As Rick pointed out I'd check your firewall settings.
I also question if there is something wrong with gmail settings or limitations. I know at one time they limited your ability to do this for more than 99 emails per day. Once you hit the limit ya gotta wait 24 hours - perhaps this is your problem???

some good info here might help:

https://support.google.com/a/answer/176600?hl=en
https://www.digitalocean.com/community/tutorials/how-to-use-google-s-smtp-server



>I don't think the port is even getting involved yet, the connection to stunnel just seems to stop on its own after 30 seconds without even trying to send it on to gmail. The username and password are passed in, but just not involved at this point. I have tried with 587 too, with the same result.
>
>>Pretty sure those settings are not correct. The server port AFAIK is smtp.gmail.com:587. You'll also need username and password passed.
>>
>>
>>Here's an example of using wwSmtp (part of West Wind Client Tools) to send mail to GMail:
>>
>>

>>DO wwSmtp && load libraries
>>
>>LOCAL loSMTP as wwSmtp
>>loSmtp=CREATEOBJECT("wwSmtp")
>>loSmtp.nMailMode = 0  && 2 - wwIPStuff mode (Win32 - default)   0 - .NET wwSmtp
>>
>>loSmtp.cMailServer="smtp.gmail.com:587"
>>loSmtp.lUseSsl = .T.
>>loSmtp.cSenderEmail="rstrahl@mydomain.com"
>>loSmtp.cSenderName="Mr. Testa"
>>
>>
>>*** Optional Username
>>loSmtp.cUsername = "ricks@gmail.com"
>>loSmtp.cPassword = "secret"
>>
>>
>>loSmtp.cRecipient="somebody@sweat.com,another@bust.com"
>>loSmtp.cCCList="rstrahl@east-wind.com,looser@nobody.com"
>>loSmtp.cSubject="wwSmtp Test Message"
>>
>>*** Optionally specify content type - text/plain is default
>>loSmtp.cContentType = "text/html"  
>>loSmtp.cMessage="Who said this had to be <b>difficult</b>?"
>>
>>*** Optionally provide an alternate content type or plain text fallback
>>loSmtp.cAlternateContentType = "text/plain"
>>loSmtp.cAlternateText = "Plain text can go here."
>>
>>*** Optionally send file attachments
>>loSmtp.AddAttachment("c:\temp\somefile.pdf")
>>
>>llResult = loSmtp.SendMail()      
>>
>>IF !llResult
>>   Wait window loSmtp.cErrorMsg
>>ENDIF
>>

>>
>>
>>+++ Rick ---
>>
>>
>>
>>>Hi,
>>>
>>>I have been using blat successfully for a while now but I now need to use it to send email which requires SSL/TSL (I am using gmail as a test). So I've installed stunnel and configured it like this:
>>>
>>>client = yes
>>>[ssmtp]
>>>accept = 25
>>>connect = smtp.gmail.com:465
>>>
>>>
>>>Unfortunately when I send my email it's not working. I get this in the log file:
>>>
>>>2015.05.08 13:33:35 LOG7[4]: Service [ssmtp] started
>>>2015.05.08 13:33:35 LOG5[4]: Service [ssmtp] accepted connection from 127.0.0.1:54592
>>>2015.05.08 13:33:35 LOG7[4]: SSL state (accept): before/accept initialization
>>>2015.05.08 13:34:05 LOG3[4]: SSL_accept: Peer suddenly disconnected
>>>2015.05.08 13:34:05 LOG5[4]: Connection reset: 0 byte(s) sent to SSL, 0 byte(s) sent to socket
>>>2015.05.08 13:34:05 LOG7[4]: Local socket (FD=596) closed
>>>2015.05.08 13:34:05 LOG7[4]: Service [ssmtp] finished (0 left)
>>>
>>>So after 30 seconds the Peer suddenly disconnects.
>>>
>>>Any ideas what I need to do?