When I use my gmail account to send e-mails to @ufl.edu accounts, my e-mails get bouced back with this error message:
Technical details of permanent failure:
Google tried to deliver your message, but it was rejected by the recipient domain. We recommend contacting the other email provider for further information about the cause of this error. The error that the other server returned was: 550 550 5.7.0 This message looks too much like SPAM to accept. (state 18).
When I use my webmail account, the e-mail sends fine.