messing around with email services

As I’ve mentioned in a few recent posts, I’ve been looking at alternatives to Gmail. I’m not really in any hurry to switch, and I like messing around with this kind of stuff, so I’ve been doing just that: messing around. My two main reasons to switch would be (1) privacy and (2) using my own domain.

I’ve continued to experiment with ProtonMail. Their webmail interface does (almost) everything I need it to do, and their iOS app is reasonably good. The main issue I have with ProtonMail is their current lack of IMAP support. I’ve also discovered that there’s no way to do a full-text search on your email, which is a problem for me. The (obvious) reason for lack of full-text search is that they store all of your email in an encrypted form, so there’s just no way to search through it. (You can search based on sender and/or subject line, so that’s helpful, but not quite useful enough for me.) So ProtonMail is out of the running for me, for now. If they ever get their IMAP bridge out of beta, I might try them again. (IMAP would, among other things, eliminate the search issue, since I could search in Outlook on my desktop.)

I also spent a little time messing with my 1&1 email. Since I’m already paying for it, I figured I might as well mess around with it a bit more. Their webmail interface is actually pretty good, but it’s got a few quirks that I’m not sure I like. So I set that aside and moved on.

I currently have an Office 365 Home subscription, and an Outlook.com account, so I thought maybe Outlook Premium would be an interesting choice, since it would allow me to use my own domain. (Whether or not Microsoft’s privacy policy is better than Google’s is arguable, but I think it is, at least a bit.) I actually went as far as signing up for it this morning, and adding one of my domains to the account. I like a lot of things about outlook.com, but there are a number of problems and feature gaps that make it difficult to use, and finding help for it isn’t easy either. First, it really wasn’t clear as to whether or not they were going to charge me for Premium. The sign-up screen was a bit confusing: it said the subscription would be free, and had a $50/year rate crossed out, but then it had a $20/year rate shown below that, and not crossed out. In the end, it was free, apparently, since they never asked for a credit card and it doesn’t show on my Microsoft services screen.

Setting up the custom domain wasn’t too hard. They step you through adding some DNS records. I had some trouble figuring out how to deal with some of these in the 1&1 interface, but that’s more 1&1’s problem than Microsoft’s. Once you’re set up, it works fine, though you’re pretty limited with what you can do. You can set up a few aliases on the domain, for instance, but you can’t set up a catch-all.

The big problem I had, though, was when I decided that I didn’t want to stick with Outlook.com Premium. It turns out that there’s no way to cancel the account or tell it to stop handling the domain. For paid Premium accounts, you can apparently cancel them from your MS subscription page. But free accounts don’t show there, and there’s no other way to cancel. It might be possible to cancel via MS support, but I found a forum thread that indicated that contacting MS support isn’t really helpful either. So, for now, my Outlook.com account still thinks it’s handling my domain, but I’ve removed the DNS entries so it isn’t. I don’t know if that’s going to cause any problems down the road. For now, I’m just going to hope it doesn’t.

I’ve been trying to avoid signing up for a FastMail trial, but I finally gave in and did that today. Signing up was quick and easy. I also went ahead and added my own domain to FastMail. They make it a lot easier than Microsoft by giving you the option to let them host the DNS for the domain. So I just had to set the DNS servers at 1&1 to point to FastMail’s servers. Then, FastMail just adds all the necessary DNS entries on its own. (The downside of this is that you can’t really use that domain for anything other than email once you’ve done that. But that’s fine. I’m not using the same domain for email as I am for my blog. And if you want to have more flexibility, they do allow you to keep hosting your own DNS and just add the records yourself.)

My main issue with FastMail’s web interface is that it only supports regular folders, and not tags/labels like Gmail and some other providers. I have a certain workflow in Gmail that relies, to some extent, on using labels in a way that’s not going to be possible in FastMail, but I think I can work something out so I won’t be too inconvenienced. I’m just going to have to change my workflow a bit.

Right now, I’m stuck in a bit of a limbo, where the nameserver change hasn’t quite propagated out everywhere, so some email to my domain is still going to Outlook instead of FastMail. So I guess I should lay off this stuff for a while and come back to it tomorrow, after work, and see if everything’s settled down.

At this point, I think there’s a fair chance that I’m going to stick with FastMail and gradually move stuff over from Gmail. I’ll start by moving some newsletter subscriptions and stuff like that, then eventually start changing all my various online accounts to use the new address. Thinking about how many accounts I have using my Gmail address, that’s going to be a long process. (The nice thing, though, is that once this is all under a domain I own, I can change email providers without having to change my email address again.)

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