Can't Move Items to iCloud Calendar

I'm running Office 2013, and today I started receiving errors when I'd try to drag an item from a different calendar in Outlook to my iCloud calendar. I've done this before with several hundred items (large family, I get in make sure everyone has what they need on their calendar). So, today the error I received was
"Cannot copy the items. Failed to INSERT Message in Z1Cache: near "#IND": syntax error. SQL INSERT INTO IPM.Appointment" and then a ton of numbers.
At first I just disconnected my account from iCloud, restarted the computer, restarted Outlook clean, then reconnected my iCloud account. That didn't help, so I uninstalled iCloud all together, reboot, opened Outlook, closed Outlook, cleaned my Apple folders in AppData, reboot, then downloaded a new copy of iCloud and installed it. Lo and behold the I got the error again.
Any ideas what I can do to get rid of this?

Hello nicolefromwinterthur,
The article below may help explain how Microsoft Outlook calendars appear on your computer and iOS device. Are you making your new entries in the iCloud calendar on your PC ?(see pink highlight in the image below). I've highlighted the information about Outlook Calendar for you. Click on the link for complete details.
iCloud: Microsoft Exchange behavior with iCloud - Apple Support
http://support.apple.com/en-za/HT202375
Microsoft Outlook Calendar: Outlook also displays iCloud and Exchange data separately. Exchange data typically appears within the My Calendars section, as in the example below with Calendar under My Calendars.
Outlook has a descriptive note about which collection your calendars belong to next to the Calendar title in the left panel of Outlook. Your local Outlook data (that is, data not belonging to either iCloud or Exchange) also appears within the My Calendars section of Outlook. Local Outlook data will have the description Outlook Data File next to the calendar title, while Exchange data will have your Exchange email address or account name next to the Calendar title. iCloud calendars have iCloud next to the calendar title, and appear in the iCloud section of Outlook Calendar instead of the My Calendars section.
Cheers,
- Judy

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