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Productivity · head to head

HEY vs Microsoft 365

HEY logo

HEY

Productivity

Flat annual subscription email service from 37signals, with its own hey.com domain and a distinctive Screener

From
$99/year
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

  • Each has a real cost: HEY there is no free tier and no monthly billing option, so trying it beyond the trial means committing to a full year upfront.; 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: HEY covers The Screener, Microsoft 365 covers Office applications.
  • Prices and features above were last checked on 1 September 2026.

Where they differ

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

Attributes where HEY and Microsoft 365 differ
AttributeHEYMicrosoft 365
Starting price$99/year$7/month
Pricing modelPer user per monthsubscription
PlatformsMac, Windows, Web, iOS, AndroidWeb

Identical on both: 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 HEY

  • The Screener
  • Imbox, Feed and Paper Trail
  • Reply Later stack
  • Focus and Reply mode
  • Screen sharing style clips
  • No tracking pixels

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.

HEY

  • Someone who wants to replace Gmail or iCloud Mail entirely with an email service built around approving senders before they reach the inboxnot Microsoft 365
  • A user overwhelmed by newsletters and receipts who wants them automatically separated from person to person conversationnot Microsoft 365
  • A family that wants shared but individually addressed email under one annual plannot Microsoft 365
  • A small company wanting HEY for Work on its own domain with the Screener model for the whole teamnot Microsoft 365

Microsoft 365

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

Where each one falls short

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

HEY

  • There is no free tier and no monthly billing option, so trying it beyond the trial means committing to a full year upfront.
  • Adopting HEY means changing your actual email address, not just installing a new client, which is a bigger migration than switching apps on an existing address.
  • The Screener and categorisation model is a real departure from a standard inbox, and some users take time to adjust or find it gets in the way for high volume mail.
  • Short vanity addresses carry steep additional annual fees, up to 999 US dollars a year for a two character address.
  • It does not connect to or manage existing Gmail, Outlook or iCloud accounts, so it cannot be used as a general client the way Mimestream or Apple Mail can.

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

HEY

$99/year
  • HEY for You$99/year
    • One hey.com email address
    • Screener, Imbox, Feed and Paper Trail
    • Billed annually only, no monthly option
  • HEY for Families$179/year
    • Covers up to five family members
    • Same features as HEY for You per member
  • HEY for Work$12/month
    • Per user, for organisations on a company domain
    • Admin controls for a team

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 HEY if

  • You need the screener.
  • You work on Mac, Windows, Web, iOS, Android.
  • You also want imbox, feed and paper trail.
HEY review

Choose Microsoft 365 if

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

Questions people ask

Is HEY or Microsoft 365 better?
Neither clearly leads. HEY starts at $99/year and Microsoft 365 at $7/month, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, HEY or Microsoft 365?
HEY starts at $99/year and Microsoft 365 at $7/month.
Does HEY or Microsoft 365 run on more platforms?
HEY runs on Mac, Windows, Web, iOS, Android. Microsoft 365 runs on Web.
What is HEY best used for?
HEY is most often used for someone who wants to replace gmail or icloud mail entirely with an email service built around approving senders before they reach the inbox, a user overwhelmed by newsletters and receipts who wants them automatically separated from person to person conversation, a family that wants shared but individually addressed email under one annual plan, a small company wanting hey for work on its own domain with the screener model for the whole team. Of those, someone who wants to replace gmail or icloud mail entirely with an email service built around approving senders before they reach the inbox and a user overwhelmed by newsletters and receipts who wants them automatically separated from person to person conversation are not what Microsoft 365 is typically brought in for.
What can HEY do that Microsoft 365 cannot?
HEY covers The Screener, Imbox, Feed and Paper Trail, Reply Later stack, Focus and Reply mode. Microsoft 365 covers Office applications, Hosted services, Teams, Microsoft Entra ID.

Answered from the vendors’ own pages

HEY: Can I use HEY with my existing Gmail address?

No. HEY provides its own hey.com email address; it is not a client layered over an existing Gmail or other account.

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.

HEY: Is there a free plan?

No. HEY offers a trial but bills annually only, with no free tier and no month to month option for individuals.

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.

HEY: What is the Screener?

A feature that holds mail from any new sender until the user explicitly approves them, before it appears in the inbox at all.

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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