From f0d5f1298bf73fdb164e5cfedf736cffa4534887 Mon Sep 17 00:00:00 2001
From: ericmaddox <eric.maddox@outlook.com>
Date: Fri, 28 Aug 2026 22:43:08 -0400
Subject: [PATCH] fix(caching): prevent whitespace-only text blocks in prompt
 cache prefix splits

---
 agent/prompt_cache_boundary.py            |  9 +++---
 agent/prompt_caching.py                   | 34 ++++++++++++-----------
 tests/agent/test_prompt_cache_boundary.py |  4 ++-
 3 files changed, 26 insertions(+), 21 deletions(-)

diff --git a/agent/prompt_cache_boundary.py b/agent/prompt_cache_boundary.py
index b55ce55303..9f88277a88 100644
--- a/agent/prompt_cache_boundary.py
+++ b/agent/prompt_cache_boundary.py
@@ -67,10 +67,11 @@ def register_stable_prefix(prefix: str) -> None:
 
 
 def find_stable_prefix(content: str) -> Optional[str]:
-    """Longest registered prefix that is a *proper* prefix of ``content``.
+    """Longest registered prefix that is a *proper* prefix of ``content`` with non-whitespace tail.
 
-    Proper (``len(content) > len(prefix)``) so the split never produces an
-    empty volatile text block, which Anthropic rejects on the wire.
+    Proper with non-whitespace tail (``bool(content[len(prefix):].strip())``) so the
+    split never produces an empty or whitespace-only volatile text block, which
+    Anthropic rejects on the wire (HTTP 400).
 
     A hit refreshes the entry's LRU position: a scaffold fired every minute
     by cron must not be evicted by a burst of one-off skill invocations,
@@ -79,7 +80,7 @@ def find_stable_prefix(content: str) -> Optional[str]:
     with _lock:
         best: Optional[str] = None
         for prefix in _prefixes:
-            if len(content) > len(prefix) and content.startswith(prefix):
+            if content.startswith(prefix) and bool(content[len(prefix):].strip()):
                 if best is None or len(prefix) > len(best):
                     best = prefix
         if best is not None:
diff --git a/agent/prompt_caching.py b/agent/prompt_caching.py
index 2304c9ddd2..d947d7c164 100644
--- a/agent/prompt_caching.py
+++ b/agent/prompt_caching.py
@@ -63,20 +63,22 @@ def _apply_cache_marker(msg: dict, cache_marker: dict, native_anthropic: bool =
         if role == "user":
             stable_prefix = find_stable_prefix(content)
             if stable_prefix is not None:
-                # Builder-declared boundary (#81867): the scaffold carries the
-                # breakpoint, the volatile invocation tail rides unmarked so a
-                # changed ticket ID or timestamp no longer invalidates the
-                # whole skill body. Request-local only — the canonical session
-                # message stays a plain string.
-                msg["content"] = [
-                    {
-                        "type": "text",
-                        "text": stable_prefix,
-                        "cache_control": cache_marker,
-                    },
-                    {"type": "text", "text": content[len(stable_prefix):]},
-                ]
-                return
+                suffix = content[len(stable_prefix):]
+                if suffix.strip():
+                    # Builder-declared boundary (#81867): the scaffold carries the
+                    # breakpoint, the volatile invocation tail rides unmarked so a
+                    # changed ticket ID or timestamp no longer invalidates the
+                    # whole skill body. Request-local only — the canonical session
+                    # message stays a plain string.
+                    msg["content"] = [
+                        {
+                            "type": "text",
+                            "text": stable_prefix,
+                            "cache_control": cache_marker,
+                        },
+                        {"type": "text", "text": suffix},
+                    ]
+                    return
         msg["content"] = [
             {"type": "text", "text": content, "cache_control": cache_marker}
         ]
@@ -204,7 +206,7 @@ def _apply_system_cache_markers(
         and content.startswith(static_system_prefix)
     ):
         suffix = content[len(static_system_prefix):]
-        if suffix:
+        if suffix.strip():
             suffix_part: dict = {"type": "text", "text": suffix}
             if mark_suffix:
                 suffix_part["cache_control"] = cache_marker
@@ -217,7 +219,7 @@ def _apply_system_cache_markers(
                 suffix_part,
             ]
             return 2 if mark_suffix else 1
-        # Empty suffix: the stored prompt IS the static prefix. Mark it as
+        # Empty/whitespace-only suffix: the stored prompt IS the static prefix. Mark it as
         # one whole block — a [marked-prefix, ""] split would put an empty
         # text block on the wire (HTTP 400 on native Anthropic).
         _apply_cache_marker(message, cache_marker, native_anthropic=native_anthropic)
diff --git a/tests/agent/test_prompt_cache_boundary.py b/tests/agent/test_prompt_cache_boundary.py
index 0449f04ed4..d155473f91 100644
--- a/tests/agent/test_prompt_cache_boundary.py
+++ b/tests/agent/test_prompt_cache_boundary.py
@@ -80,8 +80,10 @@ class TestRegistry:
     def test_requires_proper_prefix(self):
         register_stable_prefix("scaffold")
         assert find_stable_prefix("scaffold volatile") == "scaffold"
-        # Exact match would leave an empty volatile block — never split.
+        # Exact match or whitespace-only tail would leave an empty/whitespace volatile block — never split.
         assert find_stable_prefix("scaffold") is None
+        assert find_stable_prefix("scaffold   ") is None
+        assert find_stable_prefix("scaffold\n\n\t") is None
         assert find_stable_prefix("other") is None
 
     def test_longest_registered_prefix_wins(self):