Question: Does Olympus DSS Player Pro R5 support email accounts using TLS & SSL security protocols?
Yes, the Olympus DSS Player Pro Release 5 Dictation & Transcription Modules support email accounts using both TLS and SSL security protocols. 
When using TLS and/or SSL, I’ve found the best way to configure the email account is to add it as an account in MS Outlook, then create an Email account in the Olympus using select the ‘Outlook’ option.
Verification Source: In-house testing & Digualle, Olympus Product Manager