@ IceBrain:

The server is running it’s own smtp so that WordPress can send out notifications, but the incoming email is handled by Gmail. I set it up via Dreamhost back in the day, and they handled most of the work but I think it mostly involved setting up a “apps for your domain” account on Google and then pointing the MX records at their mail servers. Never really had any problems with it, or any need to tinker and hence I don’t even remember the details.

Google doesn’t seem to mind emails sent from weird servers. Their Spam filter is fantastic IMHO and instead of running blacklists/whitelists they just do heuristics on the content.

Google has gotten so good at identifying 419 emails that the scammers recently started moving towards obfuscation methods. The latest scam mail I had no body, no subject and a badly scanned JPG attachment of a printed letter hand signed by the Crown Prince of all Nigeia and the president of Nigeian National Bank as it’s sole content. :P

Meanwhile the emails sent by my bash scripts go through without an issue.

What do you use for mail delivery? Nowadays I run my own mail server, so I can whitelist these emails, but back when I used Gmail I was always worried it’d get caught on the spam filter, since it came from essentially unknown and therefore untrusted servers. The alternative is creating an account on some delivery service and doing the whole smarthost configuration, but that sounds overkill for a personal VPS.