John, I run into this a lot as I do several different transcription jobs and some of them require timestamps. I find if I make sure the software is opened up underneath the document I'm writing into, it will do the Cntrl T/Cntrl V to insert the timestamp. Then it will do it consistently for the rest of that particular piece you're on. Sometimes I attach the Word document to the recording in the software and this helps as they are joined already. I hope this helps.