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First let me say that I understand what you are saying about it not always being you who breaks things but in this case I have had the same Android version for quite some time and this issue started the same day I got the 1.4.1 update.
In the previous message when I said shutdown I meant powered off not sleeping.
When I quit listening I always do the same thing: I pause and hit 'home' or 'back'. I never do a 'Quit Winamp'.
When I return to the app I always do it by clicking the lighting bolt on the Winamp Widget (small).
What I noticed today with 1.4.2 is that it saved position 1:30:01 in the file and so far has been 1:30:01 every time I return to the app. That is the position where I first paused it this morning.
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