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16 Tips for Mail on Mac

Some more pro user tips coming up. People seem to like these. This time I am taking a look at Apple Mail on the Mac. The tips are split into three sections, Writing email, Managing email and a Misc section. As per my usual format please feel free to click on any of the below to jump straight to that tip.

A small heads up - This was a bit of a difficult one for privacy reasons and so I apologise up front for not having gifs to show every tip on this particular post.

Writing email:

Managing email:


Writing Email

Drag and drop file onto mail icon to auto attach

You don’t always have to start an email in the Mail app. To speed things up try dragging a file or photo from the file system over the top of the mail app. This will open an email with your file already attached.

  1. Drag a File onto the Mail app icon

Create a group to send to multiple people

If you frequently send emails to the same groups of people you may find creating a group in your contacts beneficial. By creating a group you no longer need to add everyone individually to your email. Instead, you can simply add the group. There are a few ways of creating a Group in your contacts and you can always review the documentation for more.

  1. Open Contacts

  2. Select your contacts while holding Command ⌘

  3. File > New Group from Selection

  4. Open a new email and type in your new group

Use smart groups to create an intelligent groups that can update automatically. Great for grouping people from the same company.

Use your iPhone to add photos, scanned docs or create a sketch

This a feature I always forget about but you can add photos, scan documents or create a sketch on the fly if you have a Mac and iPhone/iPad that are both connected to the same iCloud account and have both WiFi and Bluetooth turned on.

  1. New email

  2. File > Insert From iPhone or iPad > “Select your option”

  3. Capture or create content on iPhone/iPad

Handoff - Start on iPhone finish on mac

Handoff enables you to start writing an email on one device and then seamlessly finish it on another. There are just a few things you need to make sure of before giving it a go.

  • Devices are signed in to iCloud with the same Apple ID.

  • Devices have Bluetooth turned on.

  • Devices have Wi-Fi turned on.

  • Devices have Handoff turned on

The example I show is me starting on my iPhone and finishing up on my Mac

  1. Start an email on your iPhone

  2. Jump on your mac and select the mail icon from the dock

  3. Finish off your email

Send read receipts

This one is a little bit outside of the box as we need to enter a command line into the terminal. This also means that there is no option to pick and choose whether or not you send a read receipt.

Turn on Read Receipts

  1. Open a Terminal Console

  2. Enter the below command

defaults read UserHeaders

Turn off Read Receipts

  1. Open a Terminal Console

  2. Enter the below command

defaults delete UserHeaders

If you receive the following error “The domain/default pair of (, UserHeaders) does not exist.” Follow the below steps

  • In a Terminal Window enter the below and be sure to replace “Name” with your name and “email@address” with your email address

defaults write UserHeaders ‘{“Disposition-Notification-To” = “Name <email@address>”; }’
  • Now enter the original command

defaults read UserHeaders

Use Quick Look to preview attachments

What I thought was an obvious tip but I was speaking to a long time Mac user the other day and they didn’t know or hadn’t thought about it. You can use Quick Look to view your mail attachments.

  1. Select your Attachment

  2. Press the Spacebar ␣

Previous Recipients

You can access previous email addresses that you have used in the past but are not in your contacts list. These are the ones that pop up when you start entering an email address in the To: field. From this window, you can also remove the ones you no longer need or do not want to pop up anymore.

  1. Window > Previous Recipients

  2. Delete or add an address to contacts

Redirect instead of forward

When forwarding an email, Apple Mail will indent the previous email in a quote which I think ruins the formatting of my messages. You can use the Redirect command to forward an email in its as-is state.

  1. open you email

  2. Message > Redirect (⇧ + ⌘ + E)

Managing Mail

Smart mailboxes

Much like smart folders in Finder, these mailboxes dynamically collect emails based on a set of criteria. By default, Apple Mail has one that only shows emails from Today but you can create them for a wide range of filters. As an example, you could create a smart mailbox to collect all emails relating to a specific project or one to collect emails for a certain selection of people.

  1. Mailbox > New Smart Mailbox

  2. Define your criteria


I think we all know that you can use the search bar to find emails in your inbox but you may not know some of the tags that you can use to find certain emails. As an example, you can type “From:email@address” to find all emails from that address or “Date:01/11/2020” to show only emails on a specific date.


  • From:

  • To:

  • Subject:

  • Date:

  • Or:

  • And:

  • Not:

Natural Language search

Apple mail also has a built-in natural language search which means you can type in “emails from Bob last month” and Apple Mail will show you all the emails from Bob for last month.

Use and change filters

You can use filters to narrow down what emails mail shows to you. Quicker than searching but not as specific. By default, the filter menu, when activated, shows all unread emails but you can change this to filter by other criteria.

  1. Ensure filtering is on ⌘ + L

  2. Click and hold the Filter Icon

  3. Select a filter option

Use Tabs

If you do a lot of email having a few tabs open could make your life just that little bit easier. Although not quite as sophisticated as tabs in a web browser, tabs in Mail allows you to have multiple emails open in the same window.

  1. View> Show Tab Bar

  2. Click the + icon to open a new tab


iCloud email addresses can send large files with Mail Drop

Most email providers limit the size of attachments that you can send but if you use an iCloud email address you can send attachments up to 5GB in size. This is a feature called Mail Drop and works on all iOS devices including iPhones, iPads and Macs.

Quit and keep windows for next time

This is actually a universal feature of Mac OS and will work with most programs but if you hold Option while selecting Mail from the menu bar, you will see the option for Quit and Keep Windows (⌥ + ⌘ + Q)

This operation will quit the app but remember which windows you had open. That means the next time you launch the app your previously open windows will also be there.

Hide your email (iCloud+)

Unfortunately, this is an iCloud+ feature but if you do have iCloud+ you can choose to hide your email. This is great when you're signing up to gain access to some online content or you just want to keep things private.

Keyboard Shortcuts

⌘ + N Create New Mail

⇧ + ⌘ + L Flag

⌘ + R Reply

⌘ + Shift + F Forward

⇧ + ⌘ + D Send Email

⇧ + ⌘ + N Get new mail

⇧ + ⌘ + U Mark as read

⇧ + ⌘ + J Move to Junk

CTRL + ⌘ + A Archive email

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