I’ve been gone for awhile. I mean, not really, just from A Better Geek. I met a special someone, so that took up a lot of my time. Then said Special Someone got a job with IBM in Virginia, and we packed up and moved 700 miles to Fairfax from Lafayette back in mid-September 2009. I’m looking for work and spending my time being a server administrator, because we decided to go for Verizon Business FiOS and are hosting everything (including our websites) from our home.
Let me tell you, this has been one huge educational experience that never seems to end. My server is now running my LAN’s internal DHCP and DNS. It’s also a game application server, an internal samba file server, and an internal and external web server.
One of the things apps like WordPress, PunBB, and other content systems use is email. I’ve already discussed in the past how to make sendmail in Linux play nicely with Apache and PHP, but I realized that things were changing as I started migrating our websites and projects to an entirely different environment - Windows Server 2008 R2 Enterprise and IIS 7.0. There are some growing pains, but at least it gives me a lot to write about!
Anyhow, I realized shortly after the migration of Dan’s game servers (and related websites) that the server wasn’t sending mail. Since, you know, I hadn’t set up an SMTP service in Windows. “So what?” I thought to myself, “I’ll just install it and everything will be hunky-dory, right?”
Wrong.
It turns out that in 2009, every large mail service provider on the Internet really hates relaying email that comes from suspicious locations, including IP addresses that are part of residential ISPs. Even though we have a static IP address through Verizon Business, it’s still part of Verizon’s greater IP pool - which includes all their dynamic IPs for residential FiOS and DSL services.
Google blacklisted me the second I tried to send a message to an @gmail.com address. It was just downhill from there. I found out from some people on IRC that I needed a reverse DNS entry if I wanted anyone to relay my email, so I called up Verizon and got that taken care of. Yahoo, MSN, and AOL started relaying my mail, but Google kept delaying delivery, claiming that an “unusual amount of unsolicited email” was coming from my IP address.
After many hours on IRC and doing additional research on Google, I decided it probably wasn’t worth it to keep wrestling to make the big mail servers of cyberspace deem my rinky-dink little server worthy of their approval. It was time to look for other solutions.
I decided right from the start that I did not want to deal with hosting mail. I have no interest in trying to mitigate mass quantities of spam. My friend Julie over The Gadgeteer got on the Gmail Apps boat and moved her own email over to Google. It seemed appealing enough, so I decided to give it a shot. Google Apps offers a free version to cheapskates like me who can’t or don’t want to pay yet another monthly fee. The free version includes Google mail, calendar, sites, chat, and docs. Works for me!
Google was brilliant about the whole thing. I signed up, and when I clicked in the web-based control panel to set up email, it automagically discovered that my domain (polatrite.com, in this case) was registered with 1and1.com, so it directed me to a 1and1-specific how-to on setting up the MX records for my domain. About 18 hours later, 1and1 and Google had both updated their servers and records, and I was in business. Now it was time to figure out how to make my web server send email through Google’s SMTP servers.
Which is why we’re here today. If you’re still paying attention, that is. As always, this is a little screenshot-heavy, so hit the jump to carry onward.