diff --git a/agent/chat_completion_helpers.py b/agent/chat_completion_helpers.py
index e352f40ca9..a8b4098989 100644
--- a/agent/chat_completion_helpers.py
+++ b/agent/chat_completion_helpers.py
@@ -3270,6 +3270,10 @@ def handle_max_iterations(agent, messages: list, api_call_count: int) -> str:
         # tool_call was summarized away; Responses API rejects that as
         # "No tool call found for function call output".
         api_messages = agent._sanitize_api_messages(api_messages)
+        # Same send-path vision eviction as the main loop (#89296).
+        from agent.context_compressor import evict_stale_outbound_tool_images
+
+        evict_stale_outbound_tool_images(api_messages)
 
         # Same safety net as the main loop: drop thinking-only assistant
         # turns so Anthropic-family providers don't 400 the summary call.
diff --git a/agent/context_compressor.py b/agent/context_compressor.py
index a70ea5a300..7612383945 100644
--- a/agent/context_compressor.py
+++ b/agent/context_compressor.py
@@ -1772,6 +1772,23 @@ def _retire_stale_tool_result_images(
     return pruned
 
 
+def evict_stale_outbound_tool_images(
+    api_messages: List[Dict[str, Any]],
+    keep_newest: int = _MAX_KEEP_TOOL_IMAGES,
+) -> int:
+    """Drop stale screenshot/vision payloads from the per-call API copy.
+
+    Compression's keep-newest pass only runs when prune/compress fires, and
+    the Anthropic adapter's screenshot eviction only sees nested
+    ``tool_result`` blocks. OpenAI-style ``image_url`` tool results
+    otherwise ride every subsequent request until a 413 forces the reactive
+    strip (#89286). Call this on the cloned ``api_messages`` list after
+    sanitization so older frames never leave the box (#89296). Do not pass
+    persisted history — the rewrite is send-path only.
+    """
+    return _retire_stale_tool_result_images(api_messages, keep_newest=keep_newest)
+
+
 def _truncate_tool_call_args_json(args: str, head_chars: int = 200) -> str:
     """Shrink long string values inside a tool-call arguments JSON blob while
     preserving JSON validity.
diff --git a/agent/conversation_loop.py b/agent/conversation_loop.py
index e8f466bc09..77e502ee48 100644
--- a/agent/conversation_loop.py
+++ b/agent/conversation_loop.py
@@ -2743,6 +2743,13 @@ def run_conversation(
         # gated on context_compressor — so orphans from session loading or
         # manual message manipulation are always caught.
         api_messages = agent._sanitize_api_messages(api_messages)
+        # Send-path vision eviction (#89296): compression only strips stale
+        # screenshots when prune fires, and the Anthropic adapter's keep-window
+        # never sees OpenAI-style tool-result image_url parts. The per-call
+        # clone is rewritten in place; persisted history is untouched.
+        from agent.context_compressor import evict_stale_outbound_tool_images
+
+        evict_stale_outbound_tool_images(api_messages)
 
         # One-time repeated-heal escalation notice (#96870): if the sanitizer
         # above just crossed the per-session heal threshold, deliver the
diff --git a/tests/agent/test_outbound_stale_vision.py b/tests/agent/test_outbound_stale_vision.py
new file mode 100644
index 0000000000..1cab4234a0
--- /dev/null
+++ b/tests/agent/test_outbound_stale_vision.py
@@ -0,0 +1,119 @@
+"""Send-path eviction of stale vision_analyze / screenshot tool payloads.
+
+Issue #89296: compression only retires older image-bearing tool results when
+prune/compress fires, so OpenAI-style screenshots are re-serialized on every
+later turn until a 413. ``evict_stale_outbound_tool_images`` is the
+unconditional per-call chokepoint.
+"""
+
+from __future__ import annotations
+
+from agent.agent_runtime_helpers import sanitize_api_messages
+from agent.context_compressor import (
+    _MAX_KEEP_TOOL_IMAGES,
+    _tool_content_has_images,
+    evict_stale_outbound_tool_images,
+)
+
+
+def _image_tool(i: int, *, blob: str = "A" * 80) -> list[dict]:
+    return [
+        {
+            "role": "assistant",
+            "content": None,
+            "tool_calls": [
+                {
+                    "id": f"call_{i}",
+                    "type": "function",
+                    "function": {
+                        "name": "vision_analyze",
+                        "arguments": f'{{"image_url":"shot{i}.png"}}',
+                    },
+                }
+            ],
+        },
+        {
+            "role": "tool",
+            "tool_call_id": f"call_{i}",
+            "content": [
+                {"type": "text", "text": f"Image attached natively shot {i}"},
+                {
+                    "type": "image_url",
+                    "image_url": {"url": f"data:image/png;base64,{blob}{i}"},
+                },
+            ],
+        },
+    ]
+
+
+def _history_with_screenshots(n: int) -> list[dict]:
+    msgs: list[dict] = [{"role": "user", "content": "look at these"}]
+    for i in range(n):
+        msgs.extend(_image_tool(i))
+    msgs.append({"role": "user", "content": "compare them"})
+    return msgs
+
+
+def _image_bearing_tool_ids(messages: list[dict]) -> list[str]:
+    return [
+        m["tool_call_id"]
+        for m in messages
+        if m.get("role") == "tool" and _tool_content_has_images(m.get("content"))
+    ]
+
+
+class TestOutboundStaleVisionEviction:
+    def test_sanitize_alone_keeps_every_screenshot(self):
+        """The previous send chokepoint does not close #89296 by itself."""
+        history = _history_with_screenshots(5)
+        sanitized = sanitize_api_messages(history)
+        assert _image_bearing_tool_ids(sanitized) == [f"call_{i}" for i in range(5)]
+
+    def test_eviction_keeps_only_newest_window(self):
+        history = _history_with_screenshots(5)
+        outbound = sanitize_api_messages(history)
+        pruned = evict_stale_outbound_tool_images(outbound)
+        assert pruned == 5 - _MAX_KEEP_TOOL_IMAGES
+        kept = _image_bearing_tool_ids(outbound)
+        assert kept == [f"call_{i}" for i in range(5 - _MAX_KEEP_TOOL_IMAGES, 5)]
+
+        oldest = next(m for m in outbound if m.get("tool_call_id") == "call_0")
+        assert isinstance(oldest["content"], list)
+        assert not _tool_content_has_images(oldest["content"])
+        assert any(
+            isinstance(part, dict)
+            and part.get("type") == "text"
+            and "screenshot removed" in str(part.get("text", ""))
+            for part in oldest["content"]
+        )
+
+    def test_does_not_rewrite_persisted_history(self):
+        from agent.conversation_loop import _clone_message_for_send
+
+        history = _history_with_screenshots(5)
+        outbound = [_clone_message_for_send(m) for m in history]
+        evict_stale_outbound_tool_images(outbound)
+        assert _image_bearing_tool_ids(history) == [f"call_{i}" for i in range(5)]
+        assert _image_bearing_tool_ids(outbound) == [
+            f"call_{i}" for i in range(5 - _MAX_KEEP_TOOL_IMAGES, 5)
+        ]
+
+    def test_user_uploads_are_not_evicted(self):
+        history = [
+            {
+                "role": "user",
+                "content": [
+                    {"type": "text", "text": "look"},
+                    {
+                        "type": "image_url",
+                        "image_url": {"url": "data:image/png;base64,USERUPLOAD"},
+                    },
+                ],
+            }
+        ]
+        for i in range(_MAX_KEEP_TOOL_IMAGES + 2):
+            history.extend(_image_tool(i))
+        outbound = sanitize_api_messages(history)
+        evict_stale_outbound_tool_images(outbound)
+        user = next(m for m in outbound if m.get("role") == "user")
+        assert user["content"][1]["image_url"]["url"].endswith("USERUPLOAD")