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

Jason Yeung 61

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

Mor Levi 11 Reputation points

2022-04-28T09:45:22.783+00:00

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!

6 answers

Francesco Mantovani 1 Reputation point

2022-05-03T08:36:46.983+00:00

Yes, @Mor Levi , I wrote a post about it and you can read it here.

Let me know if this helps.
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Tooth Fairy's Tale 1 Reputation point

2021-09-15T13:03:54.45+00:00

If the above is correct, it is set at that... so I wonder what I am missing or doing wrong?
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Francesco Mantovani 1 Reputation point

2021-09-15T20:03:10.44+00:00

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/

Tooth Fairy's Tale 1 Reputation point

2021-09-15T23:20:15.12+00:00

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! :))

Francesco Mantovani 1 Reputation point

2021-09-16T19:20:48.243+00:00

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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Tooth Fairy's Tale 1 Reputation point

2021-09-15T13:00:09.357+00:00

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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Tooth Fairy's Tale 1 Reputation point

2021-09-15T12:53:45.997+00:00

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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Tom Phillips 17,716 Reputation points

2021-09-15T15:33:49.733+00:00

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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Francesco Mantovani 1 Reputation point

2021-06-10T08:48:05.093+00:00

nartac didn't worked.
It's particularly bad because I'm using Windows Authentication
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Tom Phillips 17,716 Reputation points

2021-09-15T12:46:43.597+00:00

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

Lucas Igbins 0 Reputation points

2024-01-12T23:04:17.0366667+00:00

@Francesco Mantovani how did you fix your issue? I am getting similar error message. Any help. The mail could not be sent to the recipients because of the mail server failure. (Sending Mail using Account 1 (2024-01-12T22:30:04). Exception Message: Cannot send mails to mail server. (Error in processing. The server response was: 5.7.3 STARTTLS is required to send mail [namprd11.prod.outlook.com :]).
) Smtp client authen is enable for the mailbox. Server/smart hostsmtp.office365.comPortPort 587 (recommended) or port 25TLS/StartTLSEnabledUsername/email address and passwordSign in credentials of Microsoft 365 or Office 365 mailbox the printer uses
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