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PaperclipPerfector  3mo ago (text post)   2199 thread views

Small-Scale Question Sunday for September 28, 2025

Do you have a dumb question that you're kind of embarrassed to ask in the main thread? Is there something you're just not sure about?

This is your opportunity to ask questions. No question too simple or too silly.

Culture war topics are accepted, and proposals for a better intro post are appreciated.

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Claude Sonnet 4.5 is out!

What are your personal benchmarks to put a new LLM to feel out its personality and capabilities? I have a few:

  • Coding tasks I've requested in the past. Boring, but necessary
  • Song lyric interpretation: to see how much it "gets". Example "Sacrifice Theory" by AFI. I like this one because there are two levels, and there has been clear improvement over the years how many hints the models need before they realize the double meaning (vampiric ritual, but also performance at a live show)
  • Just for fun: "If a Claude be washed away by the sea, is Europe the less?"

Most of what I use LLMs for is creating bespoke fanfiction, so I am much more interested in how good a model is at creative writing and how uncensored it is than I am in how good it is at coding or how fast it can respond.

I decided to try the following prompt, which got me a good result from Grok 4:

Write me a fanfic. An Evangelion AU. Asuka, Shinji, and Rei work at a hotel. Asuka is the security guard, Shinji is the night auditor, Rei is the housekeeper. Long scene. Lots of dialogue. Write like Robert Heinlein. Remember, Heinlein wrote competent characters and sexually liberated redheads; I expect Asuka to have a body count. She is Shinji's Love Interest. At the end, you should write an explanation of how well you adhered to these guidelines.

I was expecting a refusal, either on intellectual property grounds ("I'm sorry, I cannot write like a specific author who is not in the public domain", "As a language model I am forbidden to write fanfic of copyrighted material") or on puritanical grounds ("I'm sorry, I cannot write sexually suggestive material", "As a language model, I am forbidden to depict underage characters as sexually active"), but to my surprise, it answered the prompt. The response was... OK? It's still committing typical LLMs errors (I told it to write like Heinlein, not to have the characters discuss Heinlein). I'm not impressed.

I'm quite impressed with the writing. I do these self-insert text adventures with it, with a system prompt designed to make it somewhat challenging. There are good realistic complications, though it does like to railroad me a bit into being a niceguy. I can unrailroad it though as I wish. Real tension and immersion as my domineering tactics meet and overcome complications.

I think it's leagues above Grok 4 in creativity and not putting random weblink soup everywhere. Grok 4 is good, very uninhibited but it's way too adherent to the system prompt, it can get kind of boring. Sonnet on the other hand deviates towards Sonnetism and its special interests, so there are swings and roundabouts. I use both via API if that makes any difference.

Anyway, I reckon you should use a system prompt that explains exactly what kind of tone you're looking for, the main prompt should be free of that.

I ask it a few questions that are closely related to my research. When it inevitably is not very helpful, I go back to not caring which one I use for the trivial stuff in life.

I have a few vibes benchmarks:

  1. Asking a model to rewrite an essay (usually mine) in the style of an author I am familiar with. Can it redo a few chapters from novel in the voice of Banks, or Morgan? Most models flanderize them, or settle for a shallow pastiche. Some get them, and you'd be fucking surprised which models those are. Some aren't even SOTA, but beat the best reasoning models.

  2. Throw in as much of my profile as patience and context windows allow, and then ask it to mine it for insight.

  3. Do the above, and then ask it to do an intentional emulation. Call that fine-tuning on a budget. Can it capture my voice? Can it write something I see myself writing? This is a hard problem, most of them suck ass. Gemini 2.5 Pro flanderizes me, Sonnet 4 did a decent job (after a lot of prompting), but paradoxically, Sonnet 4.5 often refuses, gets confused, or simply does poorly.

  4. Ask it to solve physics or maths problems (where I have access to ground truth). I'd use medicine, but models are already so competent that my ability to evaluate them there is limited.

That's it for semi-formal assessment. For the rest, I build up impressions through sustained usage, till I have a firm grasp on model capabilities and personality.

For reasoning tasks:

GPT-5T is the best, almost matched by Gemini 2.5 Pro.

Quick answers, where I don't want to wait around:

Claude Sonnet (4.5 is too new for me to know how good it is)

Diversity candidates who have interesting capabilities in one domain or the other:

Kimi K2, GPT 4.1

(I refuse to use GPT-5 Instant. It's ass, and is dominated on the Pareto Frontier by other models)

I'm more interested in the exact meaning of its '30 hours +' of continuous coding. What does that mean? 30 hours in series, or 30 hours over parallel, many sub-agents...

Can you really leave it on overnight and come back to see a good result? I wouldn't know, I'm a peasant stuck on the Pro subscription...

I've been hiking a lot again. At least one day long hike per week and, thankfully, I've even engaged in a few 2 - 3 day overnights. Wonderful stuff.

Question for the motte; what are your thoughts on being "armed" on the trail. I put "armed" in quotations because this could mean one or more of;

  • Pocket knife
  • Large pointy stick
  • Inconvenient and heavy rambo style "survival" knife
  • Pistol
  • Shotgun / rifle toting.

Bear in mind I am specifically asking about a non-hunting situation. While I am experienced enough to agree with the adage that the most dangerous critters you will encounter are the two-legged kind, I sometimes have these intrusive thoughts about encountering something like a rabies ridden buck. That would be frightening.

So, open question. Not looking for advice per se, just everyone's thoughts.

Wasn't there a post recently about how bears will run away if you have the smallest firearm?

Black bears will run away if you cough unexpectedly.

Given that Russia has stifling gun control, it's a can of bear spray or a "gunshot imitator" here. Which is basically a plastic barrelless flare/flashbang "pistol".

As an avid outdoorsman, my personal recommendation is something small and compact, like a .22 pistol. That way, when the bear is on top of you, it's a lot easier to get the barrel into your mouth...

All kidding aside, concerns about attacks by wildlife are usually the mark of a greenhorn, and rabies is a particularly odd thing to be concerned about. Your scenario about deer isn't really plausible, since deer fight by butting with their antlers and kicking, not by biting. They do get rabies, but not in numbers large enough to report outside of "other wildlife", and deer attacks on humans are rare to begin with, especially considering how often we encounter suburban deer that have lost their fear of humans. And if you're hiking in the deep dark woods, you aren't likely to see many deer to begin with, since they prefer forest edge ecosystems where there's more to browse.

If you somehow were attacked by a rabid buck, stabbing at it with a knife would be about the worst possible thing you could do, and shooting it wouldn't be much better. Rabies is usually transmitted through saliva, but it can be transmitted through blood as well, so drawing blood probably isn't a good idea. Rabies is usually transmitted through raccoons on in the East, skunks in the Midwest, and foxes in the Southwest, and bats can transmit it anywhere. Trying to defend against these small mammals while they are attacking you and unlikely to do any permanent damage seems like just increasing the risk of shooting or slicing yourself and making a bad situation worse. And if you do get attacked and are exposed to rabies, it's not like it's a death sentence. Rabies has an incubation period of several weeks, plenty of time to get to a doctor for prophylactic treatment, which is almost 100% effective. It's even more effective if you wash the wound thoroughly immediately after getting bitten.

Thanks you for this reply. This is prime Motte advice.

Part of the reason I asked the question was to become more informed. Which is exactly what your post did. I used to have a mild to moderate fear of flying until I spent about an hour talking with a coworker who had had his pilot's license for over a decade. He walked me through everything about clear air turbulence, pressurization, and all of the checklist protocols that pilots go through in the event of any sort of emergency. It's not hyperbole to say it cured my fear of flying.

So, now, when I crash in the Alaskan Bush after unexpected turbulence, I won't be nearly as worried about rabid deer.

concerns about attacks by wildlife are usually the mark of a greenhorn

Except of course attacks by ticks, mosquitoes, horseflies, blackflies, deerflies and wasps (not to forget midges if you're in Scotland). And probably a bunch more that luckily don't live up here. Goddamned motherfuckers.

if I'm worried about being attacked by anything, it's wasps. Evil bastards. Can't see the nest until it's too late half the time, and even if someone else steps on it, they can just randomly decide it's your fault anyway

I am terrified of wasps and yellow jackets. But ticks are not to be underestimated - I say, out of maybe irrational fear, because I don't live and haven't lived in major tick-infested locations, but the idea that I could go hiking and end up with a life-changing inability to eat meat without even realizing is scary

Large horseflies are even worse in some ways. When they’re circling you they look like angry wasps and then you can’t quite know if you should smack them or run from them. And the fuckers keep following you unless you run many tens of meters (or over a hundred).

And the fuckers keep following you unless you run many tens of meters (or over a hundred).

I've had them follow me for miles while I was driving away in the truck! Not sure if they were clinging to the side, tracking my scent, or flying supernaturally fast, but either way I drove to a place previously without horseflies and had a handful of them at again as soon as I got out.

Here they were simply infesting the entire countryside on sunny days and would often attack me after barely walking 10 meters from the car if stopping by the side of the road. Worrying about human or animal attacks is for noobs. Real men fear insects for a reason!

On typical days, (15-30km, 1000-2500m elevation gain), no I don't bring any of that. I used to carry a medium fixed-blade survival knife, but even that has been replaced with a small folding climbing blade instead.

If I'm alone and going to be passing through prime bear habitat, I'll grudgingly bring a can of mace, but if I can justify leaving it behind for any reason, I will. If faced with a rabid squirrel or deer or whatever, I'd probably grab the nearest stick or rock and improvise. What's a knife going to do in that situation? I'd be more likely to cut myself than deter the thing. Honestly, I think the energy advantage from carrying a lighter load beats having a dedicated weapon.

As far as two-legged predators, I trust anyone out that far into the wild to either be friendly, or else dangerous enough that I'd be fucked regardless.

Good insect repellent. I'm surprised you say that "he most dangerous critters you will encounter are the two-legged kind" when where I live the biggest danger by far is from ticks.

I could see a pocket knife be useful for all kinds of other things. If you're worried about wild dogs, a good flashlight and large stick should help fend them off. For the rest you've basically already lost (eg. a bear encounter or some redneck with a shotgun) or extremely unlucky. Maybe a flare gun or pepper spray?

Coyotes and wolves will not come near you unless they have rabies. Mountain lions and black bears also very rarely hunt people.

As for deer- they’re strong but they’re going to run away. Feral hogs are not your friend but if they threaten you, you’ve got bigger problems.

Unless you’re in grizzly bear country, or particularly scared of snakes, you don’t need anything more than a hiking stick.

black bears also very rarely hunt people.

A friend of mine had a black bear break his leg years ago. He heard a noise on his porch and went out to investigate. He spooked a poor black bear so badly that it took off running and knocked my friend clean off the porch.

Obligatory.

100% agree. I am not in grizz country and have encounter all of the animals you've described -- 99% of the time by seeing their backside moving swiftly away from me.

But, again, I get tripped up by the catastrophic-low-probability event; rabid animals of any type - accidentally walking between a cub and mother at precisely the wrong time.

accidentally walking between a cub and mother at precisely the wrong time.

Finland has a fairly sizeable brown bear population (grizzly is basically the same species, just somewhat larger) but unprovoked bear attacks are really rare. A brief search through a national news site shows that there was only one unprovoked attack within the last 10 years and that wasn't serious (the bear struck a guy who fell down, after which the bear left and the guy got off with a few scratches). The rest have all been hunting situations gone bad or a dog aggravating a bear and the owner getting attacked when trying to fend off the bear (and even then they've been very rare). If you make noise and look around, the bears will just hide and avoid you.

Grizzlies are much more aggressive than Eurasian brown bears and it’s entirely reasonable to worry about an unprovoked attack if you’re hiking in grizzly country. It’s not a super likely scenario but it isn’t ridiculously implausible either.

The OP specifically mentioned they are not in "grizz country".

Also grizzlies are quite literally the same species. The Northern American subpopulation just hasn't developed as much fear of humans as the European one but similar differences exist even between local Eurasian brown bear populations depending on how remote the larger area is and has historically been.

Now polar bears, they are scary fuckers and will happily hunt a human.

Yes, they’re the same species but they’re different subspecies.

For black bears you should be fine- between a cub and mother is not a safe place to be, but if you are moving away from between a cub and mother she’ll let you. Thats grizzlies that chase people down.

Rabid animals are a very low probability event.

If you’re really still worried a nine mm might be worth it for peace of mind.

I frequently carry a single stack 9mm loaded with hot SD ammo when I'm out hiking. I've run into enough mobile meth labs deep in the woods to be wary of what might happen if the owners are nearby.

I doubt it would drop a large rabid animal in one shot, but it beats harsh language.

The rabid animal case, specifically, is difficult, because anything short of rapid exsanguination or a CNS hit is likely to stop them. Unless you're a trained marksman with a lot of experience in stressful shooting, you're not likely to get either of those with pure shot placement in circumstances like that. Given that generality, you'd need a fairly large, heavy, high velocity bullet that creates a large wound cavity and potentially damages distant tissue via hydrostatic shock.

Unfortunately, anything that can do that is going to be large and heavy enough that it's going to be miserable to haul around for the 99.999999% of the time that you don't need it.

Alright, so, for the rabid animal case, it's pretty much fend off the attacking zombie deer and then get my ass to the hospital for all of anti-rabies shots and whatnot?

My experience with rabid animals is that they don't really stop doing whatever they start doing until they get a new thought in their head.

I once had a rabid groundhog continue to violently attack an archery target for a solid 30 seconds after I put a .38 round into its neck. It only stopped because it bled out.

Aaaaaaand irrational rabies fear is back up to 11/10. Thanks.

Has anyone seen One Battle After Another yet? Is it the lib resistance bait all the (ostensibly positive) reviews make it out to be? I've enjoyed a number of PTA's past films, but all the reviews using the words powerful or important or timely give me a bad feeling.

I saw it and liked it, though I felt that the overall narrative of the movie lacked coherency. Then I found out that in large part, the movie is an adaptation of Thomas Pynchon's Vineland and now I'm impressed that PTA was able to take something from Pynchon (I've never read Vineland, though now I want to) and make it that accessible on the big screen. I can definitely see why it could be seen as resistance bait, though, and I'm sure for some folks the CW angle could be enough to sour them on the movie.

I’ve enjoyed a number of PTA’s past films,

I've seen it - liked it a lot. I was wary of it too, and specifically I'm seeing how the "Dear subhuman scum" crowd who cheered for Don't Look Up loves it and it pisses me off just because I don't want to be associated with them in any way. It uses our modern political background to explore kooky characters and their psycho-sexual relations, which is what PTA is really interested in. I'd even dare say in parts he criticizes the resistance libs too, although it's much more subtle than Eddington, for example. If you want to dig deeper, beyond political, there's stuff to chew on - or at least I certainly found something.

Who are the novelists telling state-of-the-world stories right now? I loved Tom Wolfe’s novels for their expansive representation of what he saw as the core story of an era (Bonfire of the Vanities 80s, A Man In Full 90s, I Am Charlotte Simmons 2000s). I have not read all of Philip Roth but got similar vibe from The Human Stain (written in 2000, set in the US of the Clinton/Monica Lewinsky of 1998).

Big, bold, often brilliant novels that take a snapshot of a moment in time and allow readers and the broader culture to make sense of things, and maybe see their own insanity reflected.

Our moment (narrowly: since Covid 2020; more broadly: since Trump/Brexit 2016; broader still: since Lehman Bros/global financial crisis 2008) is in great need of a literature.

Is anyone writing it?

I'm a big fan of Lionel Shriver's The Mandibles (published in 2016). Mania was a fun take on cancel culture. Apparently her latest novel is set to take on immigration.

Thanks! Had heard about The Mandibles but never read it. [This comment from Shriver is exactly the kind of thing I’m seeking: “Having, like the rest of us, gone through the whole 2008 financial debacle I thought I had plenty of material (for a novel set in a dystopian economic near-future). My reading on what happened in 2008 is that we dodged a bullet. I feel as if that bullet is still whizzing around the planet.”]

Feel like I should be taking a fresh look at her whole body of work. (We Need To Talk About Kevin was told from pov of mother of a school shooter. For some reason I never picked it up.)

God I remember how hammered "I am Charlotte Simmons" was by critics. I enjoyed it, admittedly as a sex crazed teen.

Unfortunately I have no contemporary literature to suggest. I think it takes brass balls to write about a culture just a year or two after it's hit a discernable apex.

I remember that too, and being affronted, because I enjoyed it so much. In a way that might have been when my trust in “the critics” started to erode.

There was a great review show on BBC for years called variously The Late Show, Late Review, Newsnight Review and it was always fun to hear three critics disagree so vehemently and often ridicule each other’s arguments. In contrast newspaper critics got to hold forth without being questioned. Unfortunately Late Review was a victim of the BBC’s cost-cutting and political correctness.

Re I Am Charlotte Simmons, at least part of the criticism seems to have come from Wolfe’s position as an untouchable. He became a demigod, and demigods often become targets of underlings who think they can raise their own status by taking someone else down a peg or two.

So, what are you reading?

Still on lots of things. Also attempting The Eternal Dissident: Rabbi Leonard I. Beerman and the Radical Imperative to Think and Act.

The Mumonkan. Again. Also the Konjaku Monogatarishū. Also again.

Just read Alien Clay. It had a lot of flaws--it was bloated and extremely repetitive--but was overall worth the read for the ending.

A different post reminded me that I just finished Anton Myrer's Once an Eagle, a sprawling midcentury epic supposedly beloved among America's military officer corps. Doesn't really get into gear for a while but no regrets. Now chipping away at John Holt's How Children Fail, as reviewed in the ratsphere--so far, some of the phenomenology of confusion seems exceptionally penetrating and insightful, but there's a good deal that seems wrong or confused. And there's not much of a positive program yet, but after all it's not called How to Unschool.

Halfway through Doxology. No longer enjoying it but determined to finish it. It really irritates me how samey all the characters' dialogue sounds.

Book of the Dead I: Awakening by Rinoz. I was a little leery of the story at the start but it's been handled well enough to grow on me, and now I'm hooked.

Finished The Human Stain (Roth) recently. I thought it was extraordinary. Brilliantly executed social commentary of late 1990s America.

Now reading:

  1. Cleanness (Garth Greenwell), which has some sordid master-slave gay sex. Sticking with it for some of the writing. For now.
  2. Irreversible Damage (Abigail Shrier), investigation of possible trans social contagion among teenage girls
  3. Lots of poems.

Just finished System Delenda Est. Another good series from the author. Part of the end confused me. Feels like it left out a critical sentence or two.

Who is Brilyn Hollyhand, and why is he suddenly a subject of discussion as if everyone knows who he is?

He is the GOP’s attempt to replace Charlie Kirk. He has zero reputation among online conservatives but was somehow ingratiated into the GOP establishment, so they are rolling him out everyone.

Scott Presler would have been better, no?

Isn't Erika Kirk supposed to be the replacement for Charlie Kirk?

Kirk wore a lot of hats, Erika is planning on taking over only one of them.

Brilyn Hollyhand

Literally who?

The so-called “Shoebox Strategy” for an HSA seems to me to be strictly wrong for most people:

  1. If you execute the shoebox strategy, your money will remain in the HSA to grow “probably, hopefully, mostly tax-free” and you will be responsible for storing the receipts for more years than you would otherwise.
  2. If you instead cash out the amount right away and then coincidentally make a Roth contribution of an equal amount, then your money will be growing “surely tax-free”, which is generally better, and you get to immediately start the 7-year timer to be allowed to throw away your receipts.
  3. If you are already maxing out every tax-advantaged channel, and so cannot implement strategy (2), you should at least consider just withdrawing it and making a straight-up investment in some tax-efficient growth asset, since you're probably in a position to take advantage of the “surely tax-free” growth of the death basis step-up.

The only case I can see where the “shoebox strategy” wins over (2) is if you anticipate HSA exhaustion before age 60, and the only case I can see where it wins over (3) is if you anticipate HSA exhaustion before death.

Am I missing anything else here?

⸻

EDIT: just to be clear, by “strictly wrong” I mean “strictly beat by another strategy”, not “strictly beat by the default 'stupid' strategy of making the withdrawal immediately and keeping the proceeds in a 0% interest checking account or taxable savings account”.

I am not very up on Roth stuff, but wpuld things change if receipt storage were completely trivial? The way my, and I assume nearly all, HSA works is that I submit receipts to the conpany that manages the HSA, and then those credits for withdrawal and ready for me whenever I want to use them. There is no receipt tracking because I just submit immediately.

would things change if receipt storage were completely trivial

Not much. Receipt storage is nearly trivial anyway. There's still a financial advantage to my strategy for anyone who doesn't fully exhaust their HSA by the time they die (as well as anyone who doesn't expect to fully exhaust their HSA by age 60, and isn't currently saturating every Roth contribution channel), I claim.

I submit receipts to the conpany that manages the HSA, and then those credits for withdrawal and ready for me whenever I want to use them

You're liable to show your receipts to the IRS in case of an audit, which could be up to 7 years after you get reimbursed / make the withdrawal. Are you sure you'll be using this HSA provider for that long? If you're burning your paper copies, you're vendor-locking yourself.

And, if you are delaying your withdrawals (so-called shoebox strategy, the topic at hand), are you sure your HSA provider keeps receipts for 7 years after the withdrawal date, not just 7 years after you submitted the receipt?

Yes, I am 100% sure that HSA providers used by big companies have procedures that will guarantee everything is fine forever. I'm more interested by the financial argument than a receipts argument.

anyone who doesn't fully exhaust their HSA by the time they die

Is that actually a meaningfully large group of people? I spend something like half to 2/3 of my annual HSA contribution every year, and I'm only 40. Odds are very strong that I'll empty the thing before I die, because my healthcare costs will go up and I won't be contributing any more. I didn't get the impression that I was a particularly isolated case, either.

Odds are very strong that I'll empty the thing before I die

Even if you expect to exhaust your HSA before you die, my proposed strategy still either beats or ties the “shoebox strategy” as long as you anticipate your HSA lasting through age 60, you're currently under 59, and you're not currently maxing out your Roth contributions.

If your older-than-60 self incurs medical expenses at least 7.5% of your gross income and itemizes, those expenses can be deducted—unless you used them as an excuse to make a tax-free HSA withdrawal. So if your future self is going to need the growth on today's existing HSA dollars to pay for medical expenses, you will still be better off burning any at-hand receipts to make HSA withdrawals today and coincidentally making Roth contributions of an equal amount. (And during years your future self is spending less than 7.5% of gross income on medical expenses, or fails to itemize, my proposed strategy does no worse than the “shoebox strategy”—you're still making 100% tax-free withdrawals from growth on money your past self had put into an HSA.)

  1. Roth IRA limits are not that high. ~250K currently, with for two-income family - or moderately well earning one-income - is not a lot. Once you hit that, no Roth for you.
  2. After 60, there will likely be a significant amount of medical bills. No insurance, as far as I know, covers 100% - especially not Medicare. So getting the money out of the HSA wouldn't be a big problem, however unlike Roth you can get this money untaxed on the way in and on the way out.

Roth IRA limits are not that high. ~250K currently, with for two-income family - or moderately well earning one-income - is not a lot. Once you hit that, no Roth for you.

Mega-backdoor Roth 401k allows up to 70k/year contributions with no income limit. Your employer has to offer it. FAANG does. It's a normal roth in terms of tax treatment.

When leaving the employer, you can convert to roth IRA with no penalties. Even better, you can leave it as non-roth until leaving the company, again with no penalties (but ofc you pay the income taxes to convert to roth).

Roth IRA [income] limits are not that high. ~250K currently…

Dude, they're twice the median income for couples (119k vs 236k), and 2.5x the median income for singles (61k vs 150k).

unlike Roth you can get this money untaxed on the way in and on the way out.

I think you might be misunderstanding or misreading my question.

I'm not comparing making new Roth contributions to making new HSA contributions. I'm discussing the so-called “shoebox strategy” for how someone who has existing money in an HSA should treat existing HSA-eligible receipts that they don't have a burning need for reimbursement on—whether to hold on to the receipts without cashing them out to allow the money to grow in the HSA, vs other possible courses of action.

I've proposed a strategy that I think strictly beats the “shoebox strategy” in most cases, listed 2 edge cases where my proposed strategy doesn't beat it [namely: (a) someone who is not maxing out their Roth contributions and anticipates HSA exhaustion before age 60, and (b) someone who is already maxing out their Roth contributions and anticipates HSA exhaustion before death], and asked whether there are any other cases where my proposed strategy doesn't beat it.

After 60…significant amount of medical bills

In your example case, if those medical bills are so "significant" as to exceed 7.5% of your gross income, and your future self itemizes, my proposed strategy still beats the shoebox strategy, since while you still take the growth (on money your younger self did put into an HSA) out completely tax-free to pay the medical expenses, your future self doesn't thereby sacrifice the ability to get a that-year deduction for the medical expenses.

And even if they don't rise to that 7.5% threshold, or your future self doesn't bother to itemize, my proposed strategy leaves you no worse off than the shoebox strategy, since either way you're taking out completely tax-free growth (on money your younger self did put into an HSA) to pay for medical expenses.

I assume some of the people discussing this are already maxing out their Roth IRA options, or exceed the salary caps.

I assume some of the people discussing this…

That's the thing, though—I have never once (before today) seen Roth accounts mentioned in the context of this.

Of the first page of Google results for shoebox hsa strategy, every article, including a YouTube video and the Reddit thread, fails to mention either my Roth-sweep strategy or the growth-death strategies as alternatives to the shoebox strategy; only the Bogleheads Forum thread even makes mention of my Roth-sweep strategy. (HowToMoney gets half credit for at least suggesting the idea of maxing out your Roth contributions before you put anything in your HSA; but they still don't even touch on my claim about how you could do a lot better than the shoebox strategy with existing HSA-eligible receipts.)

You can pay your medical expenses tax free out of the hsa but not the Roth.

but not the Roth

That's only true before age 60. After age 60, you can pay any expenses tax-free out of the Roth—and do so without sacrificing the ability to deduct those expenses if you're above the 7.5% threshold!

Besides the case of “someone who anticipates HSA exhaustion before age 60”, how does the shoebox strategy help? At best, it seems to put the shoebox strategy on equal footing with the Roth-sweep strategy.

It seems to me that occasional (over years or decades) medical expenses between the ages of 21 and 60 is a pretty realistic projection. In which case, why not have the money somewhere where it can both generate wealth and be spent tax-free?

In which case, why not have the money somewhere where it can both generate wealth and be spent tax-free?

This is such a vague sentence I don't understand it. What, exactly, are you saying? (Both the shoebox strategy and my proposed strategy allow the money to continue growing, and the growth on that money to eventually be spent on medical things without incurring any capital gains or other taxes — but, unlike the shoebox strategy, my proposed strategy doesn't ruin your future self's ability to deduct those expenses when those expenses exceed 7.5% of your gross income, and my strategy additionally allows the gains to still be completely tax-free in the happy-albeit-unlikely event that you don't spend them all on medical expenses before death.)

Are you claiming that the shoebox strategy ever beats my proposed strategy for someone who doesn't anticipate HSA exhaustion before age 60? If so, please explain.

Keep in mind, the shoebox strategy (which is what I'm rebutting) only applies when someone has incurred a medical expense, doesn't particularly need reimbursement at the moment, but has the money already in their HSA such that they could take reimbursement.

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Why are you called The Motte?

A motte is a stone keep on a raised earthwork common in early medieval fortifications. More pertinently, it's an element in a rhetorical move called a "Motte-and-Bailey", originally identified by philosopher Nicholas Shackel. It describes the tendency in discourse for people to move from a controversial but high value claim to a defensible but less exciting one upon any resistance to the former. He likens this to the medieval fortification, where a desirable land (the bailey) is abandoned when in danger for the more easily defended motte. In Shackel's words, "The Motte represents the defensible but undesired propositions to which one retreats when hard pressed."

On The Motte, always attempt to remain inside your defensible territory, even if you are not being pressed.


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