Apple’s latest macOS updates have introduced a new headache for some users – Outlook accounts are suddenly refusing to cooperate with Apple Mail. Reports have surfaced across Apple’s official discussion boards and Reddit threads, revealing that many users are now unable to log in to their Outlook, Hotmail, or Live accounts through the native Mail app. 
The issue manifests in various ways, with messages such as “Authentication Failed” or “Unable to verify account name or password” repeatedly appearing when users try to add their accounts.
Interestingly, this authentication issue doesn’t seem to affect everyone or every account type. Users with iCloud, Gmail, or even Microsoft 365 Exchange accounts are largely unaffected, which makes the problem all the more confusing. The issue appears to be concentrated among those using Microsoft’s free webmail services – Outlook.com, Hotmail, and Live – through Apple’s built-in Mail app.
The bug emerged in early October 2025
The timing of the issue traces back to early October 2025, around the release of macOS Tahoe 26.0.1. However, it’s not exclusive to that version; users running macOS Sequoia 15.7.1 have also reported the same authentication failures. This cross-version occurrence suggests that the problem may not lie solely in the OS version but rather in how Apple Mail communicates with Microsoft’s authentication servers. In other words, this could be a deeper compatibility conflict between Apple’s Mail protocols and Microsoft’s sign-in system.
Several users have shared their experiences to shed more light on the situation. One MacBook Pro owner reported that while Outlook functions perfectly on their iPhone and iPad, it stops working entirely on macOS following the update. Another frustrated user said Apple Support recommended updating to the latest macOS or switching to the official Outlook app – advice that didn’t resolve the issue in their case. Meanwhile, some users have noticed that Apple Mail’s account setup options have changed; the direct “Outlook.com” entry has disappeared, leaving only Exchange or manual IMAP as alternatives.
Speculations and theories
The disappearance of the dedicated Outlook.com option has led some users to believe that Apple may have modified how Mail handles Microsoft accounts, causing authentication mismatches. Others suspect that Microsoft’s Authenticator app, which plays a role in verifying logins, may be failing to sync properly on macOS systems. The absence of a clear acknowledgment from either company adds to the uncertainty, with users left in the dark about whether the problem stems from Apple, Microsoft, or a handshake misfire between the two ecosystems.
Workarounds that mostly don’t work
Some determined users have tried to restore functionality through manual configuration – entering IMAP and SMTP server settings manually (outlook.office365.com and smtp.office365.com). In a few cases, this workaround has temporarily restored access. For most others, though, it’s been a dead end. At the moment, the only consistently functional solution is to rely on Microsoft’s standalone Outlook app or simply check email through a browser. Both are less convenient alternatives for users who prefer Apple Mail’s unified inbox and integrated notifications.
The broader impact
This issue highlights a recurring frustration for Apple users: even small authentication changes can ripple across ecosystems, disrupting the seamless experience Mac owners expect. Those who manage multiple email accounts through Apple Mail are now forced to juggle multiple apps, complicating workflows and daily routines. For now, the bug seems to affect only a subset of users, but its inconsistency makes troubleshooting difficult. Neither Apple nor Microsoft has officially commented or issued a patch, leaving affected users in a limbo of trial and error.
In the meantime, the situation serves as yet another reminder to cautious Mac users: waiting before installing a new OS update might save a lot of frustration. As convenient as being on the cutting edge sounds, stability often comes from patience – especially when even a minor change in code can turn a daily-used feature like email into a source of endless authentication errors.
2 comments
had to switch to the outlook app, not as bad as i thought tbh
classic apple… update first, fix later 😂