Task Management Applications, Priced By The Ceiling

Asana's free plan stops at two people. Not two paid people. Two people total, and it's written on their own pricing page as "Up to 2 users can collaborate for free".

That one number decides more about which task management applications you end up living in than any feature grid will, because the second a third person needs access, the free option stops being free and the bill isn't for one seat. It's for all three.

Quick version for skimmers. Alone, nearly every free tier here is more than enough and you should sit on it. Two of you, Asana free works. Three or more, Trello's free plan takes up to 10 collaborators per Workspace and Asana's takes two, which is basically the whole comparison. Prices below came off each vendor's own pricing page on 28 July 2026, and one company wouldn't show me a price at all.

What The Free Tiers Actually Cap

Roundups list features. Almost none of them put the free limits side by side in matching units, which is the only view that tells you which app breaks first for the way you work.

The blanks are real blanks. Microsoft's page for To Do says you can use it free and sync your lists across the web plus iOS, Android and Windows, and then publishes no numbers whatsoever, which I'd read as "there aren't meaningful caps" but won't state as fact because they didn't.

Look at the shape of that table rather than the individual cells. Todoist caps your containers and your storage and keeps you on a one-week memory. Asana gives you unlimited projects and 100MB files and then caps the humans. Trello caps everything mildly and nothing severely. Three completely different theories of what a free tier is for, wearing the same category name.

The Third Person Costs $395.64

Here's the arithmetic that made me want to write this piece at all.

Asana Starter is $10.99 per user per month on annual billing. Three people on Starter is $32.97 a month, which is $395.64 for the year. Not $131.88 for the one extra person, because the plan applies to the workspace and everybody moves onto it together. You don't buy a seat. You buy everyone's seats.

Nearly four hundred dollars a year, triggered by one person joining, is the sort of thing that ought to be the headline of every comparison and instead sits in a footnote under a checkmark. I'm not accusing Asana of hiding it. It's on the pricing page in plain language, and the product is genuinely aimed at companies where a per-seat model is normal and expected. It's just that a couple planning a house renovation, or three friends running a small side thing, will hit that cliff without ever having thought of themselves as buyers of enterprise software.

Trello free at ten collaborators per Workspace is five times Asana's headroom on the same axis, for the same price of nothing.

Which Ceiling Costs What To Lift

The other thing nobody prints is the premium for paying monthly, so I worked it out per plan.

Somewhere between twenty and twenty-five per cent, consistently, across two unrelated companies. That's not a coincidence so much as an industry convention nobody voted on, and it means the real question isn't which plan, it's whether you're the sort of person who'll still want this in eleven months.

The Trello Enterprise row checks out against itself, incidentally. $17.50 times twelve is $210, exactly the annual figure they publish beside it. I like when the numbers on a pricing page agree with each other. It happens less often than you'd hope.

One thing I'd flag on the Asana rows. What Starter actually unlocks, for most people reading this, is the ability to have a third human in the workspace. The AI credits and the reporting are real, but the cap that binds is the one made of people, and the marketing quite reasonably leads with the features instead.

The Ones That Don't Meter You At All

Two options in this category charge nothing and have no ceiling worth writing down, and neither of them shows up in the roundups because there's no affiliate programme on free software.

Super Productivity is open source under the MIT licence, sitting at 20.9k stars on GitHub the morning I looked. It runs as a desktop app on Windows, macOS and Linux, as a web app, on iOS and Android, and it's packaged for F-Droid, Flatpak and the Snap Store. Their own site describes it as free forever and 100% offline and private with zero tracking. Sync is your problem rather than theirs, done through WebDAV or Dropbox, and it exports to JSON and CSV. Task management with subtasks and due dates, time tracking, a Pomodoro timer, Kanban and Eisenhower boards, repeating tasks, and integrations with GitHub, GitLab and Jira.

That is, feature for feature, a paid product. It's the only one on this page where nobody can change the price on you in month thirteen.

Microsoft To Do is the other one, and it's the boring correct answer for a huge number of people. Free, four platforms, list sharing, due dates, reminders, and a daily planning view. It doesn't need a Microsoft 365 subscription, which is worth saying because the page it lives on is covered in Microsoft 365 advertising and the implication is easy to pick up by accident.

The Price That Wouldn't Load

Todoist is the odd one here.

Their pricing page rendered every limit I asked for, cleanly, down to the number of custom filters on each tier, and left the actual dollar amounts blank. Pro shows "per user/month" with nothing in front of it. Business shows "plus local tax" and no figure. I tried the help centre too and got redirected to a page with no prices on it either.

So I can tell you exactly what Todoist Pro gives you, which is 300 personal projects, 100 MB uploads, full reporting history and 150 custom filters, against the free plan's 5 projects, 5 MB, one week of history and 3 filters. I can't tell you what it costs, and I'm not going to repeat a number from someone else's article and pretend I checked it.

The free tier detail worth pulling out anyway is that one-week activity history. Everything else on their free plan is a size limit, and that one is a memory limit, which is a different kind of loss. Size limits you notice. A history window closing behind you is silent.

Seven Subscribers And A Beautiful Board

I should be honest about my own credibility here, because I've done the stupid version of this.

I once put a genuinely lovely amount of effort into organising a content pipeline for a video channel. Labels, statuses, a repeating weekly review, the lot. That channel has seven subscribers. Seven. The board was immaculate and the thing the board described was not working, and I could have told you that at the time if anyone had asked me directly, which nobody did because I was busy in the board.

What I take from that isn't that task apps are bad. It's that the effort you spend inside a task application is the most legible work available to you on any given morning, it produces immediate visible output, and it is almost never the constraint. I'd guess most people reading a comparison of task management applications are, at that exact moment, avoiding something. I was.

So my honest position is that the free tier of whatever you already have installed is probably correct, and the interesting question is which limit will eventually bite, not which app has the nicest board view.

Questions That Come Up

Is a task manager the same as project management software? No, and the difference is who else is in it. Task managers are built around one person's list with sharing bolted on. Project tools are built around a team's shared state with individual lists as a view of it. Trello and Asana straddle the line, Todoist and Microsoft To Do sit clearly on the personal side.

Do I need a paid plan if I'm on my own? Almost certainly not. Every paid tier I priced today is mostly selling collaboration, admin controls or automation volume. Solo, the limits you'd hit are Todoist's five projects and Trello's ten boards, and both of those are more headroom than most single people's lives require.

Which one for a couple or a family? Trello or Microsoft To Do. Trello free carries up to ten people per Workspace, To Do is free and shares lists, and neither will surprise you with a bill. Asana free stops at two, which technically covers a couple and stops working the day a kid or a housemate needs in.

What about tasks that repeat, and where do completed ones go? That's a different question from picking an app, and it's the one that decides whether you trust the system in month six. I've gone into completed-task retention and recurrence properly in the task tracking app piece, since it's where the free plans differ most and nobody checks it before committing.

Should my task app also handle my calendar? I'd say no, mostly, and the tools that try tend to be expensive. The scheduling and time-blocking side is its own category with its own pricing weirdness, covered in apps for time management.

Is one app for everything better than four? Sometimes, and it's genuinely worth testing before you build a stack. The productivity application piece works through how much of a five-tool setup a single app can actually absorb.

How I'd Choose

Work out which ceiling applies to you before you look at a single screenshot. People, containers, file size, or history. It's almost always one of those four, and you'll know within about thirty seconds which one it is.

Then take the cheapest thing that clears it, on annual billing if you're confident and monthly if you're not, because the twenty per cent you save by committing is smaller than the money people lose to subscriptions they forgot to cancel. There's the full cost picture across a whole stack in the productivity apps breakdown, and a wider look at the category, including the free and open-source end of it, in the productivity software overview.

And if none of the ceilings apply, stay free. That's not a compromise position, it's the correct answer for most of the people asking.