Ulysses has been one of the most popular writing apps on the Mac for over a decade. It's polished, it syncs across Apple devices, and it has a loyal community. But its subscription model and Apple-only ecosystem are dealbreakers for some writers. If you're weighing Ulysses against Lettera, here's a candid comparison.

The short version

Ulysses is a library-based writing app with a unified Markdown editor, iCloud sync, and built-in publishing to WordPress, Ghost, and Micro.blog. It's designed for writers who work across Mac, iPad, and iPhone and want everything in one place. The interface is refined — three-pane navigation with groups, filters, and keywords. It feels like an app made by people who care about craft.

Lettera is a desktop-only typewriter where the page has texture and the cursor moves like a carriage. There's no sync, no cloud, no account. Your files live on your computer. There's a mode where backspace strikes through instead of deleting, a daily writing calendar called Paper Trail, and a Drawer for tucking notes alongside each chapter. Lettera feels like a tool made by someone who misses typewriters.

	Lettera	Ulysses
Price	$29 (14-day free trial)	$49.99/year
Platforms	macOS, Windows	macOS, iPad, iPhone
Windows support	✓	—
Typewriter carriage	✓	—
No-delete mode	✓ (Purist Mode)	—
Paper textures	✓	—
Cloud sync	—	✓ (iCloud)
Mobile writing	—	✓
Blog publishing	—	✓ (WordPress, Ghost)
Chapter management	✓	✓ (groups)
Per-chapter notes	✓ (the Drawer)	✓ (attachments)
Daily writing goals	✓ (Paper Trail)	✓
Grammar/style check	—	✓
Export formats	PDF, Word, Markdown, TXT	PDF, Word, ePub, HTML, Markdown
Local files	✓ (files on disk)	iCloud library (proprietary)
Account required	No	Apple ID + subscription
AI writing features	No. The words are yours.	Yes (Apple Writing Tools, ChatGPT integration)

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Where Ulysses is the better choice

If you write across devices — starting a draft on your Mac, continuing on the train with your iPad, jotting a note on your iPhone — Ulysses handles this beautifully. The iCloud sync is fast and reliable, and the experience is consistent across all three platforms. No other writing app matches this if you live in the Apple ecosystem.

Ulysses also publishes directly to WordPress, Ghost, and Micro.blog, which makes it a strong choice for bloggers and newsletter writers who want to go from draft to published post without leaving the app. The built-in grammar and style check supports over 20 languages, which is useful for multilingual writers or anyone who wants a second set of eyes built into the tool.

The library metaphor is worth mentioning too. Ulysses stores everything in a single, searchable library with smart filters and keywords. For writers who produce a lot of short-to-medium pieces, this organizational model can feel effortless.

Where Lettera is the better choice

The most obvious difference is money. Ulysses costs $49.99 a year, every year. Stop paying and you lose access to the app. Over five years, that's $250 for a writing tool. Lettera costs $29 once — try it free for 14 days first — and that's it. Never pay again. That's $221 less over five years, and Lettera never stops working.

The second difference is ownership. Ulysses stores your writing in an iCloud library using a proprietary format. You can export, but your files don't exist as plain documents on your hard drive the way they do in Lettera. With Lettera, your chapters are files on your computer. Move them, back them up, open them in another app — they're yours in every sense.

The third difference is platform. Ulysses is Apple-only. If you use Windows — or might switch someday — Ulysses can't follow you. Lettera runs on both macOS and Windows.

Ulysses has also integrated Apple's Writing Tools and ChatGPT — AI features that can rewrite, summarize, and proofread your text. Lettera has no AI. It won't rewrite your sentences or suggest what comes next. For writers who want a tool that respects the boundary between their words and a machine's, that distinction matters.

And then there's the thing that's harder to quantify: feel. Lettera's carriage movement, paper textures, and Purist Mode create a writing experience that no other app offers. The page has grain. The keys have consequence. It's the difference between typing into a cloud and typing onto a surface.

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Ulysses' philosophy

Writing should flow. From any device, to any platform, with beautiful typography and smart organization. The tool should be as fluid as the writing itself.

Lettera's philosophy

Writing should have weight. The page should have texture. The keys should have consequence. Your files should live on your computer, not in someone else's cloud.

Ulysses is built for writers who want to write everywhere. Lettera is built for writers who want to sit down somewhere — really sit down — and write.

The subscription question

Ulysses switched from a one-time purchase to a subscription model in 2017. Some long-time users never forgave them for it. Whether a subscription bothers you is personal — some writers prefer knowing the app is actively funded and updated, others resent paying rent on a tool they've already learned. For context: Lettera chose a one-time price because the person who built it believes writing tools shouldn't be a recurring expense. That's a philosophical position, not a business critique. Both models can produce great software.

Can you use both?

You can, though the use cases don't overlap as neatly as with Scrivener. Where Lettera and Ulysses might coexist: use Lettera for long, focused drafting sessions at your desk — the carriage movement, Purist Mode, and Paper Trail are designed for sustained writing. Use Ulysses for everything around the writing: organizing notes on the go, publishing blog posts, quick captures on your phone. Desktop typewriter for the hard work, cloud library for everything else.

The honest take

Ulysses is a polished, mature writing app with the best cross-device sync in the business. If you write on Apple devices and value that fluid, everything-in-sync experience, it justifies the subscription. Lettera offers something Ulysses doesn't and can't — a physical dimension to digital writing, plus true file ownership and a one-time $29 price that never renews. If you're on Windows, the choice is made for you. If you're on a Mac and the subscription cost is wearing on you, or if you've been looking for a writing app that feels like more than a text field, Lettera is worth the thirty seconds it takes to download.