Outlook logo on mobile phone screen and person using Microsoft Outlook application on a laptop..
Image: FellowNeko/Adobe Stock

Sending email messages is a huge part of our day-to-day routines. The easier we can make that process, the better. Imagine that you want to send a copy of an email message to a specific person. There are lots of situations where you’d be expected to remember to add an address to the Cc or Bcc controls when sending emails. The problem is remembering to do so. Most of us remember after sending the message, so we forward the message from the Send folder. It’s not a lot of wasted time, but it’s annoying, and you can prevent it.

SEE: Google Workspace vs. Microsoft 365: A side-by-side analysis w/checklist (TechRepublic Premium)

In this tutorial, I’ll show you how to set up a rule in Microsoft Outlook that automatically sends a copy of an email depending on the conditions that you specify. Rules are easy to implement, and once they’re in place, you won’t have to remember a thing other than to delete the rule when it’s no longer relevant.

I’m using Microsoft 365 Desktop on a Windows 10 64-bit system but you can use earlier versions of Outlook. Outlook Mail supports rules.

What is a rule in Outlook?

Simply put, a rule is a triggered set of instructions. The trigger can be many things; in this case, the trigger is sending an email. The instructions are a set of steps taken when triggered.

You need to be in the mail window to access rules as follows:

1. Click the Home tab.

2. In the Move group, click the Rules dropdown.

If an existing email is “open,” the Rules option is on the Message tab. If you’re creating a new email, this option isn’t available.

In Outlook Mail, click the Settings option and click the View All Outlook Settings link at the bottom of the Settings pane. Click Mail and then Rules. The resulting wizard is different, but you should have no problem.

How to create a rule in Outlook

Creating a rule in Outlook is a huge topic. We’re narrowing this one down to sending a copy of an email to a specific person or group. As a result, you won’t have to remember to add addresses to the Cc and Bcc controls. The rule removes a huge burden — the burden of remembering to copy other people manually.

For demonstration purposes, I recommend that you use your own email address to avoid sending a message to someone else. However, if you’re using a free mail service such as Gmail, you might not see the copy of the email, because Gmail has odd rules about resending what it considers a duplicate. When it encounters the same email addresses, it might not show you the copies. If this is the case, you might try again using a friend’s email address for testing — with their permission of course.

The first step is to outline the need for a rule. In this case, we want to send a copy of an email to someone based on a set of conditions. Fortunately, the rules wizard offers a lot of conditions, as you’ll see:

1. In the Mail window, click the Home tab.

2. In the Move group, click the Rules dropdown.

3. Choose Manage Rules & Alerts from the dropdown (Figure A).

Figure A

Select "Manage Rules & Alert" option under Microsoft Outlook "Rules" settings.
Create a new rule.

4. In the resulting dialog, click New Rule.

5. In the first wizard pane, select Apply Rule On Messages I Send (Figure B). In the next pane, you’ll add a condition to narrow that down. If you’re using Outlook Mail, all of the options are in one dialog, so you won’t be clicking Next. You won’t have nearly as many steps to complete this rule.

Figure B

Select "Apply rule on messages I send" option in the Rules Wizard pop-up window.
This option will trigger the rule every time you send a message to the person or group specified.

6. Click Next.

7. In the next pane, click the Send To People Or Public Group link in the top pane.

8. In the bottom pane, click the link and specify the person or group receiving the original message (Figure C). I’m using my email address for demonstration purposes. You should do the same to avoid sending a test email to someone unnecessarily. When applying this for real, select a person or group from the list to add it to the To list at the bottom and click OK. Doing so will replace the generic link in the bottom pane. This link identifies the recipient of your original email.

Figure C

Enter email address under the "To" section of the Rules Address window.
Identify who gets the copy of the email.

9. Click Next.

10. In the top pane click the Cc The Message To People Or Public Group to update the rule in the bottom Pane (Figure D).

Figure D

Select the actions for the message under Rules Wizard.
Specify who will receive the copy of the email message.

11. Click the People Or Public Group link in the bottom pane and repeat the instructions in step #8 for adding email addresses to the rule. I will use my own email address again, and so should you. These people will receive a copy of the message.

12. Click OK, click Finish, and then click OK.

It seems like a lot of steps, but they’re all easy ones. This isn’t a complex rule. Before we test the rule, let’s look at examples of a few choices:

  • In Step 3, you can choose Create Rule if the selected email is from the person you specify in Step 8 — the recipient(s) of the original email.
  • In Steps 7 and 8, I selected my email address for demonstration purposes only. You can choose more than one person or a group or individuals and a group, and so on.
  • The chosen people or group in Step 8 might be confusing. You are narrowing things down. You could choose the Every Email I Send option, but I don’t recommend doing so without a good reason. This choice represents who gets the original email.
  • In Step 11, identify all the people or groups who will get a copy of the email. This is the step you’re saving yourself — remembering to enter these addresses in the original email.
  • In Step 12, you could click Next and add exceptions to the rule. We didn’t do so.

With the rule in place, it’s time to test it.

How to test the rule in Outlook

Because you used your own email address as the recipient of the original message for demonstration purposes, you will identify yourself in the test email you’re sending now:

1. Click New Mail in the New group.

2. In the resulting message window, enter your email address in the To control (Figure E). You don’t need to enter anything else, but you can if you like. This address matches the one chosen in Step 8.

Figure E

The send and receive tab of Microsoft Outlook.
Enter the original recipient.

3. Click Send and confirm if you didn’t enter subject text.

4. If you control when Outlook sends email, be sure to send email manually by using the Send & Receive tab. You might have to do this twice to send and receive the test message and the copy.

You should have two copies of the email, the original one and the copy. If not and you’re using Gmail or some other free mail server, try again with another address, such as a friend or co-workers after asking for permission to do so.



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