Outlook 2016 and 2019 cheat sheet


The pundits would have you believe that email is being supplanted by texting, social media, chat apps like Slack, and direct communications software such as Skype and Google Hangouts Meet.

Don’t believe them.

Email is still big, the mainstay of workplace communications. And for countless users, email means Microsoft Outlook.

Microsoft sells its Office suite of productivity apps under two models: Individuals and businesses can pay for the software license up front and own it forever (what the company calls the “perpetual” version of the suite), or they can purchase an Office 365 or Microsoft 365 subscription, which means they have access to the software for only as long as they keep paying the subscription fee.

When you purchase a perpetual version of the suite — say, Office 2016 or Office 2019 — its applications will never get new features, whereas apps in an Office 365/Microsoft 365 subscription are continually updated with new features. (For more details, see “What are the differences between Microsoft Office 2019 and Office 365?”)

This cheat sheet gets you up to speed on the features that were introduced in Outlook 2016 and Outlook 2019, the perpetual-license versions of Outlook included with Office 2016 and Office 2019, respectively. In Microsoft 365, Outlook has all those features, plus several more. We’ll soon be publishing a separate Outlook for Microsoft 365 cheat sheet that covers all its latest features.

Most of the tips in this article apply to both Outlook 2016 and Outlook 2019 for Windows. Near the end are tips for Outlook 2019 only, and then we wrap up with handy keyboard shortcuts for both versions.

Note that the screenshots shown in this article were taken in Outlook 2019. If you’re using Outlook 2016, some screens may look slightly different.

Share this story: IT folks, we hope you’ll pass this guide on to your users to help them learn to get the most from Outlook 2016 and 2019.

Use the Ribbon

The Ribbon interface in Outlook 2016 hasn’t changed much compared to earlier versions. Because the Ribbon has been included in Office suite applications since Office 2007, we assume you’re familiar with how it works. If you need a refresher, see our Outlook 2010 cheat sheet.

The Ribbon in Outlook 2016 has a flattened look that’s cleaner and less cluttered than in Outlook 2010 and 2013. The newer Ribbon is smaller than it was in Outlook 2013, the title bar now is blue rather than the previous white, and the text for the Ribbon tabs (File, Home, Send/Receive, and so on) is a mix of upper- and lowercase rather than all caps. But it still works in the same way, and you’ll find most of the commands in the same locations as in Outlook 2013.

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The Ribbon hasn’t changed a great deal from Outlook 2013. (Click image to enlarge it.)

To find out which commands live on which tabs on the Ribbon, download our Outlook 2016 and 2019 Ribbon quick reference. Also see the nifty new Tell Me feature described below.

As in previous versions of Outlook, if you want the Ribbon commands to go away, press Ctrl-F1. (The tabs above the Ribbon stay visible.) To make them reappear, press Ctrl-F1 again.

You’ve got other options for displaying the Ribbon as well. To get to them, click the Ribbon Display Options icon at the top right of the screen, just to the left of the icons for minimizing and maximizing Outlook. From the drop-down menu, you can choose Auto-hide Ribbon (hide the entire Ribbon, both the tabs and commands underneath them), Show Tabs (show the tabs but hide the commands underneath them, as when you press Ctrl-F1), or Show Tabs and Commands (show the whole Ribbon).

And if for some reason the blue color on the title bar is too much for you, you can turn it white or gray. (In Outlook 2019, there’s also a black option.) To do it, select File > Options > General. In the “Personalize your copy of Microsoft Office” section, click the down arrow next to Office Theme and select Dark Gray or White (or Black) from the drop-down menu. To make the title bar blue again, instead choose the Colorful option from the drop-down list. Just above the Office Theme menu is an Office Background drop-down menu — here you can choose to display a pattern such as a circuit board or circles and stripes in the title bar.

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To change Outlook’s blue title bar: In the “Personalize your copy of Microsoft Office” section, click the down arrow next to Office Theme and pick dark gray, white, or (in Outlook 2019) black. (Click image to enlarge it.)

Try Tell Me for greater efficiency

Outlook is so full of features it can be tough to remember where to find commands you haven’t used in a while. Microsoft has made it easier with a new feature in Outlook 2016 and 2019 called Tell Me, which puts even buried tools you rarely use in easy reach.

To use it, click the Tell me what you want to do text to the right of the Ribbon tabs. (If you prefer keyboard shortcuts, press Alt-Q.) Then type in a task you want to do, and you’ll get a menu showing potential matches for the task.

For example, if you want to filter your mail to see only messages with attachments, type in filter email. In this instance, the top result is a Filter Email listing with an arrow to its right, indicating that it has many options. Hover your mouse over it, and you get multiple options for filtering your mail, including by Unread, Has Attachments, This Week, and others.

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The Tell Me feature in Outlook 2016 and 2019 makes it easy to perform just about any task. (Click image to enlarge it.)

Choose the option you want, and the task will be performed instantly. If you’d like more information about your task, the last two items that appear in the Tell Me menu let you select from related help topics or search for your phrase using Smart Lookup. (More on Smart Lookup below.)

For the most common basic tasks, you won’t need Tell Me. But for more complex ones, it’s worth using, because it’s much more efficient than hunting through the Ribbon to find a command. It also remembers the features you’ve previously clicked on in the box, so when you click in it, you first see a list of previous tasks you’ve searched for. That makes sure that the tasks you frequently perform are always within easy reach, while at the same time making tasks you rarely do easily accessible.

Use Smart Lookup for online research

Sometimes emails are just quick notes that don’t require much research, and you can toss them off with little or no thought. Other times, though, you’ll want to include relevant information before sending them off. Those are the times you’ll appreciate the new Smart Lookup feature. It lets you do research from right within Outlook while you’re creating an email, so you won’t have to fire up your browser, search the web, and then copy the information or pictures to your message.

To use Smart Lookup, right-click a word or group of words in an email — it can be a new draft, a message you’ve received, or one you’ve already sent — and select Smart Lookup from the menu that appears. Outlook then uses Bing to do a web search on the word or words, displaying definitions, related Wikipedia entries, pictures and other results from the web in the pane that appears on the right. If you just want a definition of the word, click the Define tab in the pane.

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Smart Lookup lets you do web research from right within Outlook. (Click image to enlarge it.)

To use Smart Lookup in Outlook or any other Office app, you might first need to enable Microsoft’s intelligent services feature, which collects your search terms and some content from your presentations and other documents. (If you’re concerned about privacy, you’ll need decide whether the privacy hit is worth the convenience of doing research from right within the app.) If you haven’t enabled it, you’ll see a screen when you click Smart Lookup asking you to turn it on. Once you do so, it will be turned on across all your Office applications.

Find attachments more easily — and share ‘cloud attachments’

We’ve all been there: We want to attach a file we were recently working on, but don’t remember its precise location — or sometimes even its name — and spend far too much time navigating and searching for it.

Outlook 2016 and 2019 solve the problem neatly. When you click the Attach File icon, a list of the twelve most recent files you’ve been using pops up. The list includes all the files you’ve been using on any device, as long as you’re signed in to your Microsoft account. So if you were working on a file on your desktop, then later in the day took your laptop to work outside your office, Outlook would show you the files you had opened on both devices. If a file is stored in OneDrive, OneDrive for Business, or SharePoint, you’ll see a cloud on its icon.

If the file you want isn’t in the list, click Browse this PC at the bottom of the menu to browse your local hard disk, or Browse Web Locations to browse OneDrive, OneDrive for Business, or SharePoint.

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Outlook shows you a list of files you’ve recently used, making it easier to find and attach them to an outgoing email. (Click image to enlarge it.)

Click the file you want to attach. What happens next depends on where the file is stored. If you choose a file that’s stored on your local hard drive, a copy of it will be attached to the email in the usual way.

In Office 2019, if you click on a file that’s stored in OneDrive, OneDrive for Business, or SharePoint, you’ll be given a choice: You can choose Attach as copy to send the file as a normal attachment or Share link to send a link to the file in its cloud location, something Microsoft informally calls a “cloud attachment.” (In Office 2016, files stored in the cloud are automatically sent as cloud attachments.)

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Sharing a link to a file stored in OneDrive, OneDrive for Business, or SharePoint lets you collaborate on the file with others. (Click image to enlarge it.)

Sharing a file as a link ensures that people will see the most recent version of the file and lets them collaborate on it. For example, if you send a link to a Word file to multiple people, when they click the link, they’ll open the file and be able to collaborate on it with each other live using Word’s collaboration features

For individuals, the default is that anyone can edit the file. If you’re in a business environment, by default anyone within your organization can edit the file. But you can change the collaboration permissions. After you’ve attached the link to the email message, click the down arrow next to the attachment icon and select Change Permissions from the drop-down menu. Individual users will have a choice between Anyone Can Edit or Anyone Can View. Business users have a few other options: Organization Can Edit, Organization Can View, Recipients Can Edit (meaning only those you’ve addressed the email to can edit the file), and Recipients Can View. Make your selection and then send the file on its way.

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Choosing collaboration permissions for a shared file link. (Click image to enlarge it.)

Note: The following tips are for Office 2019 users only. If you use Office 2016, you can skip to the handy keyboard shortcuts chart at the end of the article.

Get a more focused inbox in Outlook 2019

If you’re like the rest of the world, you suffer from email overload. Your most important messages are mixed in with the dross of everyday email life — retailing come-ons, groups begging for donations, pointless newsletters and more.

Focused Inbox helps solve the problem. Using artificial intelligence, it determines which messages are most important to you and puts them into a Focused tab, while putting everything else into an Other tab. That way you can spend most of your time handling important messages in the Focused tab, only occasionally checking the Other tab.  

Note that Focused Inbox is available only to Outlook 2019 users who have an Exchange or Outlook.com account. (It’s also available to users with Microsoft 365/Office 365 subscriptions.)

To turn on Focused Inbox, select the View tab from the Ribbon, then click the Show Focused Inbox icon. From now on, you’ll have two tabs in your Inbox, Focused and Other. The Focused tab should have the most important messages, and the Other tab should have less important messages. If that’s not the case, you can manually move messages from one folder to the other and tell Focused Inbox to automatically filter them in that way in the future.

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Turning on Focused Inbox in Office 2019. (Click image to enlarge it.)

To move a message from one tab to another, right-click the message you want to move, then select Move to Other or Move to Focused, depending on where you want the message moved. That will move the message just this once. If you want to permanently route all messages from that sender to the other tab, choose either Always Move to Other or Always Move to Focused.

Focused Inbox isn’t for everybody. If you find that Focused Inbox hinders more than it helps, you can toggle it back off by selecting View > Show Focused Inbox.



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