diff --git a/docs/configuration.md b/docs/configuration.md
index 408018c7f..d5093ebaa 100644
--- a/docs/configuration.md
+++ b/docs/configuration.md
@@ -68,6 +68,7 @@ Run `devspace init` to create both files. `devspace config set publicBaseUrl
   "oauth": {
     "accessTokenTtlSeconds": 3600,
     "refreshTokenTtlSeconds": 2592000,
+    "refreshTokenGraceSeconds": 0,
     "scopes": ["devspace"],
     "allowedResourceUrls": [],
     "allowedRedirectHosts": ["chatgpt.com", "localhost", "127.0.0.1"],
@@ -79,6 +80,19 @@ Omitted sections and keys use the defaults shown above. An empty
 `workspaces.allowedRoots` uses the current working directory. Unknown keys are
 rejected so spelling mistakes cannot silently alter behavior.
 
+`oauth.refreshTokenGraceSeconds` optionally allows a rotated refresh token to be
+retried for 0–600 seconds. The default, `0`, consumes the token immediately.
+For a trusted host that issues concurrent refreshes or retries after losing a
+response, set it to a bounded window such as `600` and restart DevSpace. On first
+use, the old token's expiry is shortened to the earlier of its original expiry
+and the grace deadline; retries never extend that deadline. New refresh tokens
+keep the configured `oauth.refreshTokenTtlSeconds`. The deadline persists across
+server restarts without a database migration.
+
+Enabling this option allows anyone holding the rotated token to reuse it during
+the window. Keep it disabled unless that compatibility behavior is needed;
+client, scope, resource, and token revocation checks still apply.
+
 `oauth.allowedResourceUrls` accepts exact alternate MCP resource URLs for
 clients that connect through a resource alias, such as a secure MCP tunnel.
 The normal `server.publicBaseUrl` `/mcp` resource remains allowed automatically.
diff --git a/schema/v1/devspace.schema.json b/schema/v1/devspace.schema.json
index cf9ce8f84..e7b42a2b5 100644
--- a/schema/v1/devspace.schema.json
+++ b/schema/v1/devspace.schema.json
@@ -330,6 +330,13 @@
           "exclusiveMinimum": 0,
           "maximum": 9007199254740991
         },
+        "refreshTokenGraceSeconds": {
+          "default": 0,
+          "description": "Allow refresh-token retries for up to this many seconds after rotation. Zero consumes tokens immediately.",
+          "type": "integer",
+          "minimum": 0,
+          "maximum": 600
+        },
         "scopes": {
           "default": [
             "devspace"
diff --git a/src/config-schema.test.ts b/src/config-schema.test.ts
index 4149f5d8e..2ecc7d933 100644
--- a/src/config-schema.test.ts
+++ b/src/config-schema.test.ts
@@ -10,6 +10,18 @@ assert.throws(
   /Unrecognized key/,
 );
 
+assert.equal(devspaceConfigSchema.parse({ configVersion: 1 }).oauth.refreshTokenGraceSeconds, 0);
+for (const refreshTokenGraceSeconds of [0, 1, 600]) {
+  assert.equal(devspaceConfigSchema.parse({
+    configVersion: 1, oauth: { refreshTokenGraceSeconds },
+  }).oauth.refreshTokenGraceSeconds, refreshTokenGraceSeconds);
+}
+for (const refreshTokenGraceSeconds of [-1, 601, 1.5, "600"]) {
+  assert.equal(devspaceConfigSchema.safeParse({
+    configVersion: 1, oauth: { refreshTokenGraceSeconds },
+  }).success, false);
+}
+
 for (const url of [
   "https://tunnel.example.com/v1/mcp/tunnel_123",
   "http://localhost:7676/mcp",
diff --git a/src/config-schema.ts b/src/config-schema.ts
index 95141fbd9..ab66e79a7 100644
--- a/src/config-schema.ts
+++ b/src/config-schema.ts
@@ -53,6 +53,8 @@ const loggingConfigSchema = z.object({
 const oauthConfigSchema = z.object({
   accessTokenTtlSeconds: z.number().int().positive().default(60 * 60),
   refreshTokenTtlSeconds: z.number().int().positive().default(30 * 24 * 60 * 60),
+  refreshTokenGraceSeconds: z.number().int().min(0).max(600).default(0)
+    .describe("Allow refresh-token retries for up to this many seconds after rotation. Zero consumes tokens immediately."),
   scopes: z.array(z.string().trim().min(1)).min(1).default(["devspace"]),
   allowedResourceUrls: z.array(z.string().trim().url().refine((value) => {
     const url = URL.parse(value);
diff --git a/src/config.test.ts b/src/config.test.ts
index ddb2fc1c3..30ed08c46 100644
--- a/src/config.test.ts
+++ b/src/config.test.ts
@@ -28,6 +28,7 @@ try {
     providers: [],
   });
   assert.deepEqual(defaults.oauth.allowedResourceUrls, []);
+  assert.equal(defaults.oauth.refreshTokenGraceSeconds, 0);
   assert.deepEqual(defaults.logging, {
     level: "info",
     format: "json",
@@ -72,6 +73,7 @@ try {
     oauth: {
       accessTokenTtlSeconds: 120,
       refreshTokenTtlSeconds: 240,
+      refreshTokenGraceSeconds: 60,
       scopes: ["devspace", "admin"],
       allowedResourceUrls: ["https://tunnel.example.com/v1/mcp/tunnel_123"],
       allowedRedirectHosts: ["chatgpt.com", "example.com"],
@@ -106,6 +108,7 @@ try {
   assert.equal(configured.subagents.instructions, "preload");
   assert.equal(configured.oauth.ownerToken, "persisted-owner-token-long-enough");
   assert.equal(configured.oauth.accessTokenTtlSeconds, 120);
+  assert.equal(configured.oauth.refreshTokenGraceSeconds, 60);
   assert.deepEqual(configured.oauth.scopes, ["devspace", "admin"]);
   assert.deepEqual(configured.oauth.allowedResourceUrls, [
     "https://tunnel.example.com/v1/mcp/tunnel_123",
diff --git a/src/config.ts b/src/config.ts
index 34fcdfc25..0e06dcacd 100644
--- a/src/config.ts
+++ b/src/config.ts
@@ -58,6 +58,7 @@ export function loadConfig(env: NodeJS.ProcessEnv = process.env): ServerConfig {
       ),
       accessTokenTtlSeconds: stored.oauth.accessTokenTtlSeconds,
       refreshTokenTtlSeconds: stored.oauth.refreshTokenTtlSeconds,
+      refreshTokenGraceSeconds: stored.oauth.refreshTokenGraceSeconds,
       scopes: stored.oauth.scopes,
       allowedResourceUrls: stored.oauth.allowedResourceUrls,
       allowedRedirectHosts: stored.oauth.allowedRedirectHosts,
diff --git a/src/oauth-provider.ts b/src/oauth-provider.ts
index 4fef99550..a4a779eed 100644
--- a/src/oauth-provider.ts
+++ b/src/oauth-provider.ts
@@ -16,6 +16,7 @@ export interface OAuthConfig {
   ownerToken: string;
   accessTokenTtlSeconds: number;
   refreshTokenTtlSeconds: number;
+  refreshTokenGraceSeconds?: number;
   scopes: string[];
   allowedResourceUrls: string[];
   allowedRedirectHosts: string[];
@@ -128,7 +129,7 @@ export class SingleUserOAuthProvider implements OAuthServerProvider {
     this.allowedResourceUrls = new Set(
       config.allowedResourceUrls.map((url) => resourceUrlFromServerUrl(url).href),
     );
-    this.oauthStore = new SqliteOAuthStore(stateDir);
+    this.oauthStore = new SqliteOAuthStore(stateDir, config.refreshTokenGraceSeconds ?? 0);
     this.clientsStore = new SqliteOAuthClientsStore(this.oauthStore, config.allowedRedirectHosts);
   }
 
diff --git a/src/oauth-refresh-grace.test.ts b/src/oauth-refresh-grace.test.ts
new file mode 100644
index 000000000..2ec06387a
--- /dev/null
+++ b/src/oauth-refresh-grace.test.ts
@@ -0,0 +1,218 @@
+import assert from "node:assert/strict";
+import { createHash } from "node:crypto";
+import { mkdtemp, rm } from "node:fs/promises";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+import { AccessDeniedError, InvalidGrantError } from "@modelcontextprotocol/sdk/server/auth/errors.js";
+import { SingleUserOAuthProvider } from "./oauth-provider.js";
+import type { OAuthConfig } from "./oauth-provider.js";
+import { SqliteOAuthStore } from "./oauth-store.js";
+
+const root = await mkdtemp(join(tmpdir(), "devspace-oauth-grace-test-"));
+const baseConfig: OAuthConfig = {
+  ownerToken: "test-owner-token-that-is-long-enough",
+  accessTokenTtlSeconds: 3600,
+  refreshTokenTtlSeconds: 2592000,
+  scopes: ["devspace", "read"],
+  allowedResourceUrls: ["https://tunnel.example.com/v1/mcp/tunnel_123"],
+  allowedRedirectHosts: ["chatgpt.com"],
+};
+const serverUrl = new URL("https://agent.example.com/mcp");
+const resource = new URL(baseConfig.allowedResourceUrls[0]!);
+const otherResource = new URL("https://other.example.com/mcp");
+const redirectUri = "https://chatgpt.com/connector_platform_oauth_redirect";
+const realDateNow = Date.now;
+
+try {
+  await testDefaultAndZeroGrace();
+  await testConcurrentReuseAndRestartPersistence();
+  await testGraceExpiryAndOriginalTtl();
+  await testGraceDoesNotRelaxRefreshPolicy();
+} finally {
+  Date.now = realDateNow;
+  await rm(root, { recursive: true, force: true });
+}
+
+async function testDefaultAndZeroGrace(): Promise<void> {
+  const defaultDir = join(root, "default");
+  const zeroDir = join(root, "zero");
+  for (const [stateDir, config] of [[defaultDir, baseConfig], [zeroDir, { ...baseConfig, refreshTokenGraceSeconds: 0 }]] as const) {
+    const provider = new SingleUserOAuthProvider(config, serverUrl, stateDir);
+    try {
+      const { client, tokens } = await issueInitialTokens(provider);
+      const rotated = await provider.exchangeRefreshToken(client, tokens.refresh_token);
+      await assert.rejects(provider.exchangeRefreshToken(client, tokens.refresh_token), InvalidGrantError);
+      assert.ok(rotated.refresh_token);
+    } finally {
+      provider.close();
+    }
+  }
+}
+
+async function testConcurrentReuseAndRestartPersistence(): Promise<void> {
+  const stateDir = join(root, "concurrent-restart");
+  const config = { ...baseConfig, refreshTokenGraceSeconds: 600 };
+  const baseSeconds = 2_000_000_500;
+  setNowSeconds(baseSeconds);
+  try {
+    const first = new SingleUserOAuthProvider(config, serverUrl, stateDir);
+    const { client, tokens } = await issueInitialTokens(first);
+    first.close();
+
+    setNowSeconds(baseSeconds + 20);
+    const left = new SingleUserOAuthProvider(config, serverUrl, stateDir);
+    const right = new SingleUserOAuthProvider(config, serverUrl, stateDir);
+    try {
+      const [leftTokens, rightTokens] = await Promise.all([
+        left.exchangeRefreshToken(client, tokens.refresh_token),
+        right.exchangeRefreshToken(client, tokens.refresh_token),
+      ]);
+      assert.ok(leftTokens.refresh_token);
+      assert.ok(rightTokens.refresh_token);
+      assert.notEqual(leftTokens.refresh_token, rightTokens.refresh_token);
+    } finally {
+      left.close();
+      right.close();
+    }
+
+    const reopened = new SingleUserOAuthProvider(config, serverUrl, stateDir);
+    try {
+      assert.equal(readRefreshExpiry(stateDir, tokens.refresh_token), baseSeconds + 20 + 600);
+      const retried = await reopened.exchangeRefreshToken(client, tokens.refresh_token);
+      assert.ok(retried.refresh_token);
+      assert.equal((await reopened.verifyAccessToken(retried.access_token)).clientId, client.client_id);
+      await reopened.revokeToken(client, { token: retried.refresh_token });
+      await assert.rejects(reopened.exchangeRefreshToken(client, retried.refresh_token), InvalidGrantError);
+
+      setNowSeconds(baseSeconds + 20 + 600);
+      const atBoundary = await reopened.exchangeRefreshToken(client, tokens.refresh_token);
+      assert.ok(atBoundary.refresh_token, "the 600-second grace token is accepted at its exact expiry second");
+      setNowSeconds(baseSeconds + 20 + 601);
+      await assert.rejects(reopened.exchangeRefreshToken(client, tokens.refresh_token), InvalidGrantError);
+    } finally {
+      reopened.close();
+    }
+  } finally {
+    Date.now = realDateNow;
+  }
+}
+
+async function testGraceExpiryAndOriginalTtl(): Promise<void> {
+  const stateDir = join(root, "expiry");
+  const config = { ...baseConfig, refreshTokenGraceSeconds: 10, refreshTokenTtlSeconds: 30 };
+  const baseSeconds = 2_000_000_000;
+  setNowSeconds(baseSeconds);
+  const provider = new SingleUserOAuthProvider(config, serverUrl, stateDir);
+  try {
+    const { client, tokens } = await issueInitialTokens(provider);
+    const oldExpiry = baseSeconds + 30;
+    assert.equal((await provider.verifyAccessToken(tokens.access_token)).expiresAt, baseSeconds + 3600);
+    assert.equal(readRefreshExpiry(stateDir, tokens.refresh_token), oldExpiry);
+
+    setNowSeconds(baseSeconds + 5);
+    const firstRotation = await provider.exchangeRefreshToken(client, tokens.refresh_token);
+    assert.equal(readRefreshExpiry(stateDir, tokens.refresh_token), baseSeconds + 15);
+    const firstNewRefreshExpiry = readRefreshExpiry(stateDir, firstRotation.refresh_token!);
+    assert.equal(firstNewRefreshExpiry, baseSeconds + 5 + 30);
+    assert.equal((await provider.verifyAccessToken(firstRotation.access_token)).expiresAt, baseSeconds + 5 + 3600);
+
+    setNowSeconds(baseSeconds + 9);
+    const secondRotation = await provider.exchangeRefreshToken(client, tokens.refresh_token);
+    assert.equal(readRefreshExpiry(stateDir, tokens.refresh_token), baseSeconds + 15);
+    assert.equal(readRefreshExpiry(stateDir, secondRotation.refresh_token!), baseSeconds + 9 + 30);
+
+    setNowSeconds(baseSeconds + 15);
+    const atBoundary = await provider.exchangeRefreshToken(client, tokens.refresh_token);
+    assert.ok(atBoundary.refresh_token, "the grace token is accepted at its exact expiry second");
+    assert.equal(readRefreshExpiry(stateDir, tokens.refresh_token), baseSeconds + 15);
+
+    setNowSeconds(baseSeconds + 16);
+    await assert.rejects(provider.exchangeRefreshToken(client, tokens.refresh_token), InvalidGrantError);
+  } finally {
+    provider.close();
+    Date.now = realDateNow;
+  }
+
+  const shortTtlDir = join(root, "short-original-ttl");
+  const shortTtlConfig = { ...baseConfig, refreshTokenGraceSeconds: 10, refreshTokenTtlSeconds: 6 };
+  setNowSeconds(baseSeconds);
+  const shortTtlProvider = new SingleUserOAuthProvider(shortTtlConfig, serverUrl, shortTtlDir);
+  try {
+    const { client, tokens } = await issueInitialTokens(shortTtlProvider);
+    assert.equal(readRefreshExpiry(shortTtlDir, tokens.refresh_token), baseSeconds + 6);
+    setNowSeconds(baseSeconds + 3);
+    await shortTtlProvider.exchangeRefreshToken(client, tokens.refresh_token);
+    assert.equal(
+      readRefreshExpiry(shortTtlDir, tokens.refresh_token),
+      baseSeconds + 6,
+      "grace must not extend a refresh token past its original earlier expiry",
+    );
+    setNowSeconds(baseSeconds + 6);
+    await shortTtlProvider.exchangeRefreshToken(client, tokens.refresh_token);
+    setNowSeconds(baseSeconds + 7);
+    await assert.rejects(shortTtlProvider.exchangeRefreshToken(client, tokens.refresh_token), InvalidGrantError);
+  } finally {
+    shortTtlProvider.close();
+    Date.now = realDateNow;
+  }
+}
+
+async function testGraceDoesNotRelaxRefreshPolicy(): Promise<void> {
+  const stateDir = join(root, "policy");
+  const config = { ...baseConfig, refreshTokenGraceSeconds: 600 };
+  const provider = new SingleUserOAuthProvider(config, serverUrl, stateDir);
+  try {
+    const { client, tokens } = await issueInitialTokens(provider);
+    const otherClient = await provider.clientsStore.registerClient?.({ redirect_uris: [redirectUri] });
+    assert.ok(otherClient);
+    await provider.exchangeRefreshToken(client, tokens.refresh_token);
+
+    await assert.rejects(provider.exchangeRefreshToken(otherClient, tokens.refresh_token), InvalidGrantError);
+    await assert.rejects(provider.exchangeRefreshToken(client, tokens.refresh_token, ["write"]), AccessDeniedError);
+    await assert.rejects(
+      provider.exchangeRefreshToken(client, tokens.refresh_token, undefined, otherResource),
+      InvalidGrantError,
+    );
+  } finally {
+    provider.close();
+  }
+}
+
+async function issueInitialTokens(provider: SingleUserOAuthProvider) {
+  const client = await provider.clientsStore.registerClient?.({
+    redirect_uris: [redirectUri],
+    client_name: "Test client",
+  });
+  assert.ok(client);
+  const code = `test-code-${Math.random()}`;
+  provider["codes"].set(code, {
+    clientId: client.client_id,
+    params: {
+      redirectUri,
+      codeChallenge: "challenge",
+      scopes: ["devspace"],
+      resource,
+    },
+    expiresAtMs: Date.now() + 60_000,
+  });
+  const tokens = await provider.exchangeAuthorizationCode(client, code, undefined, redirectUri, resource);
+  assert.ok(tokens.refresh_token);
+  return { client, tokens: { ...tokens, refresh_token: tokens.refresh_token } };
+}
+
+function readRefreshExpiry(stateDir: string, token: string): number | undefined {
+  const store = new SqliteOAuthStore(stateDir);
+  try {
+    return store.getRefreshToken(hashToken(token))?.expiresAt;
+  } finally {
+    store.close();
+  }
+}
+
+function hashToken(token: string): string {
+  return createHash("sha256").update(token).digest("base64url");
+}
+
+function setNowSeconds(seconds: number): void {
+  Date.now = () => seconds * 1000;
+}
diff --git a/src/oauth-store.ts b/src/oauth-store.ts
index 2567a40e1..e171f86ae 100644
--- a/src/oauth-store.ts
+++ b/src/oauth-store.ts
@@ -40,7 +40,7 @@ function redirectHostAllowed(redirectUri: string, allowedHosts: string[]): boole
 export class SqliteOAuthStore {
   private readonly database: DatabaseHandle;
 
-  constructor(stateDir: string) {
+  constructor(stateDir: string, private readonly refreshTokenGraceSeconds = 0) {
     this.database = openDatabase(stateDir);
     this.deleteExpiredTokens(Math.floor(Date.now() / 1000));
   }
@@ -142,9 +142,15 @@ export class SqliteOAuthStore {
   saveTokenPair(pair: PersistedTokenPair, consumedRefreshTokenHash?: string): boolean {
     const save = this.database.sqlite.transaction(() => {
       if (consumedRefreshTokenHash) {
-        const result = this.database.sqlite
-          .prepare("delete from oauth_refresh_tokens where token_hash = ?")
-          .run(consumedRefreshTokenHash);
+        const now = Math.floor(Date.now() / 1000);
+        // Retried rotations must not extend the original grace deadline or TTL.
+        const result = this.refreshTokenGraceSeconds > 0
+          ? this.database.sqlite
+              .prepare("update oauth_refresh_tokens set expires_at = min(expires_at, ?) where token_hash = ? and expires_at >= ?")
+              .run(now + this.refreshTokenGraceSeconds, consumedRefreshTokenHash, now)
+          : this.database.sqlite
+              .prepare("delete from oauth_refresh_tokens where token_hash = ?")
+              .run(consumedRefreshTokenHash);
         if (result.changes !== 1) return false;
       }