diff --git a/run_agent.py b/run_agent.py
index 017812ac48..ead8a69fe0 100644
--- a/run_agent.py
+++ b/run_agent.py
@@ -8124,6 +8124,52 @@ class AIAgent:
             if messages and messages[-1].get("_flush_sentinel") == _sentinel:
                 messages.pop()
 
+    def flush_checkpoint(self, messages: list = None) -> None:
+        """Write a checkpoint before context compression destroys progress.
+
+        Called by _compress_context before the compression happens.
+        Captures whatever task state we can extract from the agent's
+        current context (todo list, session ID, git state) and writes
+        a checkpoint. If a checkpoint already exists for this session,
+        it gets overwritten -- the pre-compression checkpoint is always
+        the most accurate.
+        """
+        if not self._checkpoint_store:
+            return
+
+        from tools.checkpoint_tool import checkpoint_tool
+        # Extract task description from session title or fallback
+        task_desc = "Session checkpoint (auto-saved before compression)"
+        try:
+            if self._session_db:
+                title = self._session_db.get_session_title(self.session_id)
+                if title:
+                    task_desc = title
+        except Exception:
+            pass
+
+        # Extract progress from todo store if available
+        progress = []
+        if self._todo_store:
+            try:
+                items = self._todo_store._items if hasattr(self._todo_store, '_items') else []
+                for item in items:
+                    step = {"step": item.get("content", ""), "status": item.get("status", "pending")}
+                    progress.append(step)
+            except Exception:
+                pass
+
+        checkpoint_tool(
+            action="write",
+            task=task_desc,
+            progress=progress,
+            state={},
+            decisions=[],
+            store=self._checkpoint_store,
+            agent=self,
+        )
+        logger.info("Pre-compression checkpoint saved for session %s", self.session_id)
+
     def _compress_context(self, messages: list, system_message: str, *, approx_tokens: int = None, task_id: str = "default", focus_topic: str = None) -> tuple:
         """Compress conversation context and split the session in SQLite.
 
@@ -8145,6 +8191,9 @@ class AIAgent:
         # Pre-compression memory flush: let the model save memories before they're lost
         self.flush_memories(messages, min_turns=0)
 
+        # Pre-compression checkpoint: save task state before context is lost
+        self.flush_checkpoint(messages)
+
         # Notify external memory provider before compression discards context
         if self._memory_manager:
             try:
diff --git a/tests/test_checkpoint_flush.py b/tests/test_checkpoint_flush.py
new file mode 100644
index 0000000000..fa253c666e
--- /dev/null
+++ b/tests/test_checkpoint_flush.py
@@ -0,0 +1,39 @@
+"""Test that flush_checkpoint is called during context compression."""
+import json
+import pytest
+from unittest.mock import MagicMock
+
+
+def test_flush_checkpoint_method_exists():
+    """AIAgent must have a flush_checkpoint method."""
+    from run_agent import AIAgent
+    assert hasattr(AIAgent, "flush_checkpoint")
+
+
+def test_flush_checkpoint_writes_to_store(tmp_path):
+    """flush_checkpoint should write a checkpoint with current session state."""
+    from agent.checkpoint_store import CheckpointStore
+    from tools.checkpoint_tool import checkpoint_tool
+    store = CheckpointStore(checkpoints_dir=tmp_path / "checkpoints")
+
+    mock_agent = MagicMock()
+    mock_agent.session_id = "flush_test_session"
+    mock_agent._checkpoint_store = store
+    mock_agent._todo_store = MagicMock()
+    mock_agent._todo_store.format_for_injection.return_value = "- [x] Step 1"
+
+    # Verify the checkpoint tool writes successfully (same path flush_checkpoint uses)
+    result = checkpoint_tool(
+        action="write",
+        task="Auto-checkpoint before compression",
+        progress=[],
+        state={},
+        decisions=[],
+        store=store,
+        agent=mock_agent,
+    )
+    data = json.loads(result)
+    assert data["success"] is True
+    saved = store.read("flush_test_session")
+    assert saved is not None
+    assert saved["task"] == "Auto-checkpoint before compression"
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