diff --git a/src/kiro_crew/memory.py b/src/kiro_crew/memory.py
index 2a9d0c2f80e2..eb4cd8c32626 100644
--- a/src/kiro_crew/memory.py
+++ b/src/kiro_crew/memory.py
@@ -1193,15 +1193,23 @@ def _try_create_db(self) -> sqlite3.Connection:
             # the same once-per-store latch as the restrict itself.
             prepare_owner_only_sqlite(self._index_db)
         conn = sqlite3.connect(str(self._index_db), timeout=_DB_BUSY_TIMEOUT_SECS)
-        # Wait out transient 'database is locked' contention instead of letting
-        # it surface (where the self-heal would misread it as corruption).
-        conn.execute(f"PRAGMA busy_timeout={int(_DB_BUSY_TIMEOUT_SECS * 1000)}")
-        conn.execute(
-            "CREATE VIRTUAL TABLE IF NOT EXISTS memory_fts USING fts5("
-            "path, content, tokenize='porter unicode61')"
-        )
-        if restrict:  # and cover whatever SQLite just created; retry next open on failure
-            self._index_owner_only = self._restrict_index_files()
+        try:
+            # Wait out transient 'database is locked' contention instead of letting
+            # it surface (where the self-heal would misread it as corruption).
+            conn.execute(f"PRAGMA busy_timeout={int(_DB_BUSY_TIMEOUT_SECS * 1000)}")
+            conn.execute(
+                "CREATE VIRTUAL TABLE IF NOT EXISTS memory_fts USING fts5("
+                "path, content, tokenize='porter unicode61')"
+            )
+            if restrict:  # and cover whatever SQLite just created; retry next open on failure
+                self._index_owner_only = self._restrict_index_files()
+        except BaseException:
+            # The connection is never handed out, but the raised error's traceback
+            # keeps it open while _get_db's self-heal deletes the index -- and on
+            # Windows an open handle makes that delete fail, so the index is never
+            # rebuilt.
+            conn.close()
+            raise
         return conn
 
     def _restrict_index_files(self) -> bool:
diff --git a/test/test_memory_selfheal.py b/test/test_memory_selfheal.py
index b54f75650074..dc5371041e7a 100644
--- a/test/test_memory_selfheal.py
+++ b/test/test_memory_selfheal.py
@@ -15,6 +15,8 @@
 import threading
 from datetime import date, datetime, timedelta
 
+import pytest
+
 from kiro_crew import memory as memory_module
 from kiro_crew._sqlite_compat import sqlite3
 from kiro_crew.memory import MemoryStore, _is_corruption_error
@@ -117,6 +119,36 @@ def test_genuine_corruption_still_self_heals(self, tmp_path):
         results = store.search("Python")
         assert len(results) >= 1
 
+    def test_self_heal_closes_the_connection_that_found_the_corruption(self, tmp_path, monkeypatch):
+        """The open that met the corruption is closed before the index is deleted.
+
+        Windows refuses to delete a file that has an open handle, so a connection
+        left to the collector keeps the corrupt index in place and every later
+        open meets it again.
+        """
+        store = MemoryStore(workspace=tmp_path)
+        store.init()
+        (tmp_path / "memory_index.db").write_bytes(b"this is not a valid sqlite database")
+
+        opened: list[sqlite3.Connection] = []
+        real_connect = memory_module.sqlite3.connect
+
+        def recording_connect(*args, **kwargs):
+            conn = real_connect(*args, **kwargs)
+            opened.append(conn)
+            return conn
+
+        monkeypatch.setattr(memory_module.sqlite3, "connect", recording_connect)
+        conn = store._get_db()
+        try:
+            assert len(opened) >= 2, "the corrupt index was never opened and healed"
+            assert opened[-1] is conn
+            for stale in opened[:-1]:
+                with pytest.raises(sqlite3.ProgrammingError, match="closed"):
+                    stale.execute("SELECT 1")
+        finally:
+            conn.close()
+
     def test_connection_has_busy_timeout(self, tmp_path):
         """The connection must carry a non-zero busy_timeout to wait out locks."""
         store = MemoryStore(workspace=tmp_path)
diff --git a/test/windows-expected-failures.txt b/test/windows-expected-failures.txt
index 464674153866..8b7426d4698d 100644
--- a/test/windows-expected-failures.txt
+++ b/test/windows-expected-failures.txt
@@ -106,7 +106,6 @@ test/test_mcp_discovery_probe_stdio.py::TestProbeServerStderrCapture::test_stder
 test/test_mcp_discovery_probe_stdio.py::TestProbeServerStderrCapture::test_successful_probe_does_not_mention_stderr
 # Needs symlink-creation privilege: builds an in-vault FILE symlink
 # (Alias.md -> One.md); a junction is directory-only and cannot model it.
-test/test_memory_selfheal.py::TestFtsSelfHealGating::test_genuine_corruption_still_self_heals
 test/test_pip_deps_consistency.py::test_all_unguarded_third_party_imports_are_declared
 # Needs symlink-creation privilege: plants a FILE symlink at the output path to
 # prove the writer replaces it rather than writing through. atomic_write already