Datto Windows Agent: Server boots into recovery mode after initial install of DWA on Windows 2008 R2

Topic

You are able to install the Datto Windows Agent on Windows Server 2008 R2 SP1, but during the initial reboot after the install, Windows Server boots into recovery mode.

Environment

• Datto Windows Agent
• Windows 2008 R2 SP1

Description

If your Windows Server is missing Windows update KB3033929 (external link), it can cause Windows Server to boot into recovery mode during the initial reboot after you install the Datto Windows Agent.

Resolution

Apply the security patch to your protected machine by using either your built-in Windows update utility or by running the standalone installer from Microsoft (external link). After applying the patch, the affected system should boot normally.