ITunes won't automatically open

When syncing my iPhone, on my phones page I have the box checked to open iTunes when phone is plugged in but it's not opening. Why not?

This may have something to do with iTunesHelper not running. I had the same issue with the latest versions of OS X and iTunes – even reinstalled iTunes recently (for another reason) but still could not get to iTunes to automatically open when I connected my iPod.
Here is what you can try.
1. Open System Preferences
2. Open Accounts
3. Select the user where you use your iTunes
4. Click on Login Items – if you see iTunesHelper there, make sure it is checked to open when you automatically when you log in. If it is already checked – I don’t know what is wrong, you can try the following steps but I am not sure. If you cannot see iTunesHelper – continue on…
5. Leave this “Login Items” window open (do not check the “+” – just leave the window open)
6. Open a finder window
7. Select Applications
8. Select iTunes – don’t click to open it – just highlight it.
9. Now, with iTunes selected, look at icons on the menu bar of “Applications”, you should see a icon that looks like a little gear called “Action” – select this and choose “Show Package Contents”
10. Then – Click Contents – Click Resources
11. Scroll way down to the almost to the bottom – there you will see the little iTunesHelper (the icon looks like iTunes)
12. Select and drag this icon to the “Login Items” window you left open in step 4 –
13. Click the little box
14. I logged out at this point, and even rebooted – YES, I know the “reboot” comes from my life with Windows – sorry, but since with an Apple it only takes about 40 Seconds – I figured it wouldn’t hurt.
15. Now, if you have already selected the “Start iTunes automatically when ….” it should start.

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