Migrate IIS SMTP to EA SMTP Server

IIS SMTP server is retired and is no longer included in Windows Server 2025 and later versions. EA SMTP Server is the replacement for IIS SMTP Server and it supports Windows Server 2012 R2 to 2025 and later versions. If you are using IIS SMTP Server, you can migrate to EA SMTP Server to continue receiving security updates and support.

This article provides the steps to migrate from IIS SMTP Server to EA SMTP Server. The migration process involves installing EA SMTP Server, configuring it, and then migrating your existing SMTP settings and data from IIS SMTP Server to EA SMTP Server.

Installation

Follow these steps to install and set up EA SMTP Server on your Windows Server:

  • Download the EA SMTP Server Installer from the official source.
  • Double-click the installer file to launch the automatic installation process. Note that the installer requires .NET Framework 4.5 or later to be pre-installed on the server.
  • After installation completes, access the EA SMTP Server Manager by navigating to Windows Start Menu > All Programs > EA SMTP Server > EA SMTP Server Manager to begin configuration.

Note

Installation Permission: An account with Administrative Privileges is required to run the installer for installing “EA SMTP Server”.

Windows Firewall Rule: The installer automatically creates a Windows Firewall rule to allow inbound connections to EA SMTP Server.

IIS SMTP Virtual Server Migration

Different from IIS SMTP Server, EA SMTP Server does not use the concept of “Virtual Servers”. Instead, it uses “Receive Connectors” to manage incoming email traffic. Each Receive Connector can be configured with specific settings such as IP address bindings, port numbers, authentication methods, and permissions. And it uses “Send Connectors” to manage outgoing email traffic. Each Send Connector can be configured with specific settings such as smart host routing, address space, and authentication methods.

To migrate your existing IIS SMTP Virtual Server settings to EA SMTP Server, follow these steps:

  • Open the EA SMTP Server Manager and navigate to the “Receive Connector” section.
  • Select an existing Receive Connector or create a new one by clicking “New Receive Connector”.
  • Configure the Receive Connector settings to match those of your IIS SMTP Virtual Server > General, Access, Messages. This includes setting the appropriate IP address bindings, port numbers, Connection Control, Relay Restrictions, authentication methods, and permissions.
  • Save the Receive Connector settings and repeat the process for any additional Receive Connectors you need to create.

Notice:

  • IIS SMTP doesn’t select SSL certificate manually, but you can select SSL certificate for each Receive Connector in EA SMTP Server if needed.
  • For message non-delivery report or bad mail folder setting, please configure in “Send Connector > Delivery” section of EA SMTP Server Manager.

Next, navigate to the “Send Connector” section in the EA SMTP Server Manager.

  • Select an existing Send Connector or create a new one by clicking “New Send Connector”.
  • Configure the Send Connector settings to match those of your IIS SMTP Virtual Server > Delivery. This includes setting the appropriate smart host routing, address space, and authentication methods.
  • Save the Send Connector settings and repeat the process for any additional Send Connectors you need to create.
  • After configuring the Receive Connectors and Send Connectors, test the email flow to ensure that emails are being sent and received correctly through EA SMTP Server.

Notice:

  • IIS SMTP doesn’t support opportunistic TLS, but EA SMTP Server does. EA SMTP Server will automatically attempt to use TLS when sending emails if the receiving server supports it. You can also configure specific TLS settings in Send Connector if needed.
  • IIS SMTP doesn’t support outbound IP address binding, but EA SMTP Server does. You can configure specific IP address bindings for each Send Connector in EA SMTP Server if needed.

Throttling Migration

IIS SMTP doesn’t support connection and message throttling. EA SMTP Server supports connection and message throttling to help manage email traffic and prevent abuse. You can configure throttling settings for each Receive Connector and Send Connector in EA SMTP Server.

DKIM Migration

IIS SMTP doesn’t support DKIM signing. If you have DKIM configurations set up in your email flow, you will need to configure DKIM settings in EA SMTP Server to ensure that your outgoing emails are signed with DKIM.

  • Open the EA SMTP Server Manager and navigate to the “DKIM Signing” section.
  • Select an existing DKIM configuration or create a new one by clicking “New DKIM Configuration”.
  • Configure the DKIM settings to match those of your IIS SMTP Server. This includes setting the appropriate domain, selector, and private key.
  • Save the DKIM settings and repeat the process for any additional DKIM configurations you need to create.
  • After configuring the DKIM settings, test the email flow to ensure that emails are being signed and validated correctly through EA SMTP Server by https://www.appmaildev.com/ or other email testing tools.

Domains Migration

If you have domains configured in your IIS SMTP Server, you will need to migrate these domains to EA SMTP Server as well. EA SMTP Server supports domain configurations, but the setup process may differ from IIS SMTP Server.

  • Open the EA SMTP Server Manager and navigate to the “Accepted Domains” section.
  • Click “New Domain” to create a new domain configuration.
  • Enter the required information for the new domain configuration, such as the domain name and any associated settings.
  • Save the domain configuration and repeat the process for any additional domains you need to create.

In EA SMTP Server, there is no concept of Alias or Remote Domain as in IIS SMTP Server. Instead, you can manage email routing and delivery through the local user and remote user list in Accepted Domains configuration. You can create local user list for domains that are hosted on your server and remote user list for domains that are hosted externally. This allows you to manage email routing and delivery based on the user lists rather than domain configurations.

Users Migration

EA SMTP Server doesn’t support windows built-in user accounts for authentication. Instead, it uses its own user management system. You will need to create new user accounts in EA SMTP Server and assign the appropriate permissions to these accounts.

  • Open the EA SMTP Server Manager and navigate to the “Users” section.
  • Click “New User” to create a new user account.
  • Enter the required information for the new user account, such as username, password, and email address.
  • Assign the appropriate permissions to the user account based on your requirements.
  • Save the user account settings and repeat the process for any additional user accounts you need to create

After migrating your settings and user accounts to EA SMTP Server, it’s important to thoroughly test the email flow to ensure that everything is working correctly.

IIS SMTP doesn’t support message throttling. You can configure message throttling settings for each user in EA SMTP Server.

Pickup Directory Migration

If you have a pickup directory configured in your IIS SMTP Server, you will need to migrate this directory to EA SMTP Server as well. EA SMTP Server supports the use of pickup directories for processing outgoing emails.

The default pickup directory of EA SMTP Server is located at Installation Path\Pickup by default. You can also edit Installation Path\Config\Pickup\PickupFolders.json file to change existing pickup directories or add more pickup directory paths if needed.

Journal Tools

IIS SMTP Server does not have a built-in message journal, but EA SMTP Server includes a message journal feature that allows you to log and track all incoming and outgoing emails. The message journal provides detailed information about each email, including sender, recipient, subject, message ID, and timestamps. This can be useful for auditing, troubleshooting, and monitoring email traffic on your server.

Message Journal

The message journal stores logs of all incoming and outgoing emails. You can search these logs by sender, recipient, subject, or message ID for auditing and troubleshooting.

The journal database is based on SQLite, and logs are stored by default at Installation Path\Log\journal.v11.db. You can also view and export logs using third-party SQLite viewers.

Queue Viewer

The queue viewer allows you to monitor the status of the submission queue and delivery queue. You can manually abort or retry messages that are stuck or failed.

Journal Setting

Configure journal settings to manage log storage and performance:

  • Journal Item Expiration Time: Set a time period to automatically delete old logs and prevent excessive disk space usage.
  • Delete Journal Table Manually: If enabled, logs are not deleted automatically; you must manually delete journal tables via the journal viewer.
  • Date-Based Table Splitting: For improved performance, logs are split into separate tables by date range. You can select which tables to view or delete in the journal viewer.
  • Max Items per Journal Table: Define the maximum number of records per journal table. When this limit is exceeded, a new table is created to store subsequent logs.

Restart EA SMTP Service

You can restart EASmtpSvc Service to restart all services of EA SMTP Server.

Restart-Service "EASmtpSvc"

Free for non-commercial use

EA SMTP Server is free for non-commercial use. You can request a trial license every 60 days, and each trial license is valid for 90 days. When your trial license is close to expiring, you can apply for a new one to continue using the server for non-commercial projects.

Free Email Support

Not enough? Please contact our technical support team.

Support@EmailArchitect.NET

Remarks

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