Sorry if this is not the correct spot for this

I cleared my Auto-Complete data in Outlook 2013/365 on Exchange.  Now to update it I am trying to "send" a message to ALL of my contacts in offline mode.  Once it hits my outbox I was going to delete the message prior to going back online.  When I try to send in offline mode I get an error instead of the message moving to the outbox to be sent once I go back online.  

Is there a better way to update the auto complete data from my contacts list or is there a trick to working offline and sending the message.  In the past with a local version of Outlook 2007 I was able to "send" emails from a plane and once I had internet connection the messages would actually send.  It seems that I cannot send a message in offline mode.  

Thanks