From deca2de60443633178efa3f29f7981ec39f67502 Mon Sep 17 00:00:00 2001
From: cliffhall <cliff@futurescale.com>
Date: Mon, 24 Aug 2026 07:46:10 -0400
Subject: [PATCH] fix(auth): require JWT shape before trusting exp as proof of
 validity
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Copilot review on #2105: jwtExpiresAtMs is lenient — it parses the second of
any two-or-more dot-separated segments — so a structured opaque token such as
`opaque.<base64url({"exp":...})>` returned a parseable exp and could still
short-circuit re-authorization, recreating the replay loop.

isAccessTokenProvablyUnexpired now checks isJwtFormat first. Tests cover a
two-segment and a four-segment token whose payload decodes to a future exp.

Signed-off-by: cliffhall <cliff@futurescale.com>
---
 .../test/core/auth/connection-state.test.ts   | 29 +++++++++++++++++++
 core/auth/connection-state.ts                 | 10 ++++++-
 2 files changed, 38 insertions(+), 1 deletion(-)

diff --git a/clients/web/src/test/core/auth/connection-state.test.ts b/clients/web/src/test/core/auth/connection-state.test.ts
index 8898b263..f8235d4a 100644
--- a/clients/web/src/test/core/auth/connection-state.test.ts
+++ b/clients/web/src/test/core/auth/connection-state.test.ts
@@ -319,6 +319,35 @@ describe("isAccessTokenProvablyUnexpired", () => {
     ).toBe(false);
   });
 
+  it("is false for a two-segment token whose payload decodes to an exp", () => {
+    // jwtExpiresAtMs only requires two dot-separated segments, so a structured
+    // opaque token carrying a decodable `{"exp":...}` would otherwise read as
+    // proof of validity. isJwtFormat is what rejects it.
+    const payload = btoa(JSON.stringify({ exp: nowSec() + 3600 }))
+      .replace(/\+/g, "-")
+      .replace(/\//g, "_")
+      .replace(/=+$/, "");
+    expect(
+      isAccessTokenProvablyUnexpired({
+        access_token: `opaque.${payload}`,
+        token_type: "Bearer",
+      }),
+    ).toBe(false);
+  });
+
+  it("is false for a four-segment token carrying a decodable exp", () => {
+    const payload = btoa(JSON.stringify({ exp: nowSec() + 3600 }))
+      .replace(/\+/g, "-")
+      .replace(/\//g, "_")
+      .replace(/=+$/, "");
+    expect(
+      isAccessTokenProvablyUnexpired({
+        access_token: `header.${payload}.sig.extra`,
+        token_type: "Bearer",
+      }),
+    ).toBe(false);
+  });
+
   it("is false when there is no access token", () => {
     expect(isAccessTokenProvablyUnexpired(undefined)).toBe(false);
     expect(
diff --git a/core/auth/connection-state.ts b/core/auth/connection-state.ts
index 58f8c0df..4ae95d4b 100644
--- a/core/auth/connection-state.ts
+++ b/core/auth/connection-state.ts
@@ -5,7 +5,7 @@ import type {
 import type { EnterpriseManagedAuthIdpConfig } from "../client/types.js";
 import { getEmaIdpLoginState, normalizeIdpIssuer } from "./ema/idpSession.js";
 import { idpOAuthStorageKey } from "./ema/storage.js";
-import { isJwtExpired, jwtExpiresAtMs } from "./ema/jwt.js";
+import { isJwtExpired, isJwtFormat, jwtExpiresAtMs } from "./ema/jwt.js";
 import type { OAuthStorage } from "./storage.js";
 import type {
   AuthProtocol,
@@ -49,11 +49,19 @@ export function isAccessTokenUsable(tokens: OAuthTokens | undefined): boolean {
  * cannot outvote a resource server that has explicitly said the token is
  * expired. Use this — not `isAccessTokenUsable` — to decide whether a
  * `token_expired` challenge is already satisfied.
+ *
+ * The shape is checked with {@link isJwtFormat} before the `exp` is trusted.
+ * {@link jwtExpiresAtMs} is deliberately lenient — it parses the second of any
+ * two-or-more dot-separated segments — so a structured opaque token that merely
+ * happens to carry a decodable `{"exp":…}` segment would otherwise be read as
+ * proof, which is exactly the "guess beats the server" failure this predicate
+ * exists to remove.
  */
 export function isAccessTokenProvablyUnexpired(
   tokens: OAuthTokens | undefined,
 ): boolean {
   if (!tokens?.access_token) return false;
+  if (!isJwtFormat(tokens.access_token)) return false;
   if (jwtExpiresAtMs(tokens.access_token) === undefined) return false;
   return !isJwtExpired(tokens.access_token);
 }