How To Fix Outlook For Web Error 500: Repeating Redirects Detected


Are you trying to log in to Outlook on the web and getting the warning message: Something went wrong: Error 500. Repeating redirects detected? This is a common issue with the web-based Outlook application and can have numerous causes and fixes. This is an issue that I recently encountered myself and it really took some figuring out.

These are ways that you can circumvent and fix the Outlook for Web repeating redirects detected error:

While I’ve personally encountered this issue, I’ve also seen it plague other users in the past too. There are temporary resolutions – letting you quickly access your emails – that I’ll explain. However, I’ll also explain potential root causes so you can permanently fix the issue and prevent it from reoccurring in the future. By the end of this blog post, you’ll have access to your emails again one way or another!

We’ve also made a video to accompany this blog post that takes you through all the potential fixes for the Error 500 issue you might encounter when using Outlook web access. Here’s our super helpful video.

I’d advise you to work through all the potential fixes I’ve listed above because any of them could fix the repeating redirects detected error.

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Try using an incognito tab (temporary resolution)

Email is an essential communication tool for most businesses, so it’s inevitably a stressful experience when you can’t sign into Outlook.

Sometimes, you can temporarily resolve the repeating redirects detected error by opening an incognito tab and signing into Office 365 through that tab.

You might be wondering why I advise using an incognito window. You’re probably thinking you should skip over this step because this type of thing never works. However, using an incognito window in any browser removes cookie and site data and essentially removes your plugins. Therefore, if cookies or plugins are preventing you from using OWA (Outlook Web Access) using an incognito window would help you determine the root issue.

Follow the steps outlined below and you should be able to access your emails using Outlook Web Access.

  1. Open an incognito window (CTRL + Shift + N [Chrome & Edge], CTRL + Shift + P [Firefox], or Command + Shift + N [Safari])
  2. Type Office.com into the address bar
  3. Log in using your Microsoft 365 credentials
  4. Select Outlook using the app launcher
  • Open an incognito window

In your browser of choice, open up an incognito window. If you’re unsure what that looks like, it should look a little something like the screenshot below.

It does look slightly different in other search engines such as Microsoft Edge, Firefox, and Safari, and might be called something different — Edge calls it InPrivate browsing — but they all perform the same function, removing cookies, site data, and plugins.

  • Type Office.com into the address bar
  • Log in using your Microsoft 365 credentials

If you’re unsure what your Microsoft 365 credentials are, it’s likely to be your work email address — for example, john.doe@examplebusiness.com — and whatever password you use to sign in to your device.

If you’re unsure, you can speak to your Microsoft 365 admin and they can reset your password for you.

  • Select Outlook using the app launcher

Once you select ‘Outlook’, that should open up your emails if you’ve followed the steps correctly. If your emails have opened correctly, this means you can determine that your issue is caused by:

  • Cookies
  • Browser plugins

If your emails don’t open and you’re still getting Error 500: Repeating redirects detected, please move onto the next step — clear your browser cookies and cache.

Clear your browser cookies and cache (temporary resolution)

If you phone tech support for anything website and browser-related the first thing they recommend is clearing your browser cookies and cache.

While cookies and your cache perform important roles and are usually beneficial to you, they can cause issues. Browsers cache websites you’ve visited so they load faster when you return, but this can cause problems if a site or software is updated since you last visited. That’s why clearing your browser cookies and cache can help you access Outlook via the web again.

The process for clearing browser cookies and cache differs from browser to browser. For the purposes of this blog post, I’ve created instructions for clearing cookies and the cache on three of the most popular browsers — Edge, Chrome, and Firefox. Select the browser you’re using for instructions on clearing cookies and cache:

Microsoft Edge: How To Clear Cookies and Cache

Here is how to clear cookies and cache in Microsoft Edge:

  1. Click the three horizontal dots to open the menu [Settings and more…]
  2. Click ‘Settings’
  3. Click ‘Cookies and site permissions’
  4. Click ‘Manage and delete cookies and site data’
  5. Click ‘See all cookies and site data’
  6. Click ‘Remove all’, then ‘Clear’ [shown in the screenshot above]

After you’ve followed these steps, follow these instructions to sign into attempt signing into Outlook Web Access.

  • Type Office.com into the address bar
  • Log in using your Microsoft 365 credentials

If you’re unsure what your Microsoft 365 credentials are, it’s likely to be your work email address — for example, john.doe@examplebusiness.com — and whatever password you use to sign in to your device.

If you’re unsure, you can speak to your Microsoft 365 admin and they can reset your password for you.

  • Select Outlook using the app launcher

Once you select ‘Outlook’, that should open up your emails if you’ve followed the steps correctly. If your emails have opened correctly, this means you can determine that your issue is caused by:

  • Cookies
  • Cache

If your emails don’t open and you’re still getting Error 500: Repeating redirects detected, please click here to move onto the next step — try a different browser.

Google Chrome: How To Clear Cookies and Cache

Here is how to clear cookies and cache on Google Chrome:

  1. Click the three vertical dots [Customize and control Google Chrome]
  2. Click ‘Settings’
  3. Click ‘Privacy and security’
  4. Click ‘Clear browsing data’
  5. Select only ‘Cookies and other site data’ and ‘Cached images and files’, then click ‘Clear data’ [Shown in screenshot above]

Once you’ve cleared cookies and cached images and files using the steps above, follow these steps to use Outlook Web Access.

  • Type Office.com into the address bar
  • Log in using your Microsoft 365 credentials

If you’re unsure what your Microsoft 365 credentials are, it’s likely to be your work email address — for example, john.doe@examplebusiness.com — and whatever password you use to sign in to your device.

If you’re unsure, you can speak to your Microsoft 365 admin and they can reset your password for you.

  • Select Outlook using the app launcher

Once you select ‘Outlook’, that should open up your emails if you’ve followed the steps correctly. If your emails have opened correctly, this means you can determine that your issue is caused by:

  • Cookies
  • Cache

If your emails don’t open and you’re still getting Error 500: Repeating redirects detected, please click here to move onto the next step — try a different browser.

Firefox: How To Clear Cookies and Cache

Please follow the instructions below to clear cookies and cache if the browser you use is Firefox:

  1. Click the three horizontal lines [Open menu]
  2. Click ‘Options’
  3. Click ‘Privacy & Security’
  4. Scroll to ‘Cookies and Site Data’, then click ‘Clear Data…’
  5. Click ‘Clear’
  6. Click ‘Clear Now’ [Shown in the screenshot above]

Once you’ve followed the steps outlined above, follow the steps below to attempt accessing Outlook for web.

  • Type Office.com into the address bar
  • Log in using your Microsoft 365 credentials

If you’re unsure what your Microsoft 365 credentials are, it’s likely to be your work email address — for example, john.doe@examplebusiness.com — and whatever password you use to sign in to your device.

If you’re unsure, you can speak to your Microsoft 365 admin and they can reset your password for you.

  • Select Outlook using the app launcher

Once you select ‘Outlook’, that should open up your emails if you’ve followed the steps correctly. If your emails have opened correctly, this means you can determine that your issue is caused by:

  • Cookies
  • Cache

If your emails don’t open and you’re still getting Error 500: Repeating redirects detected, please click here to move onto the next step — try a different browser.

Try a different browser (temporary resolution)

If the steps I’ve outlined so far have not fixed the issue, it’s a good idea to try a different browser. Some websites and software work better on some browsers than others — that can be said about Microsoft 365 and Outlook Web Access.

If you’re getting the Outlook repeating redirects detected on your current browser, try another. The best browsers for Microsoft 365 are Microsoft Edge and Google Chrome. However, Safari and Firefox are two other popular browsers that you could try.

  1. Download a different browser

Once you’ve downloaded a different web browser — I recommend the ones that I’ve listed the downloads for above — follow the steps outlined here to access the web-based version of Outlook on your device.

  • Type Office.com into the address bar
  • Log in using your Microsoft 365 credentials

If you’re unsure what your Microsoft 365 credentials are, it’s likely to be your work email address — for example, john.doe@examplebusiness.com — and whatever password you use to sign in to your device.

If you’re unsure, you can speak to your Microsoft 365 admin and they can reset your password for you.

  • Select Outlook using the app launcher

Once you select ‘Outlook’, that should open up your emails if you’ve followed the steps correctly. If your emails have opened correctly, this means you can determine that your issue is caused by:

  • The browser you were using

If your emails don’t open and you’re still getting Error 500: Repeating redirects detected, please move onto the next step — adjust date/time settings.

Adjust date/time settings (potential permanent fix)

If none of the troubleshooting steps up to now have resolved the repeating redirects issue when using Outlook Web Access, the issue is likely something more permanent that can’t be fixed just by changing browser settings.

Conflicting time and date settings can cause the Error 500: repeating redirects detected issue for Microsoft 365 users trying to use the web-based Outlook. I’ve worked with users previously where their date and time settings have been out of sync, and that often causes a ton of issues.

Here’s how you can check that your date and time are synchronised correctly:

These steps are only applicable to Windows 10 users, although the process applies to older Windows operating systems too:

  1. Click the Windows key
  2. Type ‘time’ and click ‘Change the date and time’
  3. Under the heading ‘Synchronize your clock’, click the ‘Sync now’ button

At this point, you should also check that your time zone is correct. If your time zone is incorrect, this can cause the repeated redirects error too.

These steps are only applicable to Mac OS users:

  1. Press Command + Spacebar to bring up the Spotlight search field
  2. Type ‘date’, and click the ‘Date & Time’ application
  3. Check that your date and time are correct
  4. Check that your time zone and location is correct in the ‘Time Zone’ tab

Once you’ve followed the steps outlined above and synchronized your clock, follow this step-by-step process to check if you can now access Microsoft 365 and Outlook Web Access.

  • Type Office.com into the address bar
  • Log in using your Microsoft 365 credentials

If you’re unsure what your Microsoft 365 credentials are, it’s likely to be your work email address — for example, john.doe@examplebusiness.com — and whatever password you use to sign in to your device.

If you’re unsure, you can speak to your Microsoft 365 admin and they can reset your password for you.

  • Select Outlook using the app launcher

Once you select ‘Outlook’, that should open up your emails if you’ve followed the steps correctly. If your emails have opened correctly, this means you can determine that your issue is caused by:

  • Unsynchronized date and time

If your emails don’t open and you’re still getting Error 500: Repeating redirects detected, please move onto the next step — remove unnecessary licences/administrator roles — which is the issue that caused me to get the Outlook/M365 repeating redirects detected error.

Remove unnecessary licences/administrator roles (potential permanent fix)

If you’ve gone through the rest of the troubleshooting steps and you’re still encountering the repeating redirects detected error, you’re not out of luck yet. In fact, when I personally encountered this issue for the first time, the troubleshooting steps I’m going to detail now fixed the issue for me.

If your user is assigned too many roles, the Office portal can lose its cool and get into an endless redirect loop. By ‘too many roles’, I mean your Microsoft 365 user account has been assigned too many admin roles. Fortunately, this is an easy issue to resolve — depending upon how your Microsoft 365.

If you are a Global Admin — meaning you’re the person who purchased Microsoft 365 or set it up — you can follow the steps below to remove unneeded admin roles and stop the repeating redirects issue.

  1. Type Office.com into the address bar
  2. Log in using your Microsoft 365 credentials
  3. Select Admin using the app launcher
  4. Select the Users dropdown and click ‘Active Users’
  5. Find your user in the list and select it
  6. Click ‘Manage roles’ under the heading ‘Roles’
  7. Remove all admin roles other than ‘Global Administrator’ and click ‘Save changes’
  8. Close all open browser instances and wait 2 minutes before reopening your browser
  9. Type Office.com into the address bar
  10. Log in using your Microsoft 365 credentials
  11. Select Outlook using the app launcher
  • Type Office.com into the address bar
  • Log in using your Microsoft 365 credentials

If you’re unsure what your Microsoft 365 credentials are, it’s likely to be your work email address — for example, john.doe@examplebusiness.com — and whatever password you use to sign in to your device.

  • Select Admin using the app launcher
  • Select the Users dropdown and click ‘Active Users’

Selecting ‘Active users’ will bring up all the users in your organization, allowing you to change permissions and admin roles for all of them.

  • Find your user in the list and select it
  • Click ‘Manage roles’ under the heading ‘Roles’
  • Remove all admin roles other than ‘Global Administrator’

As you can see on the screenshot, the Global Administrator role gives you unlimited access to edit all settings, encompassing all the other admin roles and more. Therefore you only need the Global Administrator role assigned to your user — the other admin roles are there to let you give users access to solely what they need, rather than everything.

Most organizations have very few global administrators because it gives users complete control over your business’s Microsoft 365.

  • Close all open browser instances and wait 2 minutes before reopening your browser
  • Type Office.com into the address bar
  • Log in using your Microsoft 365 credentials
  • Select Outlook using the app launcher

If you followed the process I outlined correctly, Outlook Web Access should work for you and you should have overcome the endless redirect issue.

If you’re still having issues after precisely following all these steps, have you tried a computer restart?! Surprisingly, switching your device off and on again can fix so many issues, as you’ll know if you work in the IT industry.

If you’re still having issues, leave a comment below and we might be able to point you in the right direction.

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