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Microsoft Outlook
Microsoft's email and calendar client, in the middle of a transition from the classic Windows application to a web-based replacement.
As of 30 August 2026, Microsoft Outlook has a free plan and paid plans start at $1.99/month. Outlook is the default mail and calendar client for organisations on Exchange and Microsoft 365, and its scheduling, delegation and compliance behaviour is why. Softwr lists it under Technology.
Overview
What Microsoft Outlook does
Outlook is Microsoft's email, calendar, contacts and tasks client. It exists as several distinct products sharing a name: the classic Win32 application shipped with Microsoft 365 and Office LTSC, the new web-based Outlook for Windows that replaced the retired Mail and Calendar apps on Windows 11, Outlook for Mac, the Outlook mobile apps for iOS and Android, and Outlook on the web. It connects to Exchange Online and Exchange Server natively and to IMAP, POP and Gmail accounts with a reduced feature set. Microsoft has said the classic Windows client will be supported through at least 2029. What distinguishes it is not the mail; it is the calendar and the compliance layer behind it. Against Exchange, Outlook does free/busy lookup across an entire organisation, room and equipment booking, delegate access where an assistant manages someone else's calendar and sends on their behalf, and shared mailboxes with tracked permissions, all subject to retention policies, legal hold and eDiscovery that an administrator sets centrally. No IMAP client reproduces that, because it is a property of the server rather than the client, and it is why organisations that dislike Outlook still run it. It is bought as part of Microsoft 365 rather than on its own, so the real decision is the mail platform underneath. The trade-off currently on the table is the Windows client transition. The new Outlook does not support COM add-ins, only web add-ins, so a line-of-business integration for CRM, dictation or document management must be rewritten or the desktop stays on classic until support ends; and the new client's handling of non-Microsoft accounts routes mail through Microsoft's cloud rather than connecting directly from the machine, which some organisations' data handling rules do not permit.
What people use it 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
The honest half
Where it falls short
Concrete and checkable, so you can decide whether any of them matter to you. This is the half of a review a vendor will not write about 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.
Cross-shopped
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Pricing
What Microsoft Outlook costs
Taken from the vendor's own pricing page. Prices move, so check before you buy.
Outlook (Free)
Free
- 15 GB mailbox storage
- 5 GB cloud storage
- Web and mobile Office app access
- Standard email features
Microsoft 365 Basic
$1.99 /mo
- 100 GB mailbox storage
- 100 GB cloud storage
- Ad-free experience
- Advanced security features
Microsoft 365 Personal
$9.99 /mo
- 1 TB cloud storage
- Desktop Office apps (Word, Excel, PowerPoint, Outlook, OneNote)
- Copilot with high usage limits
- Microsoft Defender security
- Microsoft Teams with Copilot
Microsoft 365 Family
$12.99 /mo
- 1-6 users
- Up to 6 TB total cloud storage (1 TB per person)
- Same apps and features as Personal
- Shared Defender protection
Capabilities
Features
Exchange calendar integration
Organisation-wide free/busy lookup, room and equipment booking, and meeting responses tracked on the server
Delegate access
Grants another person permission to manage a mailbox or calendar and send on the owner's behalf, with the delegation recorded
Shared mailboxes
Team mailboxes with per-user permissions that appear alongside a personal account without a second sign-in
Rules and Quick Steps
Client and server-side rules plus one-click multi-action shortcuts for repetitive mail handling
Retention, hold and eDiscovery
Administrator-set retention policies, litigation hold and search across mailboxes for compliance and legal requests
Sensitivity labels and encryption
Applies Microsoft Purview labels and message encryption, restricting forwarding or access for classified mail
Add-in platform
COM add-ins in classic Windows Outlook and cross-platform web add-ins in the new client, Mac, mobile and web
Offline cached mode
Keeps a local copy of the mailbox so classic Outlook works fully without a connection and resynchronises later
Answered, with sources
Questions people ask
Each answer names the page it came from, so you can check it rather than take our word for it.
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.
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.
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.
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.
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.
Keep looking
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- Best Technology softwareThe shortlist, and how it was cut
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Softwr does not host reviews and shows no star rating for Microsoft Outlook, because a rating we did not collect is not ours to publish. What is here is the pricing and platform detail from the vendor’s own pages, limitations we could state concretely, and alternatives a reviewer confirmed people weigh against it. Tell us if any of it is wrong.
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