Outlook, Teams and Microsoft 365 on the Mac: how to make it work well

Most companies run on Microsoft 365. Mail and calendar through Exchange Online, meetings in Teams, files in OneDrive and SharePoint. A Mac fits into that just fine, but you do have to make a few choices. Apple Mail or Outlook? Where does OneDrive put your files? Why can’t you share your screen in Teams? In this whitepaper from the series Mac and the rest of the world I go through everything you run into when you work on a Mac in a Microsoft environment, as things stand in October 2026 with macOS Golden Gate. There is also one big change happening right now that you really need to know about, so start with the first section.

First: Apple Mail and Exchange Online in October 2026

Apple Mail, Calendar, Contacts, Notes and Reminders on the Mac talk to an Exchange account through Exchange Web Services (EWS). Microsoft is switching EWS off in Exchange Online. Since 1 October 2026 Microsoft has been disabling EWS by default, organisation by organisation, unless the admin deliberately kept it on. On 1 April 2027 EWS in Exchange Online shuts down for good, with no exceptions.

What does that mean in practice?

• If Apple Mail on your Mac suddenly stops working with your work account, this is almost certainly why. It is not your password and it is not your Mac.
• Your iPhone and iPad are not affected. They use Exchange ActiveSync, not EWS.
• If your organisation still runs its own Exchange server (on-premises), nothing changes for you.
• Apple has said it is working with Microsoft on a macOS 27 update that moves Mail, Calendar, Contacts, Notes and Reminders to the Microsoft Graph API. At the time of writing that update has not shipped and there is no date.
• An admin can keep EWS switched on for the organisation until 1 April 2027. That buys time, it does not fix anything.

My advice: if you use Apple Mail with a Microsoft 365 account today, have Outlook for Mac ready as a fallback. If Apple’s Graph update arrives in time, you can choose freely again. The rest of this paper assumes that update will come, but don’t plan on it blindly.

Apple Mail and Calendar or Outlook for Mac

Outlook for Mac in 2026

There is only one Outlook for Mac worth building on: the “new” Outlook, which Microsoft now simply calls Outlook for Mac. The old one is officially called legacy Outlook for Mac. Since late 2025 the switch to go back to legacy Outlook is gone from the subscription versions. Legacy Outlook also depends on EWS and stops working with Exchange Online from October 2026. Only with an on-premises Exchange server or an Office LTSC 2024 licence is legacy Outlook still supported, until 9 October 2029.

The new Outlook is fast and talks directly to Microsoft 365. The downside is that everything lives in the cloud and very little is “local” any more. Settings you know from Outlook for Windows, like detailed sync options and COM add-ins, don’t exist on the Mac. Add-ins only work if they are built as web add-ins.

Apple Mail and Calendar

For a lot of people Apple Mail with an Exchange account is exactly enough: mail, calendar, contacts, notifications and the integration with the rest of macOS. You use the same apps as for your personal account and everything is searchable through Spotlight. The downside is that Apple Mail can’t do a number of Microsoft-specific things, such as sensitivity labels, Microsoft’s way of handling shared mailboxes and most rule management.

Shared mailboxes and shared calendars

This is where the two apps differ most in daily use.

• Outlook for Mac: you add a shared mailbox under Outlook > Settings > Accounts > Delegates and Sharing > Shared with me > Add. If you get an error, check your permissions in the Microsoft 365 admin center first. New permissions sometimes take a while to kick in. Shared and delegated calendars open in Outlook too, and you can send invites on someone’s behalf if you have the rights.
• Apple Mail: you can’t add a shared mailbox the way Outlook does. The usual workaround is to add the shared mailbox as a separate account, but that only works if the mailbox itself is allowed to sign in, and in most organisations that is switched off for good reason.
• Apple Calendar: you can add delegated calendars under Calendar > Settings > Accounts > Delegation. That works reasonably well, but for now it still depends on EWS and so on the story above.

If you work in an info@ mailbox every day or manage a colleague’s calendar, Outlook is the realistic choice.

Bringing over old .pst archives, signatures and rules

.pst and .olm

Outlook for Windows keeps archives in .pst files. Outlook for Mac has always used the .olm format. For a long time only legacy Outlook could import a .pst. According to the Microsoft 365 roadmap, .pst import in the new Outlook for Mac has been rolling out since June 2026, with .olm import and export to follow. Check under File or Tools in your own Outlook whether the import option is already there, because features like this don’t reach everyone at the same time.

Two things to know:

• A very old .pst in ANSI format (Outlook 97 to 2002) can’t be read by Outlook for Mac. Open it in Outlook for Windows first and export it again to a new .pst, which will be Unicode.
• Imported mail sits locally on your Mac, not in your mailbox. If you want it everywhere, drag it into a folder in your mailbox, or have your admin load the .pst straight into your (archive) mailbox with the Microsoft 365 import service. For large archives that is almost always the better route.

Apple Mail can’t open a .pst at all. If you use Apple Mail, putting the archive into your online mailbox is the only clean option.

Signatures and rules

Signatures from Outlook for Windows don’t come along automatically. In Outlook for Mac you recreate them under Settings > Signatures, in Apple Mail under Mail > Settings > Signatures. Copy the formatting from a web page or an email rather than from Word. If your organisation uses a central server-side signature tool, you don’t need to do anything.

For rules: rules that run on the server (created in Outlook on the web, or as server rules in Outlook for Windows) keep working whatever app you use. Rules that only ran in Outlook for Windows (“on this computer only”) don’t come along. Recreate those in Outlook on the web and they will work everywhere.

Teams on the Mac

Classic Teams was retired on 1 July 2025. You use the current Teams app, which you can recognise by its bundle ID com.microsoft.teams2. Download it from Microsoft or have your admin deploy it.

Most questions are about permissions. macOS asks for permission per app for the camera, the microphone and recording your screen. Without that last one you can’t share anything in a meeting.

1. Open System Settings > Privacy & Security.
2. Turn on Microsoft Teams under Camera and Microphone.
3. Turn on Microsoft Teams under Screen & System Audio Recording.
4. Quit Teams and open it again. Screen sharing only works after the app restarts.

If Teams is switched on but other people see a black screen, remove Teams from the list with the minus button, add it again with the plus button from the Applications folder, and restart Teams. That fixes it more often than not. In a managed setup your admin can pre-approve camera and microphone with a profile. For screen recording an admin can only allow you to switch it on yourself, even without admin rights.

OneDrive and SharePoint in the Finder

Where are your files?

OneDrive for Mac uses the macOS File Provider framework. Your files live in ~/Library/CloudStorage/OneDrive-OrganisationName and you’ll find OneDrive in the Finder sidebar under Locations. Synced SharePoint libraries show up there as well. Files On-Demand is on by default: you see all your files, but they only download when you open them. Right-click to choose “Always Keep on This Device” or “Free Up Space”.

Known issues

• Local OneDrive files count as “System Data” in Storage, because they live inside Library. It looks alarming, but it’s normal.
• If you switched between the App Store version and Microsoft’s own version, old folders are sometimes left behind in CloudStorage. Check that everything is online before you delete anything.
• Recent files in Word or Excel can point to an old path after a big update. Open the file again from the Finder.
• If you edit .docx files in OneDrive with Pages, you may see duplicate files with your device name in them. Those are sync conflicts. For shared documents, Word is the better tool.

Desktop and Documents: OneDrive or iCloud, not both

OneDrive can back up your Desktop and Documents folders (Microsoft calls this Folder Backup, or Known Folder Move). iCloud Drive can do the same with its “Desktop & Documents Folders” option. The two don’t get along, so pick one. On a work Mac that’s usually OneDrive, because then the files sit in your employer’s environment. In that case turn iCloud off first under System Settings > [your name] > iCloud > iCloud Drive. Your files stay in iCloud Drive and you get empty local folders, so move them back yourself afterwards. Note that Folder Backup only works with the OneDrive version you download from Microsoft, not the App Store version.

Word, Excel and PowerPoint: App Store or Microsoft?

Both are the same Office apps from the Current Channel. The differences are in installation and licensing:

• Mac App Store: handy for individual users, updates through the App Store. Word, Excel, PowerPoint and Outlook need a Microsoft 365 subscription. A one-time purchase like Office Home & Business 2024 won’t activate here.
• Download from Microsoft: needed for one-time and volume licences (LTSC), and the usual route for organisations that deploy through Intune or another MDM. Updates come through Microsoft AutoUpdate.

Check your licence. Microsoft 365 Business Basic and Office 365 E1 don’t include the desktop apps, so you can sign in but not edit. With a licence that does include them, you can activate the apps on several devices and manage those activations from your account on office.com. If you’re offline for more than 30 days, Office drops into reduced functionality mode until you reconnect.

Keyboard shortcuts that are different

The main rule: where you use Ctrl on Windows, you use Command (⌘) on the Mac. A few exceptions you’ll run into often:

On a MacBook, F1 to F12 are system keys by default. Hold Fn, or set the function keys as standard under System Settings > Keyboard if you live in Excel.

Office files in Pages, Numbers and Keynote

Pages, Numbers and Keynote open .docx, .xlsx and .pptx and can export back to those formats. For a letter, a simple spreadsheet or a presentation you only need to view, that works fine. Where it goes wrong: macros (VBA) don’t run, complex Excel functions and pivot tables don’t always survive, corporate templates shift around, and real-time co-editing with colleagues in Microsoft 365 only works in the Office apps. My rule of thumb: if a file comes from a colleague and goes back to a colleague, use Word, Excel or PowerPoint.

Signing in: Edge, Chrome, Safari and Company Portal

Many organisations use Conditional Access: you only get to company data if your Mac is managed and compliant. For that, your browser has to be able to tell which Mac you’re on. Microsoft Edge does this on its own once you’re signed in with your work account. Chrome needs the Microsoft Single Sign On extension. Safari works through the Enterprise SSO extension that comes with Company Portal. If a browser keeps telling you your device doesn’t meet requirements, try Edge first.

If your Mac is managed with Intune, you install Company Portal and enrol your Mac with it, or your Mac is enrolled automatically through Apple Business the first time it starts up. How to set that up for a small business is covered in my whitepaper on Apple Business, Entra ID and Intune for small businesses.

Decision table: Apple Mail or Outlook

In short: if you mostly work in your own mailbox and calendar, Apple Mail is a fine choice once Apple ships its Graph update. If you work with shared mailboxes, delegation, labels or lots of Teams meetings, go with Outlook.

Step-by-step plan

1. Ask your admin about the EWS status in your Microsoft 365 tenant and whether Apple Mail still works after October 2026.
2. Install Outlook for Mac, even if you want to keep using Apple Mail, so you have a fallback.
3. Use the decision table to pick your main mail app.
4. Add shared mailboxes and calendars in Outlook, or delegated calendars in Apple Calendar.
5. Move old .pst archives into your online (archive) mailbox, or import them into Outlook for Mac.
6. Recreate your signature and move rules over to Outlook on the web.
7. Install Teams and allow camera, microphone and Screen & System Audio Recording. Restart Teams.
8. Install OneDrive from Microsoft, choose between OneDrive Folder Backup and iCloud Desktop & Documents, and turn the other one off.
9. Install Word, Excel and PowerPoint through the route that fits your licence.
10. Use Edge, or Chrome with the Microsoft Single Sign On extension, if your organisation uses Conditional Access.

And with Apple?

To be fair: for most people Apple’s own apps work fine with Microsoft 365. Mail, Calendar and Contacts do what they should, your iPhone and iPad sync without fuss, and you don’t have to maintain two worlds side by side. Right now Microsoft’s move to the Graph API is a real bump on the Mac, and until Apple ships its update, Outlook for Mac is the safe choice for Exchange Online. Outlook is also still needed if you work with shared mailboxes, extensive delegation or sensitivity labels. Teams, OneDrive and the Office apps are fully capable on the Mac. Set them up properly and you’ll notice little difference from your colleagues on Windows.

This whitepaper describes the situation in October 2026 with macOS Golden Gate (macOS 27) and the current versions of Microsoft 365 for Mac. Microsoft and Apple update their apps regularly, especially around the EWS retirement, so always check the latest information from Microsoft and Apple before you make big changes.

Need help setting this up for your organisation? Email frank@analystict.nl.

This article is part of the Mac and the rest of the world series, where you’ll find every part in one place.