https://bugs.exim.org/show_bug.cgi?id=2255

Thorsten <thorsten.ha...@freenet.ag> changed:

           What    |Removed                     |Added
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                 CC|                            |thorsten.ha...@freenet.ag

--- Comment #5 from Thorsten <thorsten.ha...@freenet.ag> ---
Hi,

we are experiencing the same problem. The detail about the 
previous IMAP connection in this bug report
allowed us to develop a workaround. Notice that the changelog
mentions that SSL tickets were disabled in Exim 4.90. 
Conclusion must be that Outlook get confused and terminates
the SSL connection if it has a ticket from IMAP, but on
subsequent SMTP is offered none with an empty session ID.

We disabled SSL sessions[1] on our SSL termination layer and
were able to send mails through Outlook. It remains to 
determine whether Outlook or Exim is the guilty party.

Best regards, 
 Thorsten

[1] Add NO_TICKET to context options and set session id to NULL

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