STARTTLS is required when trying to send an email within SQL Server

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JasonYeung-2529 asked Mar 19, '21 FrancescoMantovani-8046 answered May 3, '22

STARTTLS is required when trying to send an email within SQL Server

Hi,
I'm trying to setup a couple of alerts on SQL Server which sends me a message when the alert executes. I've setup an account in Database Mail, which sends an email via "smtp.office365.com", using port 587. Below is the settings I used (I removed the domain of the accounts for security purposes):

When I to send a test message, I get the following errors, depending on whether I have the "This server requires a secure connection" checkbox checked.

If this checkbox is not checked, I get:
Exception message: cannot send mails to mail. The server response was 5.7.3 STARTTLS is required to send mail

If this checkbox is checked, I get:
The server response was 5.7.57 Client not authenticated to send mail.

I also tried port 25, basic and anonymous authentication and a variety of users when using basic authentication, but the same errors appear. I was wondering how do I set the account up so I could send a message from SQL Server?

Sincerely,

Jason

sql-server-general

bssi-jira-settings-database-mail.jpg (87.9 KiB)

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MorLevi-1850 · Apr 28 at 09:45 AM

Have the same error! in my 365mail marked autenticated SMTP...

and in my logged - "General Error System.Net.Mail.SmtpException: Error in processing. The server response was: 5.7.3 STARTTLS is required to send mail [**.eurprd02.prod.outlook.com]
at System.Net.Mail.MailCommand.CheckResponse(SmtpStatusCode statusCode, String response)
at System.Net.Mail.MailCommand.Send(SmtpConnection conn, Byte[] command, MailAddress from, Boolean allowUnicode)
at System.Net.Mail.SmtpTransport.SendMail(MailAddress sender, MailAddressCollection recipients, String deliveryNotify, Boolean allowUnicode, SmtpFailedRecipientException& exception)
at System.Net.Mail.SmtpClient.Send(MailMessage message)
at NotificationLib.SmtpMailSender.Send(Dictionary`2 config)"

Do you have eny solution ? getting crazy because of that
Thank you!

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Answer 1 · 2021-03-19T06:15:11.253Z

AmeliaGu-msft answered Mar 19, '21 ToothFairysTale-1298 edited Sep 15, '21

Hi JasonYeung-2529,
What the version of SQL Server and OS are you using?
Please refer to this doc to check if TLS 1.2 is supported for your OS and SQL Server, and make sure the TLS 1.2 is enabled.
And here is a tool which may help you to manage protocols.

Best Regards,
Amelia

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ToothFairysTale-1298 · Sep 15, 2021 at 12:20 PM

I am having a problem with sending my email from a certain program. Even though it is set up using STARTTLS, I am getting an error message saying 451 5.7.3 STARTTLS is required to send mail [BYAPR11CA0103.namprd11.prod.outlook.com] I am so frustrated with this! Can someone PLEASE help me!! Thank you!!

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Answer 2 · 2021-06-10T08:48:05.093Z

FrancescoMantovani-8046 answered Jun 10, '21 TomPhillips-1744 commented Sep 15, '21

nartac didn't worked.
It's particularly bad because I'm using Windows Authentication

swordmail.png (33.0 KiB)

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TomPhillips-1744 · Sep 15, 2021 at 12:46 PM

The box "This Server requires a secure connection (SSL)" must be checked.

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Answer 3 · 2021-09-15T12:53:45.997Z

ToothFairysTale-1298 answered Sep 15, '21 TomPhillips-1744 commented Sep 15, '21

Thank you TomPhillips-1744 for replying!! when I click the box, then it says, "The token supplied to the function is invalid" ?? (this is the program I am trying to send emails from called IBP) Is there another place I need to check that box?

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TomPhillips-1744 · Sep 15, 2021 at 03:33 PM

This error is related to this problem.
https://support.microsoft.com/en-us/topic/ms12-006-vulnerability-in-ssl-tls-could-allow-information-disclosure-january-10-2012-41786996-65e1-ad9e-7536-fdc4017a81a1

Use regedit to change SCHANNEL to 2.

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Answer 4 · 2021-09-15T13:00:09.357Z

ToothFairysTale-1298 answered Sep 15, '21

Should incoming mail be set at: SSL/TLS and outgoing set as: STARTTLS? However, in the outlook account settings, I'm not seeing a box to check for SSL?

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Answer 5 · 2021-09-15T13:03:54.45Z

ToothFairysTale-1298 answered Sep 15, '21 FrancescoMantovani-8046 commented Sep 16, '21

If the above is correct, it is set at that... so I wonder what I am missing or doing wrong?

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FrancescoMantovani-8046 · Sep 15, 2021 at 08:03 PM

Hi, I wrote an article that might help you out: https://www.jeeja.biz/2021/07/01/sql-server-why-your-database-mail-is-not-working-and-probably-never-will/

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ToothFairysTale-1298 FrancescoMantovani-8046 · Sep 15, 2021 at 11:20 PM

Oh wow, so you created this yourself? And it's free? I wish I understood computers more and how to install it, I am so new at all this... but I am going to keep this and see if I can attempt it one day. I'm just afraid I will mess something up in my computer that i won't be able to fix... sigh! But thanks for this, it is greatly appreciated! :))

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FrancescoMantovani-8046 ToothFairysTale-1298 · Sep 16, 2021 at 07:20 PM

Don't be afraid. Edit the first few lines, paste it in a SSMS tab and press F5.
The query will install the account for you.
If it doesn't work or if it brakes stuff.... this is how we all learnt.

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Answer 6 · 2022-05-03T08:36:46.983Z

FrancescoMantovani-8046 answered May 3, '22

Yes, @MorLevi-1850 , I wrote a post about it and you can read it here.

Let me know if this helps.

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