Silently Discarding Email Messages

Sunday May 14, 2023 — oldfolio

In a thread, Hugo Landau wrote:

A particular requirement I have for any email provider I use is the following rule: An incoming email which it is technically feasible to deliver must be delivered. In other words, mail must not be rejected for “policy” reasons...

I insist on this because I don’t want to not receive a potentially important message, but also because it’s in my view against my interests for my email provider to preempt my own decisionmaking on what mail I do and don’t want to receive. I wouldn’t find it remotely acceptable if my physical mailman started throwing away letters in purple envelopes without even telling me because he thinks they’re “probably” spam.

There’s also an issue that large mail providers rejecting incoming mail due to arbitrary criteria is one of the ways in which they effectively bully other, smaller mail providers into doing their bidding, and in which large mail providers make it harder for other mail providers to compete. So I see this as both a user-disempowering practice and one which is detrimental to the email ecosystem.

This is exactly my own thinking on the issue. Silently rejecting messages that were sent to me is a deal-breaker for me. I do not care how good your email service otherwise is, or what features you offer, if you silently discard any messages, then I will not use your service as my primary email hosting.

Tags: email

Email Hosting

Thursday December 8, 2022 — oldfolio

A few months ago, Carlos Fenollosa (the creator of bashblog, the script I use to generate this site) wrote about his decision to quit self-hosting his email after more than twenty years of doing so. He lays out the problems faced by individuals who self-host email and concludes:

One cannot reliably deploy independent email servers...

You cannot set up a home email server.

You cannot set it up on a VPS.

You cannot set it up on your own datacenter.

Fenollosa’s post generated significant discussion at in which Fastmail’s Rob Mueller offers some very thoughtful reflections on the state of email today. Because many of the problems faced by Fenollosa are driven by the pervasiveness of spam (as Fenollosa himself recognizes) Mueller elaborates on the problem of spam. Spam is big business and driven by big money.

There’s different ways to count it, but there’s capital-B Billions lost to this shit every year. And with that comes small-country-sized amounts of resources to throw at making sure the spam gets through...

People sending spam can and do spend good money...; they’ll pay for the top-tier accounts...

That is the email environment in which we operate today.

Tags: email

Self-Hosted vs. Third-Party Email

Thursday June 25, 2020 — oldfolio

Self-hosted email is probably my ideal, but for all sorts of practical reasons I inevitably go back to paying a third-party provider. It was bad enough when you had to worry about recipients not seeing your messages because their providers directed your messages to their spam folders – or, worse, completely discarded your messages without ever notifying you or your recipients. Microsoft was – and still is – notorious in this regard. The mysteriously unreliable algorithms that condemn a significant number of legitimate messages to the spam folder remain one of Microsoft’s many corporate secrets.

The situation today, though, is even worse. In addition to worrying about whether your recipients will ever see your messages, you now have to worry about the messages of your potential correspondents reaching your own mail server. Some email providers no longer deliver messages to privately run email servers. I discovered this during my most recent foray into self-hosting. I had mistakenly assumed that whatever trouble I might have getting my outbound messages into recipients’ inboxes, I at least would not have to worry about missing incoming messages because my third-party mail provider had ‘helpfully’ rejected them on suspicion of being spam. I discovered that some mail servers were not even attempting to deliver to my server. (Yes, my MX, rDNS, SPF, DKIM, and DMARC records were all properly configured and connections to my server were secured with a Let’s Encrypt certificate.) Subsequently, I discovered other email providers complaining about this same issue. A discussion at the MXroute forum confirmed that some email sending servers block sending to some destinations, presumably to the inexpensive servers that might be leased by an individual or small business.

So, at this point, I am back to relying on a third-party host for my email.

Tags: email

Self-Hosted Email, Part 2

Friday June 19, 2020 — oldfolio

In my last post, I speculated that my experiment with self-hosted email might be "just another leg of the journey in my restless migration from one host to another." One of the big appeals of self-hosting is the ability to look at server logs when diagnosing problems. The corresponding downside is that you need to be monitoring those server logs all the time. That is exactly the sort of tedious task that I would like to hand over to someone else.

In any case, I currently have my email hosted with Runbox, but I ran across a script by Luke Smith that sets up and configures an email server on Debian-based systems that is close to the way that I set up email servers manually for myself. So, I am thinking that if I am ever tempted to run my own email server in the future I should try the script. The script is elegant in its simplicity and has all the comments you need to understand what it is doing.

Tags: email

Self-Hosting My Email

Tuesday June 9, 2020 — oldfolio

Over the years, I have periodically set up and run my own email server. For the most part, these experiments were simply for learning purposes. I wanted to understand for myself what was involved in running a mail server, but I always took for granted that I would entrust the hosting of my primary email address to someone else -- someone who maintained mail servers for a living, someone working full-time at maintaining the mail server where my address would be managed.

Through all these years, though, I never found an email provider that fully suited me. There are a number of solid, reliable email hosts out there. Inevitably, though, there would be details about each of their services that bothered me. I ended up migrating from one email host to another, never quite satisfied with any of them. So, a couple of weeks ago, I bit the bullet and moved email for my primary domain to a server I am managing myself. Today, I moved email for my secondary domain to that server as well. (Don't worry: I have additional, lower-priority MX records pointing to a backup email solution.)

The final straw was discovering that my provider was silently discarding legitimate messages in an overly aggressive attempt to combat spam. Some of these were personal messages. Some were log-in verification codes that some services send when you log in from a new IP address. The point is that these messages were definitely not spam. I wanted to receive them. In the case of the log-in verification codes, I needed them. If the provider thought that the messages were suspicious, then the messages could have been directed to a spam folder. They weren't. They were simply discarded before they ever reached my account. That is a deal breaker for me.

I don't know how long my foray into self-hosting will last. It may be just another leg of the journey in my restless migration from one host to another. I do know this, though: I really like being able to look at the server logs myself. I'm not sure I could go back to a solution where I cannot do that.

Tags: email