diff --git a/headroom/cache/compression_cache.py b/headroom/cache/compression_cache.py
index a8cfc5f53..30f2ae103 100644
--- a/headroom/cache/compression_cache.py
+++ b/headroom/cache/compression_cache.py
@@ -10,6 +10,7 @@ import copy
 import hashlib
 import json
 import logging
+import time
 from collections import OrderedDict
 from dataclasses import dataclass
 
@@ -82,6 +83,8 @@ class CompressionCache:
     def __init__(self, max_entries: int = 10000) -> None:
         self.max_entries = max_entries
         self._cache: OrderedDict[str, _CacheEntry] = OrderedDict()
+        self._stable_hashes: set[str] = set()
+        self._first_seen: dict[str, float] = {}
         self._hits: int = 0
         self._misses: int = 0
         self._total_tokens_saved: int = 0
@@ -115,10 +118,51 @@ class CompressionCache:
             _, evicted = self._cache.popitem(last=False)
             self._total_tokens_saved -= evicted.tokens_saved
 
+    def mark_stable(self, content_hash: str) -> None:
+        """Mark a content hash as stable (unchanged, not compressed).
+
+        Used for tool_results that the content router excluded or skipped.
+        These messages appear verbatim every turn, so they are prefix-stable
+        even though no compressed version exists in the cache.
+        """
+        self._stable_hashes.add(content_hash)
+
+    def mark_stable_from_messages(self, messages: list[dict], up_to: int) -> None:
+        """Mark all tool_result hashes in messages[:up_to] as stable."""
+        for msg in messages[:up_to]:
+            if _is_tool_result_message(msg):
+                content = _extract_tool_result_content(msg)
+                if content is not None:
+                    self._stable_hashes.add(self.content_hash(content))
+
+    def should_defer_compression(
+        self,
+        content_hash: str,
+        ttl_seconds: float = 300.0,
+        batch_window: float = 30.0,
+    ) -> bool:
+        """Whether to defer compressing this content to avoid mid-TTL busts.
+
+        Returns True if the content was first seen recently enough that
+        compressing it now would bust the cached prefix with no TTL benefit.
+        Returns False near the TTL boundary (within batch_window of expiry),
+        meaning we should compress now and accept one bust.
+        """
+        now = time.time()
+        first_seen = self._first_seen.get(content_hash)
+        if first_seen is None:
+            self._first_seen[content_hash] = now
+            return True  # First time seeing this — defer
+        age = now - first_seen
+        if age >= ttl_seconds - batch_window:
+            return False  # Near TTL boundary — compress now (batch window)
+        return True  # Still within TTL — defer to preserve cache
+
     def get_stats(self) -> dict:
         """Return cache statistics."""
         return {
             "entries": len(self._cache),
+            "stable_hashes": len(self._stable_hashes),
             "hits": self._hits,
             "misses": self._misses,
             "tokens_saved": self._total_tokens_saved,
@@ -151,7 +195,7 @@ class CompressionCache:
                 content = _extract_tool_result_content(msg)
                 if content is not None:
                     h = self.content_hash(content)
-                    if h not in self._cache:
+                    if h not in self._cache and h not in self._stable_hashes:
                         break
                 else:
                     # tool_result with non-string content; treat as unstable
@@ -200,6 +244,8 @@ class CompressionCache:
             if orig_content is None or comp_content is None:
                 continue
             if orig_content == comp_content:
+                # Content unchanged — mark as stable for frozen count walk
+                self._stable_hashes.add(self.content_hash(orig_content))
                 continue
             h = self.content_hash(orig_content)
             tokens_saved = len(orig_content) // 4 - len(comp_content) // 4
diff --git a/headroom/cache/prefix_tracker.py b/headroom/cache/prefix_tracker.py
index 56453bb3d..8e0fc0129 100644
--- a/headroom/cache/prefix_tracker.py
+++ b/headroom/cache/prefix_tracker.py
@@ -18,6 +18,7 @@ from __future__ import annotations
 
 import copy
 import hashlib
+import json
 import logging
 import time
 from dataclasses import dataclass
@@ -228,19 +229,45 @@ class PrefixCacheTracker:
 
     @staticmethod
     def _estimate_message_tokens(messages: list[dict[str, Any]]) -> list[int]:
-        """Rough token count per message (chars / 3.5)."""
+        """Rough token count per message (chars / 3.5).
+
+        Counts text, tool_result content, and tool_use input fields
+        for accurate Anthropic-format estimation.
+        """
         counts = []
         for msg in messages:
             content = msg.get("content", "")
             if isinstance(content, str):
                 chars = len(content)
             elif isinstance(content, list):
-                chars = sum(
-                    len(str(block.get("text", ""))) for block in content if isinstance(block, dict)
-                )
+                chars = 0
+                for block in content:
+                    if not isinstance(block, dict):
+                        continue
+                    block_type = block.get("type", "")
+                    if block_type == "text":
+                        chars += len(block.get("text", ""))
+                    elif block_type == "tool_result":
+                        inner = block.get("content", "")
+                        if isinstance(inner, str):
+                            chars += len(inner)
+                        elif isinstance(inner, list):
+                            chars += sum(
+                                len(b.get("text", "")) for b in inner if isinstance(b, dict)
+                            )
+                    elif block_type == "tool_use":
+                        inp = block.get("input")
+                        if isinstance(inp, str):
+                            chars += len(inp)
+                        elif isinstance(inp, dict):
+                            chars += len(json.dumps(inp, separators=(",", ":")))
+                    else:
+                        text = block.get("text", "")
+                        if text:
+                            chars += len(text)
             else:
                 chars = 0
-            # Add overhead for role, tool_use blocks, etc.
+            # Add overhead for role, block structure, etc.
             chars += 20
             counts.append(max(1, int(chars / 3.5)))
         return counts
diff --git a/headroom/proxy/handlers/anthropic.py b/headroom/proxy/handlers/anthropic.py
index ad59da3ee..6f32729f7 100644
--- a/headroom/proxy/handlers/anthropic.py
+++ b/headroom/proxy/handlers/anthropic.py
@@ -458,6 +458,35 @@ class AnthropicHandlerMixin:
         tokenizer = get_tokenizer(model)
         original_tokens = tokenizer.count_messages(messages)
 
+        # Enterprise Security: scan request before compression
+        _security_ctx = None
+        if self.security:
+            try:
+                messages, _security_ctx = self.security.scan_request(
+                    messages,
+                    {
+                        "provider": "anthropic",
+                        "model": model,
+                        "request_id": str(request_id),
+                        "user_id": headers.get("x-api-key", "")[:16],
+                    },
+                )
+            except Exception as e:
+                if hasattr(e, "reason"):
+                    from fastapi.responses import JSONResponse as _JSONResp
+
+                    return _JSONResp(
+                        status_code=403,
+                        content={
+                            "type": "error",
+                            "error": {
+                                "type": "security_block",
+                                "message": str(e),
+                            },
+                        },
+                    )
+                logger.warning(f"[{request_id}] Security scan error: {e}")
+
         # Hook: pre_compress — let hooks modify messages before compression
 
         if self.config.hooks and not is_cache_mode(self.config.mode):
@@ -538,6 +567,41 @@ class AnthropicHandlerMixin:
                     # Safety: never freeze beyond provider-confirmed cached prefix.
                     cache_frozen_count = comp_cache.compute_frozen_count(messages)
                     frozen_message_count = min(frozen_message_count, cache_frozen_count)
+                    # Record all tool_results in the verified frozen prefix as stable
+                    comp_cache.mark_stable_from_messages(messages, frozen_message_count)
+
+                    # TTL-aware deferral: extend freeze to cover messages whose
+                    # first-time compression would bust the cache mid-TTL window.
+                    # This batches first-time compressions near the 5-min TTL
+                    # boundary, trading one big bust for many small ones.
+                    ttl_frozen = frozen_message_count
+                    from headroom.cache.compression_cache import (
+                        _extract_tool_result_content,
+                        _is_tool_result_message,
+                    )
+
+                    for idx in range(frozen_message_count, len(messages)):
+                        msg = messages[idx]
+                        if _is_tool_result_message(msg):
+                            tr_content = _extract_tool_result_content(msg)
+                            if tr_content is not None:
+                                h = comp_cache.content_hash(tr_content)
+                                # Already compressed or stable — keep going
+                                if h in comp_cache._cache or h in comp_cache._stable_hashes:
+                                    ttl_frozen = idx + 1
+                                elif comp_cache.should_defer_compression(h):
+                                    # New content within TTL — defer and freeze
+                                    comp_cache.mark_stable(h)
+                                    ttl_frozen = idx + 1
+                                else:
+                                    break  # TTL expired — compress this turn
+                            else:
+                                break
+                        else:
+                            # Non-tool_result messages are stable (user/assistant text)
+                            ttl_frozen = idx + 1
+
+                    frozen_message_count = ttl_frozen
 
                     result = await asyncio.wait_for(
                         asyncio.to_thread(
@@ -966,6 +1030,7 @@ class AnthropicHandlerMixin:
                     memory_user_id=memory_user_id,
                     pipeline_timing=pipeline_timing,
                     prefix_tracker=prefix_tracker,
+                    original_messages=original_client_messages,
                 )
             else:
                 response = await self._retry_request("POST", url, headers, body)
@@ -1358,6 +1423,23 @@ class AnthropicHandlerMixin:
                 if _compression_failed:
                     response_headers["x-headroom-compression-failed"] = "true"
 
+                # Enterprise Security: scan response + de-anonymize
+                if self.security and _security_ctx and resp_json:
+                    try:
+                        resp_json = self.security.scan_response(resp_json, _security_ctx)
+                        response = httpx.Response(
+                            status_code=200,
+                            content=json.dumps(resp_json).encode(),
+                            headers=response_headers,
+                        )
+                        return Response(
+                            content=response.content,
+                            status_code=response.status_code,
+                            headers=response_headers,
+                        )
+                    except Exception as sec_err:
+                        logger.warning(f"[{request_id}] Security response scan error: {sec_err}")
+
                 return Response(
                     content=response.content,
                     status_code=response.status_code,
diff --git a/headroom/proxy/handlers/streaming.py b/headroom/proxy/handlers/streaming.py
index 80c6656c8..5480d8fd6 100644
--- a/headroom/proxy/handlers/streaming.py
+++ b/headroom/proxy/handlers/streaming.py
@@ -450,6 +450,7 @@ class StreamingMixin:
         memory_user_id: str | None = None,
         pipeline_timing: dict[str, float] | None = None,
         prefix_tracker: Any | None = None,
+        original_messages: list[dict] | None = None,
     ) -> StreamingResponse:
         """Stream response with metrics tracking and memory tool handling.
 
@@ -551,9 +552,13 @@ class StreamingMixin:
                         # real-time clients (LangGraph, LangChain, etc.)
                         yield chunk
 
-                        if memory_enabled:
-                            # Also buffer for post-stream memory processing
-                            buffered_chunks.append(chunk)
+                        # Buffer SSE data for memory processing and/or prefix tracker
+                        _track_sse = memory_enabled or (
+                            prefix_tracker is not None and provider == "anthropic"
+                        )
+                        if _track_sse:
+                            if memory_enabled:
+                                buffered_chunks.append(chunk)
                             full_sse_data += chunk_str
                             if len(full_sse_data) > MAX_SSE_BUFFER_SIZE:
                                 logger.warning(
@@ -696,10 +701,31 @@ class StreamingMixin:
 
                 # Update prefix cache tracker for next turn (streaming path)
                 if prefix_tracker is not None:
+                    import copy as _copy
+
+                    forwarded_messages = body.get("messages", [])
+                    next_forwarded = _copy.deepcopy(forwarded_messages)
+                    next_original = _copy.deepcopy(original_messages or forwarded_messages)
+
+                    # Reconstruct assistant response from SSE data so the
+                    # prefix tracker accounts for it in the cached prefix
+                    if full_sse_data and provider == "anthropic":
+                        _parsed = (
+                            parsed_response
+                            if parsed_response is not None
+                            else self._parse_sse_to_response(full_sse_data, provider)
+                        )
+                        if _parsed:
+                            asst_msg = self._assistant_message_from_response_json(_parsed)
+                            if asst_msg is not None:
+                                next_forwarded.append(_copy.deepcopy(asst_msg))
+                                next_original.append(_copy.deepcopy(asst_msg))
+
                     prefix_tracker.update_from_response(
                         cache_read_tokens=cache_read_tokens,
                         cache_write_tokens=cache_write_tokens,
-                        messages=body.get("messages", []),
+                        messages=next_forwarded,
+                        original_messages=next_original,
                     )
 
                 if self.cost_tracker:
diff --git a/tests/test_cache/test_prefix_tracker.py b/tests/test_cache/test_prefix_tracker.py
index 2eb4e63f1..4a79356ea 100644
--- a/tests/test_cache/test_prefix_tracker.py
+++ b/tests/test_cache/test_prefix_tracker.py
@@ -212,6 +212,66 @@ class TestPrefixCacheTracker:
         assert len(counts) == 1
         assert counts[0] > 100
 
+    def test_estimate_tool_result_content(self):
+        """Token estimation should count tool_result content field."""
+        tool_content = "x" * 3500  # ~1000 tokens
+        messages = [
+            {
+                "role": "user",
+                "content": [
+                    {
+                        "type": "tool_result",
+                        "tool_use_id": "t1",
+                        "content": tool_content,
+                    }
+                ],
+            },
+        ]
+        counts = PrefixCacheTracker._estimate_message_tokens(messages)
+        assert len(counts) == 1
+        # Should be ~1000 tokens, definitely > 100
+        assert counts[0] > 100
+
+    def test_estimate_tool_use_input(self):
+        """Token estimation should count tool_use input field."""
+        messages = [
+            {
+                "role": "assistant",
+                "content": [
+                    {
+                        "type": "tool_use",
+                        "id": "t1",
+                        "name": "Read",
+                        "input": {"file_path": "/very/long/path/" + "x" * 700},
+                    }
+                ],
+            },
+        ]
+        counts = PrefixCacheTracker._estimate_message_tokens(messages)
+        assert len(counts) == 1
+        # Should count the serialized input dict
+        assert counts[0] > 50
+
+    def test_estimate_tool_result_nested_blocks(self):
+        """Token estimation should handle nested content blocks in tool_result."""
+        messages = [
+            {
+                "role": "user",
+                "content": [
+                    {
+                        "type": "tool_result",
+                        "tool_use_id": "t1",
+                        "content": [
+                            {"type": "text", "text": "A" * 3500},
+                        ],
+                    }
+                ],
+            },
+        ]
+        counts = PrefixCacheTracker._estimate_message_tokens(messages)
+        assert len(counts) == 1
+        assert counts[0] > 100
+
     def test_session_ttl_expiry(self):
         """Tracker should report as expired after TTL."""
         config = PrefixFreezeConfig(session_ttl_seconds=1)
diff --git a/tests/test_compression_cache.py b/tests/test_compression_cache.py
index 1e7f5c45d..6e9f14caf 100644
--- a/tests/test_compression_cache.py
+++ b/tests/test_compression_cache.py
@@ -172,6 +172,111 @@ class TestCompressionCacheFrozenCount:
         ]
         assert cache.compute_frozen_count(messages) == 2
 
+    def test_stable_hash_allows_frozen_count_past_uncached_tool_result(
+        self, cache: CompressionCache
+    ) -> None:
+        """Tool_results marked stable should not stop the frozen count walk."""
+        tool_content = "excluded Read output — big file contents"
+        h = CompressionCache.content_hash(tool_content)
+        cache.mark_stable(h)
+
+        messages = [
+            {"role": "user", "content": "hello"},
+            {
+                "role": "user",
+                "content": [
+                    {"type": "tool_result", "tool_use_id": "t1", "content": tool_content}
+                ],
+            },
+            {"role": "user", "content": "follow up"},
+        ]
+        # Without mark_stable, this would stop at msg[1] → frozen=1.
+        # With stable hash, the walk continues past msg[1] → frozen=3.
+        assert cache.compute_frozen_count(messages) == 3
+
+    def test_update_from_result_identical_content_marks_stable(
+        self, cache: CompressionCache
+    ) -> None:
+        """When orig == compressed, update_from_result marks the hash as stable."""
+        tool_content = "unchanged tool output"
+        originals = [
+            {"role": "user", "content": "hi"},
+            {
+                "role": "user",
+                "content": [
+                    {"type": "tool_result", "tool_use_id": "t1", "content": tool_content}
+                ],
+            },
+        ]
+        # Compressed is identical to originals (no compression happened)
+        compressed = [
+            {"role": "user", "content": "hi"},
+            {
+                "role": "user",
+                "content": [
+                    {"type": "tool_result", "tool_use_id": "t1", "content": tool_content}
+                ],
+            },
+        ]
+        cache.update_from_result(originals, compressed)
+
+        h = CompressionCache.content_hash(tool_content)
+        assert h in cache._stable_hashes
+
+        # Frozen count should now walk past this tool_result
+        messages = [
+            {"role": "user", "content": "hello"},
+            {
+                "role": "user",
+                "content": [
+                    {"type": "tool_result", "tool_use_id": "t1", "content": tool_content}
+                ],
+            },
+            {"role": "user", "content": "more stuff"},
+        ]
+        assert cache.compute_frozen_count(messages) == 3
+
+    def test_mark_stable_from_messages(self, cache: CompressionCache) -> None:
+        """mark_stable_from_messages records hashes for tool_results."""
+        content_a = "tool output A"
+        content_b = "tool output B"
+        messages = [
+            {"role": "user", "content": "hi"},
+            {
+                "role": "user",
+                "content": [
+                    {"type": "tool_result", "tool_use_id": "t1", "content": content_a}
+                ],
+            },
+            {
+                "role": "user",
+                "content": [
+                    {"type": "tool_result", "tool_use_id": "t2", "content": content_b}
+                ],
+            },
+        ]
+        # Mark first 2 messages (msg[0] + msg[1])
+        cache.mark_stable_from_messages(messages, 2)
+
+        ha = CompressionCache.content_hash(content_a)
+        hb = CompressionCache.content_hash(content_b)
+        assert ha in cache._stable_hashes
+        assert hb not in cache._stable_hashes  # msg[2] not included
+
+    def test_should_defer_compression_new_content(self, cache: CompressionCache) -> None:
+        """First-time content should be deferred."""
+        h = CompressionCache.content_hash("brand new content")
+        assert cache.should_defer_compression(h, ttl_seconds=300, batch_window=30) is True
+
+    def test_should_defer_compression_near_ttl(self, cache: CompressionCache) -> None:
+        """Content near TTL boundary should NOT be deferred."""
+        import time
+
+        h = CompressionCache.content_hash("old content")
+        # Backdate first_seen to simulate age near TTL
+        cache._first_seen[h] = time.time() - 280  # 280s old, TTL=300, window=30
+        assert cache.should_defer_compression(h, ttl_seconds=300, batch_window=30) is False
+
 
 class TestCompressionCacheApplyAndUpdate:
     def test_apply_cached_swaps_tool_results(self, cache: CompressionCache) -> None: