Technology · head to head
Microsoft Outlook vs Userpilot
Microsoft Outlook
Technology
Microsoft's email and calendar client, in the middle of a transition from the classic Windows application to a web-based replacement.
- From
- Free
- Rated
- -
Userpilot
Technology
Product analytics and in-app onboarding platform.
- From
- Free
- Rated
- -
The short version
- Each has a real cost: Microsoft Outlook microsoft is replacing the classic Win32 client with the new web-based Outlook, and the new one runs only web add-ins, not COM add-ins, so any line-of-business integration for CRM, dictation, document management or telephony must be rewritten or the desktop stays on classic until its support window closes.; Userpilot starter tier limited to 2,000 monthly active users; even small-to-medium products may require Growth tier
- Prices and features above were last checked on 30 August 2026.
Where they differ
Only the attributes on which Microsoft Outlook and Userpilot actually diverge.
| Attribute | Microsoft Outlook | Userpilot |
|---|---|---|
| Pricing model | freemium | subscription |
| Platforms | Web | Web, iOS, Android, API |
Identical on both: starting price (Free), free tier (Yes), user rating (Not yet rated), category (Technology).
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 Outlook
- Exchange calendar integration
- Delegate access
- Shared mailboxes
- Rules and Quick Steps
- Retention, hold and eDiscovery
- Sensitivity labels and encryption
- Add-in platform
- Offline cached mode
Only in Userpilot
Nothing recorded that Microsoft Outlook does not also cover.
What people use each for
The jobs each tool is most often brought in to do.
Microsoft Outlook
- Organisations on Exchange Online or Exchange Server where free/busy scheduling and room booking across everyone is a daily requirementnot Userpilot
- Executive assistants managing someone else's calendar and mailbox through delegate access, which no IMAP client supports properlynot Userpilot
- Regulated environments that need retention policies, legal hold and eDiscovery applied to mail centrally rather than per usernot Userpilot
- Teams handling shared inboxes such as support or accounts, where permissions and tracking matter more than the mail client itselfnot Userpilot
Userpilot
- SaaS companies optimising user onboarding and activationnot Microsoft Outlook
- Product teams collecting user feedback and identifying churn drivers via session replaynot Microsoft Outlook
- Customer success teams using in-app guides and contextual helpnot Microsoft Outlook
- Growth teams orchestrating multi-channel campaigns across email and in-appnot Microsoft Outlook
- Product managers measuring adoption and engagement across user cohortsnot Microsoft Outlook
Where each one falls short
Documented limitations, not opinions. Every one is a constraint you would hit in normal use.
Microsoft Outlook
- Microsoft is replacing the classic Win32 client with the new web-based Outlook, and the new one runs only web add-ins, not COM add-ins, so any line-of-business integration for CRM, dictation, document management or telephony must be rewritten or the desktop stays on classic until its support window closes.
- The new client's handling of non-Microsoft accounts synchronises mail through Microsoft's cloud rather than connecting from the machine to the provider, which several organisations' data residency and handling policies do not allow, and it is not an optional behaviour.
- PST and OST files are a single-file, corruptible and effectively unshareable store, and the new client's reduced PST support means years of personal archives sitting in those files need an explicit migration plan rather than carrying forward.
- Large mailboxes turn software problems into administration ones: search index rebuilds, OST files of tens of gigabytes and the mailbox quotas of whichever plan was bought, and the usual fix is archiving policy rather than anything a user can do.
- Against IMAP or Gmail you lose most of what justifies it, including free/busy lookup, room booking, delegate access, and retention and compliance policies, because those are Exchange server features rather than client features.
- The five or six products sharing the Outlook name have materially different feature sets, so internal documentation, training and support procedures must be written per platform and a user moving between desktop, web and mobile finds the same task done differently in each.
Userpilot
- Starter tier limited to 2,000 monthly active users; even small-to-medium products may require Growth tier
- Large price jump from Starter ($299/mo) to Growth ($849/mo), nearly 3x increase
- Growth tier scales to 100,000 MAU but does not publish pricing for higher volumes, requiring Enterprise negotiation
- Session replay and mobile engagement are optional add-ons in Growth tier, not included in base pricing
- Enterprise pricing not published; custom negotiations required for large-scale deployments
Pricing, plan by plan
Microsoft Outlook
Free- Outlook (Free)Free
- 15 GB mailbox storage
- 5 GB cloud storage
- Web and mobile Office app access
- Microsoft 365 Basic$1.99/month
- 100 GB mailbox storage
- 100 GB cloud storage
- Ad-free experience
- Microsoft 365 Personal$9.99/month
- 1 TB cloud storage
- Desktop Office apps (Word, Excel, PowerPoint, Outlook, OneNote)
- Copilot with high usage limits
- Microsoft 365 Family$12.99/month
- 1-6 users
- Up to 6 TB total cloud storage (1 TB per person)
- Same apps and features as Personal
Userpilot
Free- Starter$299/month
- Up to 2,000 monthly active users
- In-app engagement
- User segmentation
- Growth$849/month (marked 'Most Popular')
- 2,000 to 100,000 monthly active users
- All Starter features
- Advanced product analytics
- Enterprise$undefined/variable
- Custom monthly active user levels
- All Growth features
- Premium integrations
Which should you pick?
Choose Microsoft Outlook if
- You need exchange calendar integration.
- You want to start without paying.
- You also want delegate access.
Choose Userpilot if
- You want to start without paying.
- You work on Web, iOS, Android, API.
Questions people ask
- Is Microsoft Outlook or Userpilot better?
- Neither clearly leads. Microsoft Outlook starts at Free and Userpilot at Free, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
- Which is cheaper, Microsoft Outlook or Userpilot?
- Microsoft Outlook starts at Free and Userpilot at Free.
- Does Microsoft Outlook or Userpilot run on more platforms?
- Microsoft Outlook runs on Web. Userpilot runs on Web, iOS, Android, API.
- Can I use Microsoft Outlook for free?
- Both have a free tier, so you can try either at no cost before committing.
- What is Microsoft Outlook best used for?
- Microsoft Outlook is most often used for organisations on exchange online or exchange server where free/busy scheduling and room booking across everyone is a daily requirement, executive assistants managing someone else's calendar and mailbox through delegate access, which no imap client supports properly, regulated environments that need retention policies, legal hold and ediscovery applied to mail centrally rather than per user, teams handling shared inboxes such as support or accounts, where permissions and tracking matter more than the mail client itself. Of those, organisations on exchange online or exchange server where free/busy scheduling and room booking across everyone is a daily requirement and executive assistants managing someone else's calendar and mailbox through delegate access, which no imap client supports properly are not what Userpilot is typically brought in for.
- What can Microsoft Outlook do that Userpilot cannot?
- Microsoft Outlook covers Exchange calendar integration, Delegate access, Shared mailboxes, Rules and Quick Steps.
Answered from the vendors’ own pages
Microsoft Outlook: What is the difference between classic Outlook and the new Outlook for Windows?
Classic is the long-standing Win32 application shipped with Microsoft 365 and Office LTSC. The new Outlook is a web-based client that replaced Windows Mail and Calendar. The most consequential difference is add-ins: the new client supports only web add-ins, not COM add-ins.
Userpilot: What is included in the free trial?
Userpilot offers a free 14-day trial without requiring a credit card, providing full access to the Starter tier features.
SourceMicrosoft Outlook: How long will classic Outlook be supported?
Microsoft has stated support through at least 2029. That is a planning window rather than a reprieve, and organisations with COM add-in dependencies should be scoping the replacement work now.
Userpilot: Does Userpilot include session replay?
Session replay is available in the Growth tier as an optional add-on for watching real user sessions and identifying friction points.
SourceMicrosoft Outlook: Can I use Outlook with Gmail or another IMAP provider?
Yes, but with reduced capability. You lose free/busy lookup, room booking, delegate access and server-side compliance policies, because those come from Exchange rather than from the client.
Userpilot: What integrations does Userpilot support?
Userpilot integrates with HubSpot, Salesforce, Segment, Google Analytics, Amplitude, Mixpanel, Heap, Zendesk, Intercom and Google Tag Manager. Additional integrations can be requested.
SourceMicrosoft Outlook: Is Outlook free?
Outlook on the web and the mobile apps are free with a Microsoft account, and the new Outlook for Windows is included with Windows 11. The classic desktop application requires a Microsoft 365 subscription or an Office perpetual licence.
Microsoft Outlook: Will my COM add-ins work in the new Outlook?
No. The new client supports only the cross-platform web add-in model. Vendors must publish a web add-in, and where they have not, the choice is to stay on classic Outlook or replace the integration.
Related pages
More on Microsoft Outlook
Other head to heads
- Microsoft Outlook vs Safari
- Microsoft Outlook vs Google Chrome
- Microsoft Outlook vs Mozilla Firefox
- Microsoft Outlook vs Thought Machine
- Microsoft Outlook vs Sentry
- Microsoft Outlook vs Apache Spark
- Microsoft Outlook vs GitHub Desktop
- Microsoft Outlook vs MongoDB
- Microsoft Outlook vs Asana
- Microsoft Outlook vs Figma
- Microsoft Outlook vs Greenhouse
- Microsoft Outlook vs Monday.com
- Microsoft Outlook vs Maze
- Microsoft Outlook vs PagerDuty
- Microsoft Outlook vs PyCharm
- Microsoft Outlook vs Sketch
- Microsoft Outlook vs Sublime Text
- Microsoft Outlook vs Mixpanel
- Microsoft Outlook vs Canny
- Microsoft Outlook vs Intercom
- Microsoft Outlook vs Heap
- Microsoft Outlook vs LogRocket
- Microsoft Outlook vs Pendo
- Microsoft Outlook vs PostHog
- Microsoft Outlook vs Close
- Microsoft Outlook vs Amplitude
- Microsoft Outlook vs Segment
- Microsoft Outlook vs Supabase
- Microsoft Outlook vs Personetics
- Microsoft Outlook vs Plane
- Microsoft Outlook vs Postman
- Microsoft Outlook vs Raycast
- Microsoft Outlook vs RescueTime
- Microsoft Outlook vs Superhuman
- Userpilot vs Safari
- Userpilot vs Google Chrome
- Userpilot vs Mozilla Firefox
- Userpilot vs Thought Machine
- Userpilot vs Sentry
- Userpilot vs Apache Spark
- Userpilot vs GitHub Desktop
- Userpilot vs MongoDB
- Userpilot vs Asana
- Userpilot vs Figma
- Userpilot vs Greenhouse
- Userpilot vs Monday.com
- Userpilot vs Maze
- Userpilot vs PagerDuty
- Userpilot vs PyCharm
- Userpilot vs Sketch
- Userpilot vs Sublime Text
- Userpilot vs Mixpanel
- Userpilot vs Canny
- Userpilot vs Intercom
- Userpilot vs Heap
- Userpilot vs LogRocket
- Userpilot vs Pendo
- Userpilot vs PostHog
- Userpilot vs Close
- Userpilot vs Amplitude
- Userpilot vs Segment
- Userpilot vs Supabase
- Userpilot vs Personetics
- Userpilot vs Plane
- Userpilot vs Postman
- Userpilot vs Raycast
- Userpilot vs RescueTime
- Userpilot vs Superhuman