Hi. You may not want to hear this, but I don’t think using iTunes is the best way to upload apps to your device. You’d be better served using xCode. The benefits of this are that xCode will tell you if you’ve got a problem with your certificate. As well you can view the console output of the device for debugging purposes.
Also, you should be extremely cautious about updating any of these while you are developing your app:
- OS X - Updating may invalidate your certificates and may require an xCode update.
- xCode - May also cause certificate issues.
- iOS - Same deal
I pretty much lock down my iOS dev system and devices till I’m completely done. Otherwise I find myself needing to regenerate new certificates.
If you’re willing to try it, this video shows you most of the steps you need to follow to use xCode for uploading to your device and for debugging.
https://www.youtube.com/watch?v=2h4zMMN_IGE
Note: My video assumes you have all the certificates, etc for your machine and app generated and installed.