Outbound SMTP email not being delivered, but still disappearing from the queue and pickup folder

email-bouncesemail-serversmtpwindows-server-2012-r2

After setting up my smtp server on a Windows 2012 server r2 on port 587. I tested the email functions by creating a text file labeled email with the following code inside:

From:admin@mydomain.com
to:otheremail@gmail.com
Sunject: Test Email

This is the body

.
  1. Then I saved the email.txt file.
  2. Dropped it in the pickup folder inside mailroot.
  3. After a few seconds the email.txt dissapeared from the pickup folder.
  4. It appears in the queue folder
  5. But then disspears from the queue folder

At this point I checked my gmail to see if it was delivered, but there was no mail. So I checked the badmail folder, and of course it was empty.

So my question is what is happening to my email? Is it being delivered? Do I have to make changes to the smtp server to get it to work? Is my email being blocked since it doesnt even show up in my spam folder?

UPDATE 2: Just checked the dropped folder and I've been receiving Delivery Status Notifications (failure) that says:

smtp; 550 5.1.0 Authentication required

What does that mean and what can I do to fix it?

Best Answer

I solved it! I just followed these steps.

  1. Go to IIS 6.0 manager
  2. Right click on your domain - Select properties
  3. On the delivery tab choose outbound security
  4. Select basic authentication
  5. Type up your isp username in my case it was my comcast username and password
  6. Check the box for TLS encryption and press Ok
  7. Press Apply.

Now you should be able to send mail without the error 5.1.0

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