Follow the below steps to reset the connection first, then click the 'try again' button.
In your Outlook Inbox:
1. Go to the Yesware Sidebar.
2. Select the Menu tab and sign out at the bottom where it says "Logged in As".
3. The activation window will appear next where you can re-activate/sign in with Microsoft sign-in credentials.
Please then go to app.yesware.com and click your email address in the top right-hand corner and select to log-out. When prompted, please log back in.