Hi Steven Jennings,
I can understand how frustrating that is when you’ve been running into this, especially since it started with one account and then showed up with another one as well. At this point, I recommend that you review and try the steps provided in the AI generated answer on your thread. That reply typically include the most relevant checks for this scenario.
When you have a moment, could you let me know:
- Are both affected accounts personal Outlook.com accounts or work/school Microsoft 365 accounts?
- Does this happen with both accounts in Outlook for Mac only or also on other devices?
- Are you using New Outlook for Mac or Legacy Outlook?
- Does the issue happen in one browser only, or have you seen the same result in another browser as well?
- Do you use a VPN, security software, or company network profile on this Mac?
- Did anything change shortly before this started, such as a password change, MFA prompt, account security update, or Office update?
In the meantime, please try the steps below:
1. Fully quit Outlook and reopen it
2.Make sure Outlook is up to date
- Open any Office app > Help > Check for Updates and install any available updates.
3.Open Outlook on the web in an InPrivate / Incognito window
- This helps check whether the issue is tied to cached browser data or an extension.
4.Clear browser cache and cookies for Microsoft sites, then sign in again
- Please clear cached data for Outlook / Microsoft 365 sites and test again in a fresh session.
5. Temporarily disable browser extensions and VPNs
While my initial response may not fully resolve the issue, I truly appreciate your cooperation as we work together toward identifying the most effective solution. Thank you so much for your understanding.
I hope these checks help resolve the Outlook on the web sign-in issue and make the next steps clearer. Wishing you a smooth and quick return to your email access.
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