Chris, because this bug is so pervasive for me, and the need for annotated screenshots is a key part of my workflow, I'm experimenting with other tools. I'm not sure what's happening with Evernote's support of Skitch; they tell me they have no timetable for fixing this. I'm pretty happy with CloudApp; it also has the virtue of recording videos and GIFs, if that's a need. The workflow (keyboard shortcut, annotate, drag) is pretty similar. And there is automatic upload and copy of the link to your clipboard. Only downside is I liked having the searchable screenshots as part of my Evernote library . But I'd rather have a working product with an actual roadmap than an unsupported buggy application.