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:

https://www.example-url.com/item/563c10cd-b92e-4f0a-b055-91f8fbdb398e

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, 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.