FOUND THE REASON FOR THIS, PLUS OTHER TIMES I'VE HAD ISSUES.... To help iCloud keep your information up to date, keep your data within the following limits: Calendars and Reminders Total number of calendars, events, and reminders: 25,000 Maximum combined number of calendars and reminder lists you can have: 100 Maximum size of all calendar and reminder data (not including attachments): 24 MB Maximum size of all event attachments: 300 MB Maximum size of a calendar event including attachments: 20 MB Maximum number of attachments per event: 20 Maximum number of attendees you can invite to an event: 300 Maximum number of people with whom you can share a private calendar: 100 Maximum number of characters in a reminder title: 100 Contacts Total number of contact cards: 25,000 Maximum size of a contact card: 256 KB Maximum size of a contact photo: 224 KB Maximum size of a contact group: 256 KB Maximum size of all contact cards: Card text: 24 MB Card photos: 100 MB Supported file types for a contact photo: JPEG, BMP, PNG, GIF vCard import limits: Total number of vCards: 25,000 Maximum size of a vCard: 256 KB (photo + text) Maximum photo size for a vCard: 224 KB …