[This is a follow-up to this blog post. It was inspired by the response I received through social media and different websites.]

In a previous version of Yoink, I had the following conundrum:

The checkbox “Show window near mouse pointer when drag is initiated” is inactive and needs extra steps to be activated.
If I’m a new user of the app, at first, I have no idea how to activate that checkbox. At best, it’s something I need to set in this preference panel, at worst it’s a setting in a different one.
As a new user, my only option is to blindly change settings, waiting for one to activate the checkbox so I can select it.

There are different solutions to this problem, of varying degrees of effective- and usefulness:

• A tooltip. If the checkbox is inactive and you hover over it, a tooltip appears, explaining what to do to activate the checkbox.
  It’s a quick and easy solution, however, it’s almost undiscoverable. I know of many users who don’t even know tooltips exist.
• Hiding the checkbox instead of having it be inactive.
  That’s better, as it reduces clutter (as the checkbox would be inactive anyway). But it introduces another problem – nobody knows that the option even exists.

“For that UI, I think maybe an additional improvement would be to actually hide and show the checkbox completely instead of disabling it.
Also, indent the second checkbox so that it feels like it’s a sub-section of the first.
Another option might be to split things out into radio buttons instead of checkboxes and the popup menu.
That way you could expose the additional option tied to the appropriate radio choice, which you can’t exactly do with the menu item.”

– Manton Reece, via Core Intuition’s slack channel

• Speaking of radio buttons, Adrien Maston wrote me a very detailed mail with some ideas he had about resolving the issue:
  

What I ended up doing in Yoink v3.2.1, the release that followed this discussion, was this:

Instead of having the checkbox inactive, it’s active at all times and can be clicked right away. The advantage of this is that for one, the user knows the option exists and two, the user can select the option right away without having to figure out how to activate it.
The downside, and this has been pointed out to me a couple of times, and I agree, is that clicking the checkbox changes two settings at once (the checkbox and the popup, as you can see in the GIF above). It changes a setting the user has made before. And that’s bad UX design on its own right there.
My thinking was, it’s in the same preference pane, so the user sees what’s happening right away. It still was the wrong decision (as has been pointed out to me in the comments on designernews.co).

For Yoink v3.2.5, I re-thought the whole thing and decided to make it three options in a popup.
This is the result:

It solves a couple of things:

• The inactive checkbox is a thing of the past
• The options you have for when and where Yoink should appear are much clearer
• You get a preview video for every option so you know right away how each setting affects Yoink

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