Database Mail to work on Azure VM

• terry999

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  December 4, 2023 at 7:09 pm

  #4339700

  Trying to get Database mail working sending via  outlook.office365.com or smtp.office365.com port 587 using  SSL

  Running on SQL 2019 on Windows server 2019. The machine is a VM on Azure. Port 587 is open

  Get a very generic error

  The mail could not be sent to the recipients because of the mail server failure. Exception Message: Cannot send mails to mail server. (The operation has timed out.).

  A physical SQL server machine with same account details works.

  I thought it could be TLS issue because event viewer had SChannel error at the same time I was trying to send emails.

  : "A fatal error occurred while creating a TLS client credential. The internal error state is 10013."

  I did add these reg entries (But in my case for .Net 4 Database mail config file has 4.6)

  https://www.sqlservercentral.com/forums/topic/database-mail-using-tls-1-2

  After trying these and restarting machine and SQL Service (several times) I can see that Schannel error 10013 doesn't correlate to when I tested emails. So hours later I think it could be a red herring. I also believe SQL 2019 does support TLS 1.2 by default.

  A PS simple email script works on Physical machine but not on the Azure VM. So it's not just a Database mail issue.

  Any thing else I can try I'm stumped..

   

   

• Site Owners

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  December 5, 2023 at 7:10 pm

  #4340359

  Thanks for posting your issue and hopefully someone will answer soon.

  This is an automated bump to increase visibility of your question.

• cyrusbaratt

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  December 26, 2023 at 2:36 am

  #4352284

  Do you have a Azure VPN resource setup for your VM SQL server or just your Azure VM box?

  This could solve your problem.

  Please check out this link:

  https://learn.microsoft.com/en-us/azure/virtual-network/troubleshoot-outbound-smtp-connectivity#recommended-method-of-sending-email.

  Note:

  + I would setup on a sandbox before implementing on the live site.

   

  DBASupport

• terry999

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  December 27, 2023 at 11:51 am

  #4353033

  I don't know our Azure setup, probably wouldn't understand it anyway

  I'm going to ask to get Sendgrid setup, from what I see its free up to 100 emails per day.

  Would like to know where it's blocked though as simple Powershell test network connectivity on port 587 to smtp.office365.com  works..