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Each time I boot up I end up with a DOS C: prompt and have to manually change dir to Win95, then type in Win in order to run the program. I also get a warning that the Windows Configuration Manager failed to run and some devices might not work properly.
Your registry is corrupt, and/or your hard drive is going bad.
Just ran into this problem yesterday.
Or you could have lost some start up files. But defintly run a dos scandisk, and should probably try a reinstall of windows over itself and hope that works. But are most likely looking at a fresh install to a new directory, that is if the drive is not shot.