"The request failed. Please try again error creating a Skype meeting within Outlook 2010
"The request failed.  Please try again error creating a Skype meeting within Outlook 2010
error message: "The request failed. Please try again. Make sure that you are signed into Skype for Business."
error message: "The request failed. Please try again. Make sure that you are signed into Skype for Business."
Found a solution for this issue.
  It seems to be
pertaining to the auto complete cache.   Clearing this cache either by manually clearing
it  from the outlook options menu --> mail  --> clear auto
complete cache.  or by starting outlook with the 
/cleanautocompletecache switch. 
It resolved it on the few users that have been having
this issue.