I have MS Outlook 2010 v. 14.0.7106.5003 (32 bit) and have been using it since 2010.  Lately, when I start an email in outlook and type in a name that I know I've sent mail to before or a new contact that I just added in Outlook, it cannot find the name even if I hit the To button to look for the name.  I have never understood why it sometimes makes a vcard and sometimes doesn't but it used to could find either but not now.  I have to do a general search in my old emails, find the email address and paste it into the To box.  Recently but before syncing to iCloud I was trying to create a lengthy new mailing list.  I typed in the new contacts and then had difficulty finding them to add them to the mailing list.

 I sync to my iPhone and recently began syncing to iCloud but part of the problem predated iCloud.  I have been syncing to iPhone for a long time and I think this problem started pretty recently .  It got worse when I started syncing to iCloud. When I hit the To button in email now, it cannot find anyone at all.

I love Outlook but I have a new iPad on order so I have to be able to sync with my iPhone and iPad.