diff --git a/hermes_state.py b/hermes_state.py
index ce0292708a16..2b8536e6e0b3 100644
--- a/hermes_state.py
+++ b/hermes_state.py
@@ -2709,6 +2709,7 @@ class SessionDB:
         parent_session_id: str = None,
         cwd: str = None,
         profile_name: str = None,
+        git_repo_root: str = None,
     ) -> None:
         """Insert a session row, enriching NULL metadata on conflict.
 
@@ -2727,14 +2728,25 @@ class SessionDB:
         a persisted, now-inactive row belongs to the caller's chat/thread before
         switching to it (IDOR scoping — without them the ``sessions`` table has
         no chat/thread to compare).
+
+        When ``parent_session_id`` is set (compression fork, delegate/subagent
+        spawn, branch continuation) and this row's own ``cwd``/``git_repo_root``
+        are still NULL after the insert, they are backfilled from the parent
+        row. Callers of ``create_session`` for a child session historically
+        didn't propagate these fields themselves (e.g. the compression-fork
+        path), so a lineage could silently lose its working directory and drop
+        out of the project sidebar every time it forked (#64709). This only
+        fills NULLs — an explicit ``cwd``/``git_repo_root`` on the child is
+        never overwritten.
         """
         def _do(conn):
             conn.execute(
                 """INSERT INTO sessions (
                    id, source, user_id, session_key, chat_id, chat_type, thread_id,
-                   model, model_config, system_prompt, parent_session_id, cwd, profile_name, started_at
+                   model, model_config, system_prompt, parent_session_id, cwd,
+                   profile_name, git_repo_root, started_at
                 )
-                   VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?)
+                   VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?)
                    ON CONFLICT(id) DO UPDATE SET
                        model = COALESCE(sessions.model, excluded.model),
                        model_config = COALESCE(sessions.model_config, excluded.model_config),
@@ -2745,7 +2757,8 @@ class SessionDB:
                        thread_id = COALESCE(sessions.thread_id, excluded.thread_id),
                        parent_session_id = COALESCE(sessions.parent_session_id, excluded.parent_session_id),
                        cwd = COALESCE(sessions.cwd, excluded.cwd),
-                       profile_name = COALESCE(sessions.profile_name, excluded.profile_name)""",
+                       profile_name = COALESCE(sessions.profile_name, excluded.profile_name),
+                       git_repo_root = COALESCE(sessions.git_repo_root, excluded.git_repo_root)""",
                 (
                     session_id,
                     source,
@@ -2760,9 +2773,22 @@ class SessionDB:
                     parent_session_id,
                     cwd,
                     profile_name,
+                    git_repo_root,
                     time.time(),
                 ),
             )
+            if parent_session_id:
+                conn.execute(
+                    """UPDATE sessions
+                       SET cwd = COALESCE(sessions.cwd,
+                                 (SELECT p.cwd FROM sessions p
+                                   WHERE p.id = sessions.parent_session_id)),
+                           git_repo_root = COALESCE(sessions.git_repo_root,
+                                           (SELECT p.git_repo_root FROM sessions p
+                                             WHERE p.id = sessions.parent_session_id))
+                     WHERE id = ? AND parent_session_id IS NOT NULL""",
+                    (session_id,),
+                )
         self._execute_write(_do)
 
     def create_session(self, session_id: str, source: str, **kwargs) -> str:
diff --git a/tests/test_hermes_state.py b/tests/test_hermes_state.py
index 1e7efa0115e5..db38dd2ce114 100644
--- a/tests/test_hermes_state.py
+++ b/tests/test_hermes_state.py
@@ -139,6 +139,47 @@ class TestSessionLifecycle:
         assert session["cwd"] == "/work/repo"
         assert session["git_branch"] == "pets-feature"
 
+    def test_child_session_inherits_cwd_and_git_repo_root_from_parent(self, db):
+        """A parent_session_id child born without cwd/git_repo_root (e.g. the
+        compression-fork path) must inherit both from its parent, so it
+        doesn't silently drop out of the project sidebar (#64709)."""
+        db.create_session(session_id="parent", source="cli")
+        db.update_session_cwd("parent", "/work/repo", git_repo_root="/work/repo")
+
+        db.create_session(session_id="child", source="cli", parent_session_id="parent")
+
+        child = db.get_session("child")
+        assert child["cwd"] == "/work/repo"
+        assert child["git_repo_root"] == "/work/repo"
+
+    def test_child_session_explicit_cwd_is_not_overwritten_by_parent(self, db):
+        """A child that explicitly sets its own cwd/git_repo_root keeps it —
+        parent inheritance only fills in NULLs, never clobbers."""
+        db.create_session(session_id="parent", source="cli")
+        db.update_session_cwd("parent", "/work/repo-a", git_repo_root="/work/repo-a")
+
+        db.create_session(
+            session_id="child", source="cli", parent_session_id="parent",
+            cwd="/work/repo-b", git_repo_root="/work/repo-b",
+        )
+
+        child = db.get_session("child")
+        assert child["cwd"] == "/work/repo-b"
+        assert child["git_repo_root"] == "/work/repo-b"
+
+    def test_multi_generation_lineage_inherits_cwd(self, db):
+        """cwd/git_repo_root propagate through a multi-hop compression chain
+        (root -> gen1 -> gen2), mirroring the multi-generation lineage from
+        the reported issue where a single conversation forked repeatedly."""
+        db.create_session(session_id="root", source="cli")
+        db.update_session_cwd("root", "/work/repo", git_repo_root="/work/repo")
+
+        db.create_session(session_id="gen1", source="cli", parent_session_id="root")
+        db.create_session(session_id="gen2", source="cli", parent_session_id="gen1")
+
+        assert db.get_session("gen1")["cwd"] == "/work/repo"
+        assert db.get_session("gen2")["cwd"] == "/work/repo"
+
     def test_update_session_cwd_empty_branch_does_not_clobber(self, db):
         """A failed branch probe (empty string) must not wipe a branch we
         already captured — only the cwd updates."""