There are times when I feel like I’m not giving Dragon Naturally Speaking a fair shake. I see so many people out there who swear by it. Who think it’s the best thing since sliced bread.

My experience with the software has never backed up those glowing recommendations, but I figured maybe I should give it a try. So I was going to do a new feature. A year of Dragon Naturally Speaking. A year where I used the software and really dedicated myself to getting the most I could out of the software. See if it made a difference in my productivity.

So with that in mind I busted out my recorder over the weekend and dictated some stuff. I did it in four minute increments which I’ve discovered yields about 500 words when I transcribe the file. I plugged those in and got to trying to correct them.

The only problem? Nothing was working correctly. I started correcting one four minute file and everything was fine. Then I did a second file and started working, but the whole thing froze. Dragon refused to respond for a couple of minutes. Everything else in Windows worked fine, and clicking out of Parallels showed that my Mac was working just fine as well. It was only Dragon that had completely shit the bed.

Finally it came back up and ran through all the commands I’d given it while it was frozen and I was trying to get things to work. Which resulted in a mangled mess. Dragon told me it had encountered a problem and I needed to restart.

No fucking shit.

So I restarted Dragon. I tried using it again. Only this time after doing some transcription I ran into an issue where I couldn’t correct anything. A weird error manifested that I’ve seen a couple of times now. The upshot is that I’ll tell Dragon to select text, but it selects the wrong text. It’s as though where Dragon thinks the dictated text is and where it actually is in Dragonpad gets out of sync because it always selects a part of the text that is the same distanced away from what I’m trying to select.

Needless to say this renders any corrections completely useless.

I figure maybe the problem is that I’m trying to do all of this in Parallels on my Mac. Maybe there’s something about the virtual machine that isn’t playing nice with Dragon. So I dust off my old Surface Pro and try to get it working, only to be confronted with the same out of sync text/dictation error I was getting on the Mac in Parallels.

Huh.

Finally, in desperation, I trued running Dragon for Mac. It gamely loaded up and then promptly crashed and asked if I’d like to send in an error log.

The one bit of text that I managed to go through and edit/correct using Dragon took me about twenty minutes to get through on top of the four minutes I spent dictating it into a recorder in the first place. I could’ve typed that out in twelve minutes. The errors and troubleshooting I went through trying to get Dragon to work correctly on my Mac and Surface ended up wasting a whole morning.

Needless to say my “year of Dragon Naturally Speaking” has ended before it could really get started.