If the issue occurs only on newly-inserted CalendarEntry objects pointed to by the to-many relationship, then it's possible that they don't yet have permanent object ids. This is easy to debug via just dumping the object id and checking to see if it's temporary or permanent.
I've seen this happen when the containing object in the to-many relationship is retained; it seems that so long as it is retained, the to-many contained objects in the relationship never get to a point wherein they obtain permanent ids. Somewhat easy to debug by putting the application in the background and restarting it; the backgrounding will typically force the UIManagedDocument to save, and things will start working as you expect thereafter, as the CalendarEntry entities will have been assigned permanent ids and thus will become fetchable.
So far as saving the UIManagedDocument, you don't have control over when that'll happen when using a UIManagedDocument. The best thing to do is schedule a save to occur in the future, via updateChangeCount:UIDocumentChangeDone, but again, it'll happen 'soon', but not deterministically, i.e., it's not possible to know when it'll happen.
To resolve the temporary vs. permanent object id issue, if that's what you're seeing, try the following category on NSManagedObjectContext; call it after you've completed inserting new CalendarEntry objects, in order to force the issue.
// Obtain permanent ids for any objects that have been inserted into
// this context.
//
// As of this writing (iOS 5.1), we need to manually obtain permanent
// ids for any inserted objects prior to a save being performed, or any
// objects that are currently retained, that have relationships to the
// inserted objects, won't be updated with permanent ids for the related
// objects when a save is performed unless the retained object is refetched.
// For many objects, that will never occur, so we need to force the issue.
- (BOOL)obtainPermanentIDsForInsertedObjects:(NSError **)error
{
NSSet * inserts = [self insertedObjects];
if ([inserts count] == 0) return YES;
return [self obtainPermanentIDsForObjects:[inserts allObjects]
error:error];
}