GMail - Must issue a STARTTLS command first

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GMail - Must issue a STARTTLS command first

Postby sraitken » Fri Sep 07, 2012 6:05 pm

I am getting a "5.7.0 Must issue a STARTTLS command first..." error message popping-up when trying to send a test email via GMail. Settings are:

SMTP host: smtp.gmail.com
Port: 587
UserName: <email address>
Password: <password for above>
Send From: <same as email address in UserName>

Thanks for any help.
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Postby petey » Mon Sep 10, 2012 8:28 am

SQL Backup's e-mail delivery feature does not support TLS/SSL connections.
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Postby spthorn » Tue Sep 16, 2014 3:41 pm

Is this still the case? v7.7.0.18

Will it ever be the case? Our email is provided by Amazon SES, which requires it.
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Re: GMail - Must issue a STARTTLS command first

Postby petey » Tue Sep 23, 2014 6:59 am

There is a patch available that allows you to send mail via TLS and SSL. Details of the patch and required configuration can be found in this document:

ftp://support.red-gate.com/patches/sql_ ... _patch.pdf
Peter Yeoh
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Beyond compression - SQL Backup goodies under the hood, updated for version 7
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Re: GMail - Must issue a STARTTLS command first

Postby spthorn » Tue Sep 23, 2014 2:41 pm

Peter, I installed the patch files per your attached procedure. Still not getting emails.
SMTP Host: email-smtp.us-east-1.amazonaws.com
Results are the same regardless of SMTPEncoding value in registry (TLS, SSH or blank). Doesn't appear to be any change from before.
I tried the following ports (based on http://docs.aws.amazon.com/ses/latest/D ... nnect.html):
Port Result
465 Screen freezes, after 20 seconds or so it comes back, but no email received
2465 Screen freezes, after 20 seconds or so I get error "Socket Error # 10060 Connection timed out."
25 Screen freezes, after 20 seconds or so I get error "Socket Error # 10060 Connection timed out."
587 Get error "Must issue a STARTTLS command first"
2587 Screen freezes, after 20 seconds or so I get error "Socket Error # 10060 Connection timed out."

I don't doubt that it works with Gmail and Yahoo mail. Nobody else is using Amazon SES (Simple Email Service) with SQL Backup Pro?
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Re: GMail - Must issue a STARTTLS command first

Postby petey » Tue Sep 23, 2014 5:03 pm

Were you using the SQL Backup GUI to test the sending of emails?
Peter Yeoh
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Beyond compression - SQL Backup goodies under the hood, updated for version 7
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Re: GMail - Must issue a STARTTLS command first

Postby spthorn » Tue Sep 23, 2014 5:05 pm

Yep, the Send Test Email button.
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Re: GMail - Must issue a STARTTLS command first

Postby petey » Tue Sep 23, 2014 6:17 pm

Could you please try configuring the email server settings as per the document referenced earlier for GMail (TLS, port 587 etc), and run a test backup using SSMS that sends an email e.g.

Code: Select all
EXEC master..sqlbackup '-sql "BACKUP DATABASE model TO DISK = [<AUTO>] WITH MAILTO = [<your email address here>], MAILLIB_SYN"'


Does the email get sent successfully?
Peter Yeoh
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Beyond compression - SQL Backup goodies under the hood, updated for version 7
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Re: GMail - Must issue a STARTTLS command first

Postby spthorn » Tue Sep 23, 2014 6:33 pm

Yes, it did generate the email just fine.

I went ahead and added email notification to one of my half-hourly transaction log backup jobs, just to see if that email would fail as well... and it did. Generated a SQL Backup warning "Warning 151: MAILTO error: Failed to send mail. (Must issue a STARTTLS command first)".
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Re: GMail - Must issue a STARTTLS command first

Postby petey » Wed Sep 24, 2014 1:19 am

In the job you modified, did you add the MAILLIB_SYN switch e.g.

EXEC master..sqlbackup '-sql "BACKUP DATABASE model TO DISK = [<AUTO>] WITH MAILTO = [me@me.com], MAILLIB_SYN"'
Peter Yeoh
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Beyond compression - SQL Backup goodies under the hood, updated for version 7
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