I've been having a lot of issues with Skitch. I think they started around when I upgraded OSX. Sometimes, I'll try to drag an image, and I just get a blank. Sometimes, it gets into a funky state where it doesn't drop off images.
I like to drag and drop into Slack, and I get this sometimes:
Failed to compile /var/folders/xb/zm03wqls70gf3thlfy0d67bh0000gn/T/DMD84DD4A20-630F-40F4-9013-62D848BAB409/1__root_sftp___home_tcg__ssh__and_2__vim__vim__and_FE_.png: Asked for /var/folders/xb/zm03wqls70gf3thlfy0d67bh0000gn/T/DMD84DD4A20-630F-40F4-9013-62D848BAB409/1__root_sftp___home_