With the release of 15.39 (170905), we release a new feature to trigger authentication prompt when account is disconnected.

Previously, if you dismiss the authentication prompt of the disconnected account in Outlook, you will have to quit and relaunch Outlook to show the prompt again for authentication.

Now, with this new feature, you can trigger authentication prompt for the disconnected account on-demand, by clicking on the "disconnected" icon on the sidebar next to the disconnected account, or using the "Send & Receive" button on the Ribbon.

1. "disconnected" icon on the sidebar

2. Send & Receive" button

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