send: 'ehlo [192.168.11.2]\r\n' reply: b'250-mx.google.com at your service, [221.185.210.247]\r\n' reply: b'250-SIZE 35651584\r\n' reply: b'250-8BITMIME\r\n' reply: b'250-STARTTLS\r\n' reply: b'250 ENHANCEDSTATUSCODES\r\n' reply: retcode (250); Msg: b'mx.google.com at your service, [221.185.210.247]\nSIZE 35651584\n8BITMIME\nSTARTTLS\nENHANCEDSTATUSCODES' send: 'STARTTLS\r\n' reply: b'220 2.0.0 Ready to start TLS\r\n' reply: retcode (220); Msg: b'2.0.0 Ready to start TLS' send: 'ehlo [192.168.11.2]\r\n' reply: b'250-mx.google.com at your service, [221.185.210.247]\r\n' reply: b'250-SIZE 35651584\r\n' reply: b'250-8BITMIME\r\n' reply: b'250-AUTH LOGIN PLAIN\r\n' reply: b'250 ENHANCEDSTATUSCODES\r\n' reply: retcode (250); Msg: b'mx.google.com at your service, [221.185.210.247]\nSIZE 35651584\n8BITMIME\nAUTH LOGIN PLAIN\nENHANCEDSTATUSCODES' Connecting Login 220 b'2.0.0 Ready to start TLS' Traceback (most recent call last): File "smtptest.py", line 21, in session.login(smtpuser, smtppass) File "c:\python30\lib\smtplib.py", line 580, in login AUTH_PLAIN + " " + encode_plain(user, password)) File "c:\python30\lib\smtplib.py", line 545, in encode_plain return encode_base64("\0%s\0%s" % (user, password)) File "c:\python30\lib\email\base64mime.py", line 96, in body_encode enc = b2a_base64(s[i:i + max_unencoded]).decode("ascii") TypeError: b2a_base64() argument 1 must be string or buffer, not str