R5 is discontinued, no longer supported and as you have found not Windows 10 compatible.

The version you have R5.0.14 was called DSS Player Pro and was replaced by version 6 of the software which also changed its name to ODMS. Have you upgraded to Windows 10? How are you finding it? Leave us a comment or tweet us #Dictate We approached Olympus for official confirmation of Windows 10 compatibility with Olympus Dictation Management System (ODMS) and as yet there is none, but we can be assured that a) the Olympus techs are hard at work testing every little detail of ODMS and Windows 10 and b) as soon as we hear about it we will tell you. Of course the first thing we did was check Olympus ODMS, both dictation module and transcription module and initial tests are good, no obvious compatibility issues. The upgrade itself was fairly quick, taking around 15 minutes and one reboot. With the launch of Windows 10 worldwide on July 29th, 2015 and the subsequent slow rollout to those who had reserved their copy, we have finally received our update from Windows 8.1 to Windows 10 today. **Update April 2017** If you are using ODMS, either dictation or transcription module, on Windows 10 and/or with Microsoft Office 365 please apply the latest free patch from Olympus – details in this blog Olympus ODMS Patch0016