Software · head to head
Outlook Calendar vs Square Appointments

Outlook Calendar
Software
Professional calendar management for Microsoft 365
- From
- Free
- Rated
- -
The short version
- Each has a real cost: Outlook Calendar offline support limited to only past 30 days of events, older events unavailable; Square Appointments the free plan is aimed at solo professionals; booking across multiple staff requires the paid Plus plan
- They diverge on capability: Outlook Calendar covers Meeting scheduling, Square Appointments covers Online booking.
Where they differ
Only the attributes on which Outlook Calendar and Square Appointments actually diverge.
| Attribute | Outlook Calendar | Square Appointments |
|---|---|---|
| Pricing model | Unknown | subscription |
| Platforms | Web, Windows, macOS, iOS, Android | Web, Ios, Android |
| Founded | 1975 | 2009 |
Identical on both: starting price (Free), free tier (Yes), user rating (Not yet rated), category (Unknown).
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 Outlook Calendar
- Meeting scheduling
- Shared calendars
- Room booking
- Availability sharing
- Recurring events
- Microsoft Teams
- OneDrive
- SharePoint
Only in Square Appointments
- Online booking
- Client management
- Point of sale
- Payment processing
- Automated reminders
- Instagram booking
- Google booking
- Mobile app
Both cover
- Web support
What people use each for
The jobs each tool is most often brought in to do.
Outlook Calendar
- Schedulingnot Square Appointments
- Appointment bookingnot Square Appointments
- Time trackingnot Square Appointments
- Resource managementnot Square Appointments
- Team coordinationnot Square Appointments
Square Appointments
- Online appointment booking for salons, barbers and personal servicesnot Outlook Calendar
- Taking card payments and deposits at the time of bookingnot Outlook Calendar
- Managing staff calendars, waitlists and no-show policiesnot Outlook Calendar
Where each one falls short
Documented limitations, not opinions. Every one is a constraint you would hit in normal use.
Outlook Calendar
- Offline support limited to only past 30 days of events, older events unavailable
- Shared calendars and group calendars not available offline
- Cached Exchange Mode issues can limit available offline data
- Occasional sync conflicts when coming back online
Square Appointments
- The free plan is aimed at solo professionals; booking across multiple staff requires the paid Plus plan
- Cancellation policies, no-show fees and waitlists require the Plus plan
- Resource management, service cost tracking and the future bookings report require the Premium plan
- Custom processing rates are reserved for Square Pro, which is aimed at businesses processing over $250,000 a year
- Card processing fees are charged on top of the plan fee on every tier including the free one
Pricing, plan by plan
Outlook Calendar
Free- FreeFree
- Outlook.com email and calendar
- 50MB attachment limit
- 1GB cloud storage
- Microsoft 365 Basic$19.99/year
- Outlook with limited features
- Cloud storage
- Microsoft 365 Personal$99.99/year
- Premium Outlook
- Ad-free email
- 100GB mailbox storage
- Microsoft 365 Business Basic$6/month
- Business-class email
- 1TB cloud storage
- Microsoft Teams
Square Appointments
Free- FreeFree
- Unlimited appointments
- Online booking
- Client management
- Plus$29/month
- Everything in Free
- Multiple staff calendars
- No-show protection
- Premium$69/month
- Everything in Plus
- Multi-location
- Staff management
Which should you pick?
Choose Outlook Calendar if
- You need meeting scheduling.
- You want to start without paying.
- You work on Web, Windows, macOS, iOS, Android.
- You also want shared calendars.
Choose Square Appointments if
- You need online booking.
- You want to start without paying.
- You work on Web, Ios, Android.
- You also want client management.
Questions people ask
- Is Outlook Calendar or Square Appointments better?
- Neither clearly leads. Outlook Calendar starts at Free and Square Appointments at Free, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
- Which is cheaper, Outlook Calendar or Square Appointments?
- Outlook Calendar starts at Free and Square Appointments at Free.
- Does Outlook Calendar or Square Appointments run on more platforms?
- Outlook Calendar runs on Web, Windows, macOS, iOS, Android. Square Appointments runs on Web, Ios, Android.
- Can I use Outlook Calendar for free?
- Both have a free tier, so you can try either at no cost before committing.
- What is Outlook Calendar best used for?
- Outlook Calendar is most often used for scheduling, appointment booking, time tracking, resource management. Of those, scheduling and appointment booking are not what Square Appointments is typically brought in for.
- What can Outlook Calendar do that Square Appointments cannot?
- Outlook Calendar covers Meeting scheduling, Shared calendars, Room booking, Availability sharing. Square Appointments covers Online booking, Client management, Point of sale, Payment processing. Both handle Web support.
Answered from the vendors’ own pages
Outlook Calendar: Is Outlook Calendar free?
Outlook.com with calendar is free via a Microsoft account. Outlook Calendar also comes with Microsoft 365 Personal ($99.99/year), Family ($129.99/year), or Business plans starting at $6/user/month.
SourceOutlook Calendar: Does Outlook Calendar work offline?
Outlook Calendar has limited offline support. New Outlook caches only the past 30 days of calendar items. Shared calendars and group calendars are not supported offline. Changes sync when you reconnect.
SourceOutlook Calendar: What platforms does Outlook Calendar support?
Outlook Calendar is available on Windows (desktop and web), macOS (desktop and web), iOS, and Android. Real-time synchronization works across all devices.
SourceOutlook Calendar: Does Outlook Calendar integrate with Slack?
Yes. Outlook Calendar integrates with Slack to sync your status and receive meeting notifications. You can RSVP to invites directly in Slack and join Microsoft Teams meetings from Slack reminders.
SourceOutlook Calendar: Can you share calendars and set delegate permissions?
Yes. Outlook Calendar supports calendar sharing with delegate permissions, color categories for organization, and the Scheduling Assistant to view attendee availability for meeting times.
SourceRelated pages
More on Outlook Calendar
More on Square Appointments
Keep looking
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- Square Appointments vs Clockify
- Square Appointments vs Microsoft To Do
- Square Appointments vs OmniFocus
- Square Appointments vs Amie
- Square Appointments vs Float
- Square Appointments vs Google Tasks
- Square Appointments vs YouCanBook.me
- Square Appointments vs Cron Calendar
- Square Appointments vs Harvest Forecast
- Square Appointments vs Resource Guru
- Square Appointments vs SavvyCal
- Square Appointments vs Skedda
- Square Appointments vs Timepage
- Square Appointments vs Woven
- Square Appointments vs Assistant.to
- Square Appointments vs Calendly
- Square Appointments vs Cal.com
- Square Appointments vs Motion
- Square Appointments vs Acuity Scheduling
- Square Appointments vs Appointlet
- Square Appointments vs Appointy
- Square Appointments vs Setmore
- Square Appointments vs 10to8
- Square Appointments vs Booksy
- Square Appointments vs Boulevard
- Square Appointments vs Doodle
- Square Appointments vs Fresha
- Square Appointments vs GlossGenius
- Square Appointments vs Schedulicity
- Square Appointments vs When2meet
- Square Appointments vs Zenoti
- Square Appointments vs Airbnb
- Square Appointments vs Booker by Mindbody

