Hi there Robbie,
squid is an HTTP and HTTPS proxy cache, it is not a POP3 or SMTP cache.
Having said that, your proxy cache is probably also a firewall, and you could open up ports 110 and 25 through to the gmail.com servers.
This has a complexity, as the pop.gmail.com and smtp.gmail.com have multiple IP Addresses... so this might make it difficult...
Your other alternative would be to setup a POP3 proxy and SMTP proxy, you can google both of those terms to find several.
Once the POP3 proxy and SMTP proxy is setup, you should just configure actionmailer as if you did not have a proxy and it should all be good.
If you need help with this professionally, feel free to contact me off list, otherwise, report back what you find and I am sure between all of us RoRo folk we can steer you in the right direction.
Regards
Mikel Lindsaar
http://rubyx.com/
http://lindsaar.net/
We're using this http://postageapp.com in production, it might help your cause.
Matta
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