diff --git a/packages/gitbook/src/lib/api-token.test.ts b/packages/gitbook/src/lib/api-token.test.ts
new file mode 100644
index 000000000..370ab3d4e
--- /dev/null
+++ b/packages/gitbook/src/lib/api-token.test.ts
@@ -0,0 +1,32 @@
+import { describe, expect, it } from 'bun:test';
+import jwt from 'jsonwebtoken';
+
+import { isAPITokenExpired } from './api-token';
+
+function signToken(exp: number | undefined) {
+    return jwt.sign(exp === undefined ? {} : { exp }, 'secret');
+}
+
+describe('isAPITokenExpired', () => {
+    const now = Math.floor(Date.now() / 1000);
+
+    it('returns false for a token valid for a while', () => {
+        expect(isAPITokenExpired(signToken(now + 3600))).toBe(false);
+    });
+
+    it('returns true for an expired token', () => {
+        expect(isAPITokenExpired(signToken(now - 60))).toBe(true);
+    });
+
+    it('returns true for a token expiring within the margin', () => {
+        expect(isAPITokenExpired(signToken(now + 60))).toBe(true);
+    });
+
+    it('returns false for a token without an expiration', () => {
+        expect(isAPITokenExpired(signToken(undefined))).toBe(false);
+    });
+
+    it('returns false for a token that cannot be decoded', () => {
+        expect(isAPITokenExpired('not-a-jwt')).toBe(false);
+    });
+});
diff --git a/packages/gitbook/src/lib/api-token.ts b/packages/gitbook/src/lib/api-token.ts
new file mode 100644
index 000000000..4bf1d1d87
--- /dev/null
+++ b/packages/gitbook/src/lib/api-token.ts
@@ -0,0 +1,26 @@
+import { jwtDecode } from 'jwt-decode';
+
+import type { SiteAPIToken } from '@gitbook/api';
+
+/**
+ * Refresh slightly ahead of the real expiry so the token survives the rest of the request.
+ * The API mints tokens on a UTC-midnight bucket that stay valid until 00:05 the next day, so this
+ * margin must stay under that 5min overlap: outside it, a refresh returns the very same token.
+ */
+const EXPIRATION_MARGIN_SECONDS = 120;
+
+/**
+ * Check if a site API token is expired, or about to expire.
+ */
+export function isAPITokenExpired(apiToken: string): boolean {
+    try {
+        const decoded = jwtDecode<SiteAPIToken & { exp?: number }>(apiToken);
+        return (
+            typeof decoded.exp === 'number' &&
+            decoded.exp < Date.now() / 1000 + EXPIRATION_MARGIN_SECONDS
+        );
+    } catch {
+        // A token we cannot decode is not one we can refresh.
+        return false;
+    }
+}
diff --git a/packages/gitbook/src/lib/data/lookup.ts b/packages/gitbook/src/lib/data/lookup.ts
index 71fbddc08..aa7a0fd17 100644
--- a/packages/gitbook/src/lib/data/lookup.ts
+++ b/packages/gitbook/src/lib/data/lookup.ts
@@ -1,13 +1,17 @@
-import type { PublishedSiteContentLookup, SiteVisitorPayload } from '@gitbook/api';
+import type { GitBookAPI, PublishedSiteContentLookup, SiteVisitorPayload } from '@gitbook/api';
 
 import { apiClient } from './api';
 import { getExposableError } from './errors';
 import type { DataFetcherResponse } from './types';
 import { getURLLookupAlternatives, stripURLSearch } from './urls';
+import { isAPITokenExpired } from '@/lib/api-token';
 import { race, tryCatch } from '@/lib/async';
+import { getLogger } from '@/lib/logger';
 import { joinPath, joinPathWithBaseURL } from '@/lib/paths';
 import { trace } from '@/lib/tracing';
 
+type ResolveBody = Parameters<GitBookAPI['urls']['resolvePublishedContentByUrl']>[0];
+
 interface LookupPublishedContentByUrlInput {
     url: string;
     redirectOnError: boolean;
@@ -28,24 +32,50 @@ export async function lookupPublishedContentByUrl(
 
     const result = await race(lookup.urls, async (alternative, { signal }) => {
         const api = apiClient({ apiToken: input.apiToken });
-        const callResult = await trace(
+        const resolveURL = (cacheBust?: string) =>
+            tryCatch(
+                api.urls.resolvePublishedContentByUrl(
+                    {
+                        url: alternative.url,
+                        ...(input.visitorPayload ? { visitor: input.visitorPayload } : {}),
+                        redirectOnError: input.redirectOnError,
+                        // Temporary: the API caches this POST by request body, so an unknown
+                        // field is enough to miss the cache and get a freshly minted token.
+                        ...(cacheBust ? { cacheBust } : {}),
+                    } as ResolveBody, //TODO: remove cast when we are sure that everything is good
+                    { signal }
+                )
+            );
+
+        let callResult = await trace(
             {
                 operation: 'resolvePublishedContentByUrl',
                 name: alternative.url,
             },
-            () =>
-                tryCatch(
-                    api.urls.resolvePublishedContentByUrl(
-                        {
-                            url: alternative.url,
-                            ...(input.visitorPayload ? { visitor: input.visitorPayload } : {}),
-                            redirectOnError: input.redirectOnError,
-                        },
-                        { signal }
-                    )
-                )
+            () => resolveURL()
         );
 
+        const resolved = callResult.error ? null : callResult.data.data;
+        if (
+            resolved &&
+            !('redirect' in resolved) &&
+            // Only alternatives we'd actually accept are worth a second round-trip.
+            (alternative.primary || resolved.complete) &&
+            isAPITokenExpired(resolved.apiToken)
+        ) {
+            getLogger().warn(
+                'resolvePublishedContentByUrl returned an expired API token, retrying without cache'
+            );
+            callResult = await trace(
+                {
+                    operation: 'resolvePublishedContentByUrlUncached',
+                    name: alternative.url,
+                },
+                // The value only needs to differ between calls, so `Math.random` is enough.
+                () => resolveURL(Math.random().toString(36).slice(2))
+            );
+        }
+
         if (callResult.error) {
             if (alternative.primary) {
                 // We only return an error for the primary alternative (full URL),