diff --git a/tests/test_session.py b/tests/test_session.py
new file mode 100644
index 0000000..1e447e9
--- /dev/null
+++ b/tests/test_session.py
@@ -0,0 +1,96 @@
+"""Session persistence + auto-reload.
+
+The long-running background server loads the session once at startup. These tests
+pin down the behavior that lets a fresh ``og-veil login`` reach that running
+server: the in-memory session re-reads ``session.json`` when another process
+rewrites it, instead of forever using its stale (expired/revoked) token.
+"""
+
+from __future__ import annotations
+
+import json
+import time
+
+import pytest
+
+from veil.config import session_path
+from veil.session import AuthError, Session
+
+
+@pytest.fixture
+def home(tmp_path, monkeypatch):
+    monkeypatch.setenv("OG_VEIL_HOME", str(tmp_path))
+    return tmp_path
+
+
+def _bundle(access_token: str, *, expires_at: float) -> dict:
+    return {
+        "type": "opengradient-cli-auth",
+        "access_token": access_token,
+        "refresh_token": "refresh-xyz",
+        "expires_at": expires_at,
+        "user": {"email": "me@example.com"},
+        "config": {
+            "supabase_url": "https://supabase.example",
+            "supabase_anon_key": "anon",
+            "chat_api_base_url": "https://chat.example",
+        },
+    }
+
+
+def _write_session(data: dict) -> None:
+    session_path().write_text(json.dumps(data))
+
+
+def test_fresh_login_on_disk_is_picked_up_without_restart(home):
+    # The server loaded a session whose token is already expired and whose refresh
+    # token would be rejected upstream — the exact state behind the reported 401.
+    _write_session(_bundle("stale-token", expires_at=time.time() - 3600))
+    session = Session.load()
+
+    # The user runs `og-veil login`, which writes a brand-new, valid session to
+    # disk from another process. The running server must adopt it.
+    _write_session(_bundle("fresh-token", expires_at=time.time() + 3600))
+
+    # No refresh network call should be needed: the reloaded token is still valid.
+    assert session.access_token() == "fresh-token"
+    assert session.user_email == "me@example.com"
+
+
+def test_unchanged_session_is_not_reloaded_and_no_refresh(home):
+    _write_session(_bundle("good-token", expires_at=time.time() + 3600))
+    session = Session.load()
+
+    # Make any refresh attempt explode so the test fails loudly if one happens.
+    def _boom():
+        raise AssertionError("should not refresh a still-valid token")
+
+    session._refresh = _boom  # type: ignore[assignment]
+    assert session.access_token() == "good-token"
+
+
+def test_refresh_writes_back_without_triggering_self_reload(home):
+    # A token that's expired in memory but has no fresh login on disk must still go
+    # through refresh; the write-back must not look like an external change.
+    _write_session(_bundle("expired-token", expires_at=time.time() - 3600))
+    session = Session.load()
+
+    calls = {"n": 0}
+
+    def _fake_refresh():
+        calls["n"] += 1
+        session._data["access_token"] = "refreshed-token"
+        session._data["expires_at"] = time.time() + 3600
+        session.save()
+
+    session._refresh = _fake_refresh  # type: ignore[assignment]
+    assert session.access_token() == "refreshed-token"
+    # A second call sees its own write (unchanged mtime), so it neither reloads nor
+    # refreshes again.
+    assert session.access_token() == "refreshed-token"
+    assert calls["n"] == 1
+
+
+def test_load_without_session_file_raises(home):
+    with pytest.raises(AuthError):
+        Session.load()
diff --git a/veil/session.py b/veil/session.py
index a8ed95f..66e36c2 100644
--- a/veil/session.py
+++ b/veil/session.py
@@ -16,6 +16,7 @@
 from __future__ import annotations
 
 import json
+import os
 import threading
 import time
 import webbrowser
@@ -66,9 +67,14 @@ def from_dict(cls, d: dict) -> "NetworkConfig":
 class Session:
     """A persisted Chat session: tokens + network config, with auto-refresh."""
 
-    def __init__(self, data: dict):
+    def __init__(self, data: dict, mtime: Optional[float] = None):
         self._data = data
         self.config = NetworkConfig.from_dict(data.get("config", {}))
+        # Serializes refresh/reload across the threaded server's request handlers.
+        self._lock = threading.Lock()
+        # mtime of session.json as we last read/wrote it, so a long-running server
+        # can notice when another process (e.g. `og-veil login`) rewrites it.
+        self._mtime = mtime
 
     # --- persistence -------------------------------------------------------
     @classmethod
@@ -77,7 +83,7 @@ def load(cls) -> "Session":
         if not path.exists():
             raise AuthError("not logged in — run `og-veil login` first")
         try:
-            return cls(json.loads(path.read_text()))
+            return cls(json.loads(path.read_text()), mtime=_file_mtime(path))
         except (OSError, json.JSONDecodeError) as exc:
             raise AuthError(f"could not read saved session: {exc}") from exc
 
@@ -88,6 +94,28 @@ def save(self) -> None:
             path.chmod(0o600)  # the file holds a live session token
         except OSError:
             pass
+        # Record our own write so reload-on-change doesn't re-read it needlessly.
+        self._mtime = _file_mtime(path)
+
+    def _reload_if_changed(self) -> None:
+        """Re-read session.json if another process rewrote it (e.g. a fresh login).
+
+        The background server loads the session once at startup and keeps it in
+        memory. Without this, a successful ``og-veil login`` — which writes a new
+        token to disk — would never reach the running server, so requests would
+        keep failing with the stale (expired/revoked) token until a restart.
+        """
+        path = session_path()
+        disk_mtime = _file_mtime(path)
+        if disk_mtime is None or disk_mtime == self._mtime:
+            return
+        try:
+            data = json.loads(path.read_text())
+        except (OSError, json.JSONDecodeError):
+            return  # mid-write or unreadable; keep what we have and try again later
+        self._data = data
+        self.config = NetworkConfig.from_dict(data.get("config", {}))
+        self._mtime = disk_mtime
 
     # --- accessors ---------------------------------------------------------
     @property
@@ -99,9 +127,13 @@ def auth_headers(self) -> dict:
         return {"Authorization": f"Bearer {self.access_token()}"}
 
     def access_token(self) -> str:
-        if self._is_expired():
-            self._refresh()
-        token = self._data.get("access_token")
+        with self._lock:
+            # Pick up a fresh login written by another process before deciding
+            # whether the in-memory token needs refreshing.
+            self._reload_if_changed()
+            if self._is_expired():
+                self._refresh()
+            token = self._data.get("access_token")
         if not token:
             raise AuthError("session has no access token — run `og-veil login` to sign in again")
         return token
@@ -257,3 +289,11 @@ def _require(d: dict, key: str) -> str:
     if not value:
         raise AuthError(f"CLI-auth config is missing '{key}'")
     return value
+
+
+def _file_mtime(path) -> Optional[float]:
+    """Last-modified time of ``path`` in nanoseconds, or None if it's missing."""
+    try:
+        return os.stat(path).st_mtime_ns
+    except OSError:
+        return None