I don’t change my stirrup leather length until I’m jumping over 3’. And even then it’s just one hole.
I totally agree with you… outside of it being “easier” to sit the gaits because there’s more leg on to provide the friction (I don’t know how to well describe what I’m trying to say, but it is easier to sit all gaits with a longer leg for me, personally), there is really no reason to shorten/lengthen stirrups.
I shorten my stirrups five holes when I’m jumping 1.10m and up because my horse is a big rubber ball and that works best for both of us. I can jump him with no stirrups at all or in a bareback pad, so the length isn’t what is keeping me in the saddle or anything, but it’s simply easier on his back if my stirrups are shorter. It depends on the horse and the rider and what is most effective for them. I don’t go around peering at other people’s stirrup length; I care about what works for me and that’s it.
I agree that it’s not useful to always flat in one length and jump in another, but the benefit of usually flatting with longer stirrups is exactly as has been said, which is that you get more leg real estate on the horse, making it easier to do lateral work and such. Every one of my eventer friends has a dressage saddle and a jumping saddle, and my trainers also have XC saddles that are different from their stadium saddles (much more forward flap, billets set back farther, for example) for some of their UL horses. They all seem to handle multiple stirrup lengths and saddle styles just fine!
So, it seems to make sense that if your horse isn’t responding to your aids with shorter stirrups your flatwork probably needs improvement. If I’m jumping big I flat and begin jumping with my longer stirrups until the fences go up and then I shorten them, again for his back. If there is a big shift in how the horse goes when one does that one simply has to figure out where the holes are (core strength, effectiveness of seat, balance, etc.), and work to get rid of them. If your horse jumps sort of flat, or you never jump over bigger fences then there probably isn’t much point in changing the length. But again, it all depends on what works best for that horse and rider combination.
Someone else mentioned the idea that perfect dressage isn’t going to produce perfect jumping. That is absolutely true, but it’s an essential part of it for most pairs at the higher levels, I think. Jumping is flatwork with jumps. If you watch the best jumper riders in the world their horses are going around beautifully connected, responsive to the aids, able to go from a gallop to a much shorter stride without losing balance in the blink of an eye, and so on. How do you think those tools are developed in the first place?
My wonderful trainer who passed away a couple of years ago was an incredible dressage instructor, and he always used to say that my flatwork didn’t need to be perfect like the dressage or eventer people, since I don’t usually compete in that ring. Sometimes we do a CT or a dressage schooling show, although I’m terrible at remembering the tests. He said that my flatwork DID have to be effective, though, because when the jumps go up and the questions get harder the holes in the flatwork will be very apparent. Up to 1.10m with my current horse I was able to get away with having those holes because my horse is a stellar athlete, but moving up to 1.20m they became problems I had to fix for us to be competitive.
It’s a way of thinking about riding more holistically that has really helped me, especially with this particular horse, but again, everyone has different approaches!
[ETA: I am sorry for the novella. I’m getting ready for a new semester so of course this is more entertaining than writing a syllabus! I’ll get back to work now… 
]
For jumping, I want my horse to be straight, rhythmic, and on the aids. The flat work I do to establish this includes basic “dressage” movements such as leg yield, shoulder in, haunches in/out, etc. I have my stirrups longer because all of this lateral work is much more effective with longer stirrups. When my horse is warmed up and ready to jump, I shorten my stirrups so I can have a lighter seat for jumping. Hopefully I’ve done my homework and my horse is indeed straight, rhythmic, and on the aids.
There are a lot of reasons to change stirrup lengths when going between flatting and jumping. But to your question of, what I would call as a school teacher “teaching to the test”, you school your horse so they understand the cues and movements in isolation, so that they can get really good at it before they incorporate in to more challenging tests. So, you teach things like lengthening, collection, moving off the leg laterally, etc on the flat. This is generally accomplished easier with a longer stirrup so that the communication is clearer. When you start adding those skills in to jumping, you should have already established a basic level of understanding with the horse about the expectations. Jumping adds a level of difficulty, but it also has its own consequences. When a horse ignores your aids on the flat, they get stronger aids, but that is generally the only consequence. When a horse ignores your aids while jumping, they make jumping more difficult for themselves. So the jumps can help reinforce why they are being asked to do the skill. The rider is still cuing the horse as to what they want, it just may not be as precise as on the flat, but that is where the horse has to start making connections and thinking for themselves. That is one of the differences at times between a dressage horse and a jumping horse, thinking for themselves. It is not always necessary for a dressage horse to be thinking on their own, although a good dressage rider will want a horse who is, yes, obedient, but also thinking. For jumping, it is necessary for the horse to think for themselves,
To your point about horses not understanding the cues as well when the stirrups are a different length, that tells me the horse is not very well schooled. I have a 5 year old horse who is still learning many of the basics, but generally has a good foundation. I am 5’10, obviously a bit taller than most women. Just about every other person who has ridden my horse is at least 2’’ shorter than me, and at least one weighs about 95lbs and is about 5’2". He does just fine and he figures it out.
That’s what we all want to know. I was wondering why you thought it was such an easy fix.
Shorter stirrups allow your joints to act more effectively as shock absorbers.
This making it harder, because your position is in a prime position to counterbalance the “bounce”, to instead absorb it.
This was going to be exactly my point. If we are to extrapolate the logic that there is no reason to school a horse at different stirrup lengths because the horse is tuned to respond to just one narrow band, then there would be no way riders of various leg lengths and shapes could successfully ride that horse. Which I hope we can all agree is a training hole at least and handicap at worst.
I don’t understand how stirrup lengths have any effect on influencing the biomechanics that need to happen to supple a lower level horse. Do people really think dressage means long stirrups? Sure at the upper levels but if you’re just using it as a tool it’s the biomechanics that matter not the stirrup length. I can bend a neck and move shoulders and hind quarters in both short and long stirrups. Sometimes it’s a we bit harder to get a leg yield with short stirrups and a crop, but short stirrups and a dressage whip can work… As long as the horse is coming over the back and improving its okay to start that way and lengthen as the horse develops and the rider gets comfortable over time.
I put my fourth level dressage horse in the jumping saddle once a week or so to play around with canter poles. My stirrups are probably four holes shorter in the jumping saddle than my dressage saddle. And yet, miraculously, my horse understands “exactly” the same leg aids, no translation necessary.
I don’t know why everyone got caught up in stirrup length as some litmus test for “real dressage”. There were arguments being made that Horse X is a finely tuned instrument that cannot be exposed to a longer leg. That is the angle I was responding to.
You are a sample size of 1. Maybe you are a very accomplished experienced rider. Maybe you are able to expertly signal to your horse from a monkey crouch like Willy Shoemaker for all I know.
Many/most riders will find it helpful to lengthen their stirrups to get a more open hip angle and drape more of their leg around the horse, thus better effectuating leg aids.
Does this mean you need stirrups at some designated length to do “real” dressage? No. Dressage is merely a deliberate philosophy of training that can be done with any horse, in just about any equipment.
Might it be easier for most riders to find better leg contact through longer stirrups? Yes.
Is it some huge arduous task to pop one’s stirrups up and down during a ride? Seems so, although my pony club leaders would have anyone complaining riding WITHOUT stirrups for a good 20 passes around the arena.
They aren’t fictional at all. Just because you haven’t run into them doesn’t mean no one else has. I’ve run into two of them, who acted just like described, mocking me (I come from a HJ background and hadn’t had lessons in over a decade) and ridiculing my OTTB as useless. They basically turned me off to anyone who touts themselves as a dressage trainer. I’ve ended up at an eventing barn where I’m finally learning dressage. So yeah, I get that you haven’t had this happen, lucky you!
Well, when I was 12, some fancy HJ kids spit on my rescue horse at a clinic and called her a glue stick but I choose not to take a couple of isolated events to represent an entire riding culture.
Whoa! What monsters raised those monsters?
I didn’t say an entire riding culture,I said two. They did impact me; I made the adult decision to find other instructors. I didn’t get butt-hurt, I moved on to someone who didn’t berate me or my horse or tell me I could never do “real” dressage with him. 
it so happens this person is an eventing instructor, but teaches dressage and is lovely.
I’m just pointing out that yeah, in the dressage world some few do act as snooty gate-keepers, but no one you’ve interacted with has that’s all.
Just as you have pointed out there are “mean girls” in the H/J world.
Apparently you weren’t a member on the dressage forum about a dozen years ago. The WD skepticism and outright derision were real.
Fair enough! I suppose my concerns are largely unwarranted then.
That’s…
Ok you’re right, I’ll leave now.
Why? It’s just fine to own what you wrote and say you misspoke, or exaggerated, or had a brain fart. There’s no reason to leave.
I mean, there are going to be gate-keeper types in all disciplines. Hunter/jumpers certainly has that issue as much as any other discipline. And of course you will run into snobby, elitist people. We have a very expensive hobby that takes a lot of time and energy. But if you are trying to participate to some level, most good riders/trainers will accept you. If they don’t, why are you bothering with them?
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