diff --git a/run_agent.py b/run_agent.py
index bbcec618d..eefeb8088 100644
--- a/run_agent.py
+++ b/run_agent.py
@@ -2625,7 +2625,7 @@ class AIAgent:
             if messages and messages[-1].get("_flush_sentinel") == _sentinel:
                 messages.pop()
 
-    def _compress_context(self, messages: list, system_message: str, *, approx_tokens: int = None) -> tuple:
+    def _compress_context(self, messages: list, system_message: str, *, approx_tokens: int = None, task_id: str = "default") -> tuple:
         """Compress conversation context and split the session in SQLite.
 
         Returns:
@@ -2640,6 +2640,25 @@ class AIAgent:
         if todo_snapshot:
             compressed.append({"role": "user", "content": todo_snapshot})
 
+        # Preserve file-read history so the model doesn't re-read files
+        # it already examined before compression.
+        try:
+            from tools.file_tools import get_read_files_summary
+            read_files = get_read_files_summary(task_id)
+            if read_files:
+                file_list = "\n".join(
+                    f"  - {f['path']} ({', '.join(f['regions'])})"
+                    for f in read_files
+                )
+                compressed.append({"role": "user", "content": (
+                    "[Files already read in this session — do NOT re-read these]\n"
+                    f"{file_list}\n"
+                    "Use the information from the context summary above. "
+                    "Proceed with writing, editing, or responding."
+                )})
+        except Exception:
+            pass  # Don't break compression if file tracking fails
+
         self._invalidate_system_prompt()
         new_system_prompt = self._build_system_prompt(system_message)
         self._cached_system_prompt = new_system_prompt
@@ -3225,7 +3244,8 @@ class AIAgent:
                 for _pass in range(3):
                     _orig_len = len(messages)
                     messages, active_system_prompt = self._compress_context(
-                        messages, system_message, approx_tokens=_preflight_tokens
+                        messages, system_message, approx_tokens=_preflight_tokens,
+                        task_id=effective_task_id,
                     )
                     if len(messages) >= _orig_len:
                         break  # Cannot compress further
@@ -3752,7 +3772,8 @@ class AIAgent:
 
                         original_len = len(messages)
                         messages, active_system_prompt = self._compress_context(
-                            messages, system_message, approx_tokens=approx_tokens
+                            messages, system_message, approx_tokens=approx_tokens,
+                            task_id=effective_task_id,
                         )
 
                         if len(messages) < original_len:
@@ -3820,7 +3841,8 @@ class AIAgent:
 
                         original_len = len(messages)
                         messages, active_system_prompt = self._compress_context(
-                            messages, system_message, approx_tokens=approx_tokens
+                            messages, system_message, approx_tokens=approx_tokens,
+                            task_id=effective_task_id,
                         )
 
                         if len(messages) < original_len or new_ctx and new_ctx < old_ctx:
@@ -4173,7 +4195,8 @@ class AIAgent:
                     if self.compression_enabled and self.context_compressor.should_compress():
                         messages, active_system_prompt = self._compress_context(
                             messages, system_message,
-                            approx_tokens=self.context_compressor.last_prompt_tokens
+                            approx_tokens=self.context_compressor.last_prompt_tokens,
+                            task_id=effective_task_id,
                         )
                     
                     # Save session log incrementally (so progress is visible even if interrupted)
diff --git a/tests/tools/test_file_tools.py b/tests/tools/test_file_tools.py
index 7b71465f7..27ccf7042 100644
--- a/tests/tools/test_file_tools.py
+++ b/tests/tools/test_file_tools.py
@@ -242,6 +242,11 @@ class TestPatchHints:
 class TestSearchHints:
     """Search tool should hint when results are truncated."""
 
+    def setup_method(self):
+        """Clear read/search tracker between tests to avoid cross-test state."""
+        from tools.file_tools import clear_read_tracker
+        clear_read_tracker()
+
     @patch("tools.file_tools._get_file_ops")
     def test_truncated_results_hint(self, mock_get):
         mock_ops = MagicMock()
diff --git a/tests/tools/test_read_loop_detection.py b/tests/tools/test_read_loop_detection.py
new file mode 100644
index 000000000..dfa1c1ab3
--- /dev/null
+++ b/tests/tools/test_read_loop_detection.py
@@ -0,0 +1,383 @@
+#!/usr/bin/env python3
+"""
+Tests for the read-loop detection mechanism in file_tools.
+
+Verifies that:
+1. Re-reading the same file region produces a warning
+2. Different regions/files don't trigger false warnings
+3. Task isolation works (different tasks have separate trackers)
+4. get_read_files_summary returns accurate history
+5. clear_read_tracker resets state
+6. Context compression injects file-read history
+
+Run with:  python -m pytest tests/tools/test_read_loop_detection.py -v
+"""
+
+import json
+import unittest
+from unittest.mock import patch, MagicMock
+
+from tools.file_tools import (
+    read_file_tool,
+    search_tool,
+    get_read_files_summary,
+    clear_read_tracker,
+    _read_tracker,
+)
+
+
+class _FakeReadResult:
+    """Minimal stand-in for FileOperations.read_file return value."""
+    def __init__(self, content="line1\nline2\n", total_lines=2):
+        self.content = content
+        self._total_lines = total_lines
+
+    def to_dict(self):
+        return {"content": self.content, "total_lines": self._total_lines}
+
+
+def _fake_read_file(path, offset=1, limit=500):
+    return _FakeReadResult(content=f"content of {path}", total_lines=10)
+
+
+class _FakeSearchResult:
+    """Minimal stand-in for FileOperations.search return value."""
+    def __init__(self):
+        self.matches = []
+
+    def to_dict(self):
+        return {"matches": [{"file": "test.py", "line": 1, "text": "match"}]}
+
+
+def _make_fake_file_ops():
+    fake = MagicMock()
+    fake.read_file = _fake_read_file
+    fake.search = lambda **kw: _FakeSearchResult()
+    return fake
+
+
+class TestReadLoopDetection(unittest.TestCase):
+    """Verify that read_file_tool detects and warns on re-reads."""
+
+    def setUp(self):
+        clear_read_tracker()
+
+    def tearDown(self):
+        clear_read_tracker()
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_first_read_has_no_warning(self, _mock_ops):
+        result = json.loads(read_file_tool("/tmp/test.py", task_id="t1"))
+        self.assertNotIn("_warning", result)
+        self.assertIn("content", result)
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_second_read_same_region_has_warning(self, _mock_ops):
+        read_file_tool("/tmp/test.py", offset=1, limit=500, task_id="t1")
+        result = json.loads(
+            read_file_tool("/tmp/test.py", offset=1, limit=500, task_id="t1")
+        )
+        self.assertIn("_warning", result)
+        self.assertIn("already read", result["_warning"])
+        self.assertIn("2 times", result["_warning"])
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_third_read_is_blocked(self, _mock_ops):
+        """3rd read of the same region returns error, no content."""
+        for _ in range(2):
+            read_file_tool("/tmp/test.py", task_id="t1")
+        result = json.loads(read_file_tool("/tmp/test.py", task_id="t1"))
+        self.assertIn("error", result)
+        self.assertIn("BLOCKED", result["error"])
+        self.assertNotIn("content", result)
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_fourth_read_still_blocked(self, _mock_ops):
+        """Subsequent reads remain blocked with incrementing count."""
+        for _ in range(3):
+            read_file_tool("/tmp/test.py", task_id="t1")
+        result = json.loads(read_file_tool("/tmp/test.py", task_id="t1"))
+        self.assertIn("BLOCKED", result["error"])
+        self.assertIn("4 times", result["error"])
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_different_region_no_warning(self, _mock_ops):
+        read_file_tool("/tmp/test.py", offset=1, limit=500, task_id="t1")
+        result = json.loads(
+            read_file_tool("/tmp/test.py", offset=501, limit=500, task_id="t1")
+        )
+        self.assertNotIn("_warning", result)
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_different_file_no_warning(self, _mock_ops):
+        read_file_tool("/tmp/a.py", task_id="t1")
+        result = json.loads(read_file_tool("/tmp/b.py", task_id="t1"))
+        self.assertNotIn("_warning", result)
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_different_tasks_isolated(self, _mock_ops):
+        read_file_tool("/tmp/test.py", task_id="task_a")
+        result = json.loads(
+            read_file_tool("/tmp/test.py", task_id="task_b")
+        )
+        self.assertNotIn("_warning", result)
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_warning_still_returns_content(self, _mock_ops):
+        """Even with a warning, the file content is still returned."""
+        read_file_tool("/tmp/test.py", task_id="t1")
+        result = json.loads(read_file_tool("/tmp/test.py", task_id="t1"))
+        self.assertIn("_warning", result)
+        self.assertIn("content", result)
+        self.assertIn("content of /tmp/test.py", result["content"])
+
+
+class TestReadFilesSummary(unittest.TestCase):
+    """Verify get_read_files_summary returns accurate file-read history."""
+
+    def setUp(self):
+        clear_read_tracker()
+
+    def tearDown(self):
+        clear_read_tracker()
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_empty_when_no_reads(self, _mock_ops):
+        summary = get_read_files_summary("t1")
+        self.assertEqual(summary, [])
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_single_file_single_region(self, _mock_ops):
+        read_file_tool("/tmp/test.py", offset=1, limit=500, task_id="t1")
+        summary = get_read_files_summary("t1")
+        self.assertEqual(len(summary), 1)
+        self.assertEqual(summary[0]["path"], "/tmp/test.py")
+        self.assertIn("lines 1-500", summary[0]["regions"])
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_single_file_multiple_regions(self, _mock_ops):
+        read_file_tool("/tmp/test.py", offset=1, limit=500, task_id="t1")
+        read_file_tool("/tmp/test.py", offset=501, limit=500, task_id="t1")
+        summary = get_read_files_summary("t1")
+        self.assertEqual(len(summary), 1)
+        self.assertEqual(len(summary[0]["regions"]), 2)
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_multiple_files(self, _mock_ops):
+        read_file_tool("/tmp/a.py", task_id="t1")
+        read_file_tool("/tmp/b.py", task_id="t1")
+        summary = get_read_files_summary("t1")
+        self.assertEqual(len(summary), 2)
+        paths = [s["path"] for s in summary]
+        self.assertIn("/tmp/a.py", paths)
+        self.assertIn("/tmp/b.py", paths)
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_different_task_has_separate_summary(self, _mock_ops):
+        read_file_tool("/tmp/a.py", task_id="task_a")
+        read_file_tool("/tmp/b.py", task_id="task_b")
+        summary_a = get_read_files_summary("task_a")
+        summary_b = get_read_files_summary("task_b")
+        self.assertEqual(len(summary_a), 1)
+        self.assertEqual(summary_a[0]["path"], "/tmp/a.py")
+        self.assertEqual(len(summary_b), 1)
+        self.assertEqual(summary_b[0]["path"], "/tmp/b.py")
+
+
+class TestClearReadTracker(unittest.TestCase):
+    """Verify clear_read_tracker resets state properly."""
+
+    def setUp(self):
+        clear_read_tracker()
+
+    def tearDown(self):
+        clear_read_tracker()
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_clear_specific_task(self, _mock_ops):
+        read_file_tool("/tmp/test.py", task_id="t1")
+        read_file_tool("/tmp/test.py", task_id="t2")
+        clear_read_tracker("t1")
+        self.assertEqual(get_read_files_summary("t1"), [])
+        self.assertEqual(len(get_read_files_summary("t2")), 1)
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_clear_all(self, _mock_ops):
+        read_file_tool("/tmp/test.py", task_id="t1")
+        read_file_tool("/tmp/test.py", task_id="t2")
+        clear_read_tracker()
+        self.assertEqual(get_read_files_summary("t1"), [])
+        self.assertEqual(get_read_files_summary("t2"), [])
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_clear_then_reread_no_warning(self, _mock_ops):
+        read_file_tool("/tmp/test.py", task_id="t1")
+        clear_read_tracker("t1")
+        result = json.loads(read_file_tool("/tmp/test.py", task_id="t1"))
+        self.assertNotIn("_warning", result)
+
+
+class TestCompressionFileHistory(unittest.TestCase):
+    """Verify that _compress_context injects file-read history."""
+
+    def setUp(self):
+        clear_read_tracker()
+
+    def tearDown(self):
+        clear_read_tracker()
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_compress_context_includes_read_files(self, _mock_ops):
+        """After reading files, _compress_context should inject a message
+        listing which files were already read."""
+        # Simulate reads
+        read_file_tool("/tmp/foo.py", offset=1, limit=100, task_id="compress_test")
+        read_file_tool("/tmp/bar.py", offset=1, limit=200, task_id="compress_test")
+
+        # Build minimal messages for compression (need enough messages)
+        messages = [
+            {"role": "system", "content": "You are a helpful assistant."},
+            {"role": "user", "content": "Analyze the codebase."},
+            {"role": "assistant", "content": "I'll read the files."},
+            {"role": "user", "content": "Continue."},
+            {"role": "assistant", "content": "Reading more files."},
+            {"role": "user", "content": "What did you find?"},
+            {"role": "assistant", "content": "Here are my findings."},
+            {"role": "user", "content": "Great, write the fix."},
+            {"role": "assistant", "content": "Working on it."},
+            {"role": "user", "content": "Status?"},
+        ]
+
+        # Mock the compressor to return a simple compression
+        mock_compressor = MagicMock()
+        mock_compressor.compress.return_value = [
+            messages[0],  # system
+            messages[1],  # first user
+            {"role": "user", "content": "[CONTEXT SUMMARY]: Files were analyzed."},
+            messages[-1],  # last user
+        ]
+        mock_compressor.last_prompt_tokens = 5000
+
+        # Mock the agent's _compress_context dependencies
+        mock_agent = MagicMock()
+        mock_agent.context_compressor = mock_compressor
+        mock_agent._todo_store.format_for_injection.return_value = None
+        mock_agent._session_db = None
+        mock_agent.quiet_mode = True
+        mock_agent._invalidate_system_prompt = MagicMock()
+        mock_agent._build_system_prompt = MagicMock(return_value="system prompt")
+        mock_agent._cached_system_prompt = None
+
+        # Call the real _compress_context
+        from run_agent import AIAgent
+        result, _ = AIAgent._compress_context(
+            mock_agent, messages, "system prompt",
+            approx_tokens=5000, task_id="compress_test",
+        )
+
+        # Find the injected file-read history message
+        file_history_msgs = [
+            m for m in result
+            if isinstance(m.get("content"), str)
+            and "already read" in m.get("content", "").lower()
+        ]
+        self.assertEqual(len(file_history_msgs), 1,
+                         "Should inject exactly one file-read history message")
+
+        history_content = file_history_msgs[0]["content"]
+        self.assertIn("/tmp/foo.py", history_content)
+        self.assertIn("/tmp/bar.py", history_content)
+        self.assertIn("do NOT re-read", history_content)
+
+
+class TestSearchLoopDetection(unittest.TestCase):
+    """Verify that search_tool detects and blocks repeated searches."""
+
+    def setUp(self):
+        clear_read_tracker()
+
+    def tearDown(self):
+        clear_read_tracker()
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_first_search_no_warning(self, _mock_ops):
+        result = json.loads(search_tool("def main", task_id="t1"))
+        self.assertNotIn("_warning", result)
+        self.assertNotIn("error", result)
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_second_search_has_warning(self, _mock_ops):
+        search_tool("def main", task_id="t1")
+        result = json.loads(search_tool("def main", task_id="t1"))
+        self.assertIn("_warning", result)
+        self.assertIn("2 times", result["_warning"])
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_third_search_is_blocked(self, _mock_ops):
+        for _ in range(2):
+            search_tool("def main", task_id="t1")
+        result = json.loads(search_tool("def main", task_id="t1"))
+        self.assertIn("error", result)
+        self.assertIn("BLOCKED", result["error"])
+        self.assertNotIn("matches", result)
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_different_pattern_no_warning(self, _mock_ops):
+        search_tool("def main", task_id="t1")
+        result = json.loads(search_tool("class Foo", task_id="t1"))
+        self.assertNotIn("_warning", result)
+        self.assertNotIn("error", result)
+
+    @patch("tools.file_tools._get_file_ops", return_value=_make_fake_file_ops())
+    def test_different_task_isolated(self, _mock_ops):
+        search_tool("def main", task_id="t1")
+        result = json.loads(search_tool("def main", task_id="t2"))
+        self.assertNotIn("_warning", result)
+
+
+class TestTodoInjectionFiltering(unittest.TestCase):
+    """Verify that format_for_injection filters completed/cancelled todos."""
+
+    def test_filters_completed_and_cancelled(self):
+        from tools.todo_tool import TodoStore
+        store = TodoStore()
+        store.write([
+            {"id": "1", "content": "Read codebase", "status": "completed"},
+            {"id": "2", "content": "Write fix", "status": "in_progress"},
+            {"id": "3", "content": "Run tests", "status": "pending"},
+            {"id": "4", "content": "Abandoned", "status": "cancelled"},
+        ])
+        injection = store.format_for_injection()
+        self.assertNotIn("Read codebase", injection)
+        self.assertNotIn("Abandoned", injection)
+        self.assertIn("Write fix", injection)
+        self.assertIn("Run tests", injection)
+
+    def test_all_completed_returns_none(self):
+        from tools.todo_tool import TodoStore
+        store = TodoStore()
+        store.write([
+            {"id": "1", "content": "Done", "status": "completed"},
+            {"id": "2", "content": "Also done", "status": "cancelled"},
+        ])
+        self.assertIsNone(store.format_for_injection())
+
+    def test_empty_store_returns_none(self):
+        from tools.todo_tool import TodoStore
+        store = TodoStore()
+        self.assertIsNone(store.format_for_injection())
+
+    def test_all_active_included(self):
+        from tools.todo_tool import TodoStore
+        store = TodoStore()
+        store.write([
+            {"id": "1", "content": "Task A", "status": "pending"},
+            {"id": "2", "content": "Task B", "status": "in_progress"},
+        ])
+        injection = store.format_for_injection()
+        self.assertIn("Task A", injection)
+        self.assertIn("Task B", injection)
+
+
+if __name__ == "__main__":
+    unittest.main()
diff --git a/tests/tools/test_todo_tool.py b/tests/tools/test_todo_tool.py
index b0f694d72..d4fd03baf 100644
--- a/tests/tools/test_todo_tool.py
+++ b/tests/tools/test_todo_tool.py
@@ -46,11 +46,17 @@ class TestFormatForInjection:
         store.write([
             {"id": "1", "content": "Do thing", "status": "completed"},
             {"id": "2", "content": "Next", "status": "pending"},
+            {"id": "3", "content": "Working", "status": "in_progress"},
         ])
         text = store.format_for_injection()
-        assert "[x]" in text
+        # Completed items are filtered out of injection
+        assert "[x]" not in text
+        assert "Do thing" not in text
+        # Active items are included
         assert "[ ]" in text
-        assert "Do thing" in text
+        assert "[>]" in text
+        assert "Next" in text
+        assert "Working" in text
         assert "context compression" in text.lower()
 
 
diff --git a/tools/code_execution_tool.py b/tools/code_execution_tool.py
index 76a12dff8..401fc6ac7 100644
--- a/tools/code_execution_tool.py
+++ b/tools/code_execution_tool.py
@@ -78,7 +78,7 @@ _TOOL_STUBS = {
     "web_extract": (
         "web_extract",
         "urls: list",
-        '"""Extract content from URLs. Returns dict with results list of {url, title, content, error}."""',
+        '"""Extract content from URLs. Returns dict with results list of {url, content, error}."""',
         '{"urls": urls}',
     ),
     "read_file": (
@@ -616,7 +616,7 @@ _TOOL_DOC_LINES = [
      "    Returns {\"data\": {\"web\": [{\"url\", \"title\", \"description\"}, ...]}}"),
     ("web_extract",
      "  web_extract(urls: list[str]) -> dict\n"
-     "    Returns {\"results\": [{\"url\", \"title\", \"content\", \"error\"}, ...]} where content is markdown"),
+     "    Returns {\"results\": [{\"url\", \"content\", \"error\"}, ...]} where content is markdown"),
     ("read_file",
      "  read_file(path: str, offset: int = 1, limit: int = 500) -> dict\n"
      "    Lines are 1-indexed. Returns {\"content\": \"...\", \"total_lines\": N}"),
diff --git a/tools/file_tools.py b/tools/file_tools.py
index d11bac87d..cf5c12680 100644
--- a/tools/file_tools.py
+++ b/tools/file_tools.py
@@ -14,6 +14,11 @@ logger = logging.getLogger(__name__)
 _file_ops_lock = threading.Lock()
 _file_ops_cache: dict = {}
 
+# Track files read per task to detect re-read loops after context compression.
+# Key: task_id, Value: dict mapping (path, offset, limit) -> read count
+_read_tracker_lock = threading.Lock()
+_read_tracker: dict = {}
+
 
 def _get_file_ops(task_id: str = "default") -> ShellFileOperations:
     """Get or create ShellFileOperations for a terminal environment.
@@ -132,11 +137,66 @@ def read_file_tool(path: str, offset: int = 1, limit: int = 500, task_id: str =
         result = file_ops.read_file(path, offset, limit)
         if result.content:
             result.content = redact_sensitive_text(result.content)
-        return json.dumps(result.to_dict(), ensure_ascii=False)
+        result_dict = result.to_dict()
+
+        # Track reads to detect re-read loops (e.g. after context compression)
+        read_key = (path, offset, limit)
+        with _read_tracker_lock:
+            task_reads = _read_tracker.setdefault(task_id, {})
+            task_reads[read_key] = task_reads.get(read_key, 0) + 1
+            count = task_reads[read_key]
+
+        if count >= 3:
+            # Hard block: stop returning content to break the loop
+            return json.dumps({
+                "error": (
+                    f"BLOCKED: You have read this exact file region {count} times. "
+                    "The content has NOT changed. You already have this information. "
+                    "STOP re-reading and proceed with your task."
+                ),
+                "path": path,
+                "already_read": count,
+            }, ensure_ascii=False)
+        elif count > 1:
+            result_dict["_warning"] = (
+                f"You have already read this exact file region {count} times in this session. "
+                "The content has not changed. Use the information you already have instead of re-reading. "
+                "If you are stuck in a loop, stop reading and proceed with writing or responding."
+            )
+
+        return json.dumps(result_dict, ensure_ascii=False)
     except Exception as e:
         return json.dumps({"error": str(e)}, ensure_ascii=False)
 
 
+def get_read_files_summary(task_id: str = "default") -> list:
+    """Return a list of files read in this session for the given task.
+
+    Used by context compression to preserve file-read history across
+    compression boundaries.
+    """
+    with _read_tracker_lock:
+        task_reads = _read_tracker.get(task_id, {})
+        seen_paths = {}
+        for (path, offset, limit), count in task_reads.items():
+            if path not in seen_paths:
+                seen_paths[path] = []
+            seen_paths[path].append(f"lines {offset}-{offset + limit - 1}")
+        return [
+            {"path": p, "regions": regions}
+            for p, regions in sorted(seen_paths.items())
+        ]
+
+
+def clear_read_tracker(task_id: str = None):
+    """Clear the read tracker. Called when starting a new conversation."""
+    with _read_tracker_lock:
+        if task_id:
+            _read_tracker.pop(task_id, None)
+        else:
+            _read_tracker.clear()
+
+
 def write_file_tool(path: str, content: str, task_id: str = "default") -> str:
     """Write content to a file."""
     try:
@@ -185,6 +245,24 @@ def search_tool(pattern: str, target: str = "content", path: str = ".",
                 task_id: str = "default") -> str:
     """Search for content or files."""
     try:
+        # Track searches to detect repeated search loops
+        search_key = ("search", pattern, target, path, file_glob or "")
+        with _read_tracker_lock:
+            task_reads = _read_tracker.setdefault(task_id, {})
+            task_reads[search_key] = task_reads.get(search_key, 0) + 1
+            count = task_reads[search_key]
+
+        if count >= 3:
+            return json.dumps({
+                "error": (
+                    f"BLOCKED: You have run this exact search {count} times. "
+                    "The results have NOT changed. You already have this information. "
+                    "STOP re-searching and proceed with your task."
+                ),
+                "pattern": pattern,
+                "already_searched": count,
+            }, ensure_ascii=False)
+
         file_ops = _get_file_ops(task_id)
         result = file_ops.search(
             pattern=pattern, path=path, target=target, file_glob=file_glob,
@@ -195,6 +273,13 @@ def search_tool(pattern: str, target: str = "content", path: str = ".",
                 if hasattr(m, 'content') and m.content:
                     m.content = redact_sensitive_text(m.content)
         result_dict = result.to_dict()
+
+        if count > 1:
+            result_dict["_warning"] = (
+                f"You have run this exact search {count} times in this session. "
+                "The results have not changed. Use the information you already have."
+            )
+
         result_json = json.dumps(result_dict, ensure_ascii=False)
         # Hint when results were truncated — explicit next offset is clearer
         # than relying on the model to infer it from total_count vs match count.
diff --git a/tools/todo_tool.py b/tools/todo_tool.py
index a4853ac3b..7b74d01ea 100644
--- a/tools/todo_tool.py
+++ b/tools/todo_tool.py
@@ -105,8 +105,17 @@ class TodoStore:
             "cancelled": "[~]",
         }
 
-        lines = ["[Your task list was preserved across context compression]"]
-        for item in self._items:
+        # Only inject pending/in_progress items — completed/cancelled ones
+        # cause the model to re-do finished work after compression.
+        active_items = [
+            item for item in self._items
+            if item["status"] in ("pending", "in_progress")
+        ]
+        if not active_items:
+            return None
+
+        lines = ["[Your active task list was preserved across context compression]"]
+        for item in active_items:
             marker = markers.get(item["status"], "[?]")
             lines.append(f"- {marker} {item['id']}. {item['content']} ({item['status']})")