Configure Microsoft 365 with Black Pearl Mail - Using a Test/Pilot Group

Configure Microsoft 365 with Black Pearl Mail - Using a Test/Pilot Group

You may want to set up a specific group of users to test the Black Pearl Mail system before deploying to your entire organization. This article explains how to create a test group in Microsoft 365 and where to make the change in the Black Pearl Mail Flow Rule that you will or have created. If you'd prefer to set up your entire organization, follow these instructions.

STEP 1 – Log in to Microsoft 365

1) Open the Microsoft 365 admin console -

STEP 2 - Create a Group for Test Users

1) Click on the down arrow next to Groups.

2) Click on Groups.

3) Click on Add a group.

4) Select Distribution, click Next.

5) Name the Group = i.e Black Pearl Mail Test Group, click Next.

6) Enter a Group email address = i.e. blackpearlmailtest, click Next.

7) Review the settings then click Create Group.

8) To immediately add members to this new Group, click on the Exchange admin center link. Otherwise, you can wait an hour to see it appears under Groups.

9) From within the Exchange admin center, click on groups.

10) Select the Black Pearl Mail Test Group, click on the edit icon.

11) Add the individuals you wish to participate in the testing of Black Pearl Mail. Click Save.

After you have entered the users to the Test Group, you can move on to Step 3 below.

STEP 3 - Setup Inbound Connector

1) Open the Office365 admin console -
2) Click on Show all...

3) Click on Exchange.

4) Select Mail flow from the right-hand side menu.
5) Across the top menu select Connectors.
6) Click +.

7) In the pop-up window make these changes: 
  1. From: Your organization's email server.
  2. To:  Office365

8) Click Next.
9) Name: Black Pearl Mail Inbound.
  1. Ensure Turn it on is checked.
  2. Ensure Retain internal Exchange email Headers (recommended) is checked.
  3. Click Next.

10) Select By verifying that the subject name on the certificate that the sending server uses to authenticate with Office 365 match the domain name (recommended) is selected.
  1. Enter *
  2. Click Next

11) Confirm your settings are as per below, then click Save.

STEP 4 - Setup Outbound Connector

1) Select Mail flow from the right-hand side menu.
2) Across the top menu select Connectors.
3) Click +.

4) In the pop-up window make these changes: 
  1. From: Office365
  2. To:  Your organization's email Server
  3. Click Next

5) Enter the name: Black Pearl Outbound.
6) Ensure the following settings are both checked.
  1. Turn it on
  2. Retain internal Exchange email headers (recommended)

7) Click Next.
8) Check Only when I have a transport rule set up that redirects messages to this connector.

9) Click Next.
10) Click +.
11) Enter for Specify the smart host's fully qualified domain name (FQDN) or IPv4 address.

12) Click Save.
13) Click Next.

14) How should Office 365 connect to your email server?
  1. Ensure Always use Transport Layer Security (TLS) to secure the connection is checked.
  2. Select Issued by a trusted certificate authority
  3. Tick And the subject name or subject alternative name (SAN) matches this domain name:
  4. Enter *

15) Click Next.
16) Verify your settings as follows:

17) Click Next.
18) Under Validate this connector click +.

Click Ok.

19) Click Validate.

20) Click Close.

21) Ensure that Check connectivity to ‘’ succeeds. Note: “Send test email” may fail, this is not an issue. Microsoft sends the test email from an unvalidated domain which doesn’t pass security criteria.
22) Click Save

STEP 5 - Setup Mail Flow Rules

1) Click on Mail Flow, then Click on Rules.

2) Click + then select Add new rule.

3) Scroll down and click More Options.

4) Enter the following details.
      Name: Black Pearl Mail

Apply the Rule if…
  1. The Sender...

  1. is a member of this group

5) Select the Black Pearl Mail Test Group.

Under Do the following:
  1. Redirect the message to…

6) Select the following connector.

7) Select the Black Pearl Outbound.

8) Under Except if: Click add exception.

9) Select The message properties...includes the message type…

10) Select Calendaring, Click Ok.

11) Click add exception, to add another exception.

12) Select A message header…matches these text patterns.

13) Click on Enter text.

14) Enter X-BP, click Ok.

15) Click on Enter text pattens.

16) Enter ^*$
      Click + to add it.

17) Your value will now be listed below. Click Ok. 

18) Click add exception, to add another exception.

19) Select The sender's...

20) Select domain is...

21) Enter
      Click + to add it.

22) Your value will now be listed below. Click Ok.

23) Scroll down to Match sender address in message: and change to Envelope.

24)  Click Save.

That completes the settings needed in O365. You are now configured to route specific users through Black Pearl Mail. These settings can take up to an hour to complete. 

After You Have Completed Testing.

Once you have completed your testing and are ready for all members of your organization to use Black Pearl Mail, go back into the Exchange Admin Center, go to Rules, and edit the Black Pearl Mail rule. Change the Apply the Rule if... select The Sender then select is External/Internal and then select Inside the organization. This will route all users through Black Pearl Mail.

Next, you'll want to create signature templates, add user details, and lastly turn on signatures for your users. We provided helpful articles below.