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We're talking about a dialog in a Windows desktop application: enter image description here

The user types in one of the text fields, then grabs the mouse and clicks on an item in the checkbox list.

What should happen? Should the clicked item became selected and/or checked, or should the whole list get the focus first and the item checked only on the second click? Or what else?

To make it more complicated, if the focus is on the checkbox list, pressing a key will scroll the list to the first item with that letter.

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You can add a filter above the list. The advantages:

  1. It's an obvious and visible control
  2. Avoids the dilemma of the second click vs unwanted selection: The input gets focus by click or tab key
  3. It can have multiple results
  4. Only the results are visible and there is no jumping through the list

Bonus points if it filters as soon as you start typing and when you can navigate through the list with the up and down arrows on the keyboard and check items with with the space bar.

enter image description here

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Since you're talking about a Windows desktop application, I'd suggest you implement it such that the behavior is the same as other Windows applications1:

  • Clicking a checkbox will check/uncheck the box (not just provide focus)
  • "Checkbox lists" don't ever get focus, so typing a letter, arrow up/down, home/end, page up/down do nothing.

1 Based on my experience with Windows OS and other applications' implementations rather than any official guidelines.

  • While I agree that it should be consistent with the user's expectations to Windows OS, I also think that having the "pressing a button scrolls the list" functionality would be really appreciated by most users, if those lists tend to be really long. – Big_Chair Feb 12 '18 at 15:11
  • Thanks for the answer! I searched for a few examples and eg. in Windows File Explorer options there is a checkbox list and it does accept up/down and letters but only if it was clicked first (i.e. is in focus). So if the user wants to type in a letter (it's a long list indeed), first she has to click on any item, uncheck it, then press the key, which looks a bit cumbersome. – tamasrell Feb 12 '18 at 15:30
  • @TamásRell Ah, I took to File Explorer, too, when writing my answer, but I couldn't find a checkbox list that behaved that way (perhaps it was just the lists I was finding, or maybe the behavior changed with Windows 10). – maxathousand Feb 12 '18 at 15:41
  • The list is very long (OK, it's list of languages), so the majority of the users will need to scroll down. And as it is a list of languages, the user will know what they want to select, so typing the first letter is a common use case. – tamasrell Feb 12 '18 at 15:42
  • @TamásRell makes sense! – maxathousand Feb 12 '18 at 15:44

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