diff --git a/agent/conversation_compression.py b/agent/conversation_compression.py
index ba8678cc7..a0b077e3e 100644
--- a/agent/conversation_compression.py
+++ b/agent/conversation_compression.py
@@ -644,6 +644,12 @@ def try_shrink_image_parts_in_messages(api_messages: list) -> bool:
     # after a confirmed provider rejection, so the alternative is failure.
     target_bytes = 4 * 1024 * 1024
     changed_count = 0
+    # Track parts that are over the target but could NOT be shrunk under it.
+    # If any survive, retrying is pointless — the same oversized payload will
+    # be re-sent and rejected again, wasting the single retry budget.  We only
+    # report success (caller retries) when every over-threshold image was
+    # actually brought under the target.
+    unshrinkable_oversized = 0
 
     def _shrink_data_url(url: str) -> Optional[str]:
         """Return a smaller data URL, or None if shrink can't help."""
@@ -710,17 +716,34 @@ def try_shrink_image_parts_in_messages(api_messages: list) -> bool:
                 if resized:
                     image_value["url"] = resized
                     changed_count += 1
+                elif isinstance(url, str) and url.startswith("data:") \
+                        and len(url) > target_bytes:
+                    unshrinkable_oversized += 1
             elif isinstance(image_value, str):
                 resized = _shrink_data_url(image_value)
                 if resized:
                     part["image_url"] = resized
                     changed_count += 1
+                elif image_value.startswith("data:") \
+                        and len(image_value) > target_bytes:
+                    unshrinkable_oversized += 1
 
     if changed_count:
         logger.info(
             "image-shrink recovery: re-encoded %d image part(s) to fit under %.0f MB",
             changed_count, target_bytes / (1024 * 1024),
         )
+    if unshrinkable_oversized:
+        # At least one oversized image could not be shrunk under the target.
+        # Retrying would re-send it and fail identically, so signal "no
+        # progress" even if other parts shrank — the caller will surface the
+        # original error rather than burning its single retry on a no-op.
+        logger.warning(
+            "image-shrink recovery: %d oversized image part(s) could not be "
+            "shrunk under %.0f MB — not retrying (would re-send rejected payload)",
+            unshrinkable_oversized, target_bytes / (1024 * 1024),
+        )
+        return False
     return changed_count > 0
 
 
diff --git a/tests/run_agent/test_image_shrink_recovery.py b/tests/run_agent/test_image_shrink_recovery.py
index c5114ffef..86a3e6abf 100644
--- a/tests/run_agent/test_image_shrink_recovery.py
+++ b/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
diff --git a/tests/tools/test_vision_native_fast_path.py b/tests/tools/test_vision_native_fast_path.py
index 9916ca369..bb396c05d 100644
--- a/tests/tools/test_vision_native_fast_path.py
+++ b/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 ─────────────────────────────────
 
diff --git a/tools/vision_tools.py b/tools/vision_tools.py
index 23a0508fe..39a4921f1 100644
--- a/tools/vision_tools.py
+++ b/tools/vision_tools.py
@@ -311,10 +311,21 @@ def _image_to_base64_data_url(image_path: Path, mime_type: Optional[str] = None)
     return data_url
 
 
-# Hard limit for vision API payloads (20 MB) — matches the most restrictive
-# major provider (Gemini inline data limit).  Images above this are rejected.
+# Absolute hard ceiling for vision API payloads (20 MB) — above this, no major
+# provider accepts the image and we reject outright.
 _MAX_BASE64_BYTES = 20 * 1024 * 1024
 
+# Proactive embed cap (4 MB).  This is the size we resize an image DOWN to
+# before embedding it into conversation history, regardless of the 20 MB hard
+# ceiling.  Anthropic's per-image base64 limit is 5 MB; once an oversized image
+# is baked into history (e.g. a vision tool-result), it is re-sent on every
+# subsequent turn and permanently wedges the session with a 400 that retries
+# can't clear (the bad bytes are immutable history).  Capping at embed time —
+# with headroom under 5 MB — is the only durable fix.  Matches the post-failure
+# shrink target in agent.conversation_compression so behaviour is consistent
+# whether we resize proactively or reactively.
+_EMBED_TARGET_BYTES = 4 * 1024 * 1024
+
 # Target size when auto-resizing on API failure (5 MB).  After a provider
 # rejects an image, we downscale to this target and retry once.
 _RESIZE_TARGET_BYTES = 5 * 1024 * 1024
@@ -656,11 +667,21 @@ async def _vision_analyze_native(
             temp_image_path, mime_type=detected_mime_type,
         )
 
-        # Honour the same hard cap as the legacy path. Resize if needed.
-        if len(image_data_url) > _MAX_BASE64_BYTES:
+        # Proactive embed cap: this image gets baked into conversation
+        # history and re-sent on every subsequent turn.  Anthropic rejects
+        # any single base64 image over 5 MB with a 400, and because history
+        # is immutable, an oversized embed permanently wedges the session —
+        # retries can't clear bytes that are already in the request.  Resize
+        # DOWN to the embed target (4 MB, headroom under 5 MB) whenever the
+        # payload exceeds it, not just at the 20 MB hard ceiling.
+        if len(image_data_url) > _EMBED_TARGET_BYTES:
             image_data_url = _resize_image_for_vision(
                 temp_image_path, mime_type=detected_mime_type,
+                max_base64_bytes=_EMBED_TARGET_BYTES,
             )
+            # If even resizing can't get under the absolute hard ceiling,
+            # there's nothing more we can do — reject rather than embed a
+            # session-wedging payload.
             if len(image_data_url) > _MAX_BASE64_BYTES:
                 return tool_error(
                     f"Image too large for vision API: base64 payload is "