> I've always hated Gmail. I still do. But I switched jobs last year, and the new place uses Outlook instead. I struggle to find a word that adequately describes my disdain for Outlook; hate doesn't even begin to cover it. It struggles at the most basic of tasks: receiving and sending email. I'll get a notification on my phone about an email. I open the app and there's nothing. Pull down to refresh does nothing. It takes about 1-15 minutes to appear usually. Everything I do in Outlook is tedious as fuck.

The number of times at my last job I had to tell someone to re-send me an e-mail because Outlook search couldn't find anything with "GitLab Upgrade" in the subject line (let alone the twelve message thread it was part of) was staggering.

Also, my most hated functionality in Outlook: distribution groups (or whatever they call them). Instead of saying "[email protected] forwards to this list of people", you say "Devops is this group of people", so when you send an email to "Devops" it goes to all of those people. Sure, great.

Except that it means that you can't filter by that. Saying 'Devops' is just shorthand for saying "This guy, this guy, this guy, and this guy" explicitly. If you say "e-mails sent to Devops" Outlook interprets that as "e-mails with any of this group of people in the To or CC field", meaning that Outlook filters couldn't distinguish between "e-mails sent to me" and "e-mails sent to my team". Since I almost always had someone from my team CC'ed on e-mails I sent, it meant that my "e-mails sent to Devops" filter just matched every e-mail coming or going.

It ended up being that the alerting and monitoring e-mails we got I was only able to filter because the relevant tools put various headers into the e-mail (like X-Nagios-Alert or whatever) or they came from specific e-mail addresses (which was not always reliable but was often reliable enough).