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I have configured Gmail in SQL Server 2008, and it sends emails properly but after 6 Jun 2022 it does not send emails and shows email status failed with the following error:

The mail could not be sent to the recipients because of the mail server failure. (Sending Mail using Account 7 (2022-08-03T09:05:17). 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: 5.7.0 Authentication Required)

This is my configuration property

  • server name: smtp.gmail.com
  • port: 587
  • The server require secure connection : checked

Thanks in advance

Dale K
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SOHRAB
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    SQL Server 2008 and 2008 R2 have reached end of life several years ago and are now **completely unsupported**. You really should be looking at upgrading to a supported version. – marc_s Aug 03 '22 at 04:42
  • Still using TLS1.0 or similar which might be being blocked somewhere? – Dale K Aug 03 '22 at 04:44
  • You need to configure your GMAIL's App Password and use that. [Reference](https://support.google.com/accounts/answer/185833?hl=en) and [Less secure apps & your Google Account](https://support.google.com/accounts/answer/6010255?hl=en) – Squirrel Aug 03 '22 at 04:51
  • Gmail now need 2FA for smtp server. See if this question can help you: https://stackoverflow.com/questions/72577189/gmail-smtp-server-stopped-working-as-it-no-longer-support-less-secure-apps – Jim LK Yu Aug 03 '22 at 05:47
  • SQL Server 2008 would need to be updated to support TLS 1.2 (as well as the underlying operating system). And you need to configure a Gmail app password as mentioned – Charlieface Aug 03 '22 at 10:57
  • i am trying to configure GMAIL app password used your refer reference it device list it only show smartphone list not SQL Server could you please clarify a little more ? – SOHRAB Aug 06 '22 at 04:42

2 Answers2

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Personal Gmail account doesn't allow connecting from "less secure apps" anymore.

Only from Google Workspace accounts (paid). In this case, you have to allow it in administration panel.

stefmex
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I think User Gmail Server Authentication needs to reauthorized try to reconfigure SQL Server with Gmail.

Dale K
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Nalla Sanjay
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    Can you explain how to do that? – Dale K Aug 03 '22 at 05:18
  • thank you for your Quick response ,i reconfigure but still has the same error .Allow less secure apps is not working with Gmail any more can it be cause of that? – SOHRAB Aug 03 '22 at 05:53