Typically, if TT brakes will lock up easily on gravel, odds are they probably have enough braking action to brake reasonably well while being towed on pavement. It's not the most graceful way to check TT brakes; but, it's a reasonably effective check. I'd suggest finding a secluded gravel (or dirt) road and manually applying maximum braking using your truck's brake controller to see if you can lock up the brakes (all 2/4/6 of them) on gravel.
Looks like your brakes are "probably ok" mechanically. That's based on the fact the TT brakes are apparently locking-up on gravel when the TT's emergency brake is activated. Electrically, at least from the TT's emergency pull-switch to the TT's brakes, the brakes appear to be ok, too. However, due to the fact you're not getting good braking with your truck, all your truck's wiring and BC (brake controller) are suspect, plus the TT's 7-wire cable (and plug) that connects between your truck and your TT are also suspect.
If it were me, I'd check the braking voltage (should be ~12vdc with the TT's emergency brake activated) at each brake. I'd also verify braking current at each brake using any ole cheap clamp-on ammeter. You should read close to 3 amps at each brake. Current is more of a definitive check than voltage in this particular situation, because a good current reading shows you have good continuity through the brake's magnet. I'd also make this same voltage/current check while applying maximum braking using the truck's BC (manually, using the BC lever), too. Compare the two sets of readings. Based on your symptoms (less braking with the truck) I'd say you'll probably read lower voltage and current when maximum braking is applied from your truck. If that's the case, further troubleshooting will have to be done to narrow the problem down to the TT's 7-wire cable/plug (to include grounds) and/or the truck's wiring and BC.
Good luck!
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