Dear @Cristian Duran,
Thank you for posting your question in the Microsoft Q&A forum.
I understand how inconvenient it is to repeatedly encounter an Error 500 when trying to sign in.
Error 500 in Outlook on the web usually indicates a temporary disruption or a configuration problem related to the browser, mailbox, or tenant settings.
Since you did not specify whether you are an IT administrator or an end‑user, I would like to share several checks that can help identify the root cause:
Step 1: Try accessing Outlook in a clean browser session
Open a Private or Incognito window.
Sign in to your account by going to office.com > Apps > Outlook.
If the page loads correctly, return to your normal browser session.
Clear your browser’s cookies and cached data, making sure the time range is set to "All time" to fully remove old stored data.
Sign in again and test Outlook.
Step 2: Ask your organization’s IT administrator to review your account
If you are part of an organization, the issue may be related to account configuration. I recommend asking your IT admin to verify the following details:
Note: If you have an admin role assigned, you can verify this information directly in the Microsoft 365 admin center.
1/ Account roles
Too many assigned roles can conflict with Exchange settings. I recommend asking your administrator to review your current role assignments and remove any that are not required.
Sign in to the Microsoft 365 admin center using an admin account > Users > Active users > Select your account.
In the Roles section, select Manage roles.
Review the assigned roles and remove any that are unnecessary.
2/ License status
Your account must have an active license that includes Exchange Online, such as Microsoft 365 Business Standard, E3, or E5. Your administrator can check this by navigating to: Microsoft 365 admin center > Users > Active users > Select your account > Licenses and apps > Confirm that Exchange Online is enabled.
If the license appears incorrect or inactive, the admin can unassign and reassign the license. This may take up to 24 hours to fully propagate.
3/ Mailbox existence
Your IT admin can confirm whether your mailbox exists by running the following PowerShell command:
Get-Mailbox -Identity ******@domain.com
If no mailbox is found, they can create one:
New-Mailbox -UserPrincipalName ******@domain.com -FirstName 'First' -LastName 'Last'
Once the mailbox and licensing settings are correct, please try opening Outlook Web Access again in an Incognito window.
Additional information is available in the following resources:
Get-CASMailbox (ExchangePowerShell) | Microsoft Learn
Enable or disable POP3, IMAP, MAPI, Outlook Web App or ActiveSync in Microsoft 365 - Exchange | Mic…
Assign or unassign licenses for users in the Microsoft 365 admin center - Microsoft 365 admin | Mic…
Assign admin roles in the Microsoft 365 admin center - Microsoft 365 admin | Microsoft Learn
Step 3: Contact Microsoft Support
If the issue continues after your admin has reviewed all account configurations, I sincerely recommend reaching out to your IT administrator to create a support ticket via Microsoft 365 Admin Center > Support > Help & Support for further investigation.
A technical support engineer can perform a remote session to investigate the situation, verify the backend configurations, and run any necessary synchronization tools to resolve the problem. If the issue requires further attention, they can escalate it to a specialized team for deeper analysis.
As community moderators, we kindly ask for your understanding that our access to internal development details is limited. Our primary role is to guide users toward the appropriate resources and support channels. While we may not have visibility into performing deeper backend analysis, we’ll continue doing our best to support you within the scope of our responsibilities.
I hope this information is helpful. If you have any questions or need further support, please don’t hesitate to reach out at any time.
Thank you for your patience and understanding.
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