“an encrypted connection to your mail server is not available” office 365 2016

When trying to add your email account to Outlook 2016 you get the follow error

an encrypted connection to your mail server is not available

365 is obviously  encrypted which means there must be something wrong with Autodiscover

  1. Check Autodiscover

Should be a CNAME to autodiscover.outlook.com. ( Put full stop on the end )

2. Make sure you have finished setting up the domain in 365 or it won’t listen for the domain

Test Autodiscover via : https://testconnectivity.microsoft.com/

Try logging in to powershell on your 365 Tenant and disabling OAuth2 (2fa ) 

Set-OrganizationConfig -OAuth2ClientProfileEnabled:$true
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Tags: 365, an encrypted connection to your mail server is not available, autodiscover, OAuth2, Outlook 2016

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