Gmail's SMTP has a limit of 100 recipients per single message, max 500 
different recipients per day. A large number of undeliverable messages will 
get you in trouble regardless of the limits. In case of a ban, the account 
gets locked for 24h.

Yahoo has similar limitations as Gmail. Hotmail used to have a 100 
recipients per day limit and Outlook.com has this at appx. 300 per day now 
- it varies according to the account age, etc.. I'm pretty sure all 
mentioned providers take such factors into account. So a completely new 
account might get locked up much faster than on that is years old.

Lamps902, one can customize "from", "reply-to" etc. regardless of the SMTP 
server used - so no need to actually use your domain with gmail, for 
example. You just need a working SMTP... A little bit of additional code 
could also enable web2py to rotate between several SMTP servers, according 
to some simple rules... Anyway, I would recommend a private, well 
administered SMTP instead. Much less hassle.

In the GNU/linux world, having an ability to send mail locally is 
practically a given thing - most of the distributions have this 
functionality out of the box by using the ubiquitous sendmail. Even if it 
isn't actually sendmail anymore, the functionality is there (together with 
the symlink named "sendmail"). In web2py, you should be able to simply use 
localhost:25 as SMTP (might need additional authentication, might not. It 
depends...). Not quite independent of the system used, but there it is...

Regards,
Ales

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