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Productivity · head to head

Day One vs Ulysses

Day One logo

Day One

Productivity

Journalling app for iOS, Android and Mac now sold as a subscription after years as a one-time purchase

From
Free
Rated
-
Full reviewWebsite
Ulysses logo

Ulysses

Productivity

Distraction-free writing application for creative professionals

From
$5.99/month
Rated
-
Full reviewWebsite

The short version

  • Only Day One has a free tier, so it costs nothing to try first.
  • Each has a real cost: Day One it moved from a one-time purchase to a subscription after the Automattic acquisition, so long-term cost is materially higher than the original pricing implied.; Ulysses no free tier available
  • They diverge on capability: Day One covers Multiple journals, Ulysses covers Distraction-free writing.
  • Prices and features above were last checked on 1 September 2026.

Where they differ

Only the attributes on which Day One and Ulysses actually diverge.

Attributes where Day One and Ulysses differ
AttributeDay OneUlysses
Starting priceFree$5.99/month
Pricing modelFree tier plus subscriptionsubscription
Free tierYesNo
PlatformsiOS, Android, macOS, WebMacOS, IOS, IPadOS
FoundedUnknown2003

Identical on both: user rating (Not yet rated), category (Productivity).

What each one covers

Drawn from each product's published feature list. An absence here means we hold no record of it - not that the product lacks it.

Only in Day One

  • Multiple journals
  • Rich entries
  • End-to-end encryption
  • On This Day
  • Cross-platform sync
  • PDF and Day One export

Only in Ulysses

  • Distraction-free writing
  • Markdown support
  • Syntax highlighting
  • Organization with sheets and groups
  • iCloud sync
  • Dark and light themes
  • Full-screen mode
  • Search and filter

What people use each for

The jobs each tool is most often brought in to do.

Day One

  • Someone wanting a private daily journal with photos that syncs between phone and laptopnot Ulysses
  • A person keeping a travel journal that auto-attaches location and weather to each entrynot Ulysses
  • Someone who wants encrypted entries kept separate from an unencrypted general journalnot Ulysses
  • A user who wants automated daily writing prompts and On This Day nostalgia reviewnot Ulysses

Ulysses

  • Writing and editing on Apple devicesnot Day One
  • Cross-device document synchronizationnot Day One
  • Markdown-based writingnot Day One

Where each one falls short

Documented limitations, not opinions. Every one is a constraint you would hit in normal use.

Day One

  • It moved from a one-time purchase to a subscription after the Automattic acquisition, so long-term cost is materially higher than the original pricing implied.
  • The free tier caps at one journal and 25 photo entries, which is restrictive enough that anyone journalling seriously for more than a few weeks needs to pay.
  • End-to-end encryption is opt-in per journal rather than on by default, so users have to actively choose it and understand which journals are protected.
  • Cancelling Premium after using multiple journals or heavy photo storage can leave content viewable but with sync and some features disabled, so people should export before cancelling.
  • As an Automattic product, its roadmap sits behind a company whose primary focus is WordPress and Tumblr, not journalling specifically.

Ulysses

  • No free tier available
  • Only subscription model, no one-time purchase option
  • Family Sharing limited to 5 additional members (6 total users)

Pricing, plan by plan

Day One

Free
  • FreeFree
    • One journal
    • Up to 25 photo entries
    • Basic sync
  • Day One Premium$3.99/month
    • Unlimited journals and photos
    • End-to-end encryption
    • On This Day and audio transcription
  • Day One Premium Annual$34.99/year
    • Same as monthly Premium at a lower effective rate

Ulysses

$5.99/month
  • Annual Subscription$39.99/year
    • Ulysses on all Macs, iPads, and iPhones
    • Full iCloud synchronization
    • Frequent improvements and updates
  • Monthly Subscription$5.99/month
    • Ulysses on all Macs, iPads, and iPhones
    • Full iCloud synchronization
    • Frequent improvements and updates

Which should you pick?

Choose Day One if

  • You need multiple journals.
  • You want to start without paying.
  • You work on iOS, Android, macOS, Web.
  • You also want rich entries.
Day One review

Choose Ulysses if

  • You need distraction-free writing.
  • You work on MacOS, IOS, IPadOS.
  • You also want markdown support.
Ulysses review

Questions people ask

Is Day One or Ulysses better?
Neither clearly leads. Day One starts at Free and Ulysses at $5.99/month, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Day One or Ulysses?
Day One has a free tier; the other does not. Paid plans start at Free for Day One and $5.99/month for Ulysses.
Does Day One or Ulysses run on more platforms?
Day One runs on iOS, Android, macOS, Web. Ulysses runs on MacOS, IOS, IPadOS.
Can I use Day One for free?
Yes. Day One has a free tier, so you can try it without paying. Ulysses starts at $5.99/month.
What is Day One best used for?
Day One is most often used for someone wanting a private daily journal with photos that syncs between phone and laptop, a person keeping a travel journal that auto-attaches location and weather to each entry, someone who wants encrypted entries kept separate from an unencrypted general journal, a user who wants automated daily writing prompts and on this day nostalgia review. Of those, someone wanting a private daily journal with photos that syncs between phone and laptop and a person keeping a travel journal that auto-attaches location and weather to each entry are not what Ulysses is typically brought in for.
What can Day One do that Ulysses cannot?
Day One covers Multiple journals, Rich entries, End-to-end encryption, On This Day. Ulysses covers Distraction-free writing, Markdown support, Syntax highlighting, Organization with sheets and groups.

Answered from the vendors’ own pages

Day One: Is Day One still a one-time purchase?

No. Since the 2021 Automattic acquisition it is sold as Day One Premium, a subscription. Older lifetime purchasers were grandfathered but new users pay a subscription.

Ulysses: What are Ulysses pricing options?

Ulysses costs $39.99 per year (annual) or $5.99 per month (monthly). Student discounts are available. Volume licensing is available for businesses through their licensing portal.

Source
Day One: Is encryption on by default?

No, end-to-end encryption is an option users turn on per journal, not a default for all entries.

Ulysses: Does Ulysses include Family Sharing?

Yes, both annual and monthly Ulysses subscriptions include Apple Family Sharing, allowing up to five additional family members to use Ulysses on their devices at no extra cost.

Source
Day One: Can I export my entries if I cancel?

Yes, PDF and native Day One export formats are available regardless of subscription status, though some sync and premium features stop working.

Ulysses: Can I get Ulysses through a subscription service?

Yes, Ulysses is available through the Setapp subscription service as an alternative to direct subscription. Volume licensing is also available for businesses and organizations through their licensing portal.

Source
Ulysses: Does Ulysses pricing vary by location?

Prices listed apply to the U.S., and local pricing may differ in other regions. Check your regional App Store for exact pricing.

Source
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