diff --git a/agent/context_compressor.py b/agent/context_compressor.py
index b9cca84c76..e98fbb6a08 100644
--- a/agent/context_compressor.py
+++ b/agent/context_compressor.py
@@ -72,6 +72,16 @@ def _safe_int(value: Any) -> int | None:
 # with it. Context is copied per worker (``propagate_context_to_thread``), so
 # the pin reaches the retry's whole synchronous call chain and cannot leak
 # into the stalled attempt or any unrelated auxiliary call.
+#
+# Coverage is the single ``_generate_summary`` LLM call only. That is one call
+# per compression run (its only non-recursive call site is the compress path;
+# the two recursive calls are the deliberate main-model retry that must NOT
+# re-issue the pin). Lean ``tail_mode`` additionally runs
+# ``_build_chunk_digests``, which issues its own ``call_llm`` calls directly
+# and never consults the pin — during a stall-fallback retry those digests
+# still target the stalled primary and degrade to per-segment placeholders.
+# Deliberate: the digest path is a best-effort augmentation, not the summary,
+# and pinning it would require weakening the single-use contract below.
 _SUMMARY_ROUTE_PIN: contextvars.ContextVar[Optional[Dict[str, Any]]] = (
     contextvars.ContextVar("hermes_summary_route_pin", default=None)
 )
diff --git a/agent/conversation_compression.py b/agent/conversation_compression.py
index e7c032d752..05fed80da8 100644
--- a/agent/conversation_compression.py
+++ b/agent/conversation_compression.py
@@ -953,11 +953,18 @@ def _retry_compression_on_fallback_chain(
         try:
             retry_fence = new_fence()
         except Exception:
-            logger.debug(
-                "compression stall-fallback fence factory failed",
+            logger.warning(
+                "compression stall-fallback fence factory failed; the retry "
+                "will run on an unpublished fence (a /stop mid-retry cannot "
+                "serialize against its commit boundary)",
                 exc_info=True,
             )
     if not isinstance(retry_fence, CompressionCommitFence):
+        logger.warning(
+            "compression stall-fallback retry running on an unpublished fence; "
+            "hard-interrupt admission will read the aborted attempt's fence "
+            "rather than the retry's commit boundary",
+        )
         retry_fence = CompressionCommitFence()
     idle = float(route.get("timeout") or idle_timeout_seconds)
     ceiling = max(float(total_ceiling_seconds), idle)