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I'm running Ubuntu 13.04 right now. If I upgrade to Ubuntu 13.10 will I have to reinstall all of my currently installed software? Like GIMP, Dropbox, RecordMyDesktop, etc.

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It depends on how you upgrade Ubuntu :

  • If you reinstall Ubuntu from scratch (with a Live DVD or an USB key), you will likely have to reinstall everything. It depends on how your hard drive disk is partitioned, which partitions you are keeping and what those kept partitions contain. If you put everything in a single partition you will have to reinstall everything, even your personal datas.
  • If you do it from the Update Manager, it should be fine. However there are some changes in packages and some programs might be broken or might not running fine.

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