External Hard Drive Sync Issue with Deletion

So I recently set up my external hard drive to be my main music folder. The external HD runs continuously on my Mac Pro desktop. I've set it up so the external HD is mounted remotely on my laptop, so I can get all my itunes music without having to physically connect to the drive. I've set it up and everything loaded in, works fine. . . .
But then I tried to delete some files using itunes. It deleted them from my itunes library alright. But they did not delete from the external HD. Furthermore, it did not even prompt me to "keep files" or "delete from library".
I then ran an test. Could i change ID3 tags? Maybe I didn't have write permission or something. Nope, I was able to change ID3 tags just fine.
Does anybody know a way to make this work? Why it doesn't prompt me to "delete" my files?
Thanks.

is there perhaps a problem with permissions? does this problem happen whether you're using either computer or only with the laptop? maybe the laptop only has permission to delete songs from its local database and but not to delete the tracks from the shared master music folder.
i use a wireless external drive for my music too. though i've never had your problem, i have experienced something similar. if i delete a track via Finder then open iTunes, it still thinks the track is there. so if i then delete it in iTunes, it doesn't ask me if i want to keep the files or not, it only removes it from the iTunes library. in other words, i don't get prompted to keep or delete tracks if the track is already gone from the hard drive but still in the iTunes database. i haven't tried changing the tags in that scenario however.

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Hard drive syncing issues "!" HEEEELLLLPPPP!

Hard Drive syncing issues "!" HEEEELLLLPPPP!
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<hr>
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External Hard Drive Sync Issue with Deletion

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