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- BUG? Double click .screen file causes error
This one is odd. Not sure if I can get you good reproduction steps. But I will talk you through what I did.
- Have a .Screen file that is in the Project Explorer, but is not in the .Story. 
- Click the .Screen file in the Project Explorer and press Ctrl+C to Copy and Ctrl+V to Paste. 
- Rename the new file to what you want it to be named. X.Screen 
- Add it to the .Story file. 
- Double click the .Screen either from the Project Explorer or the .Story file in Storyboard or Screenflow. 
- A Windows dialog appears stating that windows cannot open the file as it doesn't regonize the filename extension. 
Info.
I have about 20 screens, but it doesn't appear to be a screen limit as I have tested it and gone over that.
I am using a workspace in a different place than normal, however this occurs when copying all the files into the normal work place as well.
I have managed to work around the problem by copying and pasting files that are in the .Story but that isn't the problem as I can also copy and paste a different .Screen file which is no longer in the .Story and it works.
I couldn't reproduce this issue. Can you send me your log file using Window > Preferences > WireframeSketcher > Report a Bug? Also make sure all your screen files use ".screen" extension. Note that the extension should be all lowercase as you keep mentioning ".Screen".