Server did not respond properly to VPN control packets. Session State: key Material Sent

Raja Meer Baz Khan 40 Reputation points
2025-03-11T14:44:22.4333333+00:00

I tried to add the certificate into azure VPN after downloading from virtual-network-gateway on Azure. It is giving me the above error when I try to connect. What are possible things that I can check to fix it?

Azure VPN Gateway
Azure VPN Gateway
An Azure service that enables the connection of on-premises networks to Azure through site-to-site virtual private networks.
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  1. Vinodh247 29,781 Reputation points MVP
    2025-03-11T16:24:56.05+00:00

    Hi ,

    Thanks for reaching out to Microsoft Q&A.

    The error message "Server did not respond properly to VPN control packets. Session State: Key Material Sent" indicates an issue with the VPN authentication or communication between your client and the Azure VPN Gateway. Here are the possible things you should check and troubleshoot:

    1. Certificate Issues

    Since you're using a certificate for authentication, verify the following:

    • Ensure that the Root and Client Certificates are correctly uploaded in the Azure VPN Gateway.
    • The client certificate must be generated from the same root certificate that was uploaded to Azure.
    • If you’re using Azure Point-to-Site (P2S) VPN, ensure the client certificate is installed on your machine under Current User > Personal > Certificates.
    • Check that the certificate is not expired.
    1. VPN Gateway Configuration
    • Ensure that the VPN Gateway SKU supports the type of authentication you’re using.
    • If using IKEv2, ensure it is enabled on the VPN Gateway.
    • If using OpenVPN, ensure the correct profile is being used.
    1. Client-Side VPN Configuration
    • Make sure you are using the correct VPN client package downloaded from the Azure portal.
    • If using Windows, check the VPN configuration under Windows Settings and verify that it is set to use the correct VPN protocol (IKEv2, SSTP, or OpenVPN).
    • Ensure the correct certificate is being selected during authentication.
    1. Network and Firewall Rules
    • Check if any firewall or antivirus software is blocking the VPN connection. Ensure that UDP ports 500, 4500, and TCP 443 are open.
    • If behind a corporate network, check if there is a proxy or network policy blocking VPN traffic.
    1. VPN Logs and Debugging
    • If using Windows, check the logs in Event Viewer > Applications and Services Logs > Microsoft > Windows > RasClient for more details.
    • Also check from powershell command, Get-WinEvent -LogName Application -MaxEvents 50 | Where-Object { $_.Message -match "RAS" }
    • Restart the IKE and IPsec services
    • Disconnect and try reconnecting after a minute.

    If the issue persists, try re-importing the certificate and re-downloading the VPN configuration package from Azure. Let me know if you need further troubleshooting!

    Please feel free to click the 'Upvote' (Thumbs-up) button and 'Accept as Answer'. This helps the community by allowing others with similar queries to easily find the solution.

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