Question SSL Setup Outlook

[jonny_alex]

Hey Pleskians

My customers always have to set up their Outlook manually and enter all details like server SSL encription and ports.
First of all, is it possible to make this happen automatically so the only enter their mail and password and all else will install automatically?

Second of all, if i set their account up, even if i use Let's encrypts on every mail and domain the error:
The server you are connected to is using a security certificate that cannot be verified. The target principal name is incorrect.

Shows up in every Outlook restart..

Does anyone have a step by step guide to solve it?

I already tried the guide How to secure a Plesk mail server with different SSL certificates (SNI support)

My Result:

echo 'Q' | openssl s_client -connect localhost:465 -servername nail-barbara.ch -showcerts 2>&1 | grep -Eo 'CN=[^/]+' | uniq
CN=nail-barbara.ch
CN=Let's Encrypt Authority X3
CN=DST Root CA X3
CN=nail-barbara.ch
CN=Let's Encrypt Authority X3

But still the error appears...?

 

[G J Piper]

I usually use the tools found here to analyze servers' autodiscover settings and see what exactly Outlook is seeing: Microsoft Remote Connectivity Analyzer

 

[robotic]

I had a similar issue, with an expired cert I got re-issued under the same name handle. It turned out that it still delivered the expired cert, although the newer one was selected. I deleted these certs and started over and then it worked.

 

[jonny_alex]

I usually use the tools found here to analyze servers' autodiscover settings and see what exactly Outlook is seeing: Microsoft Remote Connectivity Analyzer

Wich exact register and points do i have to choose to see the details?
It's really annyoing to always confirm this windows, is there someone able to help me, directly on my server? Because my knowledge is yet not big enough to handle this all alone.

 

[jonny_alex]

Is there any help possible?

 

[King555]

Concerning the SSL issue (maybe this will not help): Is the domain entered in Outlook as inbound and outbound mail server the domain for which you set the mail server certificate?

I mean, if you have the certificate for example.com there should not be mail.example.com or something like this in Outlook.