Thought this might save someone else a few headaches.
msmtp --serverinfo --host=
smtp.gmail.com --tls=on --port= 587 --tls-certcheck=off
TLS certificate information:
Owner:
Organization: Google Inc
Locality: Mountain View
State or Province: California
Country: US
Issuer:
Common Name: Google Internet Authority
Organization: Google Inc
Country: US
Validity:
Activation time: Thu Apr 22 21:02:45 2010
Expiration time: Fri Apr 22 21:12:45 2011
Fingerprints:
SHA1: 1A:6F:48:8F:BE:5B:FD:92:D8:12:30:F9:22:CE:84:49:B3:43:BD:2C
MD5: 60:39:DE:FB:0A:D9:9E:43:26:E7:75:AC:60:48:A1:B0
Capabilities:
SIZE 35651584:
Maximum message size is 35651584 bytes = 34.00 MiB
STARTTLS:
Support for TLS encryption via the STARTTLS command
AUTH:
Supported authentication methods:
PLAIN LOGIN