Synchronising twice on the same object?

I think we have to use reentrant lock for what you are trying to do. Here's a snippet from http://docs.oracle.com/javase/1.5.0/docs/api/java/util/concurrent/locks/ReentrantLock.html.

What do we mean by a reentrant lock? Simply that there is an acquisition count associated with the lock, and if a thread that holds the lock acquires it again, the acquisition count is incremented and the lock then needs to be released twice to truly release the lock. This parallels the semantics of synchronized; if a thread enters a synchronized block protected by a monitor that the thread already owns, the thread will be allowed to proceed, and the lock will not be released when the thread exits the second (or subsequent) synchronized block, but only will be released when it exits the first synchronized block it entered protected by that monitor.

Though I have not tried it, I guess if you want to do what you have above, you have to use a re-entrant lock.

Reentrant

Synchronized blocks use reentrant locks, which means if the thread already holds the lock, it can re-aquire it without problems. Therefore your code will work as you expect.

See the bottom of the Java Tutorial page Intrinsic Locks and Synchronization.

To quote as of 2015-01…

Reentrant Synchronization

Recall that a thread cannot acquire a lock owned by another thread. But a thread can acquire a lock that it already owns. Allowing a thread to acquire the same lock more than once enables reentrant synchronization. This describes a situation where synchronized code, directly or indirectly, invokes a method that also contains synchronized code, and both sets of code use the same lock. Without reentrant synchronization, synchronized code would have to take many additional precautions to avoid having a thread cause itself to block.