Question

Photo of Carrie White

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Email Setup Issue

9

I'm just trying to test a new install and am using the simplest email settings

  • Server:smtp.gmail.com
  • Port:587
  • Username:(your Gmail username "xxxx@gmail.com")
  • Password:(your Gmail password)
  • Use SSL:True (checked)

but cannot get a mail to send successfully.  I receive the following error:

Exception: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.5.1 Authentication Required. Learn more at


I have an SSL certificate installed.  I checked my password.  Not sure what to try next.  Thanks for any help!


  • Photo of Jim Michael

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    Have you tried changing to port 465 (leaving everything else the same)? 

  • Photo of Carrie White

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    Thanks Jim!  I tried that and it still failed, but my error message is

    Exception: Failure sending mail.

  • Photo of Michael Roth

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    Are you trying to use your normal free Gmail account?  Also are you on Azure by chance?

  • Photo of Carrie White

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    Just trying to get my personal gmail account to work as a starting point.  No I installed on winhost.

  • Photo of Michael Roth

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    I am not a gmail pro but was not able to get anything to work.  I ended up using Mailgun on port 2525 and it worked first try.  I tried for a long time to get Zoho and Gmail to work but gave up after too many wasted hours/days.  Someone else might be able to direct you but it was not worth the headache.

    MailGun is free and has great reports.  https://documentation.mailgun.com/quickstart-sending.html?utm_source=mailgun&utm_medium=email&utm_campaign=transactional-dns-propagation# 

    My Setup is using WInhost as the DNS and auzure as the hosting VM.  

    • Jim Michael

      Jim Michael

      Yeah, some apparently have success using Google Apps (which points to smtp-relay.gmail.com) but I'm not sure if anyone has every gotten "plain old Gmail" to work.

    • Photo of Carrie White

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      Thanks Michael!  I've tried to set up MailGun but I have an issue with it also.  When I try to send an email, I get 

      Exception: Transaction failed. The server response was: Please activate your Mailgun account. Check your inbox or log in to your control panel to resend the activation email.


      The mailgun account is active and verified.  

      I have set my transport container in Rock communication medium and have my transport set up for MailGun using port 587.  I don't see which port I should use in the Rock documentation or anywhere, but that was the default port.

      Any ideas?

    • Photo of Michael Roth

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      Can you sign up for slack for faster replies?

      rockrms.com/slack

    • Photo of Michael Roth

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      Just as a follow up for this item. Rock and winhost were setup correctly, the issue was a configure issue in mailgun. Smooth sailing from now on. 

    • Photo of Carrie White

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      Thanks so much for your help Michael!