Videos taken on the iPhone will not sync to the iPad I have several hundred pictures and a hundred or so videos that have been taken with my iPhone 4 and 5s. (90%/10% split roughly). These are all in iPhoto and have imported fine. Everything can be viewed on my laptop without issue.

I want to have all of these pictures and videos on my iPad (4). I have checked the sync all photos from iPhoto and include videos.

All pictures and most videos copy. Several videos do not. All that do not work are from the 5s. That said, I do have some of the videos that I know were taken with the 5s syncing fine. (slo mo)

I can say that I have a few 1080p videos that were synced. There were a couple that did not. There were a couple of the slo mo videos that synced and a couple that did not.

The first time I attempted to sync, I did get the warning message in iTunes that some of the videos were not compatible with the iPad, but on subsequent attempts, the message wasn't shown, iTunes just silently skipped these files. (Subsequent attempts after un-syncing, reboots, etc)

I really want to keep my photos and these types of videos in iPhoto for ease of syncing and browsing. What can I do to convince iTunes that the iPad really can play these videos that the iPhone took? Or how can I debug what the issue really is?
The fact that iTunes silently skipped informing you that it did not add the videos is most probably caused because you checked the "Do not show this message again" upon the prompt the first time. 

Are the videos in MOV or MP4 format? You can try installing the free VLC app on your iPad  and then add any video files to that app via iTunes File Sharing. Simply:


Run iTunes and connect the iPad
Enter the iPad settings in iTunes and navigate to the "Apps" tab
Select the VLC app under "File Sharing" (scroll all the way to the bottom to see "File Sharing")
Click on "Add files..." and select the videos from your PC
Click on the iTunes "Apply" button.


This should add the videos to the VLC app on your iPad from where you can access and play them.