A new version of the Trimble Positions Desktop add-in for ArcGIS Desktop (ArcMap) is available for download here. The add-in supports TerraFlex on Connect, TerraFlex Offline, TerraFlex on InSphere, TerraSync, and Esri ArcPad + Trimble Positions ArcPad extension field workflows. Please see additional information below regarding new features, improvements, and bug fixes.
Note: The initial release of Trimble Positions Desktop add-in v10.8.1.1 was posted for download on December 3rd and would have displayed as build "(140-f58876bc)" in ArcMap. In the intervening 2 weeks, a few bugs were identified (included in the section below) and fixed. The latest build, displayed as build "(17-02a82f5c)" in ArcMap, was made available for download on January 13th.
Another Note: Trimble Positions Desktop add-in Release Notes are moving to help.trimblegeospatial.com in the near future.