Question:  How can I get my MS Outlook to work with my Olympus Dictation or Transcription Module?
Upgrade your Dictation Module or Transcription Module to R5.0.11.0.  The latest release has support for Outlook 2010.  However, R50.11.0 cannot support 64bit Outlook because 32bit appications (DM/TM) cannot communicate with 64bit applications (windows system specific).
Source:  DSS Player Pro Release 5011 Fixed Bug List Summary