diff --git a/headroom/cli/__init__.py b/headroom/cli/__init__.py
index 92b28b33a..529a20d65 100644
--- a/headroom/cli/__init__.py
+++ b/headroom/cli/__init__.py
@@ -18,6 +18,7 @@ from . import (  # noqa: F401
     copilot_auth,
     evals,
     init,
+    inspect,
     install,
     learn,
     mcp,
diff --git a/headroom/cli/inspect.py b/headroom/cli/inspect.py
new file mode 100644
index 000000000..5fe001221
--- /dev/null
+++ b/headroom/cli/inspect.py
@@ -0,0 +1,183 @@
+"""`headroom inspect` — view original vs compressed message content.
+
+Headroom already exposes *quantitative* telemetry (token counts, ratios) but no
+way to *see* what the compressor changed. This command reads the proxy's
+loopback ``/transformations/feed`` endpoint — which carries the pre/post
+message snapshots when the proxy runs with ``--log-messages`` — and renders, per
+request, the original vs compressed content for each message with the changed
+segments highlighted (stdlib unified diff, no new dependencies). See issue #1267.
+"""
+
+from __future__ import annotations
+
+import difflib
+import json
+import os
+from typing import Any
+
+import click
+
+from .main import main
+
+
+def _extract_text(content: Any) -> str:
+    """Flatten a message's ``content`` (str or list of blocks) to plain text.
+
+    Handles Anthropic/OpenAI text blocks, nested ``tool_result`` content, and
+    falls back to a JSON dump for unrecognized block shapes so nothing is
+    silently dropped from the diff.
+    """
+    if content is None:
+        return ""
+    if isinstance(content, str):
+        return content
+    if isinstance(content, list):
+        parts: list[str] = []
+        for block in content:
+            if isinstance(block, str):
+                parts.append(block)
+            elif isinstance(block, dict):
+                if isinstance(block.get("text"), str):
+                    parts.append(block["text"])
+                elif isinstance(block.get("content"), (str, list)):
+                    parts.append(_extract_text(block.get("content")))
+                else:
+                    parts.append(json.dumps(block, ensure_ascii=False, sort_keys=True))
+            else:
+                parts.append(str(block))
+        return "\n".join(parts)
+    return str(content)
+
+
+def _role(msg: Any) -> str:
+    return str(msg.get("role", "?")) if isinstance(msg, dict) else "?"
+
+
+def _content_of(msg: Any) -> Any:
+    return msg.get("content") if isinstance(msg, dict) else msg
+
+
+def _render_request(transformation: dict[str, Any], *, full: bool) -> None:
+    rid = transformation.get("request_id") or "?"
+    model = transformation.get("model") or "?"
+    before = transformation.get("input_tokens_original")
+    after = transformation.get("input_tokens_optimized")
+    saved = transformation.get("tokens_saved")
+    pct = transformation.get("savings_percent")
+    transforms = ", ".join(transformation.get("transforms_applied") or []) or "none"
+
+    click.echo(click.style(f"\n━━ {rid}  {model}", bold=True))
+    click.echo(f"   tokens {before} → {after}  (saved {saved}, {pct}%)   transforms: {transforms}")
+
+    originals = transformation.get("request_messages") or []
+    compressed = transformation.get("compressed_messages") or []
+    count = max(len(originals), len(compressed))
+    any_change = False
+
+    for i in range(count):
+        original = originals[i] if i < len(originals) else {}
+        comp = compressed[i] if i < len(compressed) else {}
+        original_text = _extract_text(_content_of(original))
+        comp_text = _extract_text(_content_of(comp))
+        unchanged = original_text == comp_text
+        if unchanged and not full:
+            continue
+        any_change = True
+        role = _role(original) if original else _role(comp)
+        click.echo(click.style(f"\n  [{i}] {role}", fg="cyan"))
+        if unchanged:
+            click.echo("    (unchanged)")
+            continue
+        for line in difflib.unified_diff(
+            original_text.splitlines(),
+            comp_text.splitlines(),
+            fromfile="original",
+            tofile="compressed",
+            lineterm="",
+        ):
+            color: str | None = None
+            if line.startswith("+") and not line.startswith("+++"):
+                color = "green"
+            elif line.startswith("-") and not line.startswith("---"):
+                color = "red"
+            elif line.startswith("@@"):
+                color = "yellow"
+            click.echo("    " + (click.style(line, fg=color) if color else line))
+
+    if not any_change:
+        click.echo(
+            "   (no per-message content changes — savings came from "
+            "structural / transform-level edits)"
+        )
+
+
+@main.command("inspect")
+@click.option(
+    "--port",
+    "-p",
+    default=None,
+    type=click.IntRange(1, 65535),
+    envvar="HEADROOM_PORT",
+    help="Proxy port to query (default: 8787, env: HEADROOM_PORT)",
+)
+@click.option(
+    "--last",
+    default=1,
+    type=click.IntRange(min=1),
+    help="Show the N most recent requests (default: 1)",
+)
+@click.option(
+    "--format",
+    "output_format",
+    type=click.Choice(["text", "json"]),
+    default="text",
+    help="Output format (default: text). json emits the raw feed for offline diffing.",
+)
+@click.option(
+    "--full",
+    is_flag=True,
+    help="Show unchanged messages too (default: only messages the compressor changed)",
+)
+def inspect_cmd(port: int | None, last: int, output_format: str, full: bool) -> None:
+    """Show original vs compressed content for recent proxy requests.
+
+    \b
+    Requires a running proxy started with --log-messages (or --log-file), which
+    captures the pre/post-compression message snapshots the diff reads.
+
+    \b
+    Examples:
+        headroom inspect                 Inspect the most recent request
+        headroom inspect --last 5        Inspect the 5 most recent requests
+        headroom inspect --full          Include unchanged messages
+        headroom inspect --format json   Raw feed for piping into another tool
+    """
+    from headroom.install.health import probe_json
+
+    resolved_port = port if port is not None else int(os.environ.get("HEADROOM_PORT", "8787"))
+    base_url = f"http://127.0.0.1:{resolved_port}"
+    payload = probe_json(f"{base_url}/transformations/feed?limit={last}", timeout=5.0)
+
+    if payload is None:
+        raise click.ClickException(
+            f"No reachable proxy on {base_url}. Start one with `headroom proxy` "
+            "(or pass --port to point at a running instance)."
+        )
+    if not payload.get("log_full_messages"):
+        raise click.ClickException(
+            "The proxy isn't capturing message content, so there's nothing to diff. "
+            "Restart it with `headroom proxy --log-messages`."
+        )
+
+    transformations = payload.get("transformations") or []
+    if not transformations:
+        click.echo("No requests recorded yet. Send traffic through the proxy and retry.")
+        return
+
+    if output_format == "json":
+        click.echo(json.dumps(transformations, indent=2, ensure_ascii=False))
+        return
+
+    # The feed returns oldest→newest; show the most recent first.
+    for transformation in reversed(transformations):
+        _render_request(transformation, full=full)
diff --git a/headroom/cli/main.py b/headroom/cli/main.py
index 384d23fcb..b55c96e1e 100644
--- a/headroom/cli/main.py
+++ b/headroom/cli/main.py
@@ -68,6 +68,7 @@ def _register_commands() -> None:
         doctor,  # noqa: F401
         evals,  # noqa: F401
         init,  # noqa: F401
+        inspect,  # noqa: F401
         install,  # noqa: F401
         learn,  # noqa: F401
         mcp,  # noqa: F401
diff --git a/tests/test_cli_inspect.py b/tests/test_cli_inspect.py
new file mode 100644
index 000000000..b6ab3a790
--- /dev/null
+++ b/tests/test_cli_inspect.py
@@ -0,0 +1,105 @@
+"""Tests for the `headroom inspect` command (issue #1267).
+
+The command reads the proxy's loopback ``/transformations/feed`` endpoint and
+renders original-vs-compressed content. Tests stub ``probe_json`` so no proxy
+is required.
+
+Tests invoke the real top-level CLI (``main``) so the shipped command path —
+including subcommand registration — is exercised, not just the command object.
+"""
+
+from __future__ import annotations
+
+import json
+from unittest.mock import patch
+
+from click.testing import CliRunner
+
+from headroom.cli.inspect import _extract_text, _role
+
+
+def _run(args: list[str]):
+    from headroom.cli.main import main
+
+    return CliRunner().invoke(main, ["inspect", *args])
+
+
+def test_extract_text_handles_str_and_blocks() -> None:
+    assert _extract_text("hello") == "hello"
+    assert _extract_text([{"type": "text", "text": "a"}, {"type": "text", "text": "b"}]) == "a\nb"
+    # Nested tool_result content.
+    assert _extract_text([{"type": "tool_result", "content": [{"text": "x"}]}]) == "x"
+    # Unknown block falls back to JSON, never silently dropped.
+    assert "foo" in _extract_text([{"weird": "foo"}])
+    assert _extract_text(None) == ""
+
+
+def test_role_extraction() -> None:
+    assert _role({"role": "user"}) == "user"
+    assert _role("not a dict") == "?"
+
+
+def test_no_proxy_errors_cleanly() -> None:
+    with patch("headroom.install.health.probe_json", return_value=None):
+        result = _run([])
+    assert result.exit_code != 0
+    assert "No reachable proxy" in result.output
+
+
+def test_log_messages_disabled_hint() -> None:
+    payload = {"transformations": [], "log_full_messages": False}
+    with patch("headroom.install.health.probe_json", return_value=payload):
+        result = _run([])
+    assert result.exit_code != 0
+    assert "--log-messages" in result.output
+
+
+def test_empty_feed_message() -> None:
+    payload = {"transformations": [], "log_full_messages": True}
+    with patch("headroom.install.health.probe_json", return_value=payload):
+        result = _run([])
+    assert result.exit_code == 0
+    assert "No requests recorded" in result.output
+
+
+def _feed_payload() -> dict:
+    return {
+        "log_full_messages": True,
+        "transformations": [
+            {
+                "request_id": "req-1",
+                "model": "gpt-4o",
+                "input_tokens_original": 100,
+                "input_tokens_optimized": 40,
+                "tokens_saved": 60,
+                "savings_percent": 60.0,
+                "transforms_applied": ["SmartCrusher"],
+                "request_messages": [
+                    {"role": "user", "content": "line one\nline two\nline three"},
+                ],
+                "compressed_messages": [
+                    {"role": "user", "content": "line one\nline three"},
+                ],
+            }
+        ],
+    }
+
+
+def test_text_render_shows_diff_and_header() -> None:
+    with patch("headroom.install.health.probe_json", return_value=_feed_payload()):
+        result = _run([])
+    assert result.exit_code == 0
+    out = result.output
+    assert "req-1" in out
+    assert "gpt-4o" in out
+    assert "SmartCrusher" in out
+    # The removed line shows up on the original side of the diff.
+    assert "line two" in out
+
+
+def test_json_format_emits_raw_feed() -> None:
+    with patch("headroom.install.health.probe_json", return_value=_feed_payload()):
+        result = _run(["--format", "json"])
+    assert result.exit_code == 0
+    parsed = json.loads(result.output)
+    assert parsed[0]["request_id"] == "req-1"
diff --git a/wiki/cli.md b/wiki/cli.md
index 8dad03ee5..7b7c8cbd1 100644
--- a/wiki/cli.md
+++ b/wiki/cli.md
@@ -26,6 +26,7 @@ This page is the authoritative reference for the **Python Headroom CLI** exposed
 | `headroom proxy` | Run the Headroom proxy server | **native in container** |
 | `headroom learn` | Learn from past tool-call failures | **native in container** |
 | `headroom perf` | Summarize recent proxy performance | **native in container** |
+| `headroom inspect` | Show original vs compressed content for recent requests | **native in container** |
 | `headroom evals ...` | Run memory evaluation workflows | **native in container** |
 | `headroom memory ...` | Inspect and manage stored memories | **native in container** |
 | `headroom mcp ...` | Install, inspect, remove, or serve MCP integration | **native in container** |
@@ -330,6 +331,30 @@ The command reads `${HEADROOM_WORKSPACE_DIR}/logs/proxy.log` (defaults
 to `~/.headroom/logs/proxy.log` — see the
 [Filesystem Contract](filesystem-contract.md)).
 
+## `headroom inspect`
+
+Show the original vs compressed content for recent requests so you can *see*
+what the compressor changed (not just the token counts). Useful for building
+trust in compression and debugging quality regressions.
+
+```bash
+headroom inspect                 # inspect the most recent request
+headroom inspect --last 5        # inspect the 5 most recent requests
+headroom inspect --full          # include unchanged messages
+headroom inspect --format json   # raw feed for piping into another tool
+```
+
+| Option | Default | Meaning |
+|---|---|---|
+| `--port` / `-p` | `8787` | Proxy port to query (env: `HEADROOM_PORT`) |
+| `--last` | `1` | Number of most-recent requests to show |
+| `--format` | `text` | `text` renders a highlighted diff; `json` emits the raw feed |
+| `--full` | off | Include messages the compressor left unchanged |
+
+`inspect` queries the running proxy's loopback `/transformations/feed` endpoint,
+so the proxy must be started with `--log-messages` (or `--log-file`) for the
+pre/post-compression snapshots to be captured.
+
 ## `headroom evals`
 
 Memory evaluation command group.