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A python3.7 bug, pass the hostname to smtplib.SMTP for fixing it.
ansible/ansible#44552
Full Stacktrace:
ling.com [email protected] smtp.office365.com connect: ('smtp.office365.com', 587) connect: to ('smtp.office365.com', 587) None reply: b'220 LO2P123CA0016.outlook.office365.com Microsoft ESMTP MAIL Service ready at Tue, 7 Apr 2020 13:09:35 +0000\r\n' reply: retcode (220); Msg: b'LO2P123CA0016.outlook.office365.com Microsoft ESMTP MAIL Service ready at Tue, 7 Apr 2020 13:09:35 +0000' connect: b'LO2P123CA0016.outlook.office365.com Microsoft ESMTP MAIL Service ready at Tue, 7 Apr 2020 13:09:35 +0000' send: 'ehlo LAPTOP-SL6JSTP1.Greyhound.local\r\n' reply: b'250-LO2P123CA0016.outlook.office365.com Hello [109.255.38.119]\r\n' reply: b'250-SIZE 157286400\r\n' reply: b'250-PIPELINING\r\n' reply: b'250-DSN\r\n' reply: b'250-ENHANCEDSTATUSCODES\r\n' reply: b'250-STARTTLS\r\n' reply: b'250-8BITMIME\r\n' reply: b'250-BINARYMIME\r\n' reply: b'250-CHUNKING\r\n' reply: b'250 SMTPUTF8\r\n' reply: retcode (250); Msg: b'LO2P123CA0016.outlook.office365.com Hello [109.255.38.119]\nSIZE 157286400\nPIPELINING\nDSN\nENHANCEDSTATUSCODES\nSTARTTLS\n8BITMIME\nBINARYMIME\nCHUNKING\nSMTPUTF8' send: 'STARTTLS\r\n' reply: b'220 2.0.0 SMTP server ready\r\n' reply: retcode (220); Msg: b'2.0.0 SMTP server ready' Traceback (most recent call last): File "smtptest.py", line 86, in <module> if options.usetls: server.starttls() File "C:\Users\roman.shaikh.GREYHOUND\AppData\Local\Programs\Python\Python37\lib\smtplib.py", line 771, in starttls server_hostname=self._host) File "C:\Users\roman.shaikh.GREYHOUND\AppData\Local\Programs\Python\Python37\lib\ssl.py", line 423, in wrap_socket session=session File "C:\Users\roman.shaikh.GREYHOUND\AppData\Local\Programs\Python\Python37\lib\ssl.py", line 863, in _create owner=self, session=self._session, ValueError: server_hostname cannot be an empty string or start with a leading dot.