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Not Syncing Actions Performed in Offline Mode

Kinda freaking out here. I have 100s of offline actions I performed in Entourage on a recent flight that won't sync. Each time I try and sync I get the error message below followed by 2 more error messages that basically say that I'm going to lose everything I've done unless I fix the problem. No idea where to start here. Happy to share shots of the other error boxes, but I can't afford to lose the changes I made and emails I drafted. Any ideas, tips or suggestions would be hugely appreciated!
 
sad I’m frustrated
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