An encrypted connection to your mail server is not available.

Question

I've seen various people that have experienced the issue of having the following message appear when setting up an email account in Outlook 2013 "An encrypted connection to your mail server is not available" however none of the solutions i've came
across have helped me so far.
The Windows 7 laptop I was installing office 2013 on previously ran office 2007 and the email worked fine on it (it's a Microsoft 365 email account). I had a spare license for office 2013 so I uninstalled office 2007 and installed office 2013. But when I
tried to set up the email got the message "An encrypted connection to your mail server is not available".
I tried the same email address in outlook web app and it works fine. I've tried setting it up on a Windows 8 pc and also another Windows 7 laptop both with Outlook 2013 and it works fine, so I knew it wasn't the email settings server side etc. that was causing
the problem, so I therefore thought it was a computer issue. I also tried manually setting the email up instead of using auto-discover but that didn't work either.
I have uninstalled and re-installed office again to see if that worked but experienced the same issue.
Yesterday on a whim I tried another email on the affected laptop (it's a colleagues and also same domain email and also a Microsoft 365 account) and it worked ok. I'm now thinking that there must be some file somewhere or something in the registry blocking
the email being set up again as it was previously used on the laptop.
Anyone with any suggestion I've been stuck on this for a couple of weeks now and it's really bugging me?
(I originally posted this in the office forum but they referred me here).

Answer 1

Hi Dave-Houston,
According to your description, I notice that you cannot properly configure Outlook with your primary office 365 account after reinstall Outlook client.
If I have misunderstand your concern, please don’t hesitate to let me know.
If possible, please try to configure your e-mail account on another computer. If it works fine, it indicate that the issue is relate to your computer, for example residual registry information about primary account, incorrect username and password.
Please try to open Control Panel--> User Accounts---> Credential Manager, double check whether store some incorrect credential. If so, we can delete it and try again.
Additional, please try to re-create a user account  for testing. More details about
Create a user account, please refer to:
http://windows.microsoft.com/en-us/windows/create-user-account#create-user-account=windows-7
If problem persists, please pay attention to the link below, for your reference:
https://support.microsoft.com/kb/2404385?wa=wsignin1.0
Best Regards,
Allen Wang