I have a Jailbroken iPhone 3GS, and I had 5.1GB of space consumed by the ‘Other’ category.

I eventually managed to figure out where the space was going by making use of the following tools:

Pretty simple: Macroplant Phone Disk uses MacFUSE to present the iPhone filesystem natively. GrandPerspective constructs a treemap of any directory. So, mount the phone as a disk with Phone Disk, point GrandPerspective at the disk, hit go. It definitely takes a while – on the order of 20 minutes for my 32GB phone.

Once the treemap was built it was pretty obvious that the space was being consumed by some stray movie files that somehow ended up getting synced to my iPhone. I don’t remember when or how I put them there, and I forget exactly where they were now, but I believe the folder name was related to some jailbroken media sync app that I had installed at some point.

Note that GrandPerspective is freeware but Phone Disk is a trial with 100MB transfer limit. Fortunately the total amount of metadata GrandPerspective needed to pull down to reconstruct the treemap of the filesystem was only 98MB. Also, prior to GrandPerspective I tried using Disk Inventory X (also freeware) but it crashed when I pointed it at the iPhone file system, presumably because FUSE filesystems smell different and/or don’t support whatever disk IOCTL or other bizarre thing Disk Inventory X wants to do? I was surprised, but not enough to actually try to figure out why it didn’t work.