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How to Connect mySMTP with Microsoft Exchange Server 2019 (Smart Host Setup)

This setup uses a send connector with authentication to relay all outbound mail via relay.xx.xxx (from setup email)

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Step 1: Open Exchange Admin Center (EAC)

  1. Open your browser and go to your Exchange Admin Center:
    https://<YourExchangeServer>/ecp
  2. Log in with admin credentials.

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Step 2: Create a New Send Connector

  1. In the EAC, go to Mail Flow > Send Connectors.
  2. Click the + (plus) icon to create a new connector.
  3. Name it mySMTP or similar, and set Type to Internet.
  4. Click Next.

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Step 3: Configure the Smart Host

  1. On the Network settings screen:
    • Select: Route mail through smart hosts
    • Click + Add, and enter: relayxx.xx.xxx (from setup email)
  2. Click Next.

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Step 4: Set Up Authentication

  1. On the Smart host authentication screen:
    • Select: Basic Authentication
    • Enter your mySMTP username and password
    • Check: Offer basic authentication only after starting TLS
  2. Click Next.

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Step 5: Source Server

  1. Click + Add and select your Exchange server (e.g. EXCH01).
  2. Click Finish to create the connector.

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Step 6: Test the Connection

Send a test email from a user mailbox (e.g., using Outlook or OWA) to an external email address (e.g., Gmail or your own).

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Success Checklist

  • Port: 587
  • Encryption: TLS (STARTTLS)
  • Auth: Basic (plain login)
  • Smart Host: smtp.mysmtp.com