Yes I know exactly the problem...
When I use my 256 briefcase, I am not able to use the original leather straps since they are too long for me even though I adjusted it to the shortest. If I use the original leather straps, nearly the entire 256 falls under my hip when I wear it on my back lol
So I usually use my 230 leather straps on both 230 and 256 and it seems to be better.
By the way do you think of purchasing another filson? and does your tote look perfect to you?
I've heard of people cutting a new hole into the strap, higher up so it will sit higher on their body, so that's something you could try.
There are a few other configurations you can try too. I've done one which is a bit hard to describe but I'll try. You loosen the strap to the longest it will go and then run it through between the handles and put the pad ends tucked outside, and then you basically have two loops in the strap, one on either side of the handles, and I put my arms through those and wear the briefcase like a backpack.
As for me and Filson, I've had a few items over the years, and even though it totally fits with my philosophy of quality, heritage, and my current style of Americana/Workwear and minimalist military, I've basically decided that they're just too rugged and overkill for me, just impractical really. The prices are a little high, but very fair, and available on discount so that's not my issue. My problem is they're all overbuilt, too big and chunky and heavy. For example, I bought the dopp kitt... looks cool, got a good deal, and tried it twice and realized the bag itself is heavy, huge, and just totally overbuilt. I switched to a simple cloth zippered thing I got for free somewhere and am so much happier. I bought the 257 and got rid of it. Took me several steps to button the handle, then the flap, then unzipper it, then the zipper scratches my hands and computer every time, and the thing weighs a ton so even empty it's shoulder and back breaking. I once travelled with it, and never again. No strap to go on the suitcase, and standing around at the airport this thing breaks my shoulders. So it's a fun idea but in the end I'm more or less done with Filson. Just doesn't work for my lifestyle. I've not just got a backpack which frankly I hardly ever use (too small and too heavy even when empty), and a oil canvass tote which again I think I haven't even used yet and had for 6 months. I use a thin canvass bag instead and it folds into my pocket when it's empty. So yeah, funny turnaround I guess but in the end I've just realized that even though something is great, it doesn't mean it's great for me. I love their look, style, philosophy, etc (despite all the current issues people are complaining about), but I think it's just not my thing.