Recently, as I wrote about in my Ignite Article, Microsoft is finally giving Outlook for MacOS some proper TLC. It’s no secret that Microsoft Apps on MacOS are a bit of a poop show. It’s great news that they have made some major improvements. I thought it would be good to take a walk through the new Outlook for MacOS experience because UEM engineers have been waiting for this. For a disclaimer, I want to point out this is still part of the insider preview. We are going to cover what the new Microsoft Sync technology is (that Outlook for MacOS will be using), how to switch to the new Outlook, and some of its great new features. Let’s get started together!

Microsoft Sync Technology

The new Microsoft Sync Technology has the following features:

• Does not use any middle-tier services. It goes directly from the client to Office 365.
• Replaces the Outlook device API and Stateless Protocol Translator to reduce latency between client and server.
• Introduces support for other Office 365 tenants like O365 Government Cloud and O365 DoD environments.
• All Client Protocols are consolidated, which means a single protocol is being used by all clients (Windows, iOS, Android, and now MacOS)
• Allows clients to use new features like S/MIME, IRM, and shared mailboxes.

Switching your Mac to the Insider Build

Microsoft has added some confusion to transitioning your Mac to the insider build in recent years. Many of us have transitioned to the Microsoft Apps found on the Mac App Store.

Our issue is that MacOS App Store apps are production builds. This will be part of our challenge on switching to the insider build, but nothing too insane. A hidden gem that many MacOS administrators are not familiar with is this Mac Admin Profile Reference website which can help you with building configuration files. To transition to the insider build, we have a few steps:

• Deploy a Configuration change to switch Microsoft AutoUpdate to the Insider Build
• Reboot your Mac to get the launch daemon to apply the changes
• Download and Install the Office 365 Package from the Office 365 Portal
• Apply Updates via Microsoft AutoUpdate to switch to the Insider Build

Deploy the Configuration Change for Microsoft AutoUpdate

As I have discussed in some of my older blog posts, we can accomplish the configuration change easily via a shell script and launch agent. After deploying these settings, you can reboot your Mac and it will apply seamlessly. Launch agents/daemons are powered by a script and a plist that make the magic happen.

First, we have our script which you can find on my github and I will show below sets the channel and updates to be applied automatically.

#!/bin/sh
# Variables
loggedInUser=`/bin/ls -l /dev/console | /usr/bin/awk '{ print $3 }'`
loggedInUserHome=`dscl . -read /Users/$loggedInUser NFSHomeDirectory | awk '{print $NF}'`

# backup current file
/bin/cp "/Users/$loggedInUser/Library/Preferences/com.microsoft.autoupdate2.plist" "/Users/$loggedInUser/Library/Preferences/com.microsoft.autoupdate2.plist.backup"
/bin/echo "Preference archived as: /Users/$loggedInUser/Library/Preferences/com.microsoft.autoupdate2.plist.backup"

/usr/bin/defaults write /Users/$loggedInUser/Library/Preferences/com.microsoft.autoupdate2.plist ChannelName InsiderFast
/bin/echo "Channel Name set to InsiderFast for $loggedInUser"
/usr/bin/defaults write /Users/$loggedInUser/Library/Preferences/com.microsoft.autoupdate2.plist HowToCheck AutomaticDownload
/bin/echo "Updates will now be automatically downloaded"
/usr/sbin/chown $loggedInUser /Users/$loggedInUser/Library/Preferences/com.microsoft.autoupdate2.plist

# Respawn cfprefsd to load new preferences
/usr/bin/killall cfprefsd

else

/bin/echo "Microsoft Auto Update Preferences not found for $loggedInUser"

fi

Secondly, the launch agent found here will fire the script off when the user logs in. As a reminder, launch agents run as the user when they log in whereas a daemon runs as the system.

<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
<plist version="1.0">
<dict>
	<key>Label</key>
	<string>com.chromekerberos.daemon</string>
	<key>ProgramArguments</key>
	<array>
		<string>/usr/local/outlookinsider.sh</string>
	</array>
	<key>RunAtLoad</key>
	<true/>
	<key>StandardErrorPath</key>
	<string>/usr/local/com.outlookinsider.daemon.err</string>
	<key>StandardOutPath</key>
	<string>/usr/local/com.outlookinsider.daemon.out</string>
</dict>
</plist>

For testing, you can just run the shell script, but you would use your UEM platform of choice to deploy these files to your machines. Now, we can move onto the next part!

Downloading and Install the Office Client

The download and install of the Office Client is straight forward. You just go to Office.com and download the Office client. (This presumes that the feature is enabled by your organization). The installer is around 1.5 GB so that may take a few minutes, but once done you just install the client. The good news is you don’t need to uninstall your existing client if it’s present:

Apply Updates via Microsoft AutoUpdate

I found this might be a little tricky at the beginning. You can either wait for it to pick things up on its own, or you can download and apply updates yourself. Let’s walk through the steps!

First, Open the Microsoft AutoUpdate via Finder and Disable “Apply Automatic Updates”

Click “Turn Off” to disable the automatic updates

Click “Check for Updates”

It should find some updates for you (typically 5 or so) and you can click “Update”

You will see it apply the updates and once done you can launch Outlook.

One last thing to note is after launching Outlook, you typically will need to close and re-launch it once for the settings to apply. This is typical for Microsoft applications where it doesn’t realize it needs to flip over until the initial launch. Let’s take a look at this new Outlook!

Taking a Stroll Through the New Outlook for MacOS

As you can see below, the new UI for Outlook for MacOS is very clean and modern. It’s very similar to what you might see when using Outlook for iOS/iPadOS.

Let’s cover a few of the fun new additions in Outlook for MacOS. My hope is exploring some of these items should make you as excited as I am!

Customizing the Outlook Toolbar

We start by clicking on the … icon and selecting “Customize Toolbar”

They did a gorgeous job on the customizing toolbar section. You can just click and drag stuff into the new toolbar seamlessly with minimal effort. As you will see in the video, it’s remarkably easy and very user-centric.

The New Outlook Search

Outlook’s new and improved search capabilities are something special. You always had your typical search, but now they are enhancing it with features like taking you directly into contact cards and suggestive searches powered by AI. Check out the demo, which helps do this features justice.

The My Day View

You may have noticed above, they have added a “My Day” section in your Inbox to make life much easier. This helps by showcasing what you have going on for the day.

Outlook Introduces Some Work/Life Balance Enhancements

Outlook does have a few new features, which we will showcase in a few video tutorials. Microsoft now lets you snooze conversations until a later date, ignore an entire conversation, or leverage Microsoft’s Insights powered by AI to keep you organized.

Some Additional Calendar Enhancements

Another nice addition, we can now RSVP in detail within the conversation pane making life easier once again. It’s great seeing the user experience being at the focus of the application.

We can also now access Office Groups inside of the Calendar Pane.

You can double-click on a spot on your calendar to quickly create a meeting. The one thing that sucks about this is it doesn’t support Zoom, but otherwise is a very clean solution.

A new feature, which is a good pandemic feature is the “Working Elsewhere” status.

The Unsupported

I will try to keep this updated, but I wanted to share a few of the unsupported features at this juncture. Currently, you cannot:

• Copy Mail and Events to Other Folders
• Add Shared Mailboxes or Calendars

Some Final Thoughts

As you have seen, the Outlook for MacOS experience is something special. They have continued to develop and enhance this experience, which may finally be strong. This was only possible by customers being vocal and driving Microsoft toward addressing our concerns. Recently, we have seen Microsoft Defender release for MacOS and now Outlook for MacOS. I’m feeling more optimistic about Microsoft’s respect for MacOS and its importance in enterprise.