Even for consumer software, the common 7/14/30-day free trials are bizarre.
My general use case is to download and test software to use it a single time, for some random new task I only need that day. To use the software for 5 minutes.
Then three months later, oh it turns out I need to do that thing again, or test it out in a new way. It says the trial has expired, even though I only used it for 5 minutes. And I'm not going to pay $$$ just to use it for another 5 minutes and possibly never again.
I don't understand why x-day free trials haven't been replaced with usage-based free trials. E.g. whether it's exporting a final result 20 times, or running a filter 50 times, or processing 100 input files, or whatever metric makes sense for the particular product. Or heck, keep it a 14-day free trial but count the days individually -- so if I use it on May 2 and then on May 15, that's only two days.
The idea that, as a consumer, I'm going to sit down and fully evaluate a piece of software over the course of 7/14/30 consecutive days to then make a purchasing decision is bizarre.
But to push back, if you’re talking about a 5 minute task, that you’re using once every few months, a free trial timed the way you are asking, might mean you never end up needing to purchase a license. I understand that that is useful for you, but that isn’t exactly good for someone trying to sell a piece of software. (I understand you also gave usage based examples, but even in those scenarios (which require additional work to code for trial versions, versus a pure time-lock), there is always going to be someone who says “5 saves isn’t enough” or whatever the metric is).
Maybe it’s my past life as a software reviewer (and current life as someone frequently asked about my assessment/opinion on apps), but for consumer software (SaaS, especially for business like what OP article is about, I think is different), I really don’t think this is that bizarre.
To me, a trial is really instructive because if I’m finding myself opening or using an app frequently during the trial, that’s a good indicator I’ll get value out of the application. Similarly, if I did a trial in January for one task, then came back to do that same task again in May and the trial is expired, it’s a good way for me to evaluate if it makes sense for me to buy a license or not. There are some programs I use two or three times a year that I purchase because it is useful enough for that one task, but there are others that I use infrequently enough to try to seek out other options. A time-based trial, for me, is a good forcing function to determine if I’m actually going to use the program.
IMHO some light users should be free - niche users who don't have significant budgets or would be a support burden. Others get enormous value in 5 minutes, have easy budgets for this category of software and should be paying.
I wouldn't be quick to judge either way.
It's a little weird to suggest that just because someone wants to use the product of someone else's work only for a short time, that use "should" be free.
I mean, it's not strange to think that the ideal state for software is "used as widely as possible while maximizing profit."
That's definitely a strange ideal, to put it politely. Human welfare should be maximized instead.
???
That is very strange.
I think the context of “should” matters quite a bit here. For example the claim that everyone should have free access as if by right is quite different than the claim that as the producer of said software this is your best bet.
If you are offering free samples of your product, you shouldn't get mad at the people who don't need your product for more.
This essentially is how tailscale operates (or did last I was in this space). Home/small use totally free, and experimentation seems encouraged.
I have genuinely deployed tailscale in paying locations on basis of my really positive experience on the "Personal" plan, which is effectively almost the whole product for up to three users/100 devices, for free.
I don't think there is a universally right answer for all products/services on this question though.
Counter to your counter, a person using software 5-6 times over a few years is almost never going to become a paying customer. They'll just cut you out entirely. But odds are they know similar professionals and could be a major promoter to potential power-users. Chatting with a few coworkers, none of us can come up with a single example of letting a trial expire, only to pay for isolated uses later. We had quite a few examples of software we thought might be valueable, but weren't prepared to pay having run out our trials. Three of us are in this state for Copilot alone.
It seems you're very focused on what people "oughta" pay for. But what matters is simply what people do pay for. You tell this story, but it seems very inconsistent with my experience or my understanding of pricing theory.
"It's free advertising" is an argument I see a lot, but I've never seen the numbers to see how much that actually matters in the real world. Well, I guess I've seen some, but it's always from ad companies anyways.
When it comes to free advertising/exposure as compensation I think back to my early days on the Oregon Trail:
You can die from exposure.
We accept cash, check, and cholera.
The person using this argument never accepts free advertising as a payment option and this tells everything about the effectiveness of this strategy
I own a media production company. We occasionally sell content to other media outlets. Early in our existence, we were routinely contacted by reporters asking for permission to use our content with credit to us. I used to respond by saying yes, but only if I could use some of their content, with credit to them. Obviously, they never agreed.
I don’t know who the “you” is referring to. All I said was that in my personal experience, there have been occasions (not frequent, but it has happened) where I’ll buy a perpetual license to something for a task I use a few times a year. Because the $20 or whatever the license cost was worth the time I saved. In most cases, what I said was that if I didn’t use a piece of software after the trial expired, that was a good forcing function to figure out if it was something I find value in or not. And in most cases, the answer is going to be “I don’t need to buy this.”
I’m not at all focused on what people oughta pay for so I don’t know where you are misreading this.
I also said that for business and SaaS options like the OP article is about, things are completely different (your Copilot example). The comment I replied to was about consumer software trials and how they don’t think time limits make sense. I happen to disagree.
The problem with this thinking is that you are creating dissatisfaction for 25 cents.
Let's say, you sell your software as a single-version perpetual license. You sell it for 150$. A typical user uses it 8 hours a month. After a year, that's 96 hours. So they spend less than 2$ per hour (I'm rounding in the seller's favor.) So using it for 5 minutes, 1/12h, is less than 25 cents. (Again rounding up in the seller's favor.)
Is this about not giving away 25 cents?
This is where SaaS wins over, but even there, the overhead, both for sellers and users, of managing payment for people who want to do one-shot work is never going to be worth it.
This scenario is akin to wanting an insurance payout for a stolen car after paying just the last month’s premium
That's why they want that model. Complaints like the GP's are just a thin veil over being too cheap to pay for the software they use. You can see it in the other responses to your comment.
Flip that. I find most people do the second thing first. If what I'm doing in the software takes 5 minutes, chances are I can find something else out there that will do the same thing for free as well. Sometimes the same software lets you trial it again because it's been so long. And so all the additional features you'd review them for amount to nothing when I'm just using them to remove the background in my picture.
But here is the bigger issue.
It's a horrible way for me to evaluate licensing. Why? Because, I probably want to get on with whatever task should only take 5 minutes and do something else. I don't want to spend time evaluating licensing and determine the cost benefits analysis of this software purchase (which more and more tends toward a monthly/yearly fee).
I want to do the 5 minute thing and move on, and I will spend more time searching for another free solution than pay.
You want to get me to pay you? Make that 5 minutes showcase the things I did't know I needed.
And yes, if you have the only thing that can do the thing I'm looking to do, sure. But, a monopoly isn't exactly what we are talking about here.
I took a job working at a company that made a code obfuscator/minimizer in the days before CI/CD really existed. I knew a lot about Java internals so I thought this would be good. First day I got assigned instead to an embedded Java project.
Why? They couldn’t market the obfuscator, so they were winding it down. People didn’t want a license for something they used for ten minutes four times a year.
(We did later hire an intern to fix bugs in the obfuscator. The app was constrained to a specific JAR size, and those gave us enough headroom for about another dozen features. And I made a change late in the project that got me space for two more, via suffix sorting the constant pool instead of prefix sorting it).
That is exactly the point. As a producer of the said software, if that is the user's usage pattern, and there are enough regular users to sustain/pay for these users, then I won't want to charge them. Doing so means I either lose out on potential customers or they aren't going to be a true customer anyways.
Your example just demonstrates the usefulness of a time-based trial. You personally might not come back but the next customer might.
I know everyone complains about Adobe's switch to subscription, but it would fit the model you'd want where you could pay for a month of usage and then turn it back off.
Yes, exactly.
The parent comment says they are not going to pay to use it for another 5 minutes. So if it were usage-based, would they pay to use it for the 21st times, after they run out the 20 free uses?
And they only use it once per three months. So the 21st use is 5 years later. Will the software still be maintined by the time? Will the dev still exist? Will the problem itself still exist?
I would pay for it by the 21st time.
That was my point. If I'm using something for only the 2nd time, then statistically it's very unknown whether I'll ever use a 3rd time. If I paid for it now, there's a good chance I'd be throwing away my money.
Whereas if I've used something 20 times, then it's extremely likely I'll be using it another 20, 50, 100, or 1,000 times. It's clearly worth paying for after 20 times.
In your example above (needing it every 3 months) it would take over 5 years to reach that point.
I'm going to guess that within those 5 years it's likely that the developer would have released a new major release (with a new trial period), or that you would have reinstalled your OS (resetting the trial timer), or that you would have gotten a new computer...
In other words, you'd never pay for the software.
You may be failing to see the woods for the trees. Dunno, not OP.
By the 21st time != the 21st time.
By the 21st time == at some point prior to the 21st time. Possibly the 5th or 6th time. Maybe the 10th time. Maybe the 3rd time.
That wasn't my example. It was 3 months between the first and second times.
In my experience, your need for a tool often increases gradually. You have a one-off project that needs a tool briefly, then a couple of projects a few months later you need to try it more, then it becomes a regular thing.
It's pretty rare that I go from never needing a tool to needing it constantly as an instant switch. Which is the only scenario where 7/14/30-day trials make sense.
Then that's a terrible business model.
As a business, you want both customers to come back.
If a contiguous time-based trial model results in losing half your potential customers, while a usage-based trial model results in keeping all potential customers, then the contiguous time-based trial is objectively terrible.
So it doesn't demonstrate the usefulness at all.
Honestly I don't want a customer like OP back. They come across as extremely entitled and the whole post seems to condense down to "I don't want to pay for software, give it to me for free".
I'm also assuming OP didn't really intend to pay if they're coming to a tool that they'll use for 5 minutes. They don't see the value in paying, I'm just reading between the lines there.
Maybe its still better to let them get a long free trial so they tell their friends about it, I dunno. Not a marketer, but it struck me as kind of disingenuous that if you came back to a tool after 3 months where you know you need to use it, they still don't want to pay.
Except Adobe doesn’t let you do that, you pay for an entire year month-by-month; cancelling early still leaves you with a bill.
Most of their subscriptions are available in a true month-to-month plan with cancellation at any time without a fee. But they charge a lot more for that plan. For example, $89.99 for month-to-month vs $59.99 for monthly payments toward an annual plan. Still, it’s the cheaper and better option if you’re only using it for a few months of the year.
Adobe requires annual commit and true up!
Even with large relationships, they refuse to provide utilization metrics. So our team has to implement obnoxious processes to validate your use, or pay 15-25% more than we need to.
What you say is probably true for their enterprise deals, but most of their retail plans do offer true month-to-month options for less than double the monthly price of the annual commitment. It’s a good option when one is only using it for a few months of the year.
But that's exactly what you described yourself as doing. You downloaded the software, used it, found that it satisfied your needs, and were familiar enough with the software to recognize that you needed it again three months later.
The real bizarre thing is that someone can blame the software provider for giving away free use of their software, or for "only" allowing them to use it for 30 days for free.
Honestly, I don't understand what model would actually satisfy you while also leaving a window for the software developer to get paid. If someone gave you 14 separate days to run a trial and you utilized the software on the same 3 month schedule, you'd have over 3 years to "evaluate" the software without paying a dime.
I don't understand this complaint, either. You already used the software, saw that it solved your problems, and then knew it well enough to know that you needed it again 3 months later. What more do you want? A full year to think about it while it solves your problems?
Would you prefer if the software was usable in "trial" mode indefinitely, but you couldn't actually output anything (save files, get non-watermarked output) until you purchased it? That's the only alternative I can think of that would help you try the software longer, but then you would be forced to pay on the very first use in your example above. That actually leaves you worse off, not better.
This whole conversation reminds me of why it's so much easier to deal with B2B and Enterprise software: With cheap consumer software, you get people who will complain to the ends of the earth about your $20 software or jump through hoops to avoid paying less than the cost of a couple drinks to purchase software that clearly solves their needs.
The thing is, I often get called away from whatever I was trying to do, and just don’t revisit it for a few weeks, a month. I opened the software, but never actually used it. I go back to it later, whoops, free trial expired. I think x free uses is a much better way to do it, and I as a software maker don’t really feel like I need to charge someone who only needs my stuff once or twice, the marginal cost to me is 0. If they’re getting professional value out of it, or it’s a big part of their day to day for some other reason, then I think they should pay. They’re much more likely to make demands of me if they’re in that bucket, as well.
A 14-day (or 7, or 30 day) trial is actually perfect for this situation.
But you can't make everyone happy. If someone is starting the trial and then not using the software for a week or month, that's their mistake.
There was a time when nagware software was popular: You got to use it for free, but it would nag you with a popup or delay every once in a while asking you to purchase it. You can still occasionally find software with this model, but most developers quickly learned that the more leeway you give the free trial users, the less likely they are to buy it.
No, that's your mistake as a software maker. User behavior is user behavior.
If you're losing potential paying customers because you lock them out of the trial because they didn't come back to it for a week, it's your sales that will suffer.
Business are risk averse. They don't care about that as much as the real worst case: you become winRar and you have a lot of paying customers that never convert because you gave away too much of your product. It's really hard to put thst genie back into the bottle.
You can say that it’s their mistake, but people not using your software successfully is always a mix of blame for both parties.
Yes, you can probably make more by adding more pressure than nagware did. But you’re doing it at the expense of being pro-user. I do think it’s reasonable to be less friendly than that, if it doesn’t work for you.
You can probably make even more than free trials by getting people into a monthly subscription, making it harder to cancel, and/or making it so it’s easier to forget that they’re being charged, etc. There are many ways to enrich yourself at the expense of others. And many companies seem to have justified each of these to themselves.
That's not what happens. I download it, use some tiny part of it once (like the noise reduction filter of a full audio editing suite), forgot about it, googled noise reduction 3 months later, discovered I'd already installed it 3 months ago, and now can't try it with a different file because the trial expired.
But they deserve the blame, because now I'm going to go download a different audio editing suite to try their noise reduction instead. And if now I keep having to do noise reduction because it's no longer a one-off thing, I'll purchase that competitor. Because the first piece of software stopped letting me try it out so I can't even compare anymore. Even though I'd only used it for 5 minutes.
My whole point is that "30 days for free" is meaningless if I only use it for 5 minutes. It makes much more sense for trials to be usage-metered rather than contiguous calendar days.
They lost nothing by you not using their free trial again tho you are the kind of user that we all try to avoid
If you used the program once during the trial period then came back to it again for some reason or another after the trial expired, the trial worked exactly as intended: You want to use the program again, so it's asking you to pay up.
I don't see the problem here other than "I don't want to pay for software." which isn't the programmer's concern. If you don't want to pay, the programmer likewise couldn't give a damn if you can't use his program.
Someone will drop $20 on lunch from some place with no guarantees to its quality and think nothing of it.
But asking the same amount for software requires a painstakingly thorough evaluation.
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Products like Gmail, Facebook, Dropbox etc have trained consumers that the normal price of software is $0.
This makes sense to me. To some people, nothing will be sufficient outside of free. The demand curve predicts this. What is weird is that they're talking as if the problem was with every company trying to get paid (paying the bills? that's for the weak), instead of just simply recognizing that their purchasing power is relatively low.
Well, I sell a website analytics platform, so 14 days are needed for you to gather data and get meaningful insights. Even if you forget about it, and come later, you can still see the data and test the features.
Also, the app is self-hosted, so part of the trial benefit is that users can test the installation process, which is usually the biggest push-back against self-hosting.
Would it be possible to always offer the last 14 days of stats, but only allow a login/access to that data eg 3 or 7 times ?
I wonder if that might fit the average pattern of a casual stats user a bit better (only actually checking the data when asked by the manager) to keep them hooked for a much longer 'wall clock' time and get them to eventually convert (I've been depending on this for half a year now)
Yeah, freemium with a free tier that’s useful for casual use converts me way more often than time-based trials.
Hmm, but what would make you upgrade from the free tier to premium? Because you still can't try the premium features. Wouldn't I still need to provide a trial for the premium features, for you to decide whether they are worth upgrading?
Usually if you think hard, you can find something that a casual user could progress to wanting more of. Or you can do what a lot of companies do and start everyone on a free trial of premium, and then fall back to free. Or the evil route, and make them opt out of premium to downgrade, or it bills them by default. (May they get chargebacked to hell and dropped by their payment processor)
I try to avoid all routes that are not win-win or feel "evil".
After reading more of those comments, I am still unsure what's the way to go. Maybe simply keep the trial but make it 30 days instead of 14 days.
The problem with premium features, is that I would then need a free version of the product. But I don't want to provide a free version without support, as it's a self-hosted product.
Yeah, that's fair. Many projects just let the free community edition support itself by hosting a forum for them to swap notes. And if a trial is about the level of complexity that you feel you can support, that's also ok.
A lot of companies are firmly on the evil track, looking for any dark pattern that makes the numbers go up, sadly. Good on you for not being there.
That's a good idea and, in theory, I could implement a lot of different models.
In practice, because it's self-hosted, "cracking" might be an issue. Customers might edit the files that affect the retention, for example. Maybe most customers won't do it, but I don't know. This also feels a bit like I would have to implement some "DRM", which I really don't want.
Now that you mentioned it, maybe a better trial would be a freemium model, where I can serve a different version for free that only has some features. The problem with this, is that the customer won't get all the benefits of using the product, so they might not like it enough to upgrade to the full version.
It's an analytics platform, so I could offer just basic stats for free and for premium all the other features (segments, heatmaps, recordings, A/B tests, AI integration, etc.). This could work as a good marketing technique for the top of the funnel, but then customers would still probably want to trial the pro features, so I am stuck with the same problem as before.
They want you to pay for it, don't they?
What I do think would be worth it is micropayments, so for each usage you will pay just $0.2 or so. Unfortunately such a payment scheme is not practical under current Visa/Mastercard system.
Or under any realistic payment system that end users would want to use
No offense, but micropayments have to be the most often suggested non-solution to any problem since the "402 Payment required" code was added to the HTTP spec
Idk, I’d pretty happily pay $0.50 to use an infrequently used utility once, if it was totally effortless. But everything wants like $20-30, or even worse, to lock me into some monthly subscription.
That level of effort is something I think matters a lot. If you could make it incredibly easy for people to spend $1-2 (and no more), you could get a TON of money out of people. I dunno how you'd solve that major structural issue, but if you could, it sounds like a goldmine. If nothing else, microtransactions in software would probably explode more than they already have.
I think hypothetical/magic micropayments that just work(TM) actually solve lots of problems. The problem is with the “realistic” part, which is why it always comes up.
Sadly, the only micropayments implementation we have is ad-supported apps. It's essentially micropayments. Albeit a very annoying implementation!
Scrivener has an interesting pattern where they offer 30 day trial - but they only count the days you use the software.
So if you first play with interface for few days, but end up not attempting to write more of your great next novel for two months because you were swamped with real life, you can come back and there's still most of the trial left.
BeyondCompare does this too, and even though I’ve purchased a license I have some machines where I haven’t activated it in almost a year of infrequent usage :)
Yes, it's really nice IMO that BeyondCompare has this model.
After 30 days of ACTUALLY using it (days which are sometimes few and far between, and sometimes more closely spaced) is really a point at which, yes, it's justified to purchase, showing that it has been "the tool of choice" so many times, and likely to be so into the foreseeable near to mid future, too.
The trial is critical to a) proving that it does the useful things, b) determining that that it does said specific things better than the alternatives for some relevant definition of better, and c) giving enough of a chance to really learn it well enough to make an informed decision.
The free period builds tremendous goodwill, and is a really sane and "nice to the community" choice for a tool that might get used occasionally. It shows the confidence that the market really is there for it in general. People who can/do reap value from it on an ongoing basis will convert.
I think most consumers would agree that this is the fairest model. If I pay for 30 days of Netflix, only charge me for the days I watch so then I feel like I'm using my entire purchase.
The current SaaS model is like going to the store and you can only buy 5 gallons of butter or milk and you have one week to use it. It "feels" like most of your money is being "wasted". At least that's my perception.
Exactly. Great to hear that at least one company does this. It makes perfect sense, because it matches how unpredictable people's lives can be.
Just because you offer a 7 day trial and I had time today to try it out a bit, doesn't mean I'll necessarily have any time at all over the next 6 days to finish evaluating it. Life and other work priorities happen.
Mp3tag for Mac (https://mp3tag.app/) does the same - great piece of software, I've used it 6 times and have one day of trial left :)
Browser games, they've nailed it. So if you're talking about gamification: this is what you ought to be talking about.
Could you elaborate how?
Admittedly I don't play browser games, but is it as the parent comment says, trials in browser games are usage-based?
In principle yes. That's because you want your players to be hooked before you first present them with the prospect to pay for an advantage. So you ensure a specific action is ingrained in muscle memory before it requires payment.
It'd be pretty hilarious if GoLand switched to a mobile pricing model where the IDE is free... But you have to use build gems to run things. You get a fixed number of build gems a week then you can buy more fro $9.99 or $19.99.
Your debug gems would recharge after watching a short ad.
Usage-based trials are much harder to enforce reliably.
I don't see why.
A time-based trial records the date you started to use it somewhere.
A usage-based trial records the number of times you've done something somewhere.
I can't see why there would be any difference in reliability. The mechanism of recording and checking some value is identical.
Time-based trials don't require updating trial state once it's initialized.
On the flip side (for the company, not the consumer) if you've come back to the tool 3 months later you're already mentally invested in learning the tool, know it works, and remembered it. Either that'll be a paying customer or it won't, giving them 100 input files doesn't really guarantee a sale 7 years from now (or whenever it is they run out).
I.e. too short to actually be able to try it is a problem. How long "too short" is varies a lot based on what it is you're selling. Too short to be able to try multiple times may actually be a positive for total sales though, particularly in the consumer software space. As always the answer is "test and see what changes your sales" but that not much does it this way is more likely a hint it doesn't execute well with most models rather than nobody is trying it.
Not really. In my experience, I learned only a tiny percentage of the tool -- like how to run a noise reduction filter and nothing else. I know that one thing worked the one time for that one file, but not for other files with different types of noise. And I didn't even remember it -- I googled "noise reduction software" again, discovered the top link was purple, and only then remembered I'd already installed it on my system and forgotten its name. I started it up and it says I can't use it anymore because the trial expired.
I might have a whole bunch of clips I need to noise reduce now, maybe it's going to become a regular thing at this point, but I can only test with competitors' software now...
It's not bizarre, it's a common pattern that people understand and easy to implement. Most people will accept it for that reason even if it's not ideal.
I have a lower tier that users can move to which is an effective filter to see who really wants to move forward, since our set up & initial support costs are relatively high also on trials. So that works well, even if we make a loss on smaller tiers it's a sign of commitment.
As someone who has made and sold such software, no it is not bizarre.
It's very effective.
IIUC, the user evaluated it sufficiently for that task, such that they wanted to use it repeatedly for that task, but the software can do a lot more things, and they don't want to pay the price for just that one feature they evaluated so far, before they evaluate the other features?
If we're selling consumer software, and our expectation is that people might use it only rarely, and only need a fraction of the features, but get value out of it when they do... can we do free trials without this perception?
Don't do free trials? Cripple the trial so that user can see what it can do, but user can't get the benefit they want? Break a big package/suite into many small tools sold separately, to avoid the perception of paying for more than you need or can evaluate? Pay per metered use? Renewable subscription tiers?
Weird proposition. In both cases you would pay for the second usage and the free trial just proved that you need their product and they definitely should not let you use it for free
So essentially what you're advocating for is a model where some percentage of users can use the software in some limited way, for free, possibly over the span of many months or even years, and the person who built it sees no revenue from that use at all? Sure, as the article describes, that's an unlimited-time free tier. But maybe the developer doesn't want to offer a free tier.
Except you did do that, in your example. You evaluated it over the span of 5 minutes (you didn't even need days or weeks), and then were apparently satisfied enough with it that you remembered it and came back to it months later to use it again.
And then you balk at the idea that you should have to pay for something that you already know you get value out of. I find that bizarre.
One reason not to do that is the sales and marketing lead time. Every time marketing changes something there’s a 2 week lag before they can measure the conversion impact. With your usage-based trial concept that lag time becomes indefinite.
Paying to keep the tool running for the few moments you need can be extremely expensive to pay for those moments only.
Often it's an investment in your life to free up time. You can always get and earn more money, but it's impossible to add more time to your life.
I agree not everything has to be a SaaS though, some are better as usage based, or a basic fee plus usage/overage.
Hmm I would say usage-based free trials are problematic because a small company might only use it 10 times but an enterprise might need to run 10k files to fully trial the product. So what usage level would you set it at? If you go too high the small companies can be on a free trial for years, effectively a freemium model.
Depending on the product, your trial may cost the company a decent amount of money. For example audiobooks are rather expensive to stream (due to publisher pricing, not bandwidth).
The same reason that people complain about the weapons behavior in Breath of the Wild or why no one uses the fine china: a usage-based trial actually _discourages_ usage.
As someone else said, Scrivener offers this. I downloaded it and wanted to give it a try, but I was always hesitant to fire it up. I always felt that if I did use it and realized five minutes in that today wasn't the day I was going to write a lot, then I had wasted one of my 30 days. People as a whole are loss adverse, and so it is with usage-based trials.
I think I have seen this model before, in the days of shareware. Offhand, I don’t remember the name of the tool.
A downside of this is that if you don’t choose the right metric, people might burn through a lot of their uses due to mistakes. Like, to use your input files example, imagine someone accidentally selects a huge directory with more than 100 files and then end up with no free uses left.
Some of this also comes down to overall UX design too, of course.
If you "need" to use for the second time, it is lost revenue to cover that in free trial. Free trial are to give uninterested user interest in the product. If the need is already there, free trial can only make the product impression worse.
It’s an annoying arguably dark pattern and easy to game.
Buying behavior is a psychological concept driven by time and attention. A persons mental wallet is open for a limited period of time. The goal of the trial is a conversion to sale.
The scenarios you describe are edge case-ish, and often times companies will accommodate them as edge cases.
This is exactly why they need to charge.