Issue

Users can’t access their computers via Remote Web Workplace on an Windows Small Business Server 2008. Following error is displayed:

VBScript: Remote Desktop Disconnected
And internal error has occurred (error 50331588). For more information, please contact your network administrator or Microsoft Product Support.

Cause

Issue was caused by an expired third party certificate not replaced in TS Gateway Manager on renewal. Certificate had been renewed and updated in IIS Console, however this does not automatically updates certificate in TS Gateway Manager.

Solution

Manually replace certificate in TS Gateway Manager:

• mmc.exe > File > Add/Remove Snap-in > TS Gateway Manager > Add > OK
• Select your server > Properties > SSL Certificate
• Choose “Select an existing certificate for SSL encryption (recommended)“
• Click “Browse Certificates” > Select your up to date certificate and click Install
• Click OK to close opened dialog