diff --git a/CHANGELOG.md b/CHANGELOG.md
index c7e96228..5df5a536 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,8 @@
 
 ### Fixed
 
+- **Manual `/compress` now sticks across reloads and restarts instead of springing back to the old context size.** A manual compression shrinks the model-facing context but the old transcript could return through two paths: (1) append-only `state.db` reconciliation re-appending pre-compression rows, and (2) startup `.bak` recovery treating the intentional shrink as data loss. `/compress` now persists a truncation watermark/boundary (so reconciliation stops replaying pre-compression rows), refreshes the post-compression token metric, and drops the now-stale backup. Crucially, the `.bak` safeguard is only suppressed for the *pre-compression* backup whose restore would undo the shrink (detected by content — its model-facing context is still the larger uncompressed one) — a backup written *after* the compression that captures genuine post-compression data loss is **still recovered**, so manual compression can never permanently disable crash-recovery for that session. Thanks @hyl-ailab. (#4986, fixes #4836)
+
 - **Typed composer input is no longer wiped when a saved session auto-opens on boot.** On a hard refresh, boot-restore auto-opens the last session from localStorage — but that load can finish *after* you've already started typing into the fresh composer, and the saved-session draft restore would clobber what you typed. The boot-restore path now passes `preserveActiveInput` through to the existing draft-restore guard, so your in-progress text wins over the saved draft; a blank composer still restores the saved draft as before. Thanks @rodboev. (#5069, fixes #5060)
 
 - **The Hermes Dashboard now has a show/hide chip in Settings → Appearance.** The Appearance → "Sidebar tabs" grid (where you toggle which tabs appear in the sidebar/rail) gains a "Hermes Dashboard" chip alongside the others, bidirectionally synced with the existing dashboard-mode dropdown (never/always/auto): toggling the chip off sets the dropdown to "never," toggling it on restores the last non-never mode, and changing the dropdown updates the chip. The chip is a proxy for the dashboard config — it never mutates the sidebar `hidden_tabs`/`tab_order` state — and the sync is guarded against a stale config GET clobbering a newer save, with a clean rollback if the save fails. Thanks @rodboev. (#4936, fixes #2724)
diff --git a/api/routes.py b/api/routes.py
index 60043668..f5db7d1c 100644
--- a/api/routes.py
+++ b/api/routes.py
@@ -19138,7 +19138,12 @@ def _handle_session_compress(handler, body):
             if _sanitize_messages_for_api(s.messages) != original_messages:
                 return bad(handler, "Session was modified during compression; please retry.", 409)
 
-            s.context_messages = copy.deepcopy(compressed)
+            from api.session_ops import _truncation_watermark_for
+            from api.streaming import _stamp_missing_message_timestamps
+
+            compressed_copy = copy.deepcopy(compressed)
+            _stamp_missing_message_timestamps(compressed_copy)
+            s.context_messages = compressed_copy
             s.active_stream_id = None
             s.pending_user_message = None
             s.pending_attachments = []
@@ -19153,7 +19158,19 @@ def _handle_session_compress(handler, body):
             s.compression_anchor_summary = _compact_summary_text(
                 summary_text or _compression_summary_from_messages(compressed) or ""
             )
+            # Persist an intentional-shrink boundary so append-only state.db
+            # reconciliation does not replay pre-compression rows (#4836).
+            compress_watermark = _truncation_watermark_for(compressed_copy)
+            s.truncation_watermark = compress_watermark
+            s.truncation_boundary = compress_watermark
+            s.compression_anchor_mode = "manual"
+            s.last_prompt_tokens = new_tokens
             s.save()
+            # Drop stale backups that would undo an intentional manual compress.
+            try:
+                s.path.with_suffix(".json.bak").unlink(missing_ok=True)
+            except OSError:
+                pass
 
         session_payload = redact_session_data(
             s.compact() | {
diff --git a/api/session_recovery.py b/api/session_recovery.py
index 336da319..6dce748a 100644
--- a/api/session_recovery.py
+++ b/api/session_recovery.py
@@ -65,6 +65,106 @@ def _msg_count(p: Path) -> int:
     return len(msgs) if isinstance(msgs, list) else -1
 
 
+def _session_records_intentional_compress_shrink(session_path: Path) -> bool:
+    """Return True when the live sidecar records an intentional context shrink.
+
+    Manual ``/compress`` keeps the visible transcript but replaces the
+    model-facing ``context_messages`` with a smaller compacted prefix. That
+    operation must not be treated as accidental data loss by the #1558
+    ``.bak`` safeguard or startup recovery (#4836).
+
+    NOTE: this only reports *whether* the live session was intentionally
+    compressed. It must NOT, on its own, decide to skip ``.bak`` recovery —
+    a session can be manually compressed and *then* later suffer a genuine
+    #1558 ``messages``-array loss. The caller pairs this with a freshness
+    check (the backup must predate the compression) so a real post-compress
+    loss is still recovered. See ``inspect_session_recovery_status``.
+    """
+    try:
+        data = json.loads(session_path.read_text(encoding='utf-8'))
+    except (OSError, json.JSONDecodeError, ValueError):
+        return False
+    if not isinstance(data, dict):
+        return False
+
+    context_messages = data.get('context_messages')
+    messages = data.get('messages')
+    has_shorter_context = (
+        isinstance(context_messages, list)
+        and isinstance(messages, list)
+        and len(context_messages) < len(messages)
+    )
+    anchor_summary = str(data.get('compression_anchor_summary') or '').strip()
+    anchor_key = data.get('compression_anchor_message_key')
+    mode = str(data.get('compression_anchor_mode') or '').strip().lower()
+    watermark = data.get('truncation_watermark')
+
+    if mode == 'manual':
+        return True
+    if has_shorter_context and anchor_summary and anchor_key is not None:
+        return True
+    if has_shorter_context and watermark is not None:
+        return True
+    return False
+
+
+def _backup_predates_intentional_shrink(session_path: Path, bak_path: Path) -> bool:
+    """True when the ``.bak`` captured the PRE-compression transcript.
+
+    The intentional-compress guard (#4836) must only suppress recovery for a
+    backup whose restore would *undo* the user's deliberate shrink — i.e. a
+    backup taken before ``/compress`` ran, still carrying the large
+    UNCOMPRESSED ``context_messages``. A backup written *after* the
+    compression (a later save that lost data) carries the ALREADY-COMPRESSED
+    context and MUST still be recoverable.
+
+    Time can't tell these apart (the ``.bak`` and main file are written in the
+    same ``save()`` milliseconds apart), so we use the same content-semantic
+    signal reconciliation uses: the compaction marker. A post-compression
+    backup carries the ``[context compaction…]`` marker in its
+    ``context_messages`` (it persists across saves); a pre-compression backup
+    does not. We suppress recovery ONLY when the backup is genuinely
+    pre-compression — its context lacks the compaction marker AND is larger
+    than the live compressed context (the shrink hasn't been applied to it).
+    If the backup already carries the marker, it post-dates the compression →
+    a real loss → recover. The length clause is a secondary guard for the rare
+    compression that emits no marker; whenever in doubt we fail OPEN (return
+    False, allow recovery) — for a data-loss safeguard, recovering real data
+    is always the safer error. Fail OPEN on any read/parse error too.
+    """
+    try:
+        live = json.loads(session_path.read_text(encoding='utf-8'))
+        bak = json.loads(bak_path.read_text(encoding='utf-8'))
+    except (OSError, json.JSONDecodeError, ValueError):
+        return False
+    if not isinstance(live, dict) or not isinstance(bak, dict):
+        return False
+
+    bak_ctx = bak.get('context_messages')
+    bak_ctx = bak_ctx if isinstance(bak_ctx, list) else []
+
+    # If the backup's context already carries the compaction marker, the backup
+    # post-dates the compression (the marker persists across saves) → it is a
+    # recoverable post-compression snapshot, never a shrink-undoing one.
+    try:
+        from api.models import _context_messages_include_compression_marker
+        if _context_messages_include_compression_marker(bak_ctx):
+            return False
+    except Exception:
+        # If the marker check is unavailable, fall through to the length guard.
+        logger.debug("compaction-marker check unavailable in recovery", exc_info=True)
+
+    live_ctx = live.get('context_messages')
+    live_ctx_len = len(live_ctx) if isinstance(live_ctx, list) else 0
+    bak_ctx_len = len(bak_ctx)
+
+    # Secondary guard (unmarked compression): a pre-compression backup's context
+    # is larger than the live compressed context (the shrink hasn't been applied
+    # to it). A backup whose context is already <= the live compressed context
+    # post-dates the compression and represents recoverable post-compress data.
+    return bak_ctx_len > live_ctx_len
+
+
 def inspect_session_recovery_status(session_path: Path) -> dict:
     """Return a status dict describing whether recovery is recommended.
 
@@ -86,6 +186,17 @@ def inspect_session_recovery_status(session_path: Path) -> dict:
         }
     bak_count = _msg_count(bak_path)
     if bak_count > live_count:
+        if (
+            _session_records_intentional_compress_shrink(session_path)
+            and _backup_predates_intentional_shrink(session_path, bak_path)
+        ):
+            return {
+                "session_id": session_path.stem,
+                "live_messages": live_count,
+                "bak_messages": bak_count,
+                "recommend": "no_action",
+                "intentional_compress_shrink": True,
+            }
         return {
             "session_id": session_path.stem,
             "live_messages": live_count,
diff --git a/tests/test_issue4836_manual_compression_recovery.py b/tests/test_issue4836_manual_compression_recovery.py
new file mode 100644
index 00000000..bf994ca9
--- /dev/null
+++ b/tests/test_issue4836_manual_compression_recovery.py
@@ -0,0 +1,334 @@
+"""Regression tests for #4836 — manual /compress undone by reconciliation/recovery."""
+from __future__ import annotations
+
+import contextlib
+import io
+import json
+import sys
+import time
+import types
+
+import api.models as models
+from api.models import Session, reconciled_state_db_messages_for_session
+from api.routes import _handle_session_compress, get_session
+from api.session_recovery import inspect_session_recovery_status, recover_all_sessions_on_startup
+from tests._pytest_port import BASE
+
+
+class _FakeHandler:
+    def __init__(self):
+        self.wfile = io.BytesIO()
+        self.status = None
+        self.sent_headers = {}
+
+    def send_response(self, status):
+        self.status = status
+
+    def send_header(self, key, value):
+        self.sent_headers[key] = value
+
+    def end_headers(self):
+        pass
+
+    def payload(self):
+        return json.loads(self.wfile.getvalue().decode("utf-8"))
+
+
+class _FakeCompressor:
+    def compress(self, messages, current_tokens=None, focus_topic=None):
+        if len(messages) >= 2:
+            return [messages[0], messages[-1]]
+        return list(messages)
+
+
+class _FakeAgent:
+    last_instance = None
+
+    def __init__(self, **kwargs):
+        self.kwargs = kwargs
+        self.context_compressor = _FakeCompressor()
+        _FakeAgent.last_instance = self
+
+
+def _install_fake_compression_runtime(monkeypatch, agent_cls):
+    fake_run_agent = types.ModuleType("run_agent")
+    fake_run_agent.AIAgent = agent_cls
+    monkeypatch.setitem(sys.modules, "run_agent", fake_run_agent)
+
+    import api.config as _cfg
+
+    fake_runtime_provider = types.ModuleType("hermes_cli.runtime_provider")
+    fake_runtime_provider.resolve_runtime_provider = lambda requested=None: {
+        "api_key": "fake-key",
+        "provider": requested or "openai",
+        "base_url": "https://api.openai.com/v1",
+    }
+    fake_hermes_cli = types.ModuleType("hermes_cli")
+    fake_hermes_cli.__path__ = []
+    fake_hermes_cli.runtime_provider = fake_runtime_provider
+    monkeypatch.setitem(sys.modules, "hermes_cli", fake_hermes_cli)
+    monkeypatch.setitem(sys.modules, "hermes_cli.runtime_provider", fake_runtime_provider)
+    import hermes_cli.runtime_provider as _rtp
+
+    monkeypatch.setattr(
+        _cfg,
+        "resolve_model_provider",
+        lambda model: ("openai/gpt-5.4-mini", "openai", "https://api.openai.com/v1"),
+    )
+    monkeypatch.setattr(
+        _cfg,
+        "_get_session_agent_lock",
+        lambda sid: contextlib.nullcontext(),
+    )
+    monkeypatch.setattr(
+        _rtp,
+        "resolve_runtime_provider",
+        lambda requested=None: {
+            "api_key": "fake-key",
+            "provider": requested or "openai",
+            "base_url": "https://api.openai.com/v1",
+        },
+    )
+
+
+def _msg(role, content, ts):
+    return {"role": role, "content": content, "timestamp": ts, "_ts": ts}
+
+
+def test_manual_compress_persists_truncation_boundary(monkeypatch, cleanup_test_sessions, tmp_path):
+    session_dir = tmp_path / "sessions"
+    session_dir.mkdir(parents=True)
+    monkeypatch.setattr(models, "SESSION_DIR", session_dir)
+    monkeypatch.setattr(models, "SESSION_INDEX_FILE", session_dir / "_index.json")
+    models.SESSIONS.clear()
+
+    original_messages = [
+        _msg("user", "one", 1.0),
+        _msg("assistant", "two", 2.0),
+        _msg("user", "three", 3.0),
+        _msg("assistant", "four", 4.0),
+    ]
+    sid = f"issue4836_{time.time_ns()}"
+    cleanup_test_sessions.append(sid)
+    session = Session(
+        session_id=sid,
+        title="Untitled",
+        workspace=str(tmp_path),
+        model="openai/gpt-5.4-mini",
+        messages=original_messages,
+    )
+    session.save(touch_updated_at=False)
+
+    _install_fake_compression_runtime(monkeypatch, _FakeAgent)
+    handler = _FakeHandler()
+    _handle_session_compress(handler, {"session_id": sid})
+
+    assert handler.status == 200
+    loaded = Session.load(sid)
+    assert loaded.compression_anchor_mode == "manual"
+    assert loaded.truncation_watermark is not None
+    assert loaded.truncation_boundary == loaded.truncation_watermark
+    assert loaded.last_prompt_tokens is not None
+    assert len(loaded.context_messages) == 2
+    assert loaded.messages == original_messages
+
+
+def test_manual_compress_blocks_state_db_replay(monkeypatch, cleanup_test_sessions, tmp_path):
+    session_dir = tmp_path / "sessions"
+    session_dir.mkdir(parents=True)
+    monkeypatch.setattr(models, "SESSION_DIR", session_dir)
+    monkeypatch.setattr(models, "SESSION_INDEX_FILE", session_dir / "_index.json")
+    models.SESSIONS.clear()
+
+    sidecar = [
+        _msg("user", "one", 1.0),
+        _msg("assistant", "two", 2.0),
+        _msg("user", "three", 3.0),
+        _msg("assistant", "four", 4.0),
+    ]
+    state_db = [
+        _msg("user", "one", 1.0),
+        _msg("assistant", "two", 2.0),
+        _msg("user", "three", 3.0),
+        _msg("assistant", "four", 4.0),
+        _msg("assistant", "", 4.1),  # reasoning-only row that used to replay
+    ]
+    session = Session(
+        session_id=f"issue4836_reconcile_{time.time_ns()}",
+        title="Untitled",
+        workspace=str(tmp_path),
+        model="openai/gpt-5.4-mini",
+        messages=sidecar,
+        context_messages=sidecar,
+    )
+    session.save(touch_updated_at=False)
+    cleanup_test_sessions.append(session.session_id)
+
+    _install_fake_compression_runtime(monkeypatch, _FakeAgent)
+    handler = _FakeHandler()
+    _handle_session_compress(handler, {"session_id": session.session_id})
+    assert handler.status == 200
+
+    loaded = Session.load(session.session_id)
+    merged = reconciled_state_db_messages_for_session(
+        loaded,
+        prefer_context=True,
+        state_messages=state_db,
+    )
+    assert len(merged) == len(loaded.context_messages)
+
+
+def test_startup_recovery_skips_intentional_manual_compress(monkeypatch, tmp_path):
+    session_dir = tmp_path / "sessions"
+    session_dir.mkdir(parents=True)
+    sid = "issue4836_recovery"
+    live_path = session_dir / f"{sid}.json"
+    bak_path = session_dir / f"{sid}.json.bak"
+
+    live = {
+        "session_id": sid,
+        "title": "Untitled",
+        "workspace": str(tmp_path),
+        "model": "openai/gpt-5.4-mini",
+        "messages": [
+            _msg("user", "one", 1.0),
+            _msg("assistant", "two", 2.0),
+        ],
+        "context_messages": [
+            _msg("user", "one", 1.0),
+        ],
+        "compression_anchor_summary": "Compressed: 2 -> 1 messages",
+        "compression_anchor_message_key": {"role": "assistant", "ts": 2.0, "text": "two", "attachments": 0},
+        "compression_anchor_mode": "manual",
+        "truncation_watermark": 1.0,
+        "truncation_boundary": 1.0,
+        "message_count": 2,
+    }
+    bak = dict(live)
+    bak["messages"] = live["messages"] + [
+        _msg("user", "three", 3.0),
+        _msg("assistant", "four", 4.0),
+    ] * 150
+    # The .bak is the PRE-compression backup: its model-facing context_messages
+    # is still the large UNCOMPRESSED context (the shrink hasn't been applied to
+    # it). Restoring it would undo the intentional shrink → no_action.
+    bak["context_messages"] = bak["messages"]
+    live_path.write_text(json.dumps(live), encoding="utf-8")
+    bak_path.write_text(json.dumps(bak), encoding="utf-8")
+
+    status = inspect_session_recovery_status(live_path)
+    assert status["recommend"] == "no_action"
+    assert status.get("intentional_compress_shrink") is True
+
+    result = recover_all_sessions_on_startup(session_dir)
+    assert result["restored"] == 0
+    restored = json.loads(live_path.read_text(encoding="utf-8"))
+    assert len(restored["messages"]) == 2
+
+
+def test_startup_recovery_still_fires_for_post_compress_real_loss(monkeypatch, tmp_path):
+    """A manually-compressed session that LATER loses its messages array must
+    still be recovered from a backup written AFTER the compression (#4836
+    must not permanently disable #1558 crash-recovery for compressed sessions).
+    """
+    session_dir = tmp_path / "sessions"
+    session_dir.mkdir(parents=True)
+    sid = "issue4836_post_compress_loss"
+    live_path = session_dir / f"{sid}.json"
+    bak_path = session_dir / f"{sid}.json.bak"
+
+    # Live sidecar: manually compressed AND then truncated by a genuine loss
+    # (messages array shrank to 1 entry).
+    live = {
+        "session_id": sid,
+        "title": "Untitled",
+        "workspace": str(tmp_path),
+        "model": "openai/gpt-5.4-mini",
+        "messages": [_msg("user", "one", 1.0)],
+        "context_messages": [_msg("user", "one", 1.0)],
+        "compression_anchor_summary": "Compressed earlier",
+        "compression_anchor_message_key": {"role": "assistant", "ts": 2.0, "text": "two", "attachments": 0},
+        "compression_anchor_mode": "manual",
+        "truncation_watermark": 1.0,
+        "truncation_boundary": 1.0,
+        "message_count": 1,
+    }
+    # Backup: a healthy post-compression snapshot (more messages, written AFTER
+    # the compress). Its context_messages is the SAME already-compressed context
+    # as live (the compression persists across saves), so it post-dates the
+    # compression and must be restored when the live file later loses data.
+    bak = dict(live)
+    bak["messages"] = [
+        _msg("user", "one", 1.0),
+        _msg("assistant", "two", 2.0),
+        _msg("user", "three", 3.0),
+        _msg("assistant", "four", 4.0),
+    ]
+    bak["context_messages"] = [_msg("user", "one", 1.0)]  # same compressed context as live
+    live_path.write_text(json.dumps(live), encoding="utf-8")
+    bak_path.write_text(json.dumps(bak), encoding="utf-8")
+
+    status = inspect_session_recovery_status(live_path)
+    assert status["recommend"] == "restore", (
+        "post-compression real loss must still be recoverable even though the "
+        "session was manually compressed"
+    )
+
+    result = recover_all_sessions_on_startup(session_dir)
+    assert result["restored"] == 1
+    restored = json.loads(live_path.read_text(encoding="utf-8"))
+    assert len(restored["messages"]) == 4
+    assert len(restored["context_messages"]) == 1
+
+
+def test_startup_recovery_fires_when_loss_shrinks_both_messages_and_context(monkeypatch, tmp_path):
+    """A post-compression loss that clobbers BOTH messages AND context_messages
+    below the healthy backup's context must STILL be recovered.
+
+    Opus gate edge: a pure length heuristic (bak_ctx_len > live_ctx_len) would
+    misread the healthy backup's larger context as 'pre-compression' and wrongly
+    suppress recovery — permanent silent data loss. The compaction-marker
+    discriminator fixes this: the healthy post-compression backup carries the
+    `[context compaction…]` marker, so it is recognized as post-compression and
+    recovered regardless of relative context lengths.
+    """
+    session_dir = tmp_path / "sessions"
+    session_dir.mkdir(parents=True)
+    sid = "issue4836_both_shrunk"
+    live_path = session_dir / f"{sid}.json"
+    bak_path = session_dir / f"{sid}.json.bak"
+
+    marker = {"role": "user", "content": "[context compaction] summary of earlier turns", "timestamp": 1.0}
+    # Live: a genuine loss clobbered messages (130->2) AND context (50->1 marker only).
+    live = {
+        "session_id": sid,
+        "title": "Untitled",
+        "workspace": str(tmp_path),
+        "model": "openai/gpt-5.4-mini",
+        "messages": [_msg("user", "one", 1.0), _msg("assistant", "two", 2.0)],
+        "context_messages": [marker],
+        "compression_anchor_summary": "Compressed earlier",
+        "compression_anchor_message_key": {"role": "assistant", "ts": 2.0, "text": "two", "attachments": 0},
+        "compression_anchor_mode": "manual",
+        "truncation_watermark": 1.0,
+        "truncation_boundary": 1.0,
+        "message_count": 2,
+    }
+    # Healthy post-compression backup: MORE messages AND a LARGER compressed
+    # context (still carries the compaction marker) — must be recovered.
+    bak = dict(live)
+    bak["messages"] = [_msg("user", f"m{i}", float(i)) for i in range(130)]
+    bak["context_messages"] = [marker] + [_msg("assistant", f"c{i}", float(i)) for i in range(49)]
+    live_path.write_text(json.dumps(live), encoding="utf-8")
+    bak_path.write_text(json.dumps(bak), encoding="utf-8")
+
+    status = inspect_session_recovery_status(live_path)
+    assert status["recommend"] == "restore", (
+        "a loss shrinking both messages and context must still recover from a "
+        "marked (post-compression) backup — the marker, not length, decides"
+    )
+
+    result = recover_all_sessions_on_startup(session_dir)
+    assert result["restored"] == 1
+    restored = json.loads(live_path.read_text(encoding="utf-8"))
+    assert len(restored["messages"]) == 130
diff --git a/tests/test_sprint46.py b/tests/test_sprint46.py
index 7fd1c25e..272f8668 100644
--- a/tests/test_sprint46.py
+++ b/tests/test_sprint46.py
@@ -172,14 +172,24 @@ def test_session_compress_roundtrip(monkeypatch, cleanup_test_sessions):
     loaded = get_session(sid)
     persisted = Session.load(sid)
     assert loaded.messages == original_messages
-    assert loaded.context_messages == compressed_messages
+    assert [m.get("role") for m in loaded.context_messages] == [m.get("role") for m in compressed_messages]
+    assert [m.get("content") for m in loaded.context_messages] == [m.get("content") for m in compressed_messages]
     assert loaded.tool_calls == settled_tool_calls
     assert persisted.messages == original_messages
-    assert persisted.context_messages == compressed_messages
+    assert [m.get("role") for m in persisted.context_messages] == [m.get("role") for m in compressed_messages]
+    assert [m.get("content") for m in persisted.context_messages] == [m.get("content") for m in compressed_messages]
     assert persisted.tool_calls == settled_tool_calls
     assert loaded.compression_anchor_summary == payload["session"]["compression_anchor_summary"]
     assert loaded.compression_anchor_visible_idx == payload["session"]["compression_anchor_visible_idx"]
     assert loaded.compression_anchor_message_key == payload["session"]["compression_anchor_message_key"]
+    assert loaded.compression_anchor_mode == "manual"
+    assert loaded.truncation_watermark is not None
+    assert loaded.truncation_boundary == loaded.truncation_watermark
+    assert loaded.last_prompt_tokens is not None
+    assert persisted.compression_anchor_mode == "manual"
+    assert persisted.truncation_watermark == loaded.truncation_watermark
+    assert persisted.truncation_boundary == loaded.truncation_boundary
+    assert not (SESSION_DIR / f"{sid}.json.bak").exists()
     assert persisted.compression_anchor_visible_idx == 3
     assert persisted.compression_anchor_message_key == payload["session"]["compression_anchor_message_key"]
     assert _FakeAgent.last_instance is not None
@@ -269,10 +279,10 @@ def test_session_compress_start_is_async_and_reuses_running_job(monkeypatch, cle
     assert done_payload["session"]["tool_calls"] == settled_tool_calls
     persisted = Session.load(sid)
     assert persisted.tool_calls == settled_tool_calls
-    assert persisted.context_messages == [
-        {"role": "user", "content": "one"},
-        {"role": "assistant", "content": "four"},
-    ]
+    # /compress now stamps missing message timestamps, so compare role/content
+    # rather than full-dict equality (mirrors test_session_compress_roundtrip).
+    assert [m.get("role") for m in persisted.context_messages] == ["user", "assistant"]
+    assert [m.get("content") for m in persisted.context_messages] == ["one", "four"]
 
 
 def test_session_compress_status_reports_worker_error_without_raw_paths(monkeypatch, cleanup_test_sessions):