an encrypted connection is not available - outlook 2016 to 365
Outlook cannot establish an encrypted connection to 365. "An encrypted connection to your mail server is not available"
On the surface this appears a common issue with many suggestions regard autodiscover online. However let me explain my REAL issue:
I am creating a new mail profile - via control panel, mail, profiles. (an existing profile already exists)
Latest version of office/outlook 2016/365
I can create a new profile to connect to a 365 account on a different tenant.
I can create a profile to connect to a local exchange server.
If I try to connect to problem tenant - I get the encryped error as above.
So I jump on my laptop, and get the same issue.
I remote into a different client and I can connect OK - but it is a different version of outlook. So I guess that may be the issue - although I CAN connect to other 365 tenants.
I remote into a different client that uses the same outlook version - and same problem.
But then..
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.
FYI - the exchange connectivity analyser online suggests there are no problems.
I have tried connecting via user@domain.com and also user@domain.onmicrosoft.co
I am going in circles -
is it my PC?
my outlook version?
the tenant in question?
My current guess is it doesnt like being a second profile - although this poses a problem as the reason for setup is for a mail migration to 365 - every user (40 of them) has a current profile and we need to setup a second profile connected to 365 ready for switchover.
I dont think this is becuase we still have the old domain pointing to the old mail host.
Basically - old domain - pointing to old host,, new domainname pointing to 365, after migration the old domain will be pointed to the 365, but the new domain will be the company default. So I cant see a reason for this to be related.
The 365 tenant isnt new and has been used for dynamics for a few years, and only recently had exchange/365 added to it.
The outlook support and recover tool only madee things worse my trashing any currently existing, working profile.
My only other solution/workaround would be to create a connection to 365 with the first profile, then create a new profile to connect to the old mail server - but this will require resynching email for both accounts and this client has limited bandwidth and several mailboxes over 10gb each - which is why I wanted to commence synching the new 365 profiles in batches and at night before cutover.
Any new. lateral thinking suggestions are welcome.
On the surface this appears a common issue with many suggestions regard autodiscover online. However let me explain my REAL issue:
I am creating a new mail profile - via control panel, mail, profiles. (an existing profile already exists)
Latest version of office/outlook 2016/365
I can create a new profile to connect to a 365 account on a different tenant.
I can create a profile to connect to a local exchange server.
If I try to connect to problem tenant - I get the encryped error as above.
So I jump on my laptop, and get the same issue.
I remote into a different client and I can connect OK - but it is a different version of outlook. So I guess that may be the issue - although I CAN connect to other 365 tenants.
I remote into a different client that uses the same outlook version - and same problem.
But then..
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.
FYI - the exchange connectivity analyser online suggests there are no problems.
I have tried connecting via user@domain.com and also user@domain.onmicrosoft.co
I am going in circles -
is it my PC?
my outlook version?
the tenant in question?
My current guess is it doesnt like being a second profile - although this poses a problem as the reason for setup is for a mail migration to 365 - every user (40 of them) has a current profile and we need to setup a second profile connected to 365 ready for switchover.
I dont think this is becuase we still have the old domain pointing to the old mail host.
Basically - old domain - pointing to old host,, new domainname pointing to 365, after migration the old domain will be pointed to the 365, but the new domain will be the company default. So I cant see a reason for this to be related.
The 365 tenant isnt new and has been used for dynamics for a few years, and only recently had exchange/365 added to it.
The outlook support and recover tool only madee things worse my trashing any currently existing, working profile.
My only other solution/workaround would be to create a connection to 365 with the first profile, then create a new profile to connect to the old mail server - but this will require resynching email for both accounts and this client has limited bandwidth and several mailboxes over 10gb each - which is why I wanted to commence synching the new 365 profiles in batches and at night before cutover.
Any new. lateral thinking suggestions are welcome.
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Vasil Michev (MVP)
The Control panel approach uses a different method, thus you get a different experience, and there are some other issues with it sadly. Dont ask me what the logic behind it is, but overriding the behavior via the reg key usually help,s as you have already discovered. You can also try to use the "suggested" method by going to File -> Account settings -> Change profile, then restart Outlook and follow the steps.
ASKER
No updates, this is still an issue, and the solution I found still remains the only solution