Using Office 365 SMTP hosted services with TaskCentre

Note to reader: This article was originally published on as a KnowledgeBase Article on December 20th 2012.

As most people know TaskCentre has an inbound and outbound SMTP capability and traditionally this has worked in conjunction with the company on-premise Exchange SMTP mail server. With more customers now moving over to hosted services in the cloud the inevitable question is “Can TaskCentre provide the same functionality using hosted SMTP services?”

This knowledge article addresses that question and discusses both inbound SMTP triggers and outbound SMTP email delivery with mail relay enabled.


We begin with outbound SMTP flow where TaskCentre is required to send email though Office 365 hosted facilities.

Outbound SMTP from TaskCentre to Office 365 is relatively straightforward.

TLS authentication is required and is directed to port 587 instead of port 25 used when Exchange is hosted on-premise. Open the SMTP output configuration in Tools/Output. Take note of the configuration in the screenshots. We have used an account called “TaskCentre” to provide the TLS authentication. Note Domain name is not required.



There is a relay restriction of 1500 emails per day imposed on TaskCentre by Office 365. If your requirement is likely to exceed that quantity then you should look at deploying a local SMTP server using IIS for delivery.


In the past using on-premise Exchange SMTP services if a user wished to trigger a task based on the content of an inbound email then a email routing would be set up using a contact name and a specific address space. This would have the effect of forwarding  a subset of email onto the TaskCentre server machine which hosted a MS SMTP virtual server running under IIS.

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Similar principles apply when using hosted SMTP services the administrator must configure an outbound connector which identifies a specific address space and routes email onto the TaskCentre server. In order to use this connector you must first:

1. Set up a DNS MX record that identifies the domain name that you require and maps this to the external IP address that will be used by the IIS SMTP virtual server machine.

2. Register a sub domain name in order to filter mail destined for TaskCentre server away from email destined for Office 365 mailboxes.

Once the sub domain name has been established together with registration of the IP address then the administrator can commence work on configuring the outbound connector.

1. In the office 365 Management Console under Exchange online click Manage.


2. Click on Mail Control in the left side navigation pane:


3.       Under Microsoft Forefront Online Protection for Exchange, click on Configure IP safe listing, perimeter message tracing and email policies:


4. In the FOPE Administration Centre, click the Administration tab, and then click the Company tab

5. In the Connectors section, for the Outbound Connectors, click Add to open the Outbound Connector dialog


6. In the Name field, enter a descriptive name for the outbound connector

7. In the Description field, enter descriptive information about the outbound connector

8. In the Recipient Domains field (under Connector Scope

9. Select the Deliver all messages to the following destination check box, then select the Fully Qualified sub Domain Name option

10. The Transport Layer Security (TLS) Settings section allows you to configure whether emails will be sent securely or not. Orbis Software recommends setting up opportunistic TLS initially to ensure the TLS does not impact your outbound email flow. This means that an encrypted connection will always be attempted first, but if this cannot be established, the connection falls back to unencrypted communication.

This completes the configuration of the Office 365 outbound connector. We should now consider configuration of IIS on the TaskCentre server.

IIS Virtual SMTP server.

11. Set up IIS SMTP virtual server on Windows 2008 TaskCentre Server machine using the reference article

12. Ensure the DNS record identifies this machine by its registered external IP address.

13. Ensure that the TaskCentre SMTP agent has been installed and configured correctly on the TaskCentre server machine.


14. It should now be possible to send an email through Office 365 addressed to your sub domain in our case and for this to be routed to the TaskCentre server using the MX record triggering a task to run where the email filter criteria equates to true.


15. Administrators may decide to use the TaskCentre File Management tool to purge emails that remain in the drop folder under IIS after the trigger opportunity has been met. This is in cases where the email is not delivered to a final destination and is used solely to trigger a task runtime opportunity.

Note to reader: This article was originally published on as a KnowledgeBase Article on December 20th 2012.