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

Question

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

.

Then I saved the email.txt file.
Dropped it in the pickup folder inside mailroot.
After a few seconds the email.txt dissapeared from the pickup folder.
It appears in the queue folder
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?

AFAIK, you should be using the .eml extension with your test email, not the .txt extension. — joeqwerty, Jun 22 '15 at 21:13
I followed a tutorial that said. txt. Anyway I tried your method renaming it .msg, but it still gives me the same error. It disspears from the pick up folder and thge queue folder, but then it comes back in my drop folder as a failed delivery — user3771570, Jun 22 '15 at 21:18
I misspoke in my original comment. Try using the **.eml** extension. — joeqwerty, Jun 22 '15 at 21:23
Same problem. I get a receive a drop folder message stating failure to deliver message — user3771570, Jun 22 '15 at 21:34
What's the nature of the NDR? Can you post the text of it here? — joeqwerty, Jun 22 '15 at 21:40
Action failedStatus: 5.1.0 Diagnostic code:smtp;550 5.1.0 Authentication required — user3771570, Jun 22 '15 at 21:45

score 1 · Answer 1 · edited Jun 23 '15 at 10:42

1

I solved it! I just followed these steps.

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

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

edited Jun 23 '15 at 10:42

sebix

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answered Jun 22 '15 at 22:19

user3771570

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So you're relaying through your ISP? That information would have been useful had it been included in your question. At any rate, glad you got it resolved. – joeqwerty Jun 22 '15 at 22:32
Yes, thank you anyway. I was only using it as a smart host, but I forgot to add the username and password along with the tls encryption. – user3771570 Jun 22 '15 at 22:40

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

1 Answers1