https://bugs.documentfoundation.org/show_bug.cgi?id=63388

--- Comment #21 from Jurassic Pork <[email protected]> ---
hello,
there is a problem when you use SMTP with the port 465 
you must use a smtplib.SMTP_SSL with this port.
Proposed code in mailmerge.py : 
                if port == 465:
                        self.server = smtplib.SMTP_SSL(server,
port,timeout=tout)
                else:
                        self.server = smtplib.SMTP(server, port,timeout=tout)

                if dbg and os.name != 'nt':
                        self.server.set_debuglevel(1)

                connectiontype =
xConnectionContext.getValueByName("ConnectionType")
                if dbg:
                        print("ConnectionType: " + connectiontype, file=dbgout)
                if connectiontype.upper() == 'SSL' and port != 465:
                        self.server.ehlo()
                        self.server.starttls()
                        self.server.ehlo()

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