Run showing on watch but won't upload to My Activities

I ran a 10km run tonight, which is showing on my watch but won't upload to My Activities, whichever way I try. It's late now and I'm getting very annoyed about it.
I've found the ttbin files via iTunes and have saved them onto my desktop (I'm on a Mac) The guidelines up to this point, were great, but what the hell does the one below mean?!?!

3. Place the ttbin files in the serial number directory:
Mac: [home dir]/TomTom Sports/[serial number]
4. Restart MySports Connect and connect your watch
5. Go the Settings page (click the gear icon on the top right) and press the 'Try again' button to re-upload the files.

What?
Please would someone explain 3. and 5. in layman's terms?

Best regards,
Ian