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Productivity · head to head

Microsoft 365 vs Ulysses

Microsoft 365 logo

Microsoft 365

Productivity

Subscription bundle of the Office applications with mail, storage, meetings and organisational identity

From
$7/month
Rated
-
Full reviewWebsite
Ulysses logo

Ulysses

Productivity

Distraction-free writing application for creative professionals

From
$5.99/month
Rated
-
Full reviewWebsite

The short version

  • Each has a real cost: Microsoft 365 business plans are capped at 300 seats, so an organisation that grows past that must move to Enterprise plans, which changes both the price per user and the feature mix at the moment it can least afford a migration project.; Ulysses no free tier available
  • They diverge on capability: Microsoft 365 covers Office applications, Ulysses covers Distraction-free writing.
  • Prices and features above were last checked on 30 August 2026.

Where they differ

Only the attributes on which Microsoft 365 and Ulysses actually diverge.

Attributes where Microsoft 365 and Ulysses differ
AttributeMicrosoft 365Ulysses
Starting price$7/month$5.99/month
PlatformsWebMacOS, IOS, IPadOS
FoundedUnknown2003

Identical on both: pricing model (subscription), free tier (No), 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 Microsoft 365

  • Office applications
  • Hosted services
  • Teams
  • Microsoft Entra ID
  • OneDrive storage
  • Device management and endpoint protection
  • Purview compliance
  • Copilot

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.

Microsoft 365

  • Any organisation that wants mail, documents, meetings and identity from one supplier on one bill.not Ulysses
  • A company standardising on single sign-on, where Entra ID becomes the account other services authenticate against.not Ulysses
  • Regulated work that needs retention, legal hold and eDiscovery across mail and documents, provided the tier that includes them is actually bought.not Ulysses
  • A household that needs installed Office applications on several machines rather than browser-only editing.not Ulysses

Ulysses

  • Writing and editing on Apple devicesnot Microsoft 365
  • Cross-device document synchronizationnot Microsoft 365
  • Markdown-based writingnot Microsoft 365

Where each one falls short

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

Microsoft 365

  • Business plans are capped at 300 seats, so an organisation that grows past that must move to Enterprise plans, which changes both the price per user and the feature mix at the moment it can least afford a migration project.
  • The compliance capabilities most organisations eventually need, including retention, data loss prevention, advanced eDiscovery and insider risk, sit at the top tier or in add-ons, so the real cost surfaces after an audit or a customer questionnaire rather than at purchase.
  • Annual term subscriptions commit you for the year and month-to-month terms cost measurably more per seat, so the flexibility to reduce seats during a quiet period is bought at a permanently higher rate.
  • Entra ID becomes the identity for everything else the organisation uses, which is the hardest kind of lock-in to put a number on, because leaving means re-federating every connected application rather than simply replacing a word processor.
  • The licensing model is complicated enough that most organisations are either over-licensed or quietly non-compliant, and reconciling it usually requires a partner or a specialist, which is a recurring cost that never appears in the advertised per-user figure.

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

Microsoft 365

$7/month
  • Microsoft 365 Business Basic$7/month
    • Email and calendar with 50 GB mailbox
    • Web and mobile versions of Office apps
    • Microsoft Teams included
  • Microsoft 365 Business Standard$14/month
    • Desktop versions of Word, Excel, PowerPoint, Outlook
    • Email and Teams
    • 1 TB cloud storage per user
  • Microsoft 365 E5$60/month
    • Comprehensive security and compliance
    • All productivity apps
    • Advanced analytics

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 Microsoft 365 if

  • You need office applications.
  • You also want hosted services.
Microsoft 365 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 Microsoft 365 or Ulysses better?
Neither clearly leads. Microsoft 365 starts at $7/month and Ulysses at $5.99/month, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Microsoft 365 or Ulysses?
Microsoft 365 starts at $7/month and Ulysses at $5.99/month.
Does Microsoft 365 or Ulysses run on more platforms?
Microsoft 365 runs on Web. Ulysses runs on MacOS, IOS, IPadOS.
What is Microsoft 365 best used for?
Microsoft 365 is most often used for any organisation that wants mail, documents, meetings and identity from one supplier on one bill., a company standardising on single sign-on, where entra id becomes the account other services authenticate against., regulated work that needs retention, legal hold and ediscovery across mail and documents, provided the tier that includes them is actually bought., a household that needs installed office applications on several machines rather than browser-only editing.. Of those, any organisation that wants mail, documents, meetings and identity from one supplier on one bill. and a company standardising on single sign-on, where entra id becomes the account other services authenticate against. are not what Ulysses is typically brought in for.
What can Microsoft 365 do that Ulysses cannot?
Microsoft 365 covers Office applications, Hosted services, Teams, Microsoft Entra ID. Ulysses covers Distraction-free writing, Markdown support, Syntax highlighting, Organization with sheets and groups.

Answered from the vendors’ own pages

Microsoft 365: What is the difference between Microsoft 365 and Office?

Office was a one-off licence for a specific version. Microsoft 365 is a subscription covering the applications and the hosted services together, and when payment stops the applications drop to a reduced state rather than continuing as they were.

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
Microsoft 365: Is Teams included?

Not automatically for newer customers. Microsoft unbundled Teams and now sells it alongside the suite, so check what a given quotation actually covers.

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
Microsoft 365: What happens to our files if we stop paying?

The documents remain yours and can be downloaded, but access to hosted mailboxes and sites ends after a retention window, so leaving requires a planned export rather than a cancellation.

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
Microsoft 365: Is Copilot part of the subscription?

No. It is a per-user add-on on top of the base licence, generally with its own term commitment, and it is priced per seat regardless of how much any individual uses it.

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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