Did you try to change to:
mail.settings.login = "thade...:mypass"
(without @ and server name)

This is because line in gluon/tools.py
(username, password) = self.settings.login.split(':')

On Oct 31, 2:25 am, Thadeus Burgess <[email protected]> wrote:
> Would anybody know why I can send mail using SMTP through Evolution, yet
> when using the exact same credentials for web2py Mail(), email does not get
> sent?
>
> It is quite odd actually though.
>
> mail.settings.server = mail.example.com:25
> mail.settings.sender = "[email protected]"
> mail.settings.login = "[email protected]:mypass"
>
> Now when I use a mail.send() to other email accounts within the
> @example.comdomain, the emails get delivered, however when I use
> mail.send() to outside
> of the @example.com domain, liek @gmail and @yahoo, the emails never get
> delievered.
>
> Using evolution to send, the emails get sent, using squirrelmail interface
> works as well. Using gmail's smtp will not deliver emails outside of the @
> example.com domain either.
>
> This was working until I switched the DNS A record of the root domain to a
> slicehost IP, yet leaving the mail subdomain A record pointing to the mail
> server.
>
> example.com. A 123.456.789.012
> mail.example.com A 321.321.355.012
>
> With evolution working correctly, I am baffled.
>
> Has anybody else ever run into this? Or have an idea on what is going on
> here.
>
> -Thadeus
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