"can not find" music

I keep having to "re-add" my music on a regular basis. I store all my music on an external hard drive. Does anyone have any suggestions or ideas?

Jake, the same happened to me and I am using a Mac with an external HD connected to my Time Capsule. The issue is not related to Windows or the PC. It is related to Itunes not reconnecting with the external drive. I assume that you see a bunch of ! signs, one by the side of each song.
The way to fix it is to open the external drive BEFORE opening iTunes. Just go to that drive using the OS interface and double click on any folder on that drive or any song. That will re-establish the logical connection with the drive. Once done that, open iTunes and you will see all the songs mapped properly in the library and the cannot find music message should not happen anymore.
Let me know if that works for you as this might help others too,
cheers,

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