diff --git a/hermes_cli/kanban_db.py b/hermes_cli/kanban_db.py
index 9ad61f87817..227a943ea65 100644
--- a/hermes_cli/kanban_db.py
+++ b/hermes_cli/kanban_db.py
@@ -1481,12 +1481,22 @@ def write_txn(conn: sqlite3.Connection):
     Use for any multi-statement write (creating a task + link, claiming a
     task + recording an event, etc.).  A claim CAS inside this context is
     atomic -- at most one concurrent writer can succeed.
+
+    The explicit ROLLBACK on exception is wrapped in try/except so that
+    a SQLite auto-rollback (which leaves no active transaction) does not
+    shadow the original exception with a spurious rollback error.
     """
     conn.execute("BEGIN IMMEDIATE")
     try:
         yield conn
     except Exception:
-        conn.execute("ROLLBACK")
+        try:
+            conn.execute("ROLLBACK")
+        except sqlite3.OperationalError:
+            # SQLite has already auto-rolled-back the transaction (typical
+            # under EIO, lock contention, or corruption). Nothing to undo;
+            # do not let this secondary failure shadow the real one.
+            pass
         raise
     else:
         conn.execute("COMMIT")
diff --git a/tests/hermes_cli/test_kanban_db.py b/tests/hermes_cli/test_kanban_db.py
index 07e3b957e5f..a34c659fce8 100644
--- a/tests/hermes_cli/test_kanban_db.py
+++ b/tests/hermes_cli/test_kanban_db.py
@@ -3417,3 +3417,60 @@ def test_pragmas_not_accidentally_disabled_by_migrate_path(tmp_path):
         assert conn.execute("PRAGMA cell_size_check").fetchone()[0] == 1
         assert conn.execute("PRAGMA synchronous").fetchone()[0] == 2
 
+# write_txn — rollback handler must not mask the original exception
+# ---------------------------------------------------------------------------
+
+
+def test_write_txn_preserves_original_exception_when_rollback_fails(kanban_home):
+    """When a write inside write_txn raises an OperationalError that SQLite
+    has already auto-rolled-back (e.g. ``disk I/O error``,
+    ``database is locked``, ``database disk image is malformed``), the
+    explicit ROLLBACK in ``write_txn.__exit__`` itself raises
+    ``cannot rollback - no transaction is active``. The original cause
+    must NOT be masked by the secondary rollback failure — operators rely
+    on the original cause to diagnose the underlying issue.
+    """
+
+    class FailingConnWrapper:
+        """Delegate to a real connection, simulating an EIO during an INSERT
+        that SQLite has already auto-rolled-back."""
+
+        def __init__(self, real):
+            self._real = real
+            self._fail_armed = True
+
+        def execute(self, sql, *args, **kwargs):
+            if (
+                self._fail_armed
+                and sql.lstrip().upper().startswith("INSERT")
+                and "task_events" in sql.lower()
+            ):
+                self._fail_armed = False  # one-shot
+                # Simulate SQLite auto-rolling back the transaction by
+                # issuing a real ROLLBACK now. After this, BEGIN IMMEDIATE
+                # is no longer active and an explicit ROLLBACK would error.
+                try:
+                    self._real.execute("ROLLBACK")
+                except sqlite3.OperationalError:
+                    pass
+                raise sqlite3.OperationalError("disk I/O error")
+            return self._real.execute(sql, *args, **kwargs)
+
+        def __getattr__(self, name):
+            return getattr(self._real, name)
+
+    with kb.connect() as conn:
+        wrapper = FailingConnWrapper(conn)
+        with pytest.raises(sqlite3.OperationalError) as excinfo:
+            with kb.write_txn(wrapper):
+                kb._append_event(wrapper, "t_bogus", "promoted", None)
+
+    msg = str(excinfo.value)
+    assert "disk I/O error" in msg, (
+        f"write_txn masked the original exception with rollback failure; "
+        f"got {msg!r} (expected to contain 'disk I/O error')"
+    )
+    assert "cannot rollback" not in msg, (
+        f"write_txn surfaced the rollback failure instead of the original "
+        f"OperationalError; got {msg!r}"
+    )