Why I don't consider Outlook to be a functional mail client

Author Christian Reading time 4 minutes

Photo by Pixabay: https://www.pexels.com/photo/flare-of-fire-on-wood-with-black-smokes-57461/

This topic comes up far to often, therefore I decided to make a blogpost out of it. After all copy & pasting a link is easier than repeatedly writing the same bullet points.

Also: This is my private opinion and this article should rather be treated as a rant.

  • Mail templates are separate files? And the workflow to create them is seriously that antique?
    • Under Create an email message template (microsoft.com) Microsoft details how to create an email template. But you notice something? They use the term "[...] that include information that infrequently changes [...]" means only static text is allowed.
    • Yep, you can't draft mail templates where certain values get auto-filled and the like. I mean, how many employees, consultants, etc. have to sent their weekly/monthly time-sheet to someone? Is it so hard to automatically fill in the week number, month and automatically attach the latest file with a certain file name in a specified folder?
      • Yes! Automating this with software is surely the best way. But we all know how the reality in many companies looks like, right?
    • Additionally the mail templates are stored as files on your filesystem under: C:\users\username\appdata\roaming\microsoft\templates.
      • This means: Mail templates are not treated as mails in draft mode or the like. No, you have to load an external file via a separate dialogue into Outlook. That's user experience from the 1980s?
    • Workaround: Create a folder templates, create a sub-folder templates-for-templates. Store mail drafts (with recipients, subject, text, etc.) in templates-for-templates. When needed copy to templates. Attach file. Edit text manually. Hit send.
    • Never send directly out of templates-for-templates as else your template is gone.
    • But seriously? Why is this process so old and convoluted? I suspect the feature is kept this way because Microsoft is afraid of people utilizing it to send spam. But.. Sending spam manually? I think this stopped to be a thing at May 5th, 2000 (Wikipedia) at the latest.. Every worm/virus out there has it's own build-in logic to generate different subjects/texts/etc. Why deliberately keep a feature in such a broken state and punish your legitimate users?
  • No regular expressions in filter keywords
    • This annoys me probably the most. When you specify a filter "Sort all mails, where the subject begins with Newsletter PC news into a folder", Outlook will only sort mail with the exact subject of "Newsletter PC news"
    • Which is stupid when there is a static & changing part in the subject. I mean it's 2024. Support some kind of wildcard string matching via asterisks is not really new, isn't it? Like: "Sort all mail where the subject starts with "Newsletter PC news*" and then "Newsletter PC news April 2024" will also get sorted.. No. Not in Outlook.
  • Constant nuisance: Ctrl+F doesn't bring up the search bar - Instead it opens the new mail window..
    • I mean really? Ctrl+F is the shortcut for search everywhere. Why change that!?
    • Info: Ctrl+E activates the search field on top
  • Only one organizer for events
    • Ok, technically this isn't outlook but rather CalDAV and hence Google calendar, etc. suffer the from the same problems. But I still list it as a fault.
    • Why? Microsoft has repeatedly shown the middle finger to organizations like the ISO and the like. When it suits Microsoft's market share, they basically are willing to ignore a lot of common standards (like Google, Facebook, etc..). With their Active Directory infrastructure and Office Suite they have everything in-house and 100% under their own control to make this feature work in Windows environments - which most companies do run. But they don't care.
    • I mean.. On the other hand I'm glad that they follow the standard. It just turns out so often to be a feature we are in need of that I stopped counting.
    • And you already need proprietary connectors to properly integrate your Exchange calendar into other mail programs like Mozilla Thunderbird. So this shouldn't be really a big deal-breaker either..
  • Remember Xobni? / The search is horrible
    • Outlook search is a single input field and then it searches over everything. You can't specify if the search term you used is a name, part of the name of a file or part of an email address.
    • In the early 2000s there was Xobni. Slogan: "It reverts your Inbox." - Hence the name Xobni. It was a an add-on which added another sidebar to Outlook. There it displayed all people you've mailed with. And when you clicked on a person you saw all mails, all mail threads and, most importantly, all attachments this person had sent to you (or you to them). You could even add links to the persons social media profiles, etc. It was brilliant. And made work so easy. As often I remembered only the person who sent a file to me or the thread in which it was attached - but not the actual mail or even the subject of the mail, etc. Xobni made it pretty easy to work around that. Making it possible to search Outlook in a way in which our brain works.
    • Well, sadly Yahoo bought Xobni in July 2013 and shut it down in July 2014.
    • But it's 2024 and Microsoft hasn't come up with a similar functionality yet? Really?