Data added to iphone will not synch with PC or Macbook

I currrently have a PC running Windows 7 and sync Outlook to my iphone and Macbook Air via iCloud. It works well from PC>iphone>macbook. However, data added to my iphone will not sync to either the PC or Macbook. I also noticed that sync from PC stops after 1-3 days and I must open and close Outlook to have it restart sych, which is automatic.
Thank you,
Mike

Hi pm.cm,
Welcome to Apple Support Communities.
It sounds like you’re seeing repeated prompts to authorize your computer when trying to sync purchased content to from your iPhone to your computer. Make sure your computer is authorized with all Apple IDs that were used to purchase apps on your iPhone and then try the suggestions in the article linked below.
iTunes repeatedly prompts to authorize computer to play iTunes Store purchases
I hope this helps.
-Jason

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