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I'm trying to use SQL server database mail, but it's not sending any test emails.

here is my set up page:

enter image description here

Conor8630
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    Something tells me your outgoing server is not correct. – Sean Lange Jan 24 '19 at 17:59
  • How are you trying to send a test email? – S3S Jan 24 '19 at 17:59
  • @SeanLange As in smtp-mail.outlook.com? – Conor8630 Jan 24 '19 at 18:01
  • @scsimon by right clicking database mail node and selecting send test mail – Conor8630 Jan 24 '19 at 18:02
  • Well yeah...that is what you have as the outgoing smtp server. You want your mail server there. – Sean Lange Jan 24 '19 at 18:02
  • But it is an outlook account I'm using? – Conor8630 Jan 24 '19 at 18:03
  • Did you look in the Database Mail logs? Right-click Database Mail and select View Database Mail Log. – userfl89 Jan 24 '19 at 18:06
  • So I checked it there and got this an error, mail server error – Conor8630 Jan 24 '19 at 18:09
  • https://www.lifewire.com/what-are-the-outlook-com-smtp-server-settings-1170671 Check the "This server requires a secure connection (SSL)" box – UnhandledExcepSean Jan 24 '19 at 18:20
  • @UnhandledExcepSean Yeah I have that in and still not working – Conor8630 Jan 24 '19 at 18:28
  • Can you provide the full error message you are receiving? Also, are you able to connect to outlook.com and manually log in from that computer? – UnhandledExcepSean Jan 24 '19 at 18:28
  • @UnhandledExcepSean Yep I can log in. Here's the error "01/24/2019 18:13:33,,Error,26,The mail could not be sent to the recipients because of the mail server failure. (Sending Mail using Account 4 (2019-01-24T18:13:33). Exception Message: Cannot send mails to mail server. (The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [LO2P265CA0127.GBRP265.PROD.OUTLOOK.COM]).),9580,9,,24/01/2019 18:13:33,sa" – Conor8630 Jan 24 '19 at 18:31
  • Are you sure that checkbox is checked? You picture above shows it is unchecked. – UnhandledExcepSean Jan 24 '19 at 18:32
  • Ah, That was it!! Thank you so must Sean! if you post an answer I'll accept it – Conor8630 Jan 24 '19 at 18:35

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Outlook SMTP requires SSL according to this article.

You need to check the "This server requires a secure connection (SSL)" box

UnhandledExcepSean
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