https://bugs.documentfoundation.org/show_bug.cgi?id=123641

            Bug ID: 123641
           Summary: Emailmerge: can not connect to SMTP server with TLS
           Product: LibreOffice
           Version: 6.1.4.2 release
          Hardware: All
                OS: All
            Status: UNCONFIRMED
          Severity: normal
          Priority: medium
         Component: Writer
          Assignee: [email protected]
          Reporter: [email protected]

Created attachment 149503
  --> https://bugs.documentfoundation.org/attachment.cgi?id=149503&action=edit
TLS on port 465

This bug may seem a duplicate but is not.

It is easy to reproduce by testing the SMTP server in
<Tools><Options><Writer><E-mail>

The connection type that fails:
TLS on port 465 - see screenshot

Connection succeeds with"
STARTTLS on port 25 - see screenhot

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