Ulysses Has Broken My Heart for the Last Time

Ulysses, it’s been a long road but today I’m breaking up with you.

The choice of writing app is a very personal thing. For some people, Scrivener is their go-to, others it’s IA Writer, and then there are those who, like me until recently, use Ulysses.

Here’s a simple truth: I write in Markdown.

It’s been my choice of writing syntax for more than 20 years now, through all of its many subtle iterations.

From bog-standard Windows Notepad, to Notepad++, then migrating to Graeme Gott’s phenomenal FocusWriter, and all the other various bespoke distraction-free tools that were available to me at the time. With Markdown I’ve written documents, short stories, unpublished novels, quick notes, and more articles than I can rightly point my finger at (including this one).

And I’m not about to stop writing in Markdown anytime soon.

So when I moved back to Mac in 2007 I was looking for a decent writing app that ticked a few very specific boxes. I’d heard of Ulysses, and their companion iOS app Daedalus Touch, and tried them out. Both did a fairly good job, but were too clunky to use together and far from an elegant solution.

Enter IA Writer

A big part of my writing process is not sitting at a keyboard. Which might sound strange, but as seasoned writers will tell you time and time again—your best ideas don’t come staring at a flashing cursor while you rest your fingers on a keyboard, they happen whenever, and wherever you are.

Bored. Distracted. Busy. Half asleep. During a concert. Waiting in a queue. Wherever.

So for me, the ability to have a way to take notes, sketch ideas, write down the stupidly unformed half-baked kind of ideas I have at a moments notice is seriously important.

I also hate carrying around a notebook and pen all the time, so having a decent solution on my phone is important. I’d tried using Apple Notes and then copy/pasting them into other apps but there was something about the friction that just made me loathe doing it all the time.

And that’s where I fell in love with IA Writer, a distraction-free writing app that solved one of the biggest bugbears I had with my process. Having an app that seamlessly allowed me to have full access to all my writing at any time on my iPhone or Mac was a game changer for me.

But I’m not here to talk about how I use IA Writer, even though it’s still one of my favourites.

I’m here to talk about Ulysses.

The Switch to Ulysses

2016 was a damn revelation. The Soulmen (the developers of Ulysses and Daedalus Touch, not a late-night jazz trio in some smoke filled dive bar) made a pivotal change to their app approach. They’d decided to sunset Daedalus Touch and instead push their efforts into releasing a dedicated iPhone version of Ulysses… and my writing life changed.

Finally I had found the perfect writing environment for me. Distraction-free, but with quality of life features I didn’t even know I wanted.

Where it differed from IA Writer is that Ulysses gave me the room to be opinionated about my writing environment, I could swap themes to suit what I was writing, give myself solid visible writing goals to push me to get things done, and a feature set that supported the one thing that I really wanted to do… write a damn novel.

See, one of the things that most distraction-free writing environments do very well is working with plain-text files. But the issue that plagues most plain-text file editors is the segmentation between files, especially when working on longer projects.

Where Ulysses solves this is by abstracting where the writing lives. Rather than storing your writing in a bunch of .txt or .md files stored on your hard drive, it uses its own internal database to make things more flexible.

This gives rise to incredibly powerful features like being able to glue “sheets” so you can edit scenes together, reorder sheets to swap around the order of whole chapters, and have a snapshot of every edit you’ve ever made to a sheet so you can always revert back to an earlier draft of you’d accidentally deleted something, even if it was days before.

The best thing of all was that it all synced to your iCloud account, meaning that the same features and capabilities were available across your Mac, iPhone, and iPad all in a beautiful seamless concert of writing.

Of course if I ever wanted to export my writing back to a plain text file, I could with ease. But exporting didn’t stop there. With different export themes and formats available like PDF, EPUB, and DOCX and being able to organise drafts into publish-ready works effortlessly, Ulysses was even more compelling as a writers dream… so of course, I switched immediately.

And the biggest improvement to my workflow? Tree-style folder navigation with colours and icons. This alone was worth paying the $75+ AUD for the desktop version and separately about $40 AUD for the iOS version (yes I’m Australian, so I get to pay the age-old ‘I’m from Australia’ software tax).

Not only did it give me the seamless writing experience I’d wanted, but with the additional features it felt like a true productivity boost for my long-form writing.

So I wrote, and wrote, and wrote some more. Short form blogs. Long-form articles. Fiction Shorts. And the 10,000 word short story I was struggling to work on because of file fragmentation? Done and done.

And for a while, it was glorious.

Which is why what came next was almost unforgivable.

All up with Ulysses macOS and iOS and Daedalus Touch I’d spent around $150 AUD with The Soulmen. Then August 10, 2017 they pulled the rug out from all of us.

If you’d bought the software—as I recently had—then you woke up on that day to the notification that suddenly Ulysses had moved to a subscription model, and older versions of either the macOS or iOS would no longer be updated.

So annually I had to pay for the software that I just paid for… AGAIN, and because of the ‘Australia Tax’… it was going to cost me $60+ dollars a year moving forward (that’s $39.99 USD for those playing along).

The only saving grace was a ‘lifetime' discount that existing users could claim of 25% which brought down the price to $40.99 per year.

Anyhow, enough of a history lesson, let’s fast forward almost a decade shall we?

Specifically right now. Jan 2026.

The Inevitable Slow Decline

The reason given by the Ulysses team for switching to a subscription model was simple enough: sustainability.

Their argument was that the traditional pay-once model couldn’t fund long-term development, and that a steady revenue stream would enable continuous, incremental improvements rather than infrequent, major paid upgrades.

Fair enough, developers need to eat too.

So while, like a lot of people, I rejected the move to a subscription model, I also acutely understand the need for sustainability for technology projects.

After all, if the humans who make the software can’t eat or pay rent, then we don’t get to have software that’s continually developed, patched, upgraded, secured, and bug-free, right?

But before I continue, I need to clarify:

• I’m not anti-subscription for software, where it works it works well.
• I’m anti continually paying for an app that remains creatively static.

And that’s the crux of the problem. Over the last 9 years, I’ve kept using Ulysses.

And Ulysses… kept largely staying the same.

Sure changes arrived regularly, but they were safe. Cosmetic. Tiny incremental updates. New icons here. A few minor feature tweaks there. Small conveniences that never quite added up to full, meaningful evolution.

Yes they added features like direct publishing to Medium.com, Ghost, WordPress, and Micro.Blog (not that you’ve probably ever heard of it), but the vast majority of users probably didn’t use this feature all that much.

Later they slightly improved navigation, added internal wiki-like linking between sheets (which it had needed all along), additional colour theme options, goal setting, progress tracking, merge sheets, glue sheets.

And while these sound like a laundry list of features, you have to consider the sheer number of people paying annually for this development.

While we can’t know the true number of people who pay for Ulysses—as the company does not publish user figures—its popularity in writing circles, Apple Design Award recognition in 2016, and regularly appearing in “best of apps” roundup articles suggest it has an active user base in the low hundreds of thousands.

And for a subscription app, Ulysses has begun to feel less like active development and more like careful, yet simple maintenance—the digital equivalent of repainting the walls while never touching the foundations.

But that’s not what a subscription implies. A subscription implies momentum. Direction. A sense that the product is going somewhere.

Over the years, that sense eroded and quietly evaporated.

Does it still achieve its promise of a distraction-free writing app with advanced features?

Yes, yes it does. But with one important and rather serious caveat…

The Trust Problem

For a writing app being used by thousands of people daily, data safety isn’t optional.

And yet, scattered across forums, Reddit threads, support tickets, and firsthand accounts, the same class of problems have kept resurfacing: iCloud sync failures.

And not just a few paragraphs here or there, but entire writing libraries being corrupted in the blink of an eye, caused by the way Ulysses chooses to implement Apple CloudKit to sync it’s internal database between your devices.

Simple in theory, but it turns out not in practice:

• Sometimes it happened after a conflict between macOS and iOS.
• Sometimes after an OS upgrade.
• Sometimes after CloudKit decided—opaquely and without warning—that it was suddenly out of sync with one of your devices.

To be clear, this wasn’t a single catastrophic bug that was notified, fixed, and forgotten. It was a recurring category of failure. One that cropped up just often enough to plant a seed of doubt every time any Ulysses user opened the app on a second device.

Did it happen to everyone? no, but for the people it did happen to the outcome was utterly devastating.

And once that seed is planted, you start doing things writers shouldn’t have to do, like exporting backups “just in case”, hesitating before reorganising large projects, avoiding opening the same library on multiple devices at the same time, feeling a small spike of anxiety after every OS update.

That’s not paranoia. That’s learned behaviour.

What’s finally pushed me over the edge isn’t a single catastrophic failure.
It was the accumulation of many different kinds of friction, reported quietly and repeatedly by the same groups of users.

Out of curiosity, I spent time trawling through /r/ulyssesapp—a subreddit with fewer than 800 members—looking only at posts from the past year.

What I found wasn’t outrage. It was something worse: resignation.

The issues weren’t all the same, but they fell into a few disturbingly consistent categories.

1. Data integrity and recovery anxiety

Yes, iCloud sync failures were part of it. Lost sheets, empty libraries, vanished backups. But the deeper problem wasn’t iCloud itself. It was the lack of transparent, user-controllable recovery mechanisms when something went wrong.

Users weren’t asking for miracles. They were asking for clarity. For tools. For a reliable way to inspect, backup, and restore their own work without ritual, guesswork, or hope.

2. Regression of core writing features

Features that writers relied on quietly disappeared, changed behaviour, or became harder to access:

• Full-screen and typewriter modes behaving differently—or vanishing entirely
• Interface elements reappearing unexpectedly during focused writing
• Markdown toolbars forcing themselves back into view
• Previously predictable editing modes becoming inconsistent across updates

None of these are headline features. But they’re foundational. They directly affect flow. The one thing a writing app should never interfere with.

3. Text input behaving unpredictably

Several reports described text being replaced while typing, auto-completion behaving erratically, or cursor behaviour changing mid-sentence.

These aren’t cosmetic bugs. They strike at muscle memory. At trust between writer and tool. When the editor starts second-guessing your keystrokes, you stop thinking about what you’re writing and start thinking about the software.

That’s fatal to creative work.

4. Cross-device inconsistency

Even when data wasn’t lost, behaviour differed between macOS, iPadOS, and iOS:

• Features present on one platform but not another
• Settings that didn’t carry across
• UI changes that altered workflows depending on the device you happened to be using that day

For an app whose entire value proposition is seamless cross-device writing, that inconsistency matters more than it might seem.

5. Communication breakdown

Perhaps the most striking thing wasn’t the bugs themselves. It was how often users expressed uncertainty about whether issues were known, acknowledged, or ever likely to be fixed.

No roadmap.
No post-mortems.
No clear sense of prioritisation.

Just recurring questions from paying users asking whether a problem was “by design”, “a known issue”, or simply something they were expected to live with.

A Disappointing End

None of these issues alone has made me leave.

But together they paint a picture of a product slowly drifting away from the needs of the people who actually write with it every day, and a subscription that doesn’t evolve eventually starts to regress.

Ulysses’ official feature log shows a cadence dominated by UX refinements, export tweaks, UI redesigns, and polish—not deep expansion of core writing tools or workflows.

Improvements like backlinks, internal linking, Apple AI writing tools, and publishing helpers do matter—but they are surface-level or peripheral features, not a rethinking of how long-form creative work could be managed or structured.

Ulysses didn’t fail me because it became utterly unusable, it failed me because, over time, it stopped justifying the level of trust a writing tool quietly demands.

For years, I paid because the app felt stable, familiar, and good enough. Because it had been transformative once, and because inertia is powerful when a tool holds your entire body of work inside it.

But charging a subscription is an ongoing commitment. One that implies progress, stewardship, and above all, reliability.

What ultimately broke that commitment wasn’t a single bug, or a single update, or even the subscription itself, even if it hurt initially. It was the slow accumulation of doubt.

• Doubt that core writing behaviours would remain consistent.
• Doubt that long-standing architectural risks were being addressed.
• Doubt that the people paying year after year—and the issues they’ve faced—were being meaningfully prioritised and the subscription fees were being used to make the product fundamentally better.

A writing app doesn’t need to be exciting. It doesn’t need to chase trends. But it does need to be trustworthy, predictable, and transparent about its direction. Once those qualities begin to erode, no amount of polish or UI refinement can compensate.

I haven’t stopped using Ulysses because it became bad, I’ve stopped because it stopped improving in the ways that mattered most.

Because writing is hard enough without wondering whether the tool you rely on will still be worthy of your confidence tomorrow.

And it’s the reason I’m finally letting go.

Note: This article reflects my personal experience as a long-term user of Ulysses.

This is an independent critique and is not affiliated with or endorsed by any software developer.

Observations regarding software performance and community sentiment are based on my own usage and publicly available discussions on platforms like Reddit and the Ulysses community forums.