Visionary 360 Blog

Known Issue – SMTP Relay Service for On-Premises | ConnectWise Manage

The following only applies to those running ConnectWise Manage On-Premises servers.

From ConnectWise KB article

“On February 29th, Microsoft enabled the new security defaults policy if a partner has not met Microsoft Partner Security Requirements.

For on-premises partners that use Office 365 for their outbound email, we recommend that you install the new ConnectWise SMTP Relay Service which uses Modern Authentication.”


Unfortunately if Streamline IT or other smtp outbound domains are used, this SMTP Relay Service will not properly work.

ConnectWise’s KB Article shows this is a limitation of Microsoft’s Graph API.

At Visionary 360, we found this while troubleshooting with a client.  A new service ticket was created and a status email was sent using a StreamlineIT domain.  Reviewing the Email Audit service it was found that the proper email address was being used for the outbound email, however the ticket contact received the email with a totally different email address, that of the ConnectWise Partners domain.

Uninstalling the service, then sending via the standard IIS SMTP service corrected the issue.

This poses a problem for when Microsoft tightens security for Office 365 SMTP connectors.

As a best practice note, if sending SMTP directly from your Manage server, don’t forget to add it’s IP address to your SPF & DKMI records to prevent these emails from landing in spam folders.



About Visionary 360

Visionary 360 is a team of veteran coaches focused on the technology sector, mainly IT Service Providers, helping to successfully implement their tools more effectively with a financial focus.

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