SQL Database Mail configuration with sendgrid

AJEET SINGH 1 Reputation point
2021-09-27T09:22:39.71+00:00

I have been trying to setup sendgrid on SQL Database Mail but all the time it says Cannot send mail to mail server.

This is what i have done.

I have sendgrid accound with abc@mydomain.com and created api key and SG.xxxx password.
As this is prod setup instance, i had done domain level authentication and my webmaster updated CNAME as requested by sendgrid.
Tested using TELNET smtp.sendgrid.net 587 and authenticated with SG.xxxx password Base64 encoded and this was able to send email from abc@mydomain.com to xyz@mydomain.com
I setup profile with abc@mydomoain.com as SQL notification Profile and selected Basic Authentication and provided 'apikey' as username and 'SG.xxx' as password in Database Mail - 'Configure Database Mail' option in SQL SSMS. Unchecked - 'The server requires secure authentication (SSL) connection' Port 587
I tried to 'Send Test Mail' with 'abc@keyman .com' to 'xyz@mydomain.com' but the Database Mail reflects as below screenshot error
I have tried using abc@mydomain.com and sendgrid account password in Database Mail Config wizard for Basic authentication, but sendgrid suggested they don't accept Basic authentication. Please help how and where should i pass the api key if not under Basic Authentication ?
I tried updating with msdb.dbo.sysmail_add_account_sp nad updating records but it too didn't resolve and send email from Database mail.

Any help/ guidance would be greatly appreciated or if you had faced this how have you resolved it.

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SQL Server
SQL Server
A family of Microsoft relational database management and analysis systems for e-commerce, line-of-business, and data warehousing solutions.
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3 answers

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  1. Stratos Matzouranis 36 Reputation points
    2021-09-27T11:56:26.867+00:00

    Have you tried to click "This server required a secure connection (SSL)" ?


  2. Seeya Xi-MSFT 16,461 Reputation points
    2021-09-28T06:39:37.77+00:00

    Hi @AJEET SINGH ,

    Could you refer to this troubleshooting first: https://houseofbrick.com/troubleshooting-database-mail-for-sql-server/
    Maybe it is hopeful for you.
    If it doesn't work please feel free to let me know.

    Best regards,
    Seeya


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  3. Ben Miller (DBAduck) 956 Reputation points
    2021-10-01T12:06:15.127+00:00
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