I don't even try it anymore. I've had so many times where I'd drag a file from my file manager to an app (recently Slack) and it complained about the file type or some other jibber jabber. The other day I was just sending someone a file on Slack, I didn't want slack to preview/play it, I wanted them to get the file. I got an error when I dragged it from my desktop, but when I went into Slack and browsed to it using their attachment browser it worked fine. Situations like that are when Yoink is great, when I have to find some work around to get funny.jpg to load into an app. Without Yoink I'd try it once then give up and move on. At least with it I can easily get back to the file and put it somewhere to access. At least, at a minimum, I can drag the file name into the file browser popup.

But yeah, it's goofy that this isn't a reliable use case. I feel like it is in Windows but I use it a lot less.