"Deployment validation failed" error when trying to configure Point-to-site connection in my Azure Virtual network gateway

Hi @ Jakub Śliwiński,,

Apart from what was shared earlier, if possible, could you please go to resource group and check activity logs, you may find the logs there in json. This json with failed operation is expected to have the error detail. Please check and if you get an obvious error, you can fix or do let me know. I would be glad to assist you on this.

Hi @ Jakub Śliwiński,

Welcome to Microsoft Q&A Platform.

It looks like your P2S gateway deployment is failing validation, usually because of one of two things: a mis-matched Azure AD auth block or an unsupported gateway SKU. Here’s a quick checklist to get you un-blocked:

Grab the “Inner Errors” :

In the Azure portal go to your resource group → Deployments.---> Click on the failed deployment (Microsoft.Network-…) → Details or JSON view → expand properties.error.details.

That section will show you exactly which parameter or value is invalid.

You can also run:

az group deployment show \ --name Microsoft.Network-… \ --resource-group 

and inspect the .error.details object.

Confirm your gateway SKU & VPN type:

• Point-to-site with OpenVPN (SSL) + Azure AD auth requires a Standard-family SKU (VpnGw1 or above) and RouteBased VPN type. • Basic SKU only supports IKEv2/cert auth, so if you accidentally deployed Basic, the template will reject the OpenVPN+AAD block.
• If you need to upgrade, recreate or scale your gateway to VpnGw1+ (you can’t swap a Basic SKU in place).
• Verify your Entra ID settings exactly match the App registration Field What to enter Tenant   
• Your Directory (tenant) ID GUID only – not the full login URL Audience 
• The “Application ID URI” you set under Expose an API (for example api://), not just the 8-digit app object ID Issuer https://sts.windows.net//(with the trailing slash)
• No extra spaces or line-breaks – paste them directly from the App’s Overview/Expose an API pages. • If you’re not sure, open your App Registration in Azure AD, copy the Directory ID, the exact App-ID URI, and the sts.windows.net URL, then paste them into the P2S config.

Re-deploy Once your SKU and auth settings are corrected, hit Save again. The template validation should pass and your P2S profile will generate successfully.

Here is the Issuer Format as per Microsoft Docs

Issuer: URL of the Secure Token Service. Include a trailing slash at the end of the Issuer value. Otherwise, the connection might fail. Example:- https://sts.windows.net/{Microsoft ID Entra Tenant ID}/

Tenant: TenantID for the Microsoft Entra ID tenant. Enter the tenant ID that corresponds to your configuration. Make sure the Tenant URL doesn't have a \ (backslash) at the end. Forward slash is permissible.

• Azure Public: https://login.microsoftonline.com/{TenantID}

Pleaseand “up-vote” wherever the information provided helps you, this can be beneficial to other community members.

Deployment validation failures for Point-to-site configuration are commonly caused by one of the following, based on the provided context:

1. Unsupported or misconfigured gateway SKU or tunnel/auth type
   • The gateway must be a VPN gateway (Gateway type = VPN) with a non-Basic SKU. The Basic SKU does not support IKEv2 and has limitations on P2S features. If the gateway is using Basic, delete and recreate it with a supported SKU.
   • Ensure the gateway was created as a VPN gateway and not ExpressRoute. Certificate-based connection authentication and some advanced settings are not supported for ExpressRoute connections. If the connection type is ExpressRoute, validation will fail when trying to configure VPN-style authentication.
2. Subscription or environment limitations
   • Free trial subscriptions can have restricted permissions and behaviors that cause template or peering/validation operations to fail with generic HTTP 400 or validation errors. In similar scenarios, upgrading from Free Trial to Pay-As-You-Go resolved obscure deployment/validation failures.
   • If the virtual network or gateway is in a service-managed resource group (for example, created by another managed service), some operations may be blocked and surface only as template validation errors.
3. Region or platform-side issues
   • There are documented cases where deployments fail with obscure validation errors in a given region but succeed when redeployed in another region, even with identical settings. If all configuration values are confirmed correct, try deploying the VPN gateway and P2S configuration in a different region.
4. How to proceed
   • Verify the gateway:
     • Gateway type = VPN.
     • SKU is not Basic and supports P2S/OpenVPN.
   • Confirm the subscription is not limited by Free Trial constraints. If it is, consider upgrading the subscription and retrying the configuration.
   • If possible, attempt the same configuration in another region to rule out region-specific issues.
   • If validation still fails, use the tracking ID from the error in an Azure support ticket so support can inspect the inner errors on the platform side.

The Tenant, Audience, and Issuer values described are not covered in the provided context, so only the above supported causes and actions can be confirmed.

References:

• Configure a point-to-site VPN on Windows for use with Azure Files
• Troubleshoot site-to-site connections with digital certificate authentication
• Troubleshooting: Azure point-to-site connection problems
• Azure Peering Fails with HTTP error 400 - Microsoft Q&A
• Azure Deployment Takes 70 Minutes to Fail with Obscure Error - Microsoft Q&A
• Unable to launch HDInsight (5.1, Hadoop 3.3.4) cluster - Microsoft Q&A