The standard sequence of things to try when your iPhone, iPod, or iPad start acting strangely are:
- Shut down and restart. That is a full shutdown achieved by pressing and holding the on/off/sleep/wake button at the top of the device until a shut down slide bar appears on the screen. Slide the shutdown then allow time for the device to completely power down. Wait another 30 seconds or so then restart by once again holding down the on/off/sleep button.
- Reset your iDevice by plugging it into your MBP and when iTunes launches, selecting the iDevice and clicking on the Reset button. This will...
- Backup your iDevice
- Reset the firmware and settings to the factory default
- Restore everything in the iDevice from the backup it just made. (NOTE: this can take a while, especially if there are lots of tunes and images that have to be reloaded, so be patient.
Generally that will take care of most synch and other problems with iDevices.
The other thing I have encountered from on occasion is a corrupted tune, or I suppose it could also be a corrupted calendar file, that will stop the synch process. In that case it is a matter of identifying the corrupted file and..
- delete the file
- restore the file from a backup or in the case of a tune purchased in iTunes, redownload the tune.
The log files might be helpful in identifying and offending file if that is the case.