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Is anybody successful sending email via MS SQL Server Database Mail while secure connection is set ON in account settings?

I'm trying different SMTP servers with SSL to set up - like Gmail - and none of them is working. Yes, I have "unsafe access" ON in Google settings.

Seems to me like SSL in MS SQL Server is not working properly. When I try non-secure SMTP server it's working fine.

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The error goes like this (don't know how / where to find more detailed description):

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Please, don't ask me whether password it typed correctly - it is!

I've tryed different Gmail accounts on different servers - with the same unssuccesful result.

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  • Everything with SSL works fine! Did you receive an error when you sent a test e-mail?
    – user179264
    Oct 16, 2019 at 12:42
  • Yes, general error with no details - useless for troubleshooting. Are you successful with Gmail SMTP?
    – jericzech
    Oct 16, 2019 at 13:13
  • Please, post the error. Yes, I was able to setup e-mail using Gmail SMTP.
    – user179264
    Oct 16, 2019 at 13:16
  • I did...thank you.
    – jericzech
    Oct 16, 2019 at 13:25
  • Have you tried port 465 instead of 587?
    – Jacob H
    Oct 16, 2019 at 13:51

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