I have tried connecting via and also m exactly the same issue and scenarios. I create a new USER profile on the PC (it is domain connected so basically I logged in as a different user) - and if I allow outlook to configure the account with its startup login wizard - and it connects perfectly to the problem 365 tenant.įYI - the exchange connectivity analyser online suggests there are no problems. I remote into a different client that uses the same outlook version - and same problem. So I guess that may be the issue - although I CAN connect to other 365 tenants. I remote into a different client and I can connect OK - but it is a different version of outlook. So I jump on my laptop, and get the same issue. If I try to connect to problem tenant - I get the encryped error as above. I can create a profile to connect to a local exchange server. I can create a new profile to connect to a 365 account on a different tenant. Latest version of office/outlook 2016/365 I am creating a new mail profile - via control panel, mail, profiles. On the surface this appears a common issue with many suggestions regard autodiscover online. "An encrypted connection to your mail server is not available" Outlook cannot establish an encrypted connection to 365.
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