Aimp sometimes resets all user settings. And sets all in default. Sorry for my english.
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It's set to preserve files even if it crashes/improper shutdown and you then upgrade it. However, if you set a file association within AIMP itself, it will either open in local mode or with a separate set of settings that will be lost when it's run properly next time (by starting AIMPPortable.exe). You need to manually associate AIMPPortable.exe with your files for it to work properly.
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