Iis 6 Smtp Mail Stuck In Queue

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Microsoft IIS can perform the SMTP role well, but requires a few steps to configure. Lucky for you, I’ve set up an IIS SMTP relay server and recorded all the steps!

Iis 6 Smtp Mail Stuck In Queue

Iis 6 Smtp Mail Stuck In Queue

In this article, we will cover all the steps required to successfully configure an SMTP relay server to send email sent by Office 365. Technically, we will use this SMTP relay to send email to Office 365; It works quickly for any general purpose SMTP email delivery.

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The first task you need to do to get the IIS SMTP relay setup is to install the IIS SMTP server. You need to install it

If you are not familiar with installing Windows features through Server Manager, see this article titled Installing or Uninstalling Roles, Role Services, or Features.

Installing the SMTP server feature eliminates a lot of point and clicks. Open PowerShell console as administrator and run below line:

If you send email via TLS (Office 365), you must import an SSL certificate into the server’s local machine’s private certificate store before configuring the IIS SMTP server. You can skip this step if your Office 365 SMTP relay does not have TLS.

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If you don’t have a certificate, you can get it through your local PKI (if you have one) or a public certificate using services like LetsEncrypt, Digicert.

After receiving the certificate, you need to import it into the machine’s private certificate store. If you don’t know how to import certificates using MMC Certificates, see Certificate Import and Export – Microsoft Windows.

After import, verify that the certificate chain is complete and there are no errors. If everything is fine, you should open the certificate

Iis 6 Smtp Mail Stuck In Queue

At this point you have successfully installed the SMTP server. But before using it, server settings need to be configured first.

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The SMTP server runs in IIS6 compatibility mode and does not come with built-in PowerShell support. This means you will configure the settings manually using the IIS6 management console.

(1) You want to use the destination SMTP mail server. This does not have to be the same as the computer’s FQDN. If you are configuring this SMTP server for use with Office 365

Now if you have a device you want to test, you need to add its IP address to the relay modules first. In this example, the IP address

Added to the relay controls. This IP address belongs to a computer on the same network as the server.

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If your relay server sends outgoing emails over TLS, you must verify that the IIS SMTP server knows the certificate and enable TLS encryption.

In the SMTP server properties tab, you should see the message “TLS certificate available with expiration date: XXXXXX”. If so, you’re good to go.

At this point, your SMTP server should be configured and ready to send emails. The next step is to test it. To verify that the SMTP server receives the message, you should try sending the email through the SMTP relay.

Iis 6 Smtp Mail Stuck In Queue

. This directory is where the SMTP service takes newly submitted emails for processing before transferring them to

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If successful, the file will disappear soon. This means that the SMTP service has picked it up and started processing the message.

Within a few seconds to a minute, you will receive the email sent to the specified recipient’s email address.

Open the PowerShell console and copy/paste the code below. Be sure to edit the values

Parameters. Depending on how you configured the relay server above, you can use the example below to test the TLS or non-TLS configuration.

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In this article, you learned how to configure an IIS SMTP relay server for recipient email delivery from Office 365. We tested our system using PowerShell to verify that everything is correct. Responding to a compromised email account in Office 365Dec 13, 2019 Dec 13, 2019 Removing a user from the Limited Users site after sending spam.

When you set up a multitasking device or email app with Office 365, there are some cases where the device or app can’t connect directly to Office 365. In these cases, you must configure Internet Information Services (IIS) to act as a mediator.

Before continuing, review how to set up a multitasking device or email client with Office 365, as there is no need to set up an additional server to deploy.

Iis 6 Smtp Mail Stuck In Queue

• The SMTP feature discussed in this topic is available in IIS 6.0, and the application of IIS 6.0 is complete with support for Windows 2003. This article is for reference purposes, but we recommend using a supported version of Exchange Server instead of IIS. . SMTP. We will continue to do “best effort support” on this feature, however, no bug fixes or improvements have been made to this product. We can continue to address performance questions as best we can, but we cannot help with IIS 6.0 product issues or detailed technical inquiries. Expect this product to be removed in future versions of Windows.

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Configure Exchange Online as an SMTP Relay Using Windows Server 2012 Step 1: Install Internet Information Services (IIS)

Step 4: Restart IIS service and SMTP service

• Replace contoso-com.mail.protection.outlook.com with your tenant’s mail forwarding address. This can be found by searching for your domain’s MX record at theadmin.microsoft.comportal located in the Settings section.

We use cookies to provide you with a better experience. By using this website you accept our data protection policy. The current article is dedicated to solving problems that occur when using an SMTP relay server to send mail to the Office 365 mail infrastructure.

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In the previous article, we reviewed the concept of how to configure an IIS SMTP server as a mail relay in a basic Office 365 environment.

When using the SMTP mail forwarding option in an Office 365 environment, mail flow can be considered complex because there are many components in this process, and each of these components has specific characteristics or specific configuration settings.

In the case where we indicate the problem is that the source email client (hardware device, email software, etc.) does not reach the destination (Office 365 recipient or other external recipient), the actual cause of the display capability problem is not very simple.

Iis 6 Smtp Mail Stuck In Queue

For example, a scenario where a FAX device needs to send an email message to an Office 365 recipient involves the following steps:

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In fact, there are additional steps in the mail flow that we haven’t mentioned, such as doing the DNS resolution process and so on.

Because of this complexity, we need to understand the various components of a mail flow and what troubleshooting steps, troubleshooting tools, and techniques we can use when a mail flow does not complete successfully.

Best practice is to perform “POC” (proof of concept) testing after completing all necessary configurations; This will help you verify that the email flow is executed correctly.

To test and validate the mail flow when using SMTP email relay, we will simulate the mail flow of an enterprise client trying to send an email to an Office 365 mail recipient.

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Test 1 – A simple test where we simulate an email client using the same email address and user ID used by the IIS SMTP relay server.

Test 2 – To simulate a mail client using a different email address than the user credentials used by the IIS SMTP relay server. In this case, we want to check if the required send permission is specified for the IIS SMTP mail server user account.

In our case, a “real” mail client can be hardware devices such as FAX machines, scanners or printers, or software that supports e-mail.

Iis 6 Smtp Mail Stuck In Queue

The main problem is that, often, this “email client” does not have the option to provide correct information in case of failure, i.e., the part that does not send the mail to the intended recipient.

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To get a clear view of the mail flow process, I recommended a good SMTP email client service: Basic SMTP Telnet Client.

A basic SMTP Telnet client service enables you to simulate mail flow and “see” the contents of a communication channel between mail clients.

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