Overview
This article provides a step-by-step guide on configuring Microsoft 365 (O365) connectors to route emails through the ExSign Agent for stamping. Additionally, it outlines rules to prevent Out of Office emails from being stamped.
- Connector: From O365 to ExSign Agent
- Connector: From ExSign Agent to O365
- Rule 1: Prevent Out of Office messages from being sent to ExSign Agent.
- Rule 2: Identify messages to send to ExSign Agent
Prerequisites
To complete the steps described in this guide, you need Microsoft 365 Global Administrator credentials.
Configuring Connectors
1. Connector: From O365 to ExSign Agent
This connector routes outbound emails from Microsoft 365 Exchange Online to the ExSign Agent for stamping.
Steps to Create the Connector
- Sign in to the Exchange Online Admin Portal (https://admin.exchange.microsoft.com) as an Administrator.
- Navigate to Mail Flow > Connectors.
- Click Add a New Connector.

- Specify the Mail Flow direction.

- Provide a Connector Name: From O365 to ExSign Agent.

- Configure the connector to be used when a Transport Rule redirects emails.

- Set the Smart Host to the on-premises server where ExSign Agent is installed.

- Define security options, specifying whether a secure channel should be used.

- Validate with an active mailbox that exists on the mail server. Enter a valid email address for validation.

- Review the settings and click Create Connector.

2. Connector: From ExSign Agent to O365
This connector enables processed emails to be transferred back from the ExSign Agent to Microsoft 365 Exchange Online.
Steps to Create the Connector
- Navigate to Mail Flow > Connectors.
- Click Add a New Connector.

- Set the Mail Flow from Your Organization’s Email Server to O365.

- Enter the Connector Name: From ExSign Agent to O365.

- Provide the IP address of the machine where the ExSign Agent is running.

Review the settings and click
Create Connector.

Configuring Mail Flow Rules
1. Rule: Prevent Out of Office Messages from Being Sent to ExSign Agent
This rule prevents Out of Office (OoO) messages from being processed by the ExSign Agent.
Steps to Create the Rule
- Navigate to Mail Flow > Rules.
- Click Create a New Rule.
- Name the rule: Prevent Out of Office Messages from Being Sent to ExSign Agent.
- Under Apply this rule if, select Message Properties and choose Automatic Reply.
- Under Do the following, select Modify the message properties.
- Set a header message ‘x-exsignproceed’ with the value ‘true’.

- Set the priority to High in the settings tab.

- Save and apply the rule.
2. Rule: Identify Messages to Send to ExSign Agent
This rule ensures that only selected emails are sent to the ExSign Agent for stamping.
Pre-requisite
Before creating this rule, create a security-enabled distribution list in O365.
Mail enable security group or security enable distribution.
Add only those email addresses that should be processed by the ExSign Agent.
Steps to Create the Rule
- Navigate to Mail Flow > Rules.
- Click Create a New Rule.
- Name the rule: Identify Messages to Send to ExSign Agent.
- Under Apply this rule if:
- Select The sender is internal/external.
- Specify The sender is located InOrganization.
- Select The sender is a member of this group.
- Specify the security-enabled distribution list: HC@contoso.com.
- Under Do the following:
- Select Redirect the message to the following connector.
- Specify the connector: Send to ExSign Agent.
- Under Exceptions, set the following conditions:
- The message properties include the message type ‘Calendaring’.
- Message headers include any of these words:
- Header Name: X-MS-Exchange-UnifiedGroup-SubmittedViaGroupAddress
- Header Includes: /o=ExchangeLabs/ou=Exchange Administrative Group
- Message headers match these text patterns:
- Header Name: x-exsignprocessed
- Value: HC or True
- The sender address matches any of these text patterns:
- Value: <>


- Set the rule priority lower than Rule 1.

- Save and apply the rule.
Conclusion
By following the steps outlined in this guide, you can successfully configure Microsoft 365 connectors and rules to ensure efficient email stamping via the ExSign Agent while preventing unnecessary messages from being processed.