Issue Postfix does not want to connect

[Joey van Venrooij]

I am trying to login with outlook 365 and no matter what I try I cant connect. I have tried all 3 SMTP ports. I have tried domainname and hostname. And I get either ssl_accept error with starttls or I get lost connection after EHLO with ssl/tls. I really cant get it to work. Imap seems to work fine.

Error logs included in the screens
SSL/TLS

StartTLS

 

[Maarten]

Have you tried to run Plesk Repair?

Tools & Settings -> Diagnose & Repair -> Check Mail Server

 

[Maarten]

Btw: did you enable the "New Outlook" option? It can cause problems with the mail servers that don't run MS Exchange.

 

[Joey van Venrooij]

Have you tried to run Plesk Repair?

Tools & Settings -> Diagnose & Repair -> Check Mail Server

I did try the repair but it found 0 issues

 

[Joey van Venrooij]

Btw: did you enable the "New Outlook" option? It can cause problems with the mail servers that don't run MS Exchange.

View attachment 21098

Sorry its the locally installed outlook on windows I thought that was called office 365 aswell. This is the error that I get when I try to connect

 

[Maarten]

Can you connect to the mail server on the command line and check the certs/TLS versions?

$ openssl s_client -showcerts -connect <hostneme>:465
$ openssl s_client -showcerts -connect <hostneme>:587

 

[Joey van Venrooij]

Can you connect to the mail server on the command line and check the certs/TLS versions?

$ openssl s_client -showcerts -connect <hostneme>:465
$ openssl s_client -showcerts -connect <hostneme>:587

Here is the cert data for 465, 587 gives a socket error: bad file descriptor

 

[Joey van Venrooij]

Anyone ? i cant find anything on this