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How to Fix Error on Outlook: "The request failed. Please try again. Make sure that you are signed into Skype for Business."


Symptoms:


When attempting to create a Skype meeting within Microsoft Outlook I am receiving the following error:

"The request failed. Please try again. Make sure that you are signed into Skype for Business."



Workaround:


It seems to be pertaining to the auto complete cache. clearing this cache using one of the following methods listed below:
  • manually clearing it from the outlook options menu --> mail --> Empty Auto-Complete List 


  • Or by starting outlook with the /cleanautocompletecache switch. 
  • Or to create the following registry key: 
  1. Subkey location: HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Lync\AddinPreferenceDWord
  2. Name: RecipientResolutionMode
  3. Value data (decimal): 2

It has resolved it on the few user that have been having this issue.





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