If you're using GMail you need TLS. The old wwIpstuff library doesn't support that. The newer wwSmtp library that's part of the West Wind Client Tools (
https://west-wind.com/WestwindClientTools.aspx) supports it and it has the **same** interface as wwipstuff - you basically just change the class name. wwIPstuff is so old there wasn't even and official TLS authenticated protocol at the time, so probably time to upgrade to something a little more modern :-)
There's an example in the documentation that shows how to send email with Gmail specifically:
Sending TLS Emails with GMail+++ Rick ---
>Hi,
>
>I am trying to send email using GMAIL server. For SMTP I use "smtp.gmail.com", port 465, and then user gmail user ID and password.
>But I get a message "cannot connect to the server"
>Is there a setting or something I am missing?
>
>TIA