Hitting by “Outlook Error 500 Repeating Redirects Detected” Error – Fix Instantly

An expired or corrupted authentication token is the most common cause of the “Outlook Error 500 Repeating Redirects Detected” error. This is generally linked to how enterprise browsers manage the cookie and session data. It occurs when users access multiple accounts or when sessions expire due to inactivity. These expired tokens affect the new login attempts resulting in repeating redirect loop. Resolving issues related to this Outlook error involves both manual solution and a dedicated Outlook PST Repair software designed to fix this issue. Read the blog carefully to understand this error and how it can be resolved. 

The Outlook Error 500 Repeating Redirects Detected is a HTTP server-side error. It occurs when Outlook tries to sign in the user but enters in a redirect loop during authentication. 

What Causes this Error: 500 Something Went Wrong?

Before addressing the problem, let us first try to understand what has caused the problem. Here are some reasons that explain what might have caused the error to occur:

• If the session token is expired or affects a new login attempt, Outlook will try to reauthenticate over and over. 
• Old browser cookies can affect the active login session, especially after a password reset or switching tenants.
• SSO configurations in hybrid environments can cause redirect loops if the identity provider fails to request.
• Location-based access or enforced MFA can result in a redirect loop if the conditions aren’t met.
• Companies running both on-prem Exchange and Exchange Online in hybrid setup, a poorly configureD AutoDiscover can result in redirect cycle.

Reasons to Fix Repeating Redirects Detected

The following are the reasons why one should consider fixing this issue:

1. This error will block users from managing their emails, affecting productivity and accessibility. 
2. If Outlook is inaccessible, it can disrupt important day-to-day business operations, such as customer interactions and project timelines.
3. Errors such as expired tokens and MFA conflicts, if not timely resolved, may cause security vulnerabilities.
4. There can be user frustration after the user experiences continuous failed log-in attempts. 
5. A misconfigured authentication system affects the reliability and integrity of the organization’s access management.

How to Fix Outlook Error 500 Repeating Redirects Detected?

There are two techniques for resolving this error. The first one is a manual approach, and the other one is by using professional and robust software. Users can choose either of them depending on the size, complexity, and specific needs.

Clear Browser Cache and Cookies

This is the most common and effective solution to fix this error. It removes the expired tokens and the outdated session data. 

Below are the steps to begin fixing the error:

1. Open Google Chrome.
2. Navigate to Settings > Privacy and security > Clear browsing data.
3. After that, set the Time range to All Time.
4. Also, verify Cookies and other site data and Cached images and files.
5. Click on Clear data.
6. Restart Chrome and sign in to Outlook again.

Check your Internet Connection

• Try disconnecting and reconnecting the internet.
• Restart the modem or the router.
• Try a different network.

Try Incognito or Private Browsing

This allows the user to access Outlook without involving their existing caches, cookies, or session data. 

These are the steps to resolve the 500 something went wrong error:

1. Open Chrome.
2. Go to the three dots on the upper right of the browser.
3. Select the New Incognito window. 
4. Now, open Outlook on the web and sign in using your Microsoft credentials.

Drawback: It only bypasses the cookies and cache only for that particular session. When the user will close the window, the error returns back. 

Check your Subscription

Irrespective of  which Outlook version you are using, one need to have a subscription. If you are using Outlook for personal use, then make sure your Outlook subscription is active. 

Verify Microsoft’s Service Health to fix Outlook Web Error 500 Repeating Redirects Detected

These are the steps to follow to resolve this problem:

1. Visit https://admin.microsoft.com/.
2. Log in with your Microsoft account credentials.
3. On the left-side panel, click on Health > Service Health > All services.
4. Look out for any warnings and check if everything is okay.

Delete or Modify User Roles in Office 365

Follow these steps to begin fixing the issue:

1. Go to office.com and log in with your account credentials.
2. Click those nine dots on the upper-left side.
3. Select Admin > Users > Active Users.
4. Now, choose the user account that is having issues.
5. Go to Roles > Manage Roles.
6. Uncheck the unnecessary roles and ensure that the Global Administrator is checked.
7. Click on Save Changes. 

Limitations: Admin privileges are required for this approach. 

Turn on Outlook On The Web

The following are the instructions to try to fix the Outlook error:

1. Open the Outlook App on your Computer.
2. Navigate to User profile icon > Mail > Settings > Manage email apps. 
3. Under the Manage email apps section, check if Outlook on the web is enabled.
4. Lastly, click on Save or Apply.

Fully Secure Software to Fix Outlook Error 500 Repeating Redirects Detected

The Outlook PST Repair software is a powerful solution for restoring corrupted or damaged PST files. It has the option for bulk recovery for multiple accounts and can address both minor and severe corruption. With its flexible recovery mode feature, it is an ideal choice for both IT teams and businesses. It is fully compatible with Outlook and different versions of Windows. 

Follow the steps given below to fix 500 Something Went Wrong:

1. Download and install the software.
2. Navigate to the Open button and add the corrupted PST file.
3. Choose the type of Recovery Mode and click on Ok.
4. Once the scanning process is completed, click Ok to continue.
5. Now, preview the contents of your recovered data.
6. Click on Save to export and choose the desired file format.
7. Finally, hit Ok.

Conclusion

Fixing Outlook Error 500 Repeating Redirects Detected is essential for maintaining business continuity while upholding trust in the IT system. This blog has covered the most effective methods to resolve this issue. Although a manual approach is available, it comes with several limitations. A more reliable alternative is the Outlook PST Repair software, which ensures a secure and efficient recovery of the damaged PST Files. This tool also supports bulk recovery.

Related Post: Fix Google Drive Internal Server Error 500.

Frequently Asked Questions:

Q- How do I fix a 500 error in Outlook?

Ans- Fixing a 500 error in Outlook involves resolving the issues related to the authentication loops, expired token issues, etc. Below are some of the methods to solve this:

• Try clearing the browser’s cookies and cache
• Access Outlook in Incognito Window
• Verify the Microsoft user roles
• Enable Outlook on the Web, etc.

Q- What is error 500 in Outlook Chrome?

Ans- This error occurs during a sign in session or authentication process. It primarily means that the Outlook has resulted in a continuous redirect loop. It can happen due to outdatesd session data, expired tokens, conflicts in login accounts, etc.

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