Microsoft has deprecated functionality that Penelope used to rely on, so most email/external communications issues can be resolved by switching to Centralized Email Sending (aka SendGrid!).
It should be noted that the instruction in this article assumes a default (not limited) scope. For instructions on how to create a limited scope click here.
To configure O365 Exchange (default scope) in Penelope you will need:
1. An Admin level account and an Impersonation Account at a minimum in Office 365.
2. A System Administrator account in Penelope.
In this article
Changing from EWS (Web Services) to MS Graph
Microsoft no longer supports the current EWS (Web Services) method of synchronizing events to MS Exchange/O365. We recommend all customers using Penelope 4.21.1.0 and above use MS Graph to synchronize events with MS Exchange/O365. If you have any questions please contact the Penelope Support Team.
Exchange Admin – Account Setup
1. Log in to Office 365.
2. Select Admin icon which will take you to the Microsoft 365 admin center. The icon should look similar to the one below.
3. From the left-hand side menu click on Users (1) > Active Users (2).
4. Verify that the user’s email address appears in the Active users list.
5. You will also need to check the Mail tab for each user to ensure that they have mailbox permissions.
-To do this click the Display name of the user, a window will open on the right-hand side of the screen with the Mail tab (see the image in step 6).Click the Mail tab.
-If the user does not have mailbox permissions a message similar to this will be displayed: “This user doesn’t have an Exchange Online license”. If information about mailbox permissions etc appears then the user has a mailbox.
6. You will need to verify that the following Email apps are included for each user: Authenticated SMTP, Exchange Web Services and Outlook on the web or Outlook Desktop. Select the Active user (1), Select Mail (2) and then select Manage email apps (3).
7. You can now check the Manage email apps list to ensure it includes Authenticated SMTP, Exchange web services and Outlook on the web or Outlook Desktop. If any apps are missing, add them and click Save changes.
8. From the left-hand side menu in the Microsoft 365 admin center click Exchange (a new window will open called Exchange admin center).
9. From the Exchange admin center navigate to recipients > mailboxes and verify that all users appear here as able to receive messages in their mailbox.
10. Return to the Microsoft 365 admin center (it will most likely be open in another window) list and add a new user account (click the Add a user link) to be used for the impersonation functionality in Penelope.
11. Return to the Exchange admin center (instructions in step 8) In the Admin List go to Exchange admin centre > permissions > admin roles and click the plus (+) icon to add an Impersonation Permission Role.
12. Complete the following details (e.g. enter a name e.g. PenelopeImpersonation, add the ApplicationImpersonation Role, add the account created above for impersonation usage) and click Save.
You have now completed all the required configuration in Exchange. Instructions on how to configure Penelope for MS Exchange can be found below.
Penelope – Setup
1. Log in to Penelope using a System Administrator account.
2. Click Agency Setup and navigate to the Setting tab.
3. Set the Use MS Exchange setting to Yes and click Save.
4. Return to the System Administrators My Home (click the home icon on the left-hand side of the screen) page and click MS Exchange.
5. Enter the applicable credentials including an admin level O365 account and click Save. For the admin account ensure that only the first part (minus @domain) is entered.
6. After this is configured perform a test connection. To perform a test connection you need to use an account that is not the impersonation account (e.g. admin account).
7. Log into your Exchange calendar with the account the test was completed with and ensure the message appears in the inbox.
You have now configured Penelope for MS Exchange.
Important Information
For each Worker in Penelope ensure they have their valid O365 email address entered into the Email field in the Contact Info section of the Individual Profile, and the "Use with MS Graph" checkbox must be checked.
It is important to note that this field is different than the email address in the Personal Message Settings. The email address entered in the Contacts section must exactly match the email address/username as it appears in 0365.
Common Issues and Errors
Below you will find a list of common issues and errors which occur when configuring O365 with Penelope:
Incorrect Credentials in Penelope Setup Ensure username, password, URL, domain and admin account are correct.
Missing Impersonation Permissions for accounts Ensure the account is set up with Account Impersonation role and is not a DG group.
Missing SMTP mailbox Ensure the admin account is username only. Ensure Worker accounts match exactly in Penelope and O365.Ensure Worker account, Impersonation account and Admin account have SMTP setup in O365.
Impersonation Account or worker accounts are DG groups DG groups do not have mailboxes. Ensure each account is added as a User and not a Group.
Subset of users The impersonation account can be limited to only have access to add calendar entries for a group of accounts. This is the scope field when adding the admin role in Exchange.
Have a Question?
If you have any further questions or need assistance, please contact the Penelope Support Team.