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Productivity · head to head

Day One vs Microsoft 365

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
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

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.; 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.
  • They diverge on capability: Day One covers Multiple journals, Microsoft 365 covers Office applications.
  • Prices and features above were last checked on 1 September 2026.

Where they differ

Only the attributes on which Day One and Microsoft 365 actually diverge.

Attributes where Day One and Microsoft 365 differ
AttributeDay OneMicrosoft 365
Starting priceFree$7/month
Pricing modelFree tier plus subscriptionsubscription
Free tierYesNo
PlatformsiOS, Android, macOS, WebWeb

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 Microsoft 365

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

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 Microsoft 365
  • A person keeping a travel journal that auto-attaches location and weather to each entrynot Microsoft 365
  • Someone who wants encrypted entries kept separate from an unencrypted general journalnot Microsoft 365
  • A user who wants automated daily writing prompts and On This Day nostalgia reviewnot Microsoft 365

Microsoft 365

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

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.

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

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

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 Microsoft 365 if

  • You need office applications.
  • You also want hosted services.
Microsoft 365 review

Questions people ask

Is Day One or Microsoft 365 better?
Neither clearly leads. Day One starts at Free and Microsoft 365 at $7/month, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Day One or Microsoft 365?
Day One has a free tier; the other does not. Paid plans start at Free for Day One and $7/month for Microsoft 365.
Does Day One or Microsoft 365 run on more platforms?
Day One runs on iOS, Android, macOS, Web. Microsoft 365 runs on Web.
Can I use Day One for free?
Yes. Day One has a free tier, so you can try it without paying. Microsoft 365 starts at $7/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 Microsoft 365 is typically brought in for.
What can Day One do that Microsoft 365 cannot?
Day One covers Multiple journals, Rich entries, End-to-end encryption, On This Day. Microsoft 365 covers Office applications, Hosted services, Teams, Microsoft Entra ID.

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.

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.

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.

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.

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.

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.

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.

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