Yes, I have had this problem a lot in the last few weeks. StackOverflow lacks the proposed solutions, but most of them involve rebooting or killing.
I noticed that the error message included the phrase "Connection timeout". Therefore, I was hoping that there are some settings to extend this time, and therefore the attachment will not be disabled.
There is! What worked for me was to increase the wait time.
I'm on Eclipse Kepler now (Build id: 3.0.3-20140327-1716-Typesafe)
In the Windows menu β Skills β Java β Debugging
At the bottom of the window you will see the following field: Debug timeout (ms): 3000
I added another zero, 30,000, and my problems were gone.
You may find that your breakpoints are still skipped initially, but wait! With this long timeout time, just keep walking past these breakpoints until the debugger is successfully attached and boom! You stop at control points.
Even better, run your application in "debugging" mode, fold your arms, wait 30 seconds or more ... then on it!
This led to this revelation as follows:
Getting Startup Error: Failed to connect to the remote virtual machine. Connection timed out. which is trying to debug my application on my android device
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