This can occur when there are authentication issues between your email address and Yesware. To resolve, please try authenticating in your Outlook web mailbox first by doing the following: 

• Open a Chrome browser, visit Outlook.com, sign-in to your account.
• Once logged into your mailbox, click into an email in your inbox and select the "More Actions" button (highlighted below).

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• Select Yesware > open Yesware
  
• Log-in when prompted

Once you have successfully logged into your Outlook web application, if you close out of your Outlook desktop application and re-open it, you should then be logged into Yesware in your desktop.

If you are continuing to experience issues, reach out to support@yesware.com.