Cannot Add Email Account to Outlook 2016 for Mac My college has Office365 and I have downloaded and installed Outlook 2016 on my Mac. I opened the program and started to add an account for my email address at the college. Add Another Mailbox in Outlook 2016. To add another mailbox, launch Microsoft Outlook 2016 then click the File tab > click Info tab > Account Settings. Mac paint pot colors.

I added few Gmail.com, live.com and Zoho accounts to Outlook 2016, but I just can't add a hotmail account. Two factor is not enabled. It passes the 'Establishing network connection' phase, but not the 'Searching for @hotmail.com settings': It says 'An encrypted connection to your mail server is not available. Click Next to attempt using an unencrypted connection.' So I click 'Next' and after a while Outlook says 'We are having trouble connecting to your account.

Verify the settings below and make changes if necessary' (and then I get a chance to change the email adderss.). Another word for text. What am I missing here? I managed to add Live.com which is essentially identical, no? Ok, problem solved. Very odd solution, but this is what there is: When adding account, Auto Account Setup dialog appears: I always left default ( E-mail Account) selected, as it worked with live.com (which I considered to be same as outlook.com, hotmail.com or any other Microsoft's account). But then I noticed that the other live.com account I have is of Exchange ActiveSynce type, and not IMAP/SMTP as I assumed.

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So I selected the Manual setup or additional server types and clicked Next. In the next screen I left Outlook.com or Exchange ActiveSync compatible service selected (the other option is POP or IMAP). And finally, I entered the Your Name and E-mail Address fields, and copy-pasted the Mail server from the other live.com account to this one (and of course username and password.). And that's it, never touched any port number or security option setting. The funny thing is that when I opened this newly created account a bit later, I noticed that the Mail server was different than what I pasted into it. I initially entered @hotmail.com, and it was changed to @hotmail.com. Quite strange.