Using Email at McGill university: Ongoing suffering of an open-source user, year 9

It’s 2020, and the world has changed. Well, yes, there’s that, but I meant that the world of email has changed. For reasons I won’t speculate and rant about here, the problem of spam has not been solved, and email providers have started in the last couple of years to make it much more difficult to send an email from an address which is not based at the SMTP server domain. Worse, while when an email used to always come back to you (to “bounce”) if it didn’t go through, emails sometimes now simply disappear if some mail agent along the way doesn’t like the combination of sender and origin SMTP server. These failures are happening even if the user is completely authenticated on the SMTP server and trustworthy (well, we don’t have a measure for the latter).

In the “good old” days, I could trivially send an email from anyone’s address I wanted to. In fact, I can still do that from some servers. I last made the embarassing mistake of sending a message from a colleague instead of to them about a year ago (sorry, Ellison!), but it hasn’t happened more than once or twice per decade. Most people can’t do that stuff because they use one of a very small number of email clients, which simply don’t allow such shenanigans, or don’t make it an obvious choice.

In any case, I’ve had to start matching my SMTP server to the from address I use. For instance, I use one email client (Alpine) to send both from a personal address and from my work address. Alpine has a feature to choose the SMTP server to use (ie, to send through) based on whoever you’ve picked as the sender for a particular message.

But another change in the world is that control over email has consolidated in a horrifying way. At least, it’s horrifying to those of us with a hefty resentment against Microsoft, and a love of open standards and diversity of control. That change is that, due to the large burden of spam and increasingly fussy authentication rules, people seem to be flocking more and more to Microsoft to run their email.

My rose-coloured glasses dimmed earlier this year when MIT, my alma mater and through which all my personal email still goes, switched its alumni email service over to Microsoft. This meant a reduction in options, authentication for my MIT alumni account through the Great Market Failure of 20th Century computer (ie Microsoft), and a closure of nearly my last option to avoid working with them to get basic email functionality.

You see, Microsoft still does not compile/offer its applications for GNU/Linux, so I do not even have the choice of embracing it like most of my colleagues and 100% of university administrators.

In any case, in the last year or so, McGill University has changed all of its authentication over to Microsoft, and is steadily moving more services over to Redmond, with no choice for employees or faculty. So the server was literally replaced with

That has continued to work for me, and been stupendously slow (it takes several seconds to send an email rather than an imperceptible fraction of a second with other SMTP servers). Until two days ago, where, for the 5th?? time since I took a faculty job at McGill, my email stopped working.

It turns out that McGill has now embraced two-factor authentication (2FA) for everything, made it mandatory, and everything goes through Microsoft. This is very bitter.

Of course, Microsoft’s 2FA is only supported on a small set of email clients, mostly Microsoft’s, so this represents an astonishing further limitation of choice and diversity and a complete shut down of most open source options.

The McGill web site is kind enough to mention (GNU/)Linux and suggests that one can use the Evolution email client, but (a) that is one client amount countless open source options, (b) that is a terrible option for me, and (c) their instructions for setting it up did not work at all, even though I have the latest version of Evolution.


  1. Altogether stop sending email from my McGill address. This would be professionally awkward and costly but might be appropriate given that I do not wish to subscribe to their buttressing of Microsoft’s near-monopolistic control over what used to be an open standard (SMTP).
  2. Switch to Google’s SMTP servers, which for the time being still allow me to send from any address I’ve authenticated through my account. I fear this may change with time.

I’ve implemented (2), using Alpine in a mode which chooses the server based on my sending address. My personal emails still go through MIT (err, Microsoft, but without 2FA) and take a couple of seconds to send. My McGill/professional email now gets sent through and takes only milliseconds.

Sadly, I was not able to get this to work with my primary Google account, which is a Google Apps account (that is what drives Stanford’s alumni email service). So instead I’ve used a free/normal Gmail account. I’m sure there will be downsides to this which reveal themselves in the days to come, but after more wasted hours for the Nth time since I took this job at McGill, I at least have my email sending and receiving again.

I will mention the new setup tips in a separate post. Here are the other relevant posts in this saga:

This entry was posted in Academia, Alpine, Alpine, GNU/linux, McGill University, Microsoft, software, Uncategorized and tagged , , , , , . Bookmark the permalink.

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