fix(vision): cap embedded image size before it wedges a session (#35732)

Resize vision tool-result images down to a 4 MB embed cap at load time,
not just at the 20 MB hard ceiling. A 5-20 MB image previously sailed
through the native fast path and got baked into conversation history,
where Anthropic's 5 MB per-image base64 limit rejected every subsequent
turn with a 400 — and because history is immutable, retries could never
clear it, permanently wedging the session.

Also harden the reactive shrink-recovery: it now returns False (don't
retry) when any oversized image part can't be brought under target, so
the single retry isn't burned re-sending a payload that will fail
identically. Previously it returned True after shrinking *any* part,
even when the actual oversized culprit survived.

tests/run_agent/test_image_shrink_recovery.py

@@ -273,3 +273,51 @@ class TestShrinkImagePartsHelper:
         assert agent._try_shrink_image_parts_in_messages(msgs) is False
         # Original URL still in place, not replaced by the bigger one.
         assert msgs[0]["content"][0]["image_url"]["url"] == oversized_url
+
+    def test_mixed_one_shrinkable_one_not_returns_false(self, monkeypatch):
+        """Regression for the wedged-session incident (May 2026).
+
+        When one oversized image shrinks but another oversized image can't,
+        the helper must return False — retrying would re-send the surviving
+        oversized payload and fail identically, burning the single retry on a
+        no-op.  The original bug returned True after shrinking *any* part,
+        which is what permanently wedged a session whose history held a 12 MB
+        tool-result image alongside a freshly-loaded shrinkable one.
+        """
+        agent = _make_agent()
+        shrinkable = _big_png_data_url(5000)
+        unshrinkable = _big_png_data_url(6000)
+        small = "data:image/jpeg;base64," + "C" * 500
+
+        # _resize_image_for_vision returns small for the shrinkable input but
+        # echoes the oversized payload back for the unshrinkable one.
+        def fake_resize(path, *a, **kw):
+            # The temp file written by the helper contains the decoded bytes;
+            # distinguish by size — the 6000 KB source stays "big".
+            try:
+                size = path.stat().st_size
+            except Exception:
+                size = 0
+            if size > 5500 * 1024:
+                return unshrinkable  # can't reduce — echo oversized back
+            return small
+
+        monkeypatch.setattr(
+            "tools.vision_tools._resize_image_for_vision",
+            fake_resize,
+            raising=False,
+        )
+
+        msgs = [{
+            "role": "tool",
+            "content": [
+                {"type": "image_url", "image_url": {"url": shrinkable}},
+                {"type": "image_url", "image_url": {"url": unshrinkable}},
+            ],
+        }]
+        # One part shrank, one survived oversized → must NOT retry.
+        assert agent._try_shrink_image_parts_in_messages(msgs) is False
+        # The shrinkable one was still re-encoded (mutated in place).
+        assert msgs[0]["content"][0]["image_url"]["url"] == small
+        # The unshrinkable one is left as-is (caller surfaces original error).
+        assert msgs[0]["content"][1]["image_url"]["url"] == unshrinkable

tests/tools/test_vision_native_fast_path.py

@@ -139,6 +139,44 @@ class TestVisionAnalyzeNative:
         assert isinstance(result, dict)
         assert result.get("_multimodal") is True
 
+    def test_oversized_image_resized_under_embed_cap(self, tmp_path):
+        """Regression for the wedged-session incident (May 2026).
+
+        A vision tool-result image is baked into conversation history and
+        re-sent on every subsequent turn.  Anthropic rejects any single
+        base64 image over 5 MB with a 400, and immutable history means the
+        bad bytes can't be cleared by retrying — the session is permanently
+        wedged.  The native fast path must proactively resize down to the
+        embed cap (well under 5 MB) BEFORE embedding, not just at the 20 MB
+        hard ceiling.  Skips if Pillow isn't available (resize is a no-op).
+        """
+        pytest = __import__("pytest")
+        try:
+            from PIL import Image
+        except ImportError:
+            pytest.skip("Pillow not installed — proactive resize is a no-op")
+
+        from tools.vision_tools import _EMBED_TARGET_BYTES
+
+        # Noisy PNG that base64-encodes to well over 5 MB (won't compress much).
+        big = tmp_path / "big.png"
+        Image.effect_noise((2600, 2600), 80).convert("RGB").save(big, format="PNG")
+        assert big.stat().st_size * 4 // 3 > 5 * 1024 * 1024, "test image not big enough"
+
+        result = asyncio.get_event_loop().run_until_complete(
+            _vision_analyze_native(str(big), "describe")
+        )
+        assert isinstance(result, dict) and result.get("_multimodal") is True
+        url = next(
+            p["image_url"]["url"]
+            for p in result["content"]
+            if p.get("type") == "image_url"
+        )
+        assert len(url) <= _EMBED_TARGET_BYTES, (
+            f"embedded image {len(url) / 1024 / 1024:.1f} MB exceeds embed cap "
+            f"{_EMBED_TARGET_BYTES / 1024 / 1024:.0f} MB — would wedge sessions on Anthropic"
+        )
+
 
 # ─── _handle_vision_analyze fast-path gating ─────────────────────────────────