diff --git a/tools/terminal_tool.py b/tools/terminal_tool.py
index 9f4c237541..b0ec8ff39e 100644
--- a/tools/terminal_tool.py
+++ b/tools/terminal_tool.py
@@ -272,6 +272,19 @@ def _get_sudo_password_callback():
     return getattr(_callback_tls, "sudo_password", None)
 
 
+def _current_session_key() -> str:
+    """Return the active gateway/WebUI session key, or "" outside sessions.
+
+    Single lookup point for the ``HERMES_SESSION_KEY`` ContextVar with the
+    os.environ fallback that ``get_session_env()`` applies for CLI, cron, and
+    test processes. Callers scope per-session caches by prefixing the value
+    with ``"session:"`` so two sessions never share a cache slot.
+    """
+    from gateway.session_context import get_session_env
+
+    return get_session_env("HERMES_SESSION_KEY", "")
+
+
 def _get_approval_callback():
     return getattr(_callback_tls, "approval", None)
 
@@ -297,12 +310,7 @@ def set_approval_callback(cb):
 
 def _get_sudo_password_cache_scope() -> str:
     """Return the cache scope for interactive sudo passwords."""
-    try:
-        from gateway.session_context import get_session_env
-
-        session_key = get_session_env("HERMES_SESSION_KEY", "")
-    except Exception:
-        session_key = os.getenv("HERMES_SESSION_KEY", "")
+    session_key = _current_session_key()
     if session_key:
         return f"session:{session_key}"
 
@@ -1398,12 +1406,7 @@ def _resolve_container_task_id(task_id: Optional[str]) -> str:
     # branches above: those paths already key containers per task_id, so they
     # stay authoritative where they apply and this only covers the cases that
     # would otherwise collapse to the shared "default" key (notably SSH).
-    try:
-        from gateway.session_context import get_session_env
-
-        session_key = get_session_env("HERMES_SESSION_KEY", "")
-    except Exception:
-        session_key = os.getenv("HERMES_SESSION_KEY", "")
+    session_key = _current_session_key()
     if session_key:
         return f"session:{session_key}"
     return "default"