Has anyone had luck sending dbmail via relay to an external server on an Azure VM (which appears to block SMTP outbound regardless of rules)?

Typically the servers we manage we handle a lot of the alerting for the SQL noise via operators/profiles/DBMail which gives us the most raw information about any issues that crop up on the server.

It appears that within Azure VMs, outbound via port 25 is disabled and can not be enabled (as far as my luck has gone, that is). This prevents the typical use of a relay to our mail server to then send mail to our ticketing boards.

Has anyone run into anything similar, and if so, are there any good workarounds that you found? I am sure this question is a bit confusing so please ask for whatever relevant info is needed.

Please read: Enhanced Azure Security for sending Emails – November 2017 Update which outlines the recommendations, options and restrictions for sending emails in Azure.

In particular:


For Pay-As-You-Go or Microsoft Partner Network subscriptions created
after November 15, 2017, there will be technical restrictions blocking
e-mail sent directly from VMs in these subscriptions. Customers that
need the ability to send e-mail from Azure VMs directly to external
e-mail providers (not using an authenticated SMTP relay) can make a
request to remove the restriction. Requests will be reviewed and
approved at Microsoft’s discretion and will be only granted after
additional anti-fraud checks are performed. To make a request, open a
support case with the issue type Technical --> Virtual Network -->
Connectivity --> Cannot send e-mail (SMTP/Port 25). Be sure to add
details about why your deployment needs to send mail directly to mail
providers instead of going through an authenticated relay.

StackExchange Database Administrators Q#208169, answer score: 5