It sounds bass-ackwards, but now that you have the ditch line struck off, start at the outlet end. Tilt the box slightly forward, so the material tumbles forward. It doesn't take a lot, just so it is always barely creeping on the face of the blade. Once the box blade is to full capacity, it should theoretically float across previous passes, if you have the top link adjusted properly. Rolling/moving dirt on the face of the blade moves a lot easier, than a box full of dirt just crammed in there.
I don't know if your scarifier teeth can be set at different depths, but setting them just an inch or two deeper than your cutting edge should be enough. It does take a certain amount of crowd, to force the dirt to roll on the blade, rather than trying to move a lot of fluff. After multiple passes, it should get longer and smoother.
With the leaves and debris pictured, I can only imagine you made a lot of trips, with dirt and debris in the box blade, dragging it across all of those leaves, further towards the outlet, getting a massive gob of both behind you. Personally, I would have (and maybe you did) again started at the outlet end, and made multiple passes clearing the surface of leaves, etc., just prepping it to get to the dirt, putting it off to the side, out of the way,yet close enough to retrieve it. It would make a great dressing/mulch for the spoils from the cut, to prevent it from washing.
I have no idea how far of a cut it will take to fill the box blade to capacity in that material, but guessing 10' - 15'..?? Looks like you've made enough passes, you ought to have a good idea. If you are at near grade on the outlet end, making a longer loaded pass across that portion, so as to float across may be needed. If it needs to go a lot deeper, make shorter passes, to make a cut to the end.
Once you get the gist of it, and how well it works, the end result becomes much clearer. I'm sure you'll have to make more than several adjustments along the way. but a couple turns on the top link, or nudge if it's hydraulic, or bump the 3 pt. arms to get across a low spot, gets easier, and easier.