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Interesting theory. You could send a small picture, a single pixel, and see if that works.

According to the given output the server gets to here:
System.out.println("Connected to client...

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Have you followed the suggestions in...

Add some more printlns to see exactly which line of code is the last one to be executed as expected

So the question is, "Why not?"
Follow the flow and see where things seem to go unexpected.
Does the server actually connect with the client? Does the image get sent?...somewhere along the path...