I have spent several hours looking for tips on using the email binary in
Cygwin to send email via Gmail from the command line.  The man page and help
output don’t seem to clarify this.  I seem to be timing out or not
connecting to the gmail smtp server, but I don’t get any errors from email,
even with the –V flag.  It just hangs at:

Connecting to server smtp.gmail.com on port 465
Greeting the SMTP server...
...
Here is the command I am using in my script.  This worked fine when I used
another ISP, but gmail is pickier.

email -r smtp.gmail.com -f <user>@gmail.com -n me -s "backup for %DATE%" -a
d:\backup.log <sameuser>@gmail.com

I ran email-config and specified my userid, password, smtp server, port
number, and to use TLS.  I have also specified the port and used the tls
flag in the command line.  Sending email from outlook on the same computer
works fine.

Any documentation on email with SSL or tips on alternatives would be greatly
appreciated.



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