Glassmail vs Outlook for Mac: which should you use?
Outlook for Mac is free with ads and best for Microsoft 365 work. Glassmail is a calm, native app for every account, with AI that runs on your Mac.
Short answer: use Outlook for Mac if your job runs on Microsoft 365: calendar, shared mailboxes, meeting rooms and Teams. Use Glassmail if you want a quiet, native Mac app for all your mail (work Outlook plus Gmail, iCloud or Yahoo) without ads, with an AI assistant that runs on your Mac, for a one-time price.
At a glance
| Glassmail | Outlook for Mac | |
|---|---|---|
| Price | $49 once (lower launch prices for early buyers) | Free with ads; ad-free from Microsoft 365 Basic; Copilot from Microsoft 365 Personal |
| Accounts | Gmail, iCloud, Outlook, Microsoft 365, Yahoo, Fastmail, any IMAP | Microsoft 365, Exchange, Outlook.com, Gmail, iCloud, Yahoo, IMAP |
| Calendar and contacts | Email only; adds dates from mail to Apple Calendar and Reminders | Built in |
| Exchange features | No (IMAP with Microsoft sign-in) | Full: shared mailboxes, delegation, rooms |
| AI | On your Mac, included | Copilot in the cloud, on paid plans |
| Ads | None | In the free version |
| Platforms | Mac (macOS 14+) | Mac, Windows, iPhone, Android, web |
Outlook details from Microsoft’s Outlook for Mac page, November 2026. Disclosure: Glassmail is our app. Tell us at hi@glassmail.app if anything here is wrong.
Where Outlook wins
Outlook is the full Microsoft 365 client: calendar, contacts, shared and delegated mailboxes, room booking, and Teams meetings. If your organisation lives in Microsoft 365, nothing else on the Mac does all of that.
Where Glassmail wins
- One calm inbox for everything. Mail from people first; receipts and newsletters bundled by sender in Updates.
- Native and quick. Built in Swift for macOS, so it looks and behaves like your other Mac apps.
- Private AI. Ask “what needs me today?”, get the gist of a long thread, draft a reply in your voice, all on your Mac. Copilot is cloud-based and needs a paid plan.
- No ads, no subscription. One payment, every 1.x update.
Can you use both?
Yes. Many people keep Outlook for the calendar and use Glassmail for mail. Both read the same mailbox, so archiving in one archives in the other. How to add Microsoft 365 to a Mac mail app.
Which should you choose?
- Choose Outlook if you need Exchange calendars, shared mailboxes, or Copilot across Office.
- Choose Glassmail if you want all your mail in one native, ad-free app with private AI, and pay once.
Glassmail is free for 14 days. See also the best Apple Mail alternatives.
Quick answers
Is Outlook for Mac free?
Yes, for personal accounts. Microsoft says Outlook for Mac is free to use with Outlook.com, Gmail, iCloud, Yahoo and IMAP accounts, with ads. Removing ads needs a Microsoft 365 plan, and Copilot needs Microsoft 365 Personal or higher.
Should I use Outlook or Glassmail for a work Microsoft 365 account?
If your work relies on Exchange features like shared calendars, room booking and shared mailboxes, use Outlook. Glassmail connects to Microsoft 365 with Microsoft sign-in over IMAP for mail only, which suits people who want work and personal mail in one calm inbox.
Does Glassmail have a calendar like Outlook?
No. Glassmail is focused on email, though it can add a date mentioned in an email to Apple Calendar or Reminders in one click. Outlook combines mail, calendar and contacts in one app.