Outlook 2010 iCloud Add-In causes emails not to send
I just started using iCloud to migrate my Outlook 2010 contacts and calendar to iCloud and then to my iPhone 5s.
There's an intermittent problem (although I can now make it happen, so not so intermittent anymore) where my emails will not send unless I disable the iCloud Add-In. They appear as Drafts (not italicized in my Outbox) and will not send until I disable the iCloud Add-In, and go back into them and click 'Send' again.
Disabling my iCloud Add-In means that my Contacts and Calendar do not update to iCloud (and thus not to my phone either), so I have to be careful to remember to enable the iCloud Add-In immediately after getting my emails sent.
Does anyone have this problem and/or a fix for it?
Windows PC, Windows Vista