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How to upload images from Greenshot to Jumpshare has released a Windows app that supports uploading images by drag-n-drop, however this can currently be directly included into Greenshot (I have requested the missing upload feature, let's see how that pans out).

The easiest way to upload a screenshot to Jumpshare is to use Copy to Clipboard and choose upload from Clipboard in the Jumpshare tray app.

(yes, I know you can take screenshots with Jumpshare directly, but I am a big fan of Greenshot, so I'm sticking with that)