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I have been using my outlook exchange account for a while already with Apple Mail on 10.12.3 Everything work just fine, until couple days ago, it doesn't login anymore, I get error about Username / Password combination miss match...

However, login to outlook it self from webpage works just fine. Also, I'm using same mail account with iPhone with apple mail as well. I checked the login details, and even tried that same password to iPhone and it works...

Where to start debugging ?

Edit: All other non outlook emails work just fine, unfortunately I don't have second outlook account to test with...

  • What is "Apple Outlook"? Are you using the standard Apple Mail application or Microsoft Outlook? – nohillside Feb 8 '17 at 8:24
  • I'm using Apple Mail application, where is outlook exchange account, fixed question and title – Diamonte Feb 8 '17 at 8:47
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I believe that Outlook.com actually uses Exchange 2016 (correct me if I am wrong here...) So if you are using outlook.com or a Work (MS Exchange) email account it should be similar.

I administer an Exchange 2013 server and find that from time to time Apple Mail loses it's mind (EG connectivity, etc.) with the Exchange account. I have found the best and quickest way to solve this issue is to delete and then re-add the account from Settings > Mail > Accounts.

Note that Exchange servers store everything (messages, calendar data, contacts) on the Exchange server so deleting the account doesn't cause loss of data unless you have lost connectivity and the mail.app (and Contacts and Calendar) hasn't pushed out your recent changes.

About a year ago (maybe more) I switched my work email account to the (free) Microsoft Outlook email app for IOS. It is an excellent mail client plus it has calendar and contacts built into it as well. And I have NEVER had a problem with it losing connectivity or forgetting the password. So I keep my personal email in the Apple mail.app and all the work email in Outlook. It's a good solution, IMHO.

  • Your solution might work, except I have also iCloud mail and work mails in mail app. I like that mail app on windows 10 too (yes I still need to use windows machine because some programs work only with windows), I have not used that with IOS or OS X tho. But as for your solution, removing and adding again that exchange account fixed this "issue". I can think about that using 2 separate email software as well, thought I'm using already thunderbird along apple mail app, because my personal (company and personal mail) are in apple mail app and daywork mails are in thunderbird... – Diamonte Feb 9 '17 at 10:40

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