Why I hate Outlook

Yesterday at work a co-worker sent me an email with a bulleted list of URLs that I would have to visit today, to make some configuration changes. The URLs have the format https://www.foo.com/item/<GUID>. Where <GUID> is replaced with a 36-character string like 85d8a9de-9503-457d-8815-18f277847f43. So, for example:

  • https://www.example-url.com/item/563c10cd-b92e-4f0a-b055-91f8fbdb398e
  • https://www.example-url.com/item/85d8a9de-9503-457d-8815-18f277847f43

Ever helpful, Outlook tried to pretty this up for me (or perhaps for my coworker). In any case, it helpfully added hrefs to the links, but rather stupidly. It decided that only the part up to but not including the first hyphen was the actual URL. So I got this:


That in itself is no problem. I’ve seen automatic formatting get confused like that before. Usually I can just copy and paste the text, and everything works out. Not this time!

The second thing Outlook did was much more insidious. It replaced some of the hyphens with en dash characters. So when I copied and pasted the URL to my browser, I got a 404 “Not Found” error.

This type of error is nearly impossible to spot by eye. Now that I know what to look for, I can see in the URL below that some of the “hyphens” are slightly longer than others. But it’s not something you’d spot from a quick inspection. Especially not when the URLs are displayed in a variable-width font in a bulleted list.

  • https://example-url.com/item/46815abd–52aa–4e5c-b48f–7eadfbbe7776
  • https://example-url.com/item/bfbf6faf–1ee8–42a8–9229–053db1397ed2

It took me a few minutes of trial and error before I figured out what was going on here, then a few more minutes of cussing at Outlook before I just copied the list to my trusty plain text editor and replaced the offending characters.

I really detest software that “helps” me like this.

I know, “Don’t use Outlook.” That’s not an option. When you work for a company that has a half million employees on Outlook, you use it, too. Or you suffer from poor productivity for a while before you find yourself out on the street looking for another place to work.

4 comments to Why I hate Outlook

  • MikeB

    You also have to be careful with snippets of code that contain quotes. Outlook “helps” by converting those characters to ‘smart quotes’ that confuse any compiler or interpreter.

    You are supposed to be able to configure this behavior in “Outlook Options/Mail/Compose Messages/Editor Options…/Autocorrect Options…” (could they bury it any deeper?)

    There are two tabs that I think you have to muck around with: “AutoFormat” and “AutoFormat As You Type”. I’m not sure exactly what the difference between the two is…

    However that only helps with the emails that you compose. Doesn’t help at all with the ones that you receive. Also, I seem to lose those setting pretty easily. I’m not sure if that’s a problem with the way things are administered here or if I just occasionally do something that resets my options without realizing. Also I’m not sure where these options are in the web version of Outlook (or if they even exist there), but I don’t use the web interface too often.

    I find that if I compose stuff in a plain old text editor and copy/paste it into the Outlook email the AutoFormat stuff doesn’t kick in. That’s what I typically do. But again, that only helps with what you send, not with what you get.

  • MikeB

    It looks like the “Leave a Reply” comment box on this block does some similar AutoFormatting – at least to the quotes.

    Are fancy quotes really all that much more readable than ASCII quotes to justify anyone having spent time working on implementing this irritating functionality?

  • Dax

    Buried in outlook’s options is the ability to configure/disable AutoCorrect: File -> Options -> Mail (on left) -> Spelling and Autocorrect

    Hope this helps

  • Jim

    Yes, I’m aware that I can prevent Outlook from automatically “correcting” messages that I write. As others have pointed out, that doesn’t help when somebody else sends me things.



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