You need to use SSL on your SMTP connection (loSmtp.lUseSSL = .T.) for GMail. Your other ISP probably doesn't require SSL so that works.
Make sure you use the .NET interface of wwSMTP, which support SSL connections. There's an example in the help file.
+++ Rick ---
>Is anybody out there using VFP in Parallel on a mac
>
>I am trying to use Rick Stahls wwipstuff to send emails and now am running in windows 7 pro on OSX 9.10 Mavericks
>
>I am getting this error using smtp.gmail.com as smtp server
>
>530 5.7.0 Must issue a STARTTLS command first. b10sm65145962qeg.7 - gsmtp
>
>It works fine using smtp.charter.net but that only works from home
>
>Thanks
>
>Peter