Movie not copying from Mac to iPad

[PlateStacker]

I've searched many of times for a way to resolve this issue, and have found no real answer so far.

I've got a video I'm trying to transfer from my Mac to my iPad. I've transferred hundreds of videos and never had a problem.
[Your File] was not copied to the [Device Name] because it cannot be played on this iPad. Is the message I'm getting.

Some people say you can convert the file to be iPad playable thru iTunes. When I try this, it gives me yet another error message. I even tried downloading a third party app and still nothing. Can anyone give me a way for this to work, that would be great.

Thanks


OS X Mavericks
iPad2

 

[rgarjr]

Convert the video with handbrake maybe?

 

[PlateStacker]

I don't have Handbrake. Will it work then if I get it? I can't believe no one else has givin a solution..