I found a simple fix. 1. Create and save your icon as usual 2. The window to select sizes doesn't pop up? Open task manager (CTRL+Shift+Esc for me) 3. Look for paint.net in the task manager 4. Press the arrow > and rightclick on Icon/Cursor Save Options, on my picture here I am loading a .ico file so it says Load Options. 5. Select "Switch to" and the window will pop up. Picture: http://img.picshare.at/1443282155_openpopup.png Notice that this is the Windows 8/8.1/10 Task manager, I can't test the old Windows 7-task manager, if someone could do that would be pretty. Thanks.