+
+
+def test_openai_responses_context_budget_breaks_out_static_and_live_buckets() -> None:
+    payload = {
+        "instructions": "stable instructions",
+        "tools": [
+            {
+                "type": "function",
+                "name": "read_file",
+                "description": "Read a file.",
+                "parameters": {
+                    "type": "object",
+                    "properties": {"path": {"type": "string"}},
+                    "required": ["path"],
+                },
+            }
+        ],
+        "input": [
+            {
+                "type": "function_call_output",
+                "call_id": "call_1",
+                "output": "line one\nline two\n",
+            },
+            {
+                "type": "message",
+                "role": "user",
+                "content": [{"type": "input_text", "text": "do the thing"}],
+            },
+        ],
+    }
+
+    budget = _openai_responses_context_budget(payload)
+
+    assert budget["payload_bytes"] > 0
+    assert {"instructions", "tools", "input"}.issubset(budget["buckets"])
+    assert budget["input_breakdown"]["function_call_output"]["items"] == 1
+    assert budget["input_breakdown"]["function_call_output"]["text_bytes"] == len(
+        b"line one\nline two\n"
+    )
+    assert budget["input_breakdown"]["message"]["items"] == 1
+
+
+def test_openai_tool_schema_compaction_preserves_invocation_shape() -> None:
+    verbose = " ".join(["Use this tool to read a file from the workspace."] * 40)
+    payload = {
+        "tools": [
+            {
+                "type": "function",
+                "name": "read_file",
+                "title": "Read File",
+                "description": verbose,
+                "parameters": {
+                    "$schema": "https://json-schema.org/draft/2020-12/schema",
+                    "title": "ReadFileParameters",
+                    "type": "object",
+                    "properties": {
+                        "path": {
+                            "title": "Path",
+                            "type": "string",
+                            "description": verbose,
+                            "examples": ["src/main.py"],
+                        }
+                    },
+                    "required": ["path"],
+                    "additionalProperties": False,
+                },
+            }
+        ]
+    }
+
+    compacted, modified, before, after = _compact_openai_responses_tools(payload)
+
+    assert modified is True
+    assert after < before
+    tool = compacted["tools"][0]
+    assert tool["type"] == "function"
+    assert tool["name"] == "read_file"
+    assert "title" not in tool
+    assert tool["parameters"]["type"] == "object"
+    assert tool["parameters"]["required"] == ["path"]
+    assert tool["parameters"]["additionalProperties"] is False
+    assert tool["parameters"]["properties"]["path"]["type"] == "string"
+    assert "examples" not in tool["parameters"]["properties"]["path"]
+    assert tool["parameters"]["properties"]["path"]["description"] == " ".join(verbose.split())
+
+
+def test_openai_tool_schema_compaction_is_deterministic() -> None:
+    payload = {
+        "tools": [
+            {
+                "type": "function",
+                "name": "mcp__serena__",
+                "description": "  Semantic code tools.\n\nUse for symbol-aware edits.  ",
+                "parameters": {
+                    "$schema": "https://json-schema.org/draft/2020-12/schema",
+                    "$comment": "annotation only",
+                    "type": "object",
+                    "properties": {
+                        "name_path_pattern": {
+                            "type": "string",
+                            "description": "  Name path to match.\nKeeps full semantics. ",
+                            "examples": ["Foo/bar"],
+                        }
+                    },
+                    "required": ["name_path_pattern"],
+                    "additionalProperties": False,
+                },
+            }
+        ]
+    }
+
+    first, first_modified, first_before, first_after = _compact_openai_responses_tools(payload)
+    second, second_modified, second_before, second_after = _compact_openai_responses_tools(payload)
+
+    assert first_modified is True
+    assert second_modified is True
+    assert first_before == second_before
+    assert first_after == second_after
+    assert first == second
+    assert first["tools"][0]["description"] == ("Semantic code tools. Use for symbol-aware edits.")
+    prop = first["tools"][0]["parameters"]["properties"]["name_path_pattern"]
+    assert prop["description"] == "Name path to match. Keeps full semantics."
+    assert prop["type"] == "string"
+    assert "examples" not in prop
+
+
+class _StubTokenizer:
+    def count_text(self, text: str) -> int:
+        return len(text.split())
+
+
+class _StubProvider:
+    def get_token_counter(self, model: str) -> _StubTokenizer:
+        del model
+        return _StubTokenizer()
+
+
+class _StubPipeline:
+    def __init__(self, router: ContentRouter):
+        self.transforms = [router]
+
+
+class _HandlerHarness(OpenAIHandlerMixin):
+    """Minimal subclass exposing just the deps the unit-extraction path
+    actually reads. The full HeadroomProxy ctor wires dozens of unrelated
+    services; this keeps the test focused on the gate behavior."""
+
+    def __init__(self, router: ContentRouter):
+        self.openai_pipeline: Any = _StubPipeline(router)
+        self.openai_provider: Any = _StubProvider()
+
+
+def test_codex_input_list_payload_reaches_router_without_skip() -> None:
+    """Codex's Responses payload uses `input=[...]` with no `messages` key.
+    The compression gate must accept either field as the items source —
+    otherwise the entire payload is silently passed through uncompressed,
+    which is the exact production bug surfaced in proxy.log analysis."""
+
+    router = ContentRouter(ContentRouterConfig())
+    handler = _HandlerHarness(router)
+
+    long_output = " ".join(["compressible"] * 200)
+    payload: dict[str, Any] = {
+        "type": "response.create",
+        "model": "gpt-5.5",
+        "input": [
+            {
+                "type": "function_call_output",
+                "call_id": "call_1",
+                "output": long_output,
+            }
+        ],
+        # Note: no `messages` key at all — Codex doesn't send one.
+    }
+
+    updated, modified, _saved, _transforms, _units_by_cat, _chain, _attempted = (
+        handler._compress_openai_responses_live_text_units_with_router(
+            payload,
+            model="gpt-5.5",
+            request_id="hr_codex_test_0001",
+        )
+    )
+
+    # The gate must NOT have skipped the payload. If it had, `updated`
+    # would be the input payload identity-passed through with
+    # modified=False — but the deepcopy + splice always returns a new
+    # dict object when the path executes.
+    assert updated is not payload, "Codex-shape payload was skipped at the input/messages gate"
+    # Whether or not Kompress actually compresses 200 repeated words is
+    # not the point of this test; the point is that we *entered* the
+    # extraction loop. Modified may be True or False depending on
+    # Kompress availability in CI, so we only assert non-skip semantics.
+    assert isinstance(modified, bool)
+
+
+def test_codex_payload_with_only_messages_field_also_reaches_router() -> None:
+    """The Anthropic-style shape (messages=list, no input) must also
+    flow. This is the reverse of the Codex case and guards against a
+    future regression that swings the gate too far the other way."""
+
+    router = ContentRouter(ContentRouterConfig())
+    handler = _HandlerHarness(router)
+
+    payload: dict[str, Any] = {
+        "type": "response.create",
+        "model": "gpt-5.5",
+        "messages": [
+            {
+                "type": "function_call_output",
+                "call_id": "call_2",
+                "output": " ".join(["compressible"] * 200),
+            }
+        ],
+    }
+
+    updated, _modified, _saved, _transforms, _units_by_cat, _chain, _attempted = (
+        handler._compress_openai_responses_live_text_units_with_router(
+            payload,
+            model="gpt-5.5",
+            request_id="hr_codex_test_0002",
+        )
+    )
+
+    assert updated is not payload, "messages-shape payload was skipped at the gate"
+
+
+def test_compression_pass_id_is_content_derived(caplog) -> None:
+    """Re-entrant Codex websocket passes share one `request_id` but
+    process distinct payloads. The `pass_id` field on every compression
+    event must be content-derived so dashboards can attribute each
+    unit_result to its originating pass. Distinct payloads → distinct
+    pass_ids (per-pass savings sum legitimately across passes); identical
+    payloads → identical pass_ids (idempotent retries should dedup)."""
+
+    import logging as _logging
+
+    router = ContentRouter(ContentRouterConfig())
+    handler = _HandlerHarness(router)
+
+    payload_a: dict[str, Any] = {
+        "type": "response.create",
+        "model": "gpt-5.5",
+        "input": [
+            {
+                "type": "function_call_output",
+                "call_id": "call_1",
+                "output": " ".join(["alpha"] * 200),
+            }
+        ],
+    }
+    payload_b: dict[str, Any] = {
+        "type": "response.create",
+        "model": "gpt-5.5",
+        "input": [
+            {
+                "type": "function_call_output",
+                "call_id": "call_1",
+                "output": " ".join(["bravo"] * 200),
+            }
+        ],
+    }
+
+    caplog.set_level(_logging.INFO, logger="headroom.proxy")
+    handler._compress_openai_responses_payload(
+        payload_a, model="gpt-5.5", request_id="hr_shared_request"
+    )
+    handler._compress_openai_responses_payload(
+        payload_b, model="gpt-5.5", request_id="hr_shared_request"
+    )
+    # Same content twice → same pass_id (deterministic + idempotent).
+    handler._compress_openai_responses_payload(
+        payload_a, model="gpt-5.5", request_id="hr_shared_request"
+    )
+
+    # Collect pass_ids in call order — payload bodies are no longer
+    # embedded at INFO so we can't grep for content; we rely on the
+    # 3-call sequence [a, b, a] producing a [A, B, A] pass_id sequence.
+    pass_id_sequence: list[str] = []
+    for record in caplog.records:
+        message = record.getMessage()
+        if "event=codex_compression_payload_input" not in message:
+            continue
+        match_quoted = '"pass_id":"'
+        idx = message.find(match_quoted)
+        assert idx != -1, f"pass_id missing from event: {message[:200]}"
+        start = idx + len(match_quoted)
+        end = message.find('"', start)
+        pass_id_sequence.append(message[start:end])
+
+    assert len(pass_id_sequence) == 3, (
+        f"expected exactly 3 payload_input events for 3 calls, got {len(pass_id_sequence)}"
+    )
+    # Two distinct payloads + one repeat → two distinct pass_ids overall.
+    assert len(set(pass_id_sequence)) == 2, (
+        f"expected two distinct pass_ids, got {set(pass_id_sequence)}"
+    )
+    # Repeated payload_a must be deterministic — index 0 and 2 are the
+    # same call shape so they must produce the same pass_id.
+    assert pass_id_sequence[0] == pass_id_sequence[2], (
+        f"repeated identical payload produced different pass_ids: {pass_id_sequence}"
+    )
+    assert pass_id_sequence[0] != pass_id_sequence[1]
+
+
+def test_codex_payload_without_either_field_is_skipped() -> None:
+    """The gate must still reject malformed payloads — `input` and
+    `messages` both absent (or non-list) is the genuine skip condition."""
+
+    router = ContentRouter(ContentRouterConfig())
+    handler = _HandlerHarness(router)
+
+    payload: dict[str, Any] = {
+        "type": "response.create",
+        "model": "gpt-5.5",
+        # No input, no messages — genuinely nothing to compress.
+    }
+
+    updated, modified, saved, transforms, units_by_cat, chain, attempted = (
+        handler._compress_openai_responses_live_text_units_with_router(
+            payload,
+            model="gpt-5.5",
+            request_id="hr_codex_test_0003",
+        )
+    )
+
+    assert updated is payload
+    assert modified is False
+    assert units_by_cat == {}
+    assert chain == []
+    assert attempted == 0
+    assert saved == 0
+    assert transforms == []
+
+
+def test_content_router_retries_kompress_when_structured_strategy_noops(monkeypatch) -> None:
+    router = ContentRouter(ContentRouterConfig(enable_smart_crusher=True))
+    content = " ".join("x" for _ in range(200))
+
+    class NoopCrusher:
+        def crush(self, value: str, query: str = "", bias: float = 1.0):
+            return SimpleNamespace(compressed=value)
+
+    monkeypatch.setattr(router, "_get_smart_crusher", lambda: NoopCrusher())
+    monkeypatch.setattr(
+        router,
+        "_try_ml_compressor",
+        lambda value, context, question=None: ("short summary", 2),
+    )
+
+    compressed, compressed_tokens, strategy_chain = router._apply_strategy_to_content(
+        content,
+        CompressionStrategy.SMART_CRUSHER,
+        context="",
+    )
+
+    assert compressed == "short summary"
+    assert compressed_tokens == 2
+    # The fallback chain must record both strategies it tried.
+    assert strategy_chain == ["smart_crusher", "kompress"]
diff --git a/tests/test_transforms_content_router.py b/tests/test_transforms_content_router.py
index fc82e20c3..bea4fa735 100644
--- a/tests/test_transforms_content_router.py
+++ b/tests/test_transforms_content_router.py
@@ -239,6 +239,7 @@ def test_content_router_mixed_pure_apply_and_toin(monkeypatch: pytest.MonkeyPatc
         lambda content, strategy, context, language=None, question=None, bias=1.0: (
             f"{strategy.value}:{content}",
             len(content.split()) - 1,
+            [strategy.value],
         ),
     )
     result = router._compress_mixed(mixed_content, "ctx")
@@ -252,6 +253,7 @@ def test_content_router_mixed_pure_apply_and_toin(monkeypatch: pytest.MonkeyPatc
         lambda content, strategy, context, language=None, question=None, bias=1.0: (
             "shrunk",
             1,
+            [strategy.value],
         ),
     )
     pure = router._compress_pure("some plain text", CompressionStrategy.TEXT, "ctx")