Several times in the past few months I’ve had important emails go missing. One advantage of running my own email server is that when someone claims they never got an email, I can check the server logs to make sure that I actually sent it and that it was successfully received by the recipient’s mail transfer agent (MTA). I started checking up on these and found that…
- in every case, the missing email was successfully delivered to the recipient’s MTA
- in every case, that MTA belonged to Google
As you’re probably aware, it’s almost impossible to get Google to provide any kind of technical support when gmail goes wrong. This was frustrating, though, because having messages just disappear after they were successfully sent can lead to some serious problems. The recipients, some of whom are quite technically savvy, assured me they weren’t in their gmail spam folders, but I got on my little-used gmail account and discovered that messages I sent there…
- got placed in the spam folder, though there is absolutely no indication on the default mail page that the spam folder exists or has anything in it
- got automatically deleted after a period of time
It’s worth mentioning that any MTA can declare an email as spam for any reason; that’s entirely their business. That can be frustrating, but it isn’t wrong. But to accept the mail, tell the sender it’s been accepted, and then not delivering is wrong. Very, very wrong. Google was apparently in a gray area here: they did, in fact, deliver the messages, but delivered them to a hidden folder and then deleted them before they were seen.
Since moving to the island, I haven’t had the luxury of a static IP address at home. I’ve been sending mail through a virtual private server (VPS) in the Hetzner cloud. It seems likely, reasonable even, that mail providers would view any email originating from a low-cost cloud VPS with some suspicion, thus raising my mail’s spam score.
Now that I’m retired, I no longer need to send highly-confidential emails within my own domains. The VPS worked because I created an encrypted tunnel to it and, on top of that, encrypted routes to receiving MTAs. I decided I needed to use a mail service with a good reputation (one that works hard to be sure their service isn’t abused to send spam) and that is willing to accommodate my odd setup (I just wanted to use their SMTP server and continue to use my own MTA for incoming mail). I settled on Fastmail as I have consistently heard very good things about them.
I first wrote to their customer service department and explained my rather odd proposed setup to make sure I wasn’t somehow violating their TOS. My ISP, for example, has terms prohibiting use of their SMTP server for mail whose from address doesn’t match a domain they control. I almost immediately got a reply, and the reply clearly wasn’t from a script and nicely addressed my specific concerns. Wow!
I immediately signed up, followed their excellent setup instructions, and was using the service within an hour. It’s not free, but it’s only a few dollars a month which is cheaper than using a “free” service that won’t support you when things go wrong.
Highly recommended.
—2p