IIS smtp messages stuck in inetpub/mailroot/queue - smtp

Question

I have initiated an email by using utl_mail.send
begin
utl_mail.send(
sender => <<sender mail>>,
recipients => <<recipient mail>>,
message => 'Hello World'
);
commit;
end;
/
But, the mail is not sent to recipient and stays in inetpub/mailroot/queue.
We verified all smtp server settings and looks fine.
We see that port 25 is also open.
Also, we stopped the smtp, cleared the queue, and re-start the smtp again. Still the issue is not resolved.
Kindly help with your valuable answers and experience. Every individual answer is appreciated.
Thanks in advance,
Subbu

Answer 1

Check the Event Viewer for any logs
For this you need to open the Event Viewer and goto Windows
Logs and then Application.
If its a 4.3.1 error then simply it
means the \inetpud\mailroot\ does not have proper permissions to the mailroot folder ,so give it the IIS_IUSRS and also IIS AppPool\"Your App Pool"
If the problem still persists make sure you have the vmstp setup on the local server , for this you need to have smtpclient installed on the server and go to IIS manager (not inetpub) and add a new VSMTP server .
And in the delivery choose the outbound security and then add your gmail or what ever mail you use.
And also make sure you allow port 25 through the firewall

Answer 2

Use telnet to try and confirm all is will by sending a very plain email. Instructions thanks to wiki (http://www.askstudent.com/techtips/how-to-use-telnet-to-send-email-over-port-25-using-smtp/):
Step # 1: First, open a command prompt. To open a command prompt window, click Start, Run and then type in cmd and press Enter. You can also press the +R to open the Run prompt and then type in cmd in the open text box.
Step # 2: You need to know a remote mail server. If you are still in school or working, there is the excellent opportunity to use your University mail server or your company’s mail server for this.
type in telnet RemoteMailServer 25 at the command prompt. The Remote mail server here in this command is the mail server of your school or company. It is usually mailhost..edu or compmail..com or something on those lines. When you press enter, you are shown a quick prompt that you are connecting to the remote mail server.
Step # 3: Introduce yourself to the mail server. Play around a bit.
type in helo mailhost at the command prompt. The mail server responds back with something like this
250 RemoteMailHost. Hello , pleased to meet you.
Step # 4: You can now enter your email address.
type in mail from: your email id # blah.com
The mail server responds back with a 250 … sender ok
Step # 5: You can now enter your receipient’s email address
type in rcpt to: recipient email id # blah.com
The mail server responds back with a “Recipient OK” message
Step # 6: Now, you are ready to type in the body of the email message.
type in data and press enter.
Now, type your message and then finally press Enter. To end your message type in a single period “.” . Your message is now in the queue
Step # 7: To complete and finish the process, type in quit and press enter. The mail server responds with a “Bye” after which you see a “Connection to host lost” message displaye

Answer 3

I recently ran into the same issue on server 2016. SMTP was configured using the IIS6 manager. Turns out, SMTP also had to be configured in IIS proper as well. Basically, I selected SMTP from the IIS server node, entered credentials for my smtp server and saved it. Immediately items that were stuck in the Queue folder started to get delivered. Not sure why this was necessary because I was accessing the relay from a console app, but the solution did work.

Answer 4

I ran into the same issue on Server 2019. My problem was that "From Email Address" used while sending from client wasn't matching what was setup on SMTP server. Once the client started sending with the correct "From Email Address", the mails were no longer stuck in the Queue.