diff --git a/packages/backend-common/src/tokens/ServerTokenManager.test.ts b/packages/backend-common/src/tokens/ServerTokenManager.test.ts
index 2827634aac..30d3571606 100644
--- a/packages/backend-common/src/tokens/ServerTokenManager.test.ts
+++ b/packages/backend-common/src/tokens/ServerTokenManager.test.ts
@@ -179,21 +179,21 @@ describe('ServerTokenManager', () => {
       const { token: token1 } = await tokenManager.getToken();
       await expect(tokenManager.authenticate(token1)).resolves.not.toThrow();
 
-      // Less than ten minutes before expiry, it still returns the same token
-      jest.advanceTimersByTime(49 * 60 * 1000);
+      // Right before the reissue timeout, it still returns the same token
+      jest.advanceTimersByTime(9 * 60 * 1000);
       const { token: token1Again } = await tokenManager.getToken();
       expect(token1).toEqual(token1Again);
       await expect(tokenManager.authenticate(token1)).resolves.not.toThrow();
 
-      // Right before the expiry, the old ones are still valid but returning a new token
-      jest.advanceTimersByTime(10 * 60 * 1000);
+      // Right after the reissue timeout, the old ones are still valid but returning a new token
+      jest.advanceTimersByTime(2 * 60 * 1000);
       const { token: token2 } = await tokenManager.getToken();
       expect(token1).not.toEqual(token2);
       await expect(tokenManager.authenticate(token1)).resolves.not.toThrow();
       await expect(tokenManager.authenticate(token2)).resolves.not.toThrow();
 
-      // After expiry, the newest one is still valid
-      jest.advanceTimersByTime(2 * 60 * 1000);
+      // After expiry of the first one, the newest one is still valid
+      jest.advanceTimersByTime(52 * 60 * 1000);
       await expect(
         tokenManager.authenticate(token1),
       ).rejects.toThrowErrorMatchingInlineSnapshot(
diff --git a/packages/backend-common/src/tokens/ServerTokenManager.ts b/packages/backend-common/src/tokens/ServerTokenManager.ts
index 65354f270f..1915330d26 100644
--- a/packages/backend-common/src/tokens/ServerTokenManager.ts
+++ b/packages/backend-common/src/tokens/ServerTokenManager.ts
@@ -23,7 +23,8 @@ import { TokenManager } from './types';
 
 const TOKEN_ALG = 'HS256';
 const TOKEN_SUB = 'backstage-server';
-const TOKEN_EXPIRY = Duration.fromObject({ hours: 1 });
+const TOKEN_EXPIRY_AFTER = Duration.fromObject({ hours: 1 });
+const TOKEN_REISSUE_AFTER = Duration.fromObject({ minutes: 10 });
 
 /**
  * A token manager that issues static dummy tokens and never fails
@@ -151,7 +152,9 @@ export class ServerTokenManager implements TokenManager {
       const jwt = await new SignJWT({})
         .setProtectedHeader({ alg: TOKEN_ALG })
         .setSubject(TOKEN_SUB)
-        .setExpirationTime(DateTime.now().plus(TOKEN_EXPIRY).toUnixInteger())
+        .setExpirationTime(
+          DateTime.now().plus(TOKEN_EXPIRY_AFTER).toUnixInteger(),
+        )
         .sign(this.signingKey);
       return { token: jwt };
     });
@@ -162,7 +165,7 @@ export class ServerTokenManager implements TokenManager {
       .then(() => {
         setTimeout(() => {
           this.currentTokenPromise = undefined;
-        }, TOKEN_EXPIRY.minus({ minutes: 5 }).toMillis());
+        }, TOKEN_REISSUE_AFTER.toMillis());
       })
       .catch(() => {
         this.currentTokenPromise = undefined;