I have the same issue since about 2-3 weeks : though I'm dragging the correct last fresh (unannotated, not renamed) screenshot and the thumbnail when dragging is correct too, it is the previous unannotated screenshot that is pasted. (it works if the previous screenshot was annotated)
This is an issue because there is a high risk to share a wrong screenshot to clients...
A workaround as said by jheuer is to think to add an annotation on the last screenshot to get it work... but that's it is time consuming and does not stick to my mind every time...
I'm seeing the same bug after updating to High Sierra, also. Although I seem to always get the previous screenshot when dragging/dropping. At least it's made for some entertaining conversations with customers and coworkers? I'm jumping ship to CloudApp until I hear this is resolved. Such a bummer... Skitch was an integral part of my daily workflows.
Skitch Mac Bug when dragging to another app
in Skitch for Mac Issues
Posted
I'm seeing the same bug after updating to High Sierra, also. Although I seem to always get the previous screenshot when dragging/dropping. At least it's made for some entertaining conversations with customers and coworkers? I'm jumping ship to CloudApp until I hear this is resolved. Such a bummer... Skitch was an integral part of my daily workflows.