In early October 2025, a subset of Mac users began encountering difficulties when attempting to integrate their Outlook.com, Hotmail, or Live email accounts with Apple’s native Mail application. These users reported authentication failures, receiving error messages such as Authentication Failed and Unable to verify account name or password. Notably, other email services like iCloud, Gmail, and Microsoft 365 Exchange remained unaffected.
Emergence of the Issue
The problem surfaced across various online forums, including Apple Discussions and Reddit. Some users running macOS Tahoe 26.0.1 experienced these issues following an upgrade, while others on macOS Sequoia 15.7.1 reported similar problems. This overlap suggests that the issue may not be exclusive to a particular macOS version but could indicate a broader authentication problem between Apple Mail and Microsoft’s personal email services.
User Experiences
One MacBook Pro owner noted that while Outlook functioned correctly on their iPhone and iPad, it failed to work on their Mac after the Tahoe update. Another user mentioned that Apple’s support team recommended updating the operating system or using Microsoft’s Outlook app; however, neither solution resolved the issue.
Additionally, some users observed missing account options within the Mail application. Previously, Mac users could add Outlook.com accounts directly, but newer macOS versions only offer Exchange or IMAP options. This change may be disrupting Microsoft’s authentication process. There is also speculation that the integration of Microsoft’s Authenticator app might be failing on macOS.
Potential Causes
The root of the problem appears to be linked to how Apple Mail handles Microsoft’s OAuth 2.0 modern authentication protocols. This protocol replaced the simpler username and password system known as Basic Authentication. Users have reported that the system works correctly only about 10% of the time, with the remaining 90% resulting in repeated password re-entry requests. This inconsistency suggests that Apple Mail may be failing to properly store or refresh the OAuth tokens required for ongoing authentication.
Furthermore, Safari users have encountered additional issues when accessing Outlook on the web. Safari’s Intelligent Tracking Prevention may block third-party cookies or cross-site resources that Outlook’s preview functionality depends on. This can lead to attachment previews failing to load and email content displaying incorrectly.
Temporary Solutions
Workarounds have been inconsistent. Some users have attempted to configure IMAP manually using servers like outlook.office365.com and smtp.office365.com. While a few have succeeded, others report continued failures with the same setup. The most reliable interim solution appears to be using Microsoft’s standalone Outlook app or accessing emails via webmail.
For those who prefer consolidating all their email accounts within Apple Mail, this issue necessitates juggling multiple applications, leading to frustration. However, it’s important to note that this problem does not affect all users.
Official Responses
As of now, neither Apple nor Microsoft has publicly addressed the issue. The lack of official communication leaves users speculating about whether the fault lies within Apple’s Mail app, Microsoft’s authentication servers, or a combination of both. Given the relatively small number of confirmed cases, it would be inaccurate to label this as a widespread outage. For the time being, most Mac users appear unaffected.
Conclusion
The recent authentication issues between Apple Mail and Outlook accounts highlight the complexities of integrating services from different providers. While temporary solutions exist, they may not be suitable for all users. Affected individuals are encouraged to monitor official channels for updates and consider alternative email clients if the problem persists.
