Private Endpoints Revisited: NSGs and UDRs

Private Endpoints Revisited: NSGs and UDRs

Welcome back fellow geeks!

It’s been a while since my last post. For the past few months I’ve been busy renewing some AWS certificates and putting together some Azure networking architectures on GitHub. A new post was long overdue, so I thought it would be fun to circle back to Private Endpoints yet again. I’ve written extensively about the topic over the past few years, yet there always seems more to learn.

There have historically been two major pain points with Private Endpoints which include routing complexity when trying to inspect traffic to Private Endpoints and a lack of NSG (network security groups) support. Late last year Microsoft announced in public preview a feature to help with the routing and support for NSGs. I typically don’t bother tinkering with features in public preview because the features often change once GA (generally available) or never make it to GA. Now that these two features are further along and likely close to GA, it was finally a good time to experiment with them.

I built out a simple lab with a hub and spoke architecture. There were two spoke VNets (virtual networks). The first spoke contained a single subnet with a VM, a private endpoint for a storage account, and a private endpoint for a Key Vault. The second spoke contained a single VM. Within the hub I had two subnets. One subnet contained a VM which would be used to route traffic between spokes, and the other contained a VM for testing routing changes. All VMs ran Ubuntu. Private DNS zones were defined for both Key Vault and blob storage and linked to all VNets to keep DNS simple for this test case.

Lab setup

Each spoke subnet had a custom route table assigned with a route to the other spoke set with a next hop as the VM acting as a router in the hub.

Once the lab was setup, I had to enable the preview features in the subscription I wanted to test with. This was done using the az feature command.

az feature register --namespace Microsoft.Network --name AllowPrivateEndpointNSG

The feature took about 30 minutes to finish registering. You can use the command below to track the registration process. While the feature is registering the state will report as registering, and when complete the state will be registered.

az feature show --namespace Microsoft.Network --name AllowPrivateEndpointNSG

Once the feature was ready to go, I first decided to test the new UDR feature. As I’ve covered in a prior post, creation of a private endpoint in a VNet creates a /32 route for the private endpoint’s IP address in both the VNet it is provisioned into as well as any directly peered VNets. This can be problematic when you need to route traffic coming from on-premises through a security appliance like a Palo Alto firewall running in Azure to inspect the traffic and perform IDS/IPS. Since Azure has historically selected the most specific prefix match for routing, and the GatewaySubnet in the hub would contain the /32 routes, you would be forced to create unique /32 UDRs (user-defined routes) for each private endpoint. This can created a lot of overhead and even risked hitting the maximum of 400 UDRs per route table.

With the introduction of these new features, Microsoft has made it easier to deal with the /32 routes. You can now create a more summarized UDR and that will take precedence over the more specific system route. Yes folks, I know this is confusing. Personally, I would have preferred Microsoft had gone the route of a toggle switch which would disable the /32 route from propagating into peered VNets. However, we have what we have.

Let’s take a look at it in action. The image below shows the effective routes on the network interface associated with the second VM in the hub. The two /32 routes for the private endpoints are present and active.

Effective routes for second VM in the hub

Before the summarized UDR can be added, you need to set a property on the subnet containing the Private Endpoint. There is a property on each subnet in a virtual network named PrivateEndpointNetworkPolicies. When a private endpoint is created in a subnet this property is set disabled. This property needs to be set to enabled. This is done by setting the –disable-private-endpoint-network-policies parameter to false as seen below.

az network vnet subnet update \
  --disable-private-endpoint-network-policies false \
  --name snet-pri \
  --resource-group rg-demo-routing \
  --vnet-name vnet-spoke-1

I then created a route table, added a route for with a next hop of the router at, and assigned the route table to the second VM’s subnet. The effective routes on the network interface for the second VM now show the two /32s as invalid with new route now active.

Effective routes for second VM in the hub after routing change

A quick tcpdump on the router shows the traffic flowing through the router as we have defined in our routes.

tcpdump of router

For fun, let’s try that same wget on the Key Vault private endpoint.

Uh-oh. Why aren’t I getting back a 404 and why am I not seeing the other side of conversation on the router? If you guessed asymmetric routing you’d be spot on! To fix this I would need to setup the iptables on my router to NAT (network address translation) to the router’s address. The reason attaching a route table to the spoke 1 subnet the private endpoints wouldn’t work is because private endpoints do not honor UDRs. I imagine you’re scratching your head asking why it worked with the storage account and not with Key Vault? Well folks, it’s because Microsoft does something funky at the SDN (software defined networking) layer for storage that is not done for any other service’s private endpoints. I bring this up because I wasted a good hour scratching my head as to why this was working without NAT until I came across that buried issue in the Microsoft documentation. So take this nugget of knowledge with you, storage account private endpoint networking works differently from all other PaaS service private networking in Azure. Sadly, when things move fast, architectural standards tend to be one of the things that fall into the “we’ll get back to that on a later release” bucket.

So wonderful, the pain of /32 routes is gone! Sure we still need to NAT because private endpoints still don’t honor UDRs attached to their subnet, but the pain is far less than it was with the /32 mess. One thing to take from this gain is there is a now a disclaimer to Azure routing precedence. When it comes to routing with private endpoints, UDRs take precedence over the system route even if the system route is more specific.

Now let’s take a look at NSG support. I next created an NSG and associated it to the private endpoint’s subnet. I added a deny rule blocking all https traffic from the VM in spoke 2.

NSG applied to private endpoint subnet

Running a wget on the VM in spoke 2 to the blob storage endpoint on the private endpoint in spoke 1 returns the file successfully. The NSG does not take effect simply by enabling the feature. The PrivateEndpointNetworkPolicies property I mentioned above must be set to enabled.

After setting the property, the change takes about a minute or two to complete. Once complete, running another wget from the VM in spoke 2 failed to make a connection validating the NSG is working as expected.

NSG blocking connection

One thing to be aware of is NSG flow logs will not log the connection at this time. Hopefully this will be worked out by GA.

Well folks that’s it for this post. The key things you should take aware are the following:

  • Testing these features requires registering the feature on the subscription AND setting the PrivateEndpointNetworkPolicies property to enabled on the subnet. Keep in mind setting this property is required for both UDR summarization and enabling NSG support. (Thank you to my peer Silvia Wibowo for pointing out that it is also required for UDR summarization).
  • NAT is still required to ensure symmetric routing when traffic is coming from on-premises or another spoke. The only exception are private endpoints for Azure Storage because it operates different at the SDN.
  • The UDR feature for private endpoints makes less-specific UDRs take precedence over the more specific private endpoint system route.
  • NSG and summarized UDR support for private endpoints are still in public preview and are not recommended for production until GA.
  • NSG Flow Logs do not log connection attempts to private endpoints at this time.

See you next post!

Behavior of Azure Event Hub Network Security Controls

Behavior of Azure Event Hub Network Security Controls

Welcome back fellow geeks.

In this post I’ll be covering the behavior of the network security controls available for Azure Event Hub and the “quirk” (trying to be nice here) in enforcement of those controls specifically for Event Hub. This surfaced with one of my customers recently, and while it is publicly documented, I figured it was worthy of a post to explain why an understanding of this “quirk” is important.

As I’ve mentioned in the past, my primary customer base consists of customers in regulated industries. Given the strict laws and regulations these organizations are subject to, security is always at the forefront in planning for any new workload. Unless you’ve been living under a rock, you’ve probably heard about the recent “issue” identified in Microsoft’s CosmosDB service, creatively named ChaosDB. I’ll leave the details to the researchers over at Wiz. Long story short, the “issue” reinforced the importance of practicing defense-in-depth and ensuring network controls are put in place where they are available to supplement identity controls.

You may be asking how this relates to Event Hub? Like CosmosDB and many other Azure PaaS (platform-as-a-service) services, Event Hub has more than one method to authenticate and authorize to access to both the control plane and the data plane. The differences in these planes are explained in detail here, but the gist of it is the control plane is where interactions with the Azure Resource Manager (ARM) API occurs and involves such operations as creating an Event Hub, enabling network controls like Private Endpoints, and the like. The data plane on the other hand consists of interactions with the Event Hub API and involves operations such as sending an event or receiving an event.

Azure AD authentication and Azure RBAC authorization uses modern authentication protocols such as OpenID Connect and OAuth which comes with the contextual authorization controls provided by Azure AD Conditional Access and the granularity for authorization provided by Azure RBAC. This combination allows you to identify, authenticate, and authorize humans and non-humans accessing the Event Hub on both planes. Conditional access can be enforced to get more context about a user’s authentication (location, device, multi-factor) to make better decisions as to the risk of an authentication. Azure RBAC can then be used to achieve least privilege by granting the minimum set of permissions required. Azure AD and Azure RBAC is the recommended way to authenticate and authorize access to Event Hub due to the additional security features and modern approach to identity.

The data plane has another method to authenticate and authorize into Event Hubs which uses shared access keys. There are few PaaS services in Azure that allow for authentication using shared access keys such as Azure Storage, CosmosDB, and Azure Service Bus. These shared keys are generated at the creation time of the resource and are the equivalent to root-level credentials. These keys can be used to create SAS (shared access signatures) which can then be handed out to developers or applications and scoped to a more limited level of access and set with a specific start and expiration time. This makes using SAS a better option than using the access keys if for some reason you can’t use Azure AD. However, anyone who has done key management knows it’s an absolute nightmare of which you should avoid unless you really want to make your life difficult, hence the recommendation to use Azure AD for both the control plane and data plane.

Whether you’re using Azure AD or SAS, the shared access keys remain a means to access the resource with root-like privileges. While access to these keys can be controlled at the control plane using Azure RBAC, the keys are still there and available for use. Since the usage of these keys when interacting with the data plane is outside Azure AD, it means conditional access controls aren’t an option. Your best bet in locking down the usage of these keys is to restrict access at the control plane as to who can retrieve the access keys and use the network controls available for the service. Event Hubs supports using Private Endpoints, Service Endpoint, and the IP-based restrictions via what I will refer to as the service firewall.

If you’ve used any Azure PaaS service such as Key Vault or Azure Storage, you should be familiar with the service firewall. Each instance of a PaaS service in Azure has a public IP address exposes that service to the Internet. By default, the service allows all traffic from the Internet and the method of controlling access to the service is through identity-based controls provided by the supported authentication and authorization mechanism.

Access to the service through the public IP can be restricted to a specific set of IPs, specific Virtual Networks, or to Private Endpoints. I want quickly to address a common point of confusion for customers; when locking down access to a specific set of Virtual Networks such as available in this interface, you are using Service Endpoints. This list should be empty because there are few very situations where you are required to use a Service Endpoint now because of the availability of Private Endpoints. Private Endpoints are the strategic direction for Microsoft and provide a number of benefits over Service Endpoints such as making the service routable from on-premises over an ExpressRoute or VPN connection and mitigating the risk of data exfiltration that comes with the usage of Service Endpoints. If you’ve been using Azure for any length of time, it’s worthwhile auditing for the usage of Service Endpoints and replacing them where possible.

Service Firewall options

Now this is where the “quirk” of Event Hubs comes in. As I mentioned earlier, most of the Azure PaaS services have a service firewall with a similar look and capabilities as above. If you were to set the the service firewall to the setting above where the “Selected Networks” option is selected and no IP addresses, Virtual Networks, or Private Endpoints have been exempted you would assume all traffic is blocked to the service right? If you were talking about a service such as Azure Key Vault, you’d be correct. However, you’d be incorrect with Event Hubs.

The “quirk” in the implementation of the service firewall for Event Hub is that it is still accessible to the public Internet when the Selected Networks option is set. You may be thinking, well what if I enabled a Private Endpoint? Surely it would be locked down then right? Wrong, the service is still fully accessible to the public Internet. While this “quirk” is documented in the public documentation for Event Hubs, it’s inconsistent to the behaviors I’ve observed in other Microsoft PaaS services with a similar service firewall configuration. The only way to restrict access to the public Internet is to add a single entry to the IP list.

Note in public documentation

So what does this mean to you? Well this means if you have any Event Hubs deployed and you don’t have a public IP address listed in the IP rules, then your Event Hub is accessible from the Internet even if you’ve enabled a Private Endpoint. You may be thinking it’s not a huge deal since “accessible” means open for TCP connections and that authentication and authorization still needs to occur and you have your lovely Azure AD conditional access controls in place. Remember how I covered the shared access key method of accessing the Event Hubs data plane? Yeah, anyone with access to those keys now has access to your Event Hub from any endpoint on the Internet since Azure AD controls don’t come into play when using keys.

Now that I’ve made you wish you wore your brown pants, there are a variety of mitigations you can put in place to mitigate the risk of someone exploiting this. Most of these are taken directly from the security baseline Microsoft publishes for the service. These mitigations include (but are not limited to):

  • Use Azure RBAC to restrict who has access to the share access keys.
  • Take an infrastructure-as-code approach when deploying new Azure Event Hubs to ensure new instances are configured for Azure AD authentication and authorization and that the service firewall is properly configured.
  • Use Azure Policy to enforce Event Hubs be created with correctly configured network controls which include the usage of Private Endpoints and at least one IP address in the IP Rules. You can use the built-in policies for Event Hub to enforce the Private Endpoint in combination with this community policy to ensure Event Hubs being created include at least one IP of your choosing. Make sure to populate the parameter with at least one IP address which could be a public IP you own, a non-publicly routable IP, or a loopback address.
  • Use Azure Policy to audit for existing Event Hubs that may be publicly available. You can use this policy which will look for Event Hub hubs with a default action of Allow or Event Hubs with an empty IP list.
  • Rotate the access keys on a regular basis and whenever someone who had access to the keys changes roles or leaves the organization. Note that rotating the access keys will invalidate any SAS, so ensure you plan this out ahead of time. Azure Storage is another service with access keys and this article provides some advice on how to handle rotating the access keys and the repercussions of doing it.

If you’re an old school security person, not much of the above should be new to you. Sometimes it’s the classic controls that work best. 🙂 For those of you that may want to test this out for yourselves and don’t have the coding ability to leverage one of the SDKs, take a look at the Event Hub add-in for Visual Studio Code. It provides a very simplistic interface for testing sending and receiving messages to an Event Hub.

Well folks, I hope you’ve found this post helpful. The biggest piece of advice I can give you is to ensure you read documentation thoroughly whenever you put a new service in place. Never assume one service implements a capability in the same way (I know, it hurts the architect in me as well), so make sure you do your own security testing to validate any controls which fall into the customer responsibility column.

Have a great week!

What If… Volume 2

Hi there folks!

I’ve been busy lately buried in learning and practicing Kubernetes in preparation for the Certified Kubernetes Administrator exam. Tonight I’m taking a break to bring you another entry into the “What If” series I started a few months back.

Let’s get right to it.

What if I need to access a Private Endpoint in a subscription associated with a different Azure AD tenant and I have an existing Azure Private DNS Zone already?

I’ve been helping a good friend who recently joined Microsoft to support his customer as he gets up to speed on the Azure platform. This customer consists of two very large organizations which have a high degree of independence. Each of these organizations have their own Azure AD tenant and their own Azure footprint. One organization is further along in their cloud journey than the other.

Organization A (new to Azure) needed to consume some data that existed in an Azure SQL database in an Azure subscription associated with Organization B’s tenant. Both organizations have strict security and compliance requirements so they are heavy users of Azure PrivateLink Endpoints. A site-to-site VPN (virtual private network) connection was established between the two organizations to facilitate network communication between the Azure environments.

Customer Environment

The customer environment looked similar to the above where a machine on-premises in Organization A needed to access the Azure SQL database in Organization B. If you look closely, you probably see the problem already. From a DNS perspective, we have two Azure Private DNS Zones for This means we have two authorities for the same zone.

My peer and I went back on forth with a few different solutions. One solution seemed obvious in that organization A would manually create an A record in their Azure Private DNS zone pointing to IP of the PrivateLink Endpoint in Organization B. Since the organizations had connectivity between the two environments, this would technically work. The challenge with this pattern is it would introduce a potential bottleneck depending on the size of the VPN pipe. It could also lead to egress costs for Organization A depending on how the VPN connection was implemented.

The other option we came up with was to create a Private Endpoint in Organization A’s Azure subscription which would be associated with the Azure SQL instance running in Organization B’s Azure subscription. This would avoid any egress costs, we wouldn’t be introducing a potential bottleneck, and we’d avoid the additional operational head of having to manually manage the A record in Organization A’s Azure Private DNS Zone. Neither of us had done this before and while it seemed to be possible based on Microsoft’s documentation, the how was a bit lacking when talking PaaS services.

To test this I used two separate personal tenants I keep to test scenarios that aren’t feasible to test with internal resources. My goal was to build an architecture like the below.

Target architecture

So was it possible? Why yes it was, and an added bonus I’m going to tell you how to do it.

When you create a Private Endpoint through the Azure Portal, there is a Connection Method radio button seen below. If you’re creating the Private Endpoint for a resource within the existing tenant you can choose the Connect to an Azure resource in my directory option and you get a handy guided selection tool. If you want to connect to a resource outside your tenant, you instead have to select the Connect to an Azure resource by resource ID or alias. In this field you would end the full resource ID of the resource you’re creating the Private Endpoint for, which in this case is the Azure SQL server resource id. You’ll be prompted to enter the sub-resource which for Azure SQL is SqlServer. Proceed to create the Private Endpoint.

Private Endpoint Creation

After the Private Endpoint has been created you’ll observe it has a Connection status of Pending. This is part of the approval workflow where someone with control over the resource in the destination tenant needs to approve of the connection to the Azure SQL server.

Private Endpoint in pending status

If you jump over to the other resource in the target tenant and select the Private endpoint connections menu option you’ll see there is a pending connection that needs approval along with a message from the requestor.

Private Endpoint request

Select the endpoint to approve and click the approve button. At that point the Private Endpoint in the requestor tenant and you’ll see it has been approved and is ready for use.

This was a fun little problem to work through. I was always under the assumption this would work, the documentation said it would work, but I’m a trust but verify type of person so I wanted to see and experience it for myself.

I hope you enjoyed the post and learned something new. Now back to practicing Kubernetes labs!