If I rip a song off CD via lossless, what format is it in? Will it stay in that format when transferred to iPad?

To transfer songs/movie you can only have certain formats

It will most likely be mp3. Ipad can read mp3 but prefers mp4 format

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What format is the lossless setting in iTunes?

Why do you want lossless? In 99.99% of cases you'll not hear the difference between lossy and lossless.

I'm not sure it will work, but if any settings will work these will be the ones.

First change the CD Rip settings to Apple's Lossless Encoder; found in iTunes Preferences, Then on the iPad sync settings, on the Summary page, uncheck the the bit rate conversion option.



Though, as you can tell by the settings in the screen shot, I myself don't think it's worth the trouble or loss of space on the iPad.