Thorsten <> changed:

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--- Comment #5 from Thorsten <> ---

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, 

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

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