Hello @MikeMacNeil-5031
It is recommended that you use authenticated SMTP (port 587) to sendmail from an Azure VM (SendGrid is one of the recommendations they make to use). If you have an enterprise subscription then you will have access to raising a ticket with Microsoft as seen in the document below.
For more information please read the documentation on https://learn.microsoft.com/en-us/azure/virtual-network/troubleshoot-outbound-smtp-connectivity
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