diff --git a/tests/tools/test_mcp_oauth_cold_load_expiry.py b/tests/tools/test_mcp_oauth_cold_load_expiry.py
new file mode 100644
index 000000000..a9fb19106
--- /dev/null
+++ b/tests/tools/test_mcp_oauth_cold_load_expiry.py
@@ -0,0 +1,546 @@
+"""Tests for cold-load token expiry tracking in MCP OAuth.
+
+PR #11383's consolidation fixed external-refresh reloading (mtime disk-watch)
+and 401 dedup, but left two underlying latent bugs in place:
+
+1. ``HermesTokenStorage.set_tokens`` persisted only relative ``expires_in``,
+   which is meaningless after a process restart.
+2. The MCP SDK's ``OAuthContext._initialize`` loads ``current_tokens`` from
+   storage but does NOT call ``update_token_expiry``, so
+   ``token_expiry_time`` stays None. ``is_token_valid()`` then returns True
+   for any loaded token regardless of actual age, and the SDK's preemptive
+   refresh branch at ``oauth2.py:491`` is never taken.
+
+Consequence: a token that expired while the process was down ships to the
+server with a stale Bearer header. The server's response is provider-specific
+— some return HTTP 401 (caught by the consolidation's 401 handler, which
+surfaces a ``needs_reauth`` error), others return HTTP 200 with an
+application-level auth failure in the body (e.g. BetterStack's "No teams
+found. Please check your authentication."), which the consolidation cannot
+detect.
+
+These tests pin the contract for Fix A:
+- ``set_tokens`` persists an absolute ``expires_at`` wall-clock timestamp.
+- ``get_tokens`` reconstructs ``expires_in`` from ``expires_at - now`` so
+  the SDK's ``update_token_expiry`` computes the correct absolute expiry.
+- ``HermesMCPOAuthProvider._initialize`` seeds ``context.token_expiry_time``
+  after loading, so ``is_token_valid()`` reports True only for tokens that
+  are actually still valid, and the SDK's preemptive refresh fires for
+  expired tokens with a live refresh_token.
+
+Reference: Claude Code solves this via an ``OAuthTokens.expiresAt`` absolute
+timestamp persisted alongside the access_token (``auth.ts:~180``).
+"""
+from __future__ import annotations
+
+import asyncio
+import json
+import time
+
+import pytest
+
+
+pytest.importorskip("mcp.client.auth.oauth2", reason="MCP SDK 1.26.0+ required")
+
+
+# ---------------------------------------------------------------------------
+# HermesTokenStorage — absolute expiry persistence
+# ---------------------------------------------------------------------------
+
+
+class TestSetTokensAbsoluteExpiry:
+    def test_set_tokens_persists_absolute_expires_at(self, tmp_path, monkeypatch):
+        """Tokens round-tripped through disk must encode absolute expiry."""
+        monkeypatch.setenv("HERMES_HOME", str(tmp_path))
+        from mcp.shared.auth import OAuthToken
+
+        from tools.mcp_oauth import HermesTokenStorage
+
+        storage = HermesTokenStorage("srv")
+        before = time.time()
+        asyncio.run(
+            storage.set_tokens(
+                OAuthToken(
+                    access_token="a",
+                    token_type="Bearer",
+                    expires_in=3600,
+                    refresh_token="r",
+                )
+            )
+        )
+        after = time.time()
+
+        on_disk = json.loads(
+            (tmp_path / "mcp-tokens" / "srv.json").read_text()
+        )
+        assert "expires_at" in on_disk, (
+            "Fix A: set_tokens must record an absolute expires_at wall-clock "
+            "timestamp alongside the SDK's serialized token so cold-loads "
+            "can compute correct remaining TTL."
+        )
+        assert before + 3600 <= on_disk["expires_at"] <= after + 3600
+
+    def test_set_tokens_without_expires_in_omits_expires_at(
+        self, tmp_path, monkeypatch
+    ):
+        """Tokens without a TTL must not gain a fabricated expires_at."""
+        monkeypatch.setenv("HERMES_HOME", str(tmp_path))
+        from mcp.shared.auth import OAuthToken
+
+        from tools.mcp_oauth import HermesTokenStorage
+
+        storage = HermesTokenStorage("srv")
+        asyncio.run(
+            storage.set_tokens(
+                OAuthToken(
+                    access_token="a",
+                    token_type="Bearer",
+                    refresh_token="r",
+                )
+            )
+        )
+
+        on_disk = json.loads(
+            (tmp_path / "mcp-tokens" / "srv.json").read_text()
+        )
+        assert "expires_at" not in on_disk
+
+
+class TestGetTokensReconstructsExpiresIn:
+    def test_get_tokens_uses_expires_at_for_remaining_ttl(
+        self, tmp_path, monkeypatch
+    ):
+        """Round-trip: expires_in on read must reflect time remaining."""
+        monkeypatch.setenv("HERMES_HOME", str(tmp_path))
+        from mcp.shared.auth import OAuthToken
+
+        from tools.mcp_oauth import HermesTokenStorage
+
+        storage = HermesTokenStorage("srv")
+        asyncio.run(
+            storage.set_tokens(
+                OAuthToken(
+                    access_token="a",
+                    token_type="Bearer",
+                    expires_in=3600,
+                    refresh_token="r",
+                )
+            )
+        )
+
+        # Wait briefly so the remaining TTL is measurably less than 3600.
+        time.sleep(0.05)
+
+        reloaded = asyncio.run(storage.get_tokens())
+        assert reloaded is not None
+        assert reloaded.expires_in is not None
+        # Should be slightly less than 3600 after the 50ms sleep.
+        assert 3500 < reloaded.expires_in <= 3600
+
+    def test_get_tokens_returns_zero_ttl_for_expired_token(
+        self, tmp_path, monkeypatch
+    ):
+        """An already-expired token reloaded from disk must report expires_in=0."""
+        monkeypatch.setenv("HERMES_HOME", str(tmp_path))
+        from tools.mcp_oauth import HermesTokenStorage, _get_token_dir
+
+        token_dir = _get_token_dir()
+        token_dir.mkdir(parents=True, exist_ok=True)
+        # Write an already-expired token file directly.
+        (token_dir / "srv.json").write_text(
+            json.dumps(
+                {
+                    "access_token": "a",
+                    "token_type": "Bearer",
+                    "expires_in": 3600,
+                    "expires_at": time.time() - 60,  # expired 1 min ago
+                    "refresh_token": "r",
+                }
+            )
+        )
+
+        storage = HermesTokenStorage("srv")
+        reloaded = asyncio.run(storage.get_tokens())
+        assert reloaded is not None
+        assert reloaded.expires_in == 0, (
+            "Expired token must reload with expires_in=0 so the SDK's "
+            "is_token_valid() returns False and preemptive refresh fires."
+        )
+
+    def test_get_tokens_legacy_file_without_expires_at_is_loadable(
+        self, tmp_path, monkeypatch
+    ):
+        """Existing on-disk files (pre-Fix-A) must still load without crashing.
+
+        Pre-existing token files have ``expires_in`` but no ``expires_at``.
+        Fix A falls back to the file's mtime as a best-effort wall-clock
+        proxy: a file whose (mtime + expires_in) is in the past clamps
+        expires_in to zero so the SDK refreshes on next request. A fresh
+        legacy-format file (mtime = now) keeps most of its TTL.
+        """
+        monkeypatch.setenv("HERMES_HOME", str(tmp_path))
+        from tools.mcp_oauth import HermesTokenStorage, _get_token_dir
+
+        token_dir = _get_token_dir()
+        token_dir.mkdir(parents=True, exist_ok=True)
+        # Legacy-shape file (no expires_at). Make it stale by backdating mtime
+        # well past its nominal expires_in.
+        legacy_path = token_dir / "srv.json"
+        legacy_path.write_text(
+            json.dumps(
+                {
+                    "access_token": "a",
+                    "token_type": "Bearer",
+                    "expires_in": 3600,
+                    "refresh_token": "r",
+                }
+            )
+        )
+        stale_time = time.time() - 7200  # 2hr ago, exceeds 3600s TTL
+        import os
+
+        os.utime(legacy_path, (stale_time, stale_time))
+
+        storage = HermesTokenStorage("srv")
+        reloaded = asyncio.run(storage.get_tokens())
+        assert reloaded is not None
+        assert reloaded.expires_in == 0, (
+            "Legacy file whose mtime + expires_in is in the past must report "
+            "expires_in=0 so the SDK refreshes on next request."
+        )
+
+
+# ---------------------------------------------------------------------------
+# HermesMCPOAuthProvider._initialize — seed token_expiry_time
+# ---------------------------------------------------------------------------
+
+
+@pytest.mark.asyncio
+async def test_initialize_seeds_token_expiry_time_from_stored_tokens(
+    tmp_path, monkeypatch
+):
+    """Cold-load must populate context.token_expiry_time.
+
+    The SDK's base ``_initialize`` loads current_tokens but doesn't seed
+    token_expiry_time. Our subclass must do it so ``is_token_valid()``
+    reports correctly and the preemptive-refresh path fires when needed.
+    """
+    monkeypatch.setenv("HERMES_HOME", str(tmp_path))
+    from mcp.shared.auth import OAuthClientInformationFull, OAuthToken
+    from pydantic import AnyUrl
+
+    from tools.mcp_oauth import HermesTokenStorage
+    from tools.mcp_oauth_manager import _HERMES_PROVIDER_CLS, reset_manager_for_tests
+
+    assert _HERMES_PROVIDER_CLS is not None
+    reset_manager_for_tests()
+
+    storage = HermesTokenStorage("srv")
+    await storage.set_tokens(
+        OAuthToken(
+            access_token="a",
+            token_type="Bearer",
+            expires_in=7200,
+            refresh_token="r",
+        )
+    )
+    await storage.set_client_info(
+        OAuthClientInformationFull(
+            client_id="test-client",
+            redirect_uris=[AnyUrl("http://127.0.0.1:12345/callback")],
+            grant_types=["authorization_code", "refresh_token"],
+            response_types=["code"],
+            token_endpoint_auth_method="none",
+        )
+    )
+
+    from mcp.shared.auth import OAuthClientMetadata
+
+    metadata = OAuthClientMetadata(
+        redirect_uris=[AnyUrl("http://127.0.0.1:12345/callback")],
+        client_name="Hermes Agent",
+    )
+    provider = _HERMES_PROVIDER_CLS(
+        server_name="srv",
+        server_url="https://example.com/mcp",
+        client_metadata=metadata,
+        storage=storage,
+        redirect_handler=_noop_redirect,
+        callback_handler=_noop_callback,
+    )
+
+    await provider._initialize()
+
+    assert provider.context.token_expiry_time is not None, (
+        "Fix A: _initialize must seed context.token_expiry_time so "
+        "is_token_valid() correctly reports expiry on cold-load."
+    )
+    # Should be ~7200s in the future (fresh write).
+    assert provider.context.token_expiry_time > time.time() + 7000
+    assert provider.context.token_expiry_time <= time.time() + 7200 + 5
+
+
+@pytest.mark.asyncio
+async def test_initialize_flags_expired_token_as_invalid(tmp_path, monkeypatch):
+    """After _initialize, an expired-on-disk token must report is_token_valid=False.
+
+    This is the end-to-end assertion: cold-load an expired token, verify the
+    SDK's own ``is_token_valid()`` now returns False (the consequence of
+    seeding token_expiry_time correctly), so the SDK's ``async_auth_flow``
+    will take the ``can_refresh_token()`` branch on the next request and
+    silently refresh instead of sending the stale Bearer.
+    """
+    monkeypatch.setenv("HERMES_HOME", str(tmp_path))
+    from mcp.shared.auth import OAuthClientInformationFull, OAuthClientMetadata
+    from pydantic import AnyUrl
+
+    from tools.mcp_oauth import HermesTokenStorage, _get_token_dir
+    from tools.mcp_oauth_manager import _HERMES_PROVIDER_CLS, reset_manager_for_tests
+
+    assert _HERMES_PROVIDER_CLS is not None
+    reset_manager_for_tests()
+
+    # Write an already-expired token directly so we control the wall-clock.
+    token_dir = _get_token_dir()
+    token_dir.mkdir(parents=True, exist_ok=True)
+    (token_dir / "srv.json").write_text(
+        json.dumps(
+            {
+                "access_token": "stale",
+                "token_type": "Bearer",
+                "expires_in": 3600,
+                "expires_at": time.time() - 60,
+                "refresh_token": "fresh",
+            }
+        )
+    )
+
+    storage = HermesTokenStorage("srv")
+    await storage.set_client_info(
+        OAuthClientInformationFull(
+            client_id="test-client",
+            redirect_uris=[AnyUrl("http://127.0.0.1:12345/callback")],
+            grant_types=["authorization_code", "refresh_token"],
+            response_types=["code"],
+            token_endpoint_auth_method="none",
+        )
+    )
+
+    metadata = OAuthClientMetadata(
+        redirect_uris=[AnyUrl("http://127.0.0.1:12345/callback")],
+        client_name="Hermes Agent",
+    )
+    provider = _HERMES_PROVIDER_CLS(
+        server_name="srv",
+        server_url="https://example.com/mcp",
+        client_metadata=metadata,
+        storage=storage,
+        redirect_handler=_noop_redirect,
+        callback_handler=_noop_callback,
+    )
+
+    await provider._initialize()
+
+    assert provider.context.is_token_valid() is False, (
+        "After _initialize with an expired-on-disk token, is_token_valid() "
+        "must return False so the SDK's async_auth_flow takes the "
+        "preemptive refresh path."
+    )
+    assert provider.context.can_refresh_token() is True, (
+        "Refresh should remain possible because refresh_token + client_info "
+        "are both present."
+    )
+
+
+async def _noop_redirect(_url: str) -> None:
+    return None
+
+
+async def _noop_callback() -> tuple[str, str | None]:
+    raise AssertionError("callback handler should not be invoked in these tests")
+
+
+# ---------------------------------------------------------------------------
+# Pre-flight OAuth metadata discovery
+# ---------------------------------------------------------------------------
+
+
+@pytest.mark.asyncio
+async def test_initialize_prefetches_oauth_metadata_when_missing(
+    tmp_path, monkeypatch
+):
+    """Cold-load must pre-flight PRM + ASM discovery so ``_refresh_token``
+    has the correct ``token_endpoint`` before the first refresh attempt.
+
+    Without this, the SDK's ``_refresh_token`` falls back to
+    ``{server_url}/token`` which is wrong for providers whose AS is at
+    a different origin. BetterStack specifically: MCP at
+    ``mcp.betterstack.com`` but token_endpoint at
+    ``betterstack.com/oauth/token``. Without pre-flight the refresh 404s
+    and we drop into full browser re-auth — visible to the user as an
+    unwanted OAuth browser prompt every time the process restarts.
+    """
+    monkeypatch.setenv("HERMES_HOME", str(tmp_path))
+
+    import httpx
+    from mcp.shared.auth import (
+        OAuthClientInformationFull,
+        OAuthClientMetadata,
+        OAuthToken,
+    )
+    from pydantic import AnyUrl
+
+    from tools.mcp_oauth import HermesTokenStorage
+    from tools.mcp_oauth_manager import _HERMES_PROVIDER_CLS, reset_manager_for_tests
+
+    assert _HERMES_PROVIDER_CLS is not None
+    reset_manager_for_tests()
+
+    storage = HermesTokenStorage("srv")
+    await storage.set_tokens(
+        OAuthToken(
+            access_token="a",
+            token_type="Bearer",
+            expires_in=3600,
+            refresh_token="r",
+        )
+    )
+    await storage.set_client_info(
+        OAuthClientInformationFull(
+            client_id="test-client",
+            redirect_uris=[AnyUrl("http://127.0.0.1:12345/callback")],
+            grant_types=["authorization_code", "refresh_token"],
+            response_types=["code"],
+            token_endpoint_auth_method="none",
+        )
+    )
+
+    # Route the AsyncClient used inside _prefetch_oauth_metadata through a
+    # MockTransport that mimics BetterStack's split-origin discovery:
+    #   PRM at mcp.example.com/.well-known/oauth-protected-resource -> points to auth.example.com
+    #   ASM at auth.example.com/.well-known/oauth-authorization-server -> token_endpoint at auth.example.com/oauth/token
+    def mock_handler(request: httpx.Request) -> httpx.Response:
+        url = str(request.url)
+        if url.endswith("/.well-known/oauth-protected-resource"):
+            return httpx.Response(
+                200,
+                json={
+                    "resource": "https://mcp.example.com",
+                    "authorization_servers": ["https://auth.example.com"],
+                    "scopes_supported": ["read", "write"],
+                    "bearer_methods_supported": ["header"],
+                },
+            )
+        if url.endswith("/.well-known/oauth-authorization-server"):
+            return httpx.Response(
+                200,
+                json={
+                    "issuer": "https://auth.example.com",
+                    "authorization_endpoint": "https://auth.example.com/oauth/authorize",
+                    "token_endpoint": "https://auth.example.com/oauth/token",
+                    "registration_endpoint": "https://auth.example.com/oauth/register",
+                    "response_types_supported": ["code"],
+                    "grant_types_supported": ["authorization_code", "refresh_token"],
+                    "code_challenge_methods_supported": ["S256"],
+                    "token_endpoint_auth_methods_supported": ["none"],
+                    "scopes_supported": ["read", "write"],
+                },
+            )
+        return httpx.Response(404)
+
+    transport = httpx.MockTransport(mock_handler)
+
+    # Patch the AsyncClient constructor used by _prefetch_oauth_metadata so
+    # it uses our mock transport instead of the real network.
+    import httpx as real_httpx
+
+    original_async_client = real_httpx.AsyncClient
+
+    def patched_async_client(*args, **kwargs):
+        kwargs["transport"] = transport
+        return original_async_client(*args, **kwargs)
+
+    monkeypatch.setattr(real_httpx, "AsyncClient", patched_async_client)
+
+    metadata = OAuthClientMetadata(
+        redirect_uris=[AnyUrl("http://127.0.0.1:12345/callback")],
+        client_name="Hermes Agent",
+    )
+    provider = _HERMES_PROVIDER_CLS(
+        server_name="srv",
+        server_url="https://mcp.example.com",
+        client_metadata=metadata,
+        storage=storage,
+        redirect_handler=_noop_redirect,
+        callback_handler=_noop_callback,
+    )
+
+    await provider._initialize()
+
+    assert provider.context.protected_resource_metadata is not None, (
+        "Pre-flight must cache PRM for the SDK to reference later."
+    )
+    assert provider.context.oauth_metadata is not None, (
+        "Pre-flight must cache ASM so _refresh_token builds the correct "
+        "token_endpoint URL."
+    )
+    assert str(provider.context.oauth_metadata.token_endpoint) == (
+        "https://auth.example.com/oauth/token"
+    )
+
+
+@pytest.mark.asyncio
+async def test_initialize_skips_prefetch_when_no_tokens(tmp_path, monkeypatch):
+    """Pre-flight must not run when there are no stored tokens yet.
+
+    Without this guard, every fresh-install ``_initialize`` would do two
+    extra network roundtrips that gain nothing (the SDK's 401-branch
+    discovery will run on the first real request anyway).
+    """
+    monkeypatch.setenv("HERMES_HOME", str(tmp_path))
+    import httpx
+    from mcp.shared.auth import OAuthClientMetadata
+    from pydantic import AnyUrl
+
+    from tools.mcp_oauth_manager import _HERMES_PROVIDER_CLS, reset_manager_for_tests
+    from tools.mcp_oauth import HermesTokenStorage
+
+    assert _HERMES_PROVIDER_CLS is not None
+    reset_manager_for_tests()
+
+    calls: list[str] = []
+
+    def mock_handler(request: httpx.Request) -> httpx.Response:
+        calls.append(str(request.url))
+        return httpx.Response(404)
+
+    transport = httpx.MockTransport(mock_handler)
+    import httpx as real_httpx
+
+    original = real_httpx.AsyncClient
+
+    def patched(*args, **kwargs):
+        kwargs["transport"] = transport
+        return original(*args, **kwargs)
+
+    monkeypatch.setattr(real_httpx, "AsyncClient", patched)
+
+    storage = HermesTokenStorage("srv")  # empty — no tokens on disk
+    metadata = OAuthClientMetadata(
+        redirect_uris=[AnyUrl("http://127.0.0.1:12345/callback")],
+        client_name="Hermes Agent",
+    )
+    provider = _HERMES_PROVIDER_CLS(
+        server_name="srv",
+        server_url="https://mcp.example.com",
+        client_metadata=metadata,
+        storage=storage,
+        redirect_handler=_noop_redirect,
+        callback_handler=_noop_callback,
+    )
+
+    await provider._initialize()
+
+    assert calls == [], (
+        f"Pre-flight must not fire when no tokens are stored, but got {calls}"
+    )
diff --git a/tools/mcp_oauth.py b/tools/mcp_oauth.py
index 6e1d7f5fb..7910c3cdc 100644
--- a/tools/mcp_oauth.py
+++ b/tools/mcp_oauth.py
@@ -40,6 +40,7 @@ import re
 import socket
 import sys
 import threading
+import time
 import webbrowser
 from http.server import BaseHTTPRequestHandler, HTTPServer
 from pathlib import Path
@@ -196,6 +197,35 @@ class HermesTokenStorage:
         data = _read_json(self._tokens_path())
         if data is None:
             return None
+        # Hermes records an absolute wall-clock ``expires_at`` alongside the
+        # SDK's serialized token (see ``set_tokens``). On read we rewrite
+        # ``expires_in`` to the remaining seconds so the SDK's downstream
+        # ``update_token_expiry`` computes the correct absolute time and
+        # ``is_token_valid()`` correctly reports False for tokens that
+        # expired while the process was down.
+        #
+        # Legacy token files (pre-Fix-A) have ``expires_in`` but no
+        # ``expires_at``. We fall back to the file's mtime as a best-effort
+        # wall-clock proxy for when the token was written: if (mtime +
+        # expires_in) is in the past, clamp ``expires_in`` to zero so the
+        # SDK refreshes before the first request. This self-heals one-time
+        # on the next successful ``set_tokens``, which writes the new
+        # ``expires_at`` field. The stored ``expires_at`` is stripped before
+        # model_validate because it's not part of the SDK's OAuthToken schema.
+        absolute_expiry = data.pop("expires_at", None)
+        if absolute_expiry is not None:
+            data["expires_in"] = int(max(absolute_expiry - time.time(), 0))
+        elif data.get("expires_in") is not None:
+            try:
+                file_mtime = self._tokens_path().stat().st_mtime
+            except OSError:
+                file_mtime = None
+            if file_mtime is not None:
+                try:
+                    implied_expiry = file_mtime + int(data["expires_in"])
+                    data["expires_in"] = int(max(implied_expiry - time.time(), 0))
+                except (TypeError, ValueError):
+                    pass
         try:
             return OAuthToken.model_validate(data)
         except (ValueError, TypeError, KeyError) as exc:
@@ -203,7 +233,23 @@ class HermesTokenStorage:
             return None
 
     async def set_tokens(self, tokens: "OAuthToken") -> None:
-        _write_json(self._tokens_path(), tokens.model_dump(exclude_none=True))
+        payload = tokens.model_dump(exclude_none=True)
+        # Persist an absolute ``expires_at`` so a process restart can
+        # reconstruct the correct remaining TTL. Without this the MCP SDK's
+        # ``_initialize`` reloads a relative ``expires_in`` which has no
+        # wall-clock reference, leaving ``context.token_expiry_time=None``
+        # and ``is_token_valid()`` falsely reporting True. See Fix A in
+        # ``mcp-oauth-token-diagnosis`` skill + Claude Code's
+        # ``OAuthTokens.expiresAt`` persistence (auth.ts ~180).
+        expires_in = payload.get("expires_in")
+        if expires_in is not None:
+            try:
+                payload["expires_at"] = time.time() + int(expires_in)
+            except (TypeError, ValueError):
+                # Mock tokens or unusual shapes: skip the expires_at write
+                # rather than fail persistence.
+                pass
+        _write_json(self._tokens_path(), payload)
         logger.debug("OAuth tokens saved for %s", self._server_name)
 
     # -- client info -------------------------------------------------------
diff --git a/tools/mcp_oauth_manager.py b/tools/mcp_oauth_manager.py
index 29cd79b78..7c8a91f3f 100644
--- a/tools/mcp_oauth_manager.py
+++ b/tools/mcp_oauth_manager.py
@@ -111,6 +111,131 @@ def _make_hermes_provider_class() -> Optional[type]:
             super().__init__(*args, **kwargs)
             self._hermes_server_name = server_name
 
+        async def _initialize(self) -> None:
+            """Load stored tokens + client info AND seed token_expiry_time.
+
+            Also eagerly fetches OAuth authorization-server metadata (PRM +
+            ASM) when we have stored tokens but no cached metadata, so the
+            SDK's ``_refresh_token`` can build the correct token_endpoint
+            URL on the preemptive-refresh path. Without this, the SDK
+            falls back to ``{mcp_server_url}/token`` (wrong for providers
+            whose AS is a different origin — BetterStack's MCP lives at
+            ``https://mcp.betterstack.com`` but its token endpoint is at
+            ``https://betterstack.com/oauth/token``), the refresh 404s, and
+            we drop through to full browser reauth.
+
+            The SDK's base ``_initialize`` populates ``current_tokens`` but
+            does NOT call ``update_token_expiry``, so ``token_expiry_time``
+            stays ``None`` and ``is_token_valid()`` returns True for any
+            loaded token regardless of actual age. After a process restart
+            this ships stale Bearer tokens to the server; some providers
+            return HTTP 401 (caught by the 401 handler), others return 200
+            with an app-level auth error (invisible to the transport layer,
+            e.g. BetterStack returning "No teams found. Please check your
+            authentication.").
+
+            Seeding ``token_expiry_time`` from the reloaded token fixes that:
+            ``is_token_valid()`` correctly reports False for expired tokens,
+            ``async_auth_flow`` takes the ``can_refresh_token()`` branch,
+            and the SDK quietly refreshes before the first real request.
+
+            Paired with :class:`HermesTokenStorage` persisting an absolute
+            ``expires_at`` timestamp (``mcp_oauth.py:set_tokens``) so the
+            remaining TTL we compute here reflects real wall-clock age.
+            """
+            await super()._initialize()
+            tokens = self.context.current_tokens
+            if tokens is not None and tokens.expires_in is not None:
+                self.context.update_token_expiry(tokens)
+
+            # Pre-flight OAuth AS discovery so ``_refresh_token`` has a
+            # correct ``token_endpoint`` before the first refresh attempt.
+            # Only runs when we have tokens on cold-load but no cached
+            # metadata — i.e. the exact scenario where the SDK's built-in
+            # 401-branch discovery hasn't had a chance to run yet.
+            if (
+                tokens is not None
+                and self.context.oauth_metadata is None
+            ):
+                try:
+                    await self._prefetch_oauth_metadata()
+                except Exception as exc:  # pragma: no cover — defensive
+                    # Non-fatal: if discovery fails, the SDK's normal 401-
+                    # branch discovery will run on the next request.
+                    logger.debug(
+                        "MCP OAuth '%s': pre-flight metadata discovery "
+                        "failed (non-fatal): %s",
+                        self._hermes_server_name, exc,
+                    )
+
+        async def _prefetch_oauth_metadata(self) -> None:
+            """Fetch PRM + ASM from the well-known endpoints, cache on context.
+
+            Mirrors the SDK's 401-branch discovery (oauth2.py ~line 511-551)
+            but runs synchronously before the first request instead of
+            inside the httpx auth_flow generator. Uses the SDK's own URL
+            builders and response handlers so we track whatever the SDK
+            version we're pinned to expects.
+            """
+            import httpx  # local import: httpx is an MCP SDK dependency
+            from mcp.client.auth.utils import (
+                build_oauth_authorization_server_metadata_discovery_urls,
+                build_protected_resource_metadata_discovery_urls,
+                create_oauth_metadata_request,
+                handle_auth_metadata_response,
+                handle_protected_resource_response,
+            )
+
+            server_url = self.context.server_url
+            async with httpx.AsyncClient(timeout=10.0) as client:
+                # Step 1: PRM discovery to learn the authorization_server URL.
+                for url in build_protected_resource_metadata_discovery_urls(
+                    None, server_url
+                ):
+                    req = create_oauth_metadata_request(url)
+                    try:
+                        resp = await client.send(req)
+                    except httpx.HTTPError as exc:
+                        logger.debug(
+                            "MCP OAuth '%s': PRM discovery to %s failed: %s",
+                            self._hermes_server_name, url, exc,
+                        )
+                        continue
+                    prm = await handle_protected_resource_response(resp)
+                    if prm:
+                        self.context.protected_resource_metadata = prm
+                        if prm.authorization_servers:
+                            self.context.auth_server_url = str(
+                                prm.authorization_servers[0]
+                            )
+                        break
+
+                # Step 2: ASM discovery against the auth_server_url (or
+                # server_url fallback for legacy providers).
+                for url in build_oauth_authorization_server_metadata_discovery_urls(
+                    self.context.auth_server_url, server_url
+                ):
+                    req = create_oauth_metadata_request(url)
+                    try:
+                        resp = await client.send(req)
+                    except httpx.HTTPError as exc:
+                        logger.debug(
+                            "MCP OAuth '%s': ASM discovery to %s failed: %s",
+                            self._hermes_server_name, url, exc,
+                        )
+                        continue
+                    ok, asm = await handle_auth_metadata_response(resp)
+                    if not ok:
+                        break
+                    if asm:
+                        self.context.oauth_metadata = asm
+                        logger.debug(
+                            "MCP OAuth '%s': pre-flight ASM discovered "
+                            "token_endpoint=%s",
+                            self._hermes_server_name, asm.token_endpoint,
+                        )
+                        break
+
         async def async_auth_flow(self, request):  # type: ignore[override]
             # Pre-flow hook: ask the manager to refresh from disk if needed.
             # Any failure here is non-fatal — we just log and proceed with