Apart from that, you can run some Fidder traces to capture the traffic. Using all of the above has resolved this for us when the usual workaround (just deleting the entries in Keychain) doesn't work. I'd suggest running the 'test e-mail autoconfiguration' test from Outlook to make sure no references to the erroneous value are returned in the lookups and the autodiscover.xml file itself. Select the desired email account, and you will have the option to update your email address, passwords, server, or port numbers.
A list of your available accounts will be on the left. In Outlook > Tools > Accounts > input the password into the email account(s) you're having trouble with In the upper-left hand corner, select Outlook.In Outlook > login to any accounts that you're prompted for.Open Outlook > input password to unlock login in Keychain If your email client cannot detect your email configuration from the email provider, it may attempt to recommend settings based on common server settings, which.Open Keychain Access > (View > show invisible items) > search for and remove entries related to "exchange", "office", "adal".It doesn't crop up every day/week/month, isn't related to password or other issues specific to an account, and appears to be a problem with Outlook/Keychain interaction. This is an issue that has been around for several years going back to at least Outlook 2016 for Mac. If you are working with a large number of users, you'll have to bulk modify these accounts in powershell. You might have to add their email address as the default UPN. Our users having trouble are using O365 accounts in combination with Duo (but Duo doesn't seem to be the problem). The strange thing is occasionally it will be for an e-mail address different than the mailbox (es) configured in Outlook. I wanted to add some notes about our workaround for this because sometimes just deleting those entries in keychain isn't (always) enough.
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