Lets say that I have an 8GB MicroSDHC card. I have 1GB of space left, and I want to sync three albums which can easily fit within that restriction with the right file format. The albums are stored on my hard drive in FLAC format which takes up a lot of space, but the media player that my MicroSDHC card is used by does not support FLAC, but it supports Vorbis/MP3. If I convert the files myself and put them on there, it will work properly but it won't be synchronized with my Rhythmbox library like I would prefer. Rhythmbox, due to not knowing the size difference, assumes that the files I want to sync will not fit and won't let me sync.

In circumstances (such as this example) where songs to be converted go past the filesystem's size limit, an option to transcode the files and analyze the final size before syncing should be present in the sync window upon not being able to sync. The option should only appear if the target device does not support the original format of the song files, such as in the previous example.