Modernizing Terraform Pipelines on Azure: OIDC Federation for GitHub Actions and Azure DevOps
The secret nobody wants to rotate Most Terraform-on-Azure pipelines we see still authenticate the same way they did three years ago. A long-lived ARM_CLIENT_SECRET sitting in GitHub Actions or Azure DevOps, set once, copied around, and rotated only when something breaks. It's the most ignored credential in the cloud, and statistically the most likely one to leak. A developer screenshots a variable group. A pipeline log echoes a value. A fork inherits a secret. Or the secret simply expires on a Friday evening and takes production deployments with it. Workload Identity Federation (WIF) makes this whole class of problem go away. The pipeline mints a short-lived token at runtime, exchanges it for an Azure access token via Microsoft Entra, and never touches a secret. GitHub Actions has supported it since 2021. Azure DevOps service connections went GA with WIF in February 2024. The azurerm Terraform provider has supported it since v3.7. This post walks through the pattern end-to-end, for both GitHub Actions and Azure DevOps, the way I've rolled it out across multiple customer estates. How the exchange actually works Before any YAML, it helps to picture what's happening: The CI system (GitHub or ADO) signs a short-lived JWT describing exactly what's running- which repo, which branch, which environment, which service connection. The pipeline sends that JWT to Microsoft Entra ID. Entra checks it against a federated identity credential you've configured on a managed identity or app registration. The iss, sub, and aud claims must match case-sensitively. If it matches, Entra returns an Azure access token valid for the duration of the job. Terraform uses it. The job ends. The token expires. Nothing persists. The token is bound to a specific subject like repo:contoso/platform:environment:prod or sc://contoso/platform/azure-prod. It can't be reused from another repo, branch, or pipeline. Recommended Architecture A few choices that usually hold up in production: Decision Choice Identity type User-assigned managed identity (UAMI), not app registration Identity granularity One UAMI per environment (not per pipeline) Trust scope Pinned to the environment claim, not the branch RBAC scope Resource group, not subscription Remote state OIDC + use_azuread_auth = true, shared key access disabled Why UAMIs? They live in your subscription, don't need Application Administrator rights to manage, and follow the lifecycle of the resource group they belong to. Why one per environment? Pipeline-per-identity explodes into hundreds of identities. Environment-per-identity maps cleanly to deployment scopes. Part 1 - GitHub Actions Step 1: Create the identity and federate it Two commands per environment. That's it. az identity create -g rg-platform-identity -n id-tf-prod -l eastus az identity federated-credential create \ --name github-prod \ --identity-name id-tf-prod \ --resource-group rg-platform-identity \ --issuer https://token.actions.githubusercontent.com \ --subject repo:contoso/platform:environment:prod \ --audiences api://AzureADTokenExchange Repeat for nonprod. No secret is created anywhere. Step 2: Wire it up in GitHub In repo Settings → Environments, create nonprod and prod. On prod, add required reviewers and a branch rule restricting deployments to main. Then add three environment variables (not secrets - these aren't sensitive): AZURE_CLIENT_ID, AZURE_TENANT_ID, AZURE_SUBSCRIPTION_ID. The workflow itself stays small: permissions: id-token: write contents: read jobs: apply: runs-on: ubuntu-latest environment: prod env: ARM_USE_OIDC: "true" ARM_CLIENT_ID: ${{ vars.AZURE_CLIENT_ID }} ARM_TENANT_ID: ${{ vars.AZURE_TENANT_ID }} ARM_SUBSCRIPTION_ID: ${{ vars.AZURE_SUBSCRIPTION_ID }} steps: - uses: actions/checkout@v4 - uses: hashicorp/setup-terraform@v3 - run: terraform init && terraform apply -auto-approve Three things make this secure: id-token: write is the only elevated permission, and it doesn't grant write access to anything in GitHub, it just lets the runner mint a JWT. The environment: line picks the right AZURE_CLIENT_ID and drives the sub claim. The federation refuses anything else. No azure/login step is needed for Terraform. The azurerm provider reads GitHub's OIDC environment variables automatically. Part 2 - Azure DevOps The model is identical. The mechanics are different. ADO offers two creation paths for a WIF service connection: automatic (it creates an app registration for you) and manual (you bring your own UAMI). For platform teams, manual + UAMI is almost always the better choice to ensure identity lives where governance lives. The flow is a small dance between the two portals: In Azure DevOps, create a new ARM service connection → choose Workload Identity Federation (manual) → fill in your UAMI's client ID, tenant ID, and subscription. Save as draft. ADO shows you an issuer URL and a subject identifier. In Azure, on the UAMI, add a federated credential using the values ADO showed you. The subject looks like sc://contoso/platform/azure-prod. Back in ADO, click Verify and save. In the pipeline, the service connection only "activates" if a task in the job loads it. The simplest way is the AzureCLI@2 task: - task: AzureCLI@2 inputs: azureSubscription: azure-prod # the WIF service connection scriptType: bash scriptLocation: inlineScript inlineScript: | terraform init && terraform apply -auto-approve env: ARM_USE_OIDC: "true" ARM_CLIENT_ID: $(AZURE_CLIENT_ID) ARM_TENANT_ID: $(AZURE_TENANT_ID) ARM_SUBSCRIPTION_ID: $(AZURE_SUBSCRIPTION_ID) ARM_ADO_PIPELINE_SERVICE_CONNECTION_ID: $(SERVICE_CONNECTION_ID) SYSTEM_ACCESSTOKEN: $(System.AccessToken) SYSTEM_OIDCREQUESTURI: $(System.OidcRequestUri) For teams converting dozens of legacy connections, the Azure DevOps team published a PowerShell helper that walks every ARM service connection in a project and converts them in place. There's a 7-day rollback window on each connection, which makes the migration genuinely low-risk. Don't forget the state file The Terraform state is your real blast radius. With OIDC, it's almost free to lock it down too. The same UAMI can read and write blob data without the storage account key: backend "azurerm" { resource_group_name = "rg-tfstate" storage_account_name = "sttfstateprodeastus" container_name = "platform-prod" key = "platform.tfstate" use_oidc = true use_azuread_auth = true } Grant the UAMI Storage Blob Data Contributor on the container (not the account), disable shared key access on the storage account, and you've removed the last secret in the pipeline. RBAC and break-glass Federation removes a credential, not a privilege. A few habits worth keeping: Scope role assignments to resource groups, not subscriptions. The whole point of federation is that scoping is now trivially easy. Use Role Based Access Control Administrator instead of User Access Administrator if your Terraform creates role assignments. It's a more recent, narrower role. Have a documented break-glass. If GitHub or ADO has a token-service incident, you still need a path to ship a hotfix. A single hardware-key-protected emergency app registration in a separate identity boundary works well, audited monthly. Monitor sign-ins. Every federated exchange shows up in Entra sign-in logs as a service principal sign-in. Pipe these to Sentinel and alert on anomalies like sign-ins outside expected hours, or from IPs outside GitHub's published ranges. The errors you will hit (and what they really mean) Symptom What it actually is AADSTS70021: No matching federated identity record found Case-sensitive mismatch in iss, sub, or aud. Almost always a trailing slash or a capitalised character AADSTS700016: Application not found in directory Wrong client ID or tenant. Not a federation problem 403 on a resource even though token exchange worked Federation is fine. Your RBAC isn't. Check the exact scope Unable to determine OIDC token (ADO) No task in the job loaded the service connection. Add an AzureCLI@2 step Works on main, fails on tags You pinned sub to a branch ref. Add a second federated credential for tags, or move to environment-based scoping Migrating without a maintenance window You almost never get to do this on a greenfield repo. The order that has worked for me on legacy estates: Create the new UAMI alongside the old service principal, with the same role assignments. Federate one canary pipeline. Verify it deploys equivalently. Cut over pipelines in waves, lowest-risk environment first. Once a full release cycle passes cleanly, disable the old SP's secret. Wait another cycle. Then delete the SP entirely. Add a CI gate that fails any new pipeline introducing ARM_CLIENT_SECRET. The old and new auth methods coexist on the same subscription throughout. There's no hard cutover and no maintenance window, just a steady drift toward zero secrets. Wrapping up If you do nothing else after reading this, do one thing: search your CI variable groups for ARM_CLIENT_SECRET. Every result is an outage or a breach waiting to happen. Federation is one of those rare changes that's both more secure and less work to operate. Once you've set it up, you stop thinking about credential rotation, secret expiry, and quarterly access reviews for service principals. The pipeline simply runs, and the audit trail is in Entra where it belongs. That's a good trade.
CHERIoT-Ibex: Closing the door on memory safety vulnerabilities with hardware-enforced protection
Memory safety vulnerabilities—largely arising from widely used programming languages such as C and C++—remain a leading cause of exploitable software defects across systems, from embedded devices to cloud-scale infrastructure. In simple terms, memory safety ensures that software accesses only the data it is intended to use; when this protection fails, attackers can exploit these defects to gain control of devices or disrupt critical services. Industry data shows that about 70 percent of the vulnerabilities Microsoft assigns as Common Vulnerabilities and Exposures (CVE) each year are memory safety issues, highlighting how frequently these software defects translate into real-world security risk (CISA – The Urgent Need for Memory Safety in Software Products). Hardware-enforced protections such as CHERIoT-Ibex can help eliminate these vulnerabilities at their source, reducing the likelihood that low-level software flaws can be exploited to compromise devices or disrupt workloads, supporting more trustworthy infrastructure by design. An open and certified foundation for memory-safe embedded systems CHERIoT-Ibex is the first open-source production-quality implementation of the CHERIoT instruction set architecture and among the first cores certified by the CHERI Alliance (CHERI Alliance – CHERIoT). CHERIoT is an extension of the CHERI (Capability Hardware Enhanced RISC Instructions) instruction set, with a focus on embedded and Internet of Things (IoT) applications. Ibex is an open‑source 32‑bit RISC‑V core developed by LowRISC. CHERIoT‑Ibex builds on Ibex by including CHERIoT capability extensions to provide hardware‑enforced memory safety and fine‑grained compartmentalization. It is the result of a close partnership between Microsoft Research and Azure Hardware Systems & Infrastructure, combining advanced research innovation with industry-leading silicon IP development expertise. In 2023, Microsoft open-sourced the CHERIoT Platform to bring hardware-enforced memory safety to embedded systems, including an instruction set architecture, toolchain, real-time operating system, and the RTL implementation of the CHERIoT-Ibex core. The CHERI Alliance certification recognizes its ability to provide spatial and temporal memory safety, fine-grained compartmentalization, and compatibility with the broader CHERI ecosystem. Critically, CHERIoT-Ibex achieves these security guarantees with power and area efficiency comparable to low-cost microcontrollers, demonstrating that security doesn’t have to come at a premium. Why memory safety remains a foundational security challenge Traditional embedded and microcontroller-class designs rely on software hardening and coarse-grained hardware protections that struggle to prevent attacks such as buffer overflows and use-after-free vulnerabilities, often adding complexity while still leaving gaps in protection. Consider a controller that runs privileged firmware responsible for device initialization, telemetry, and system health monitoring, while also hosting networking functionality exposed to external inputs. A memory-safe vulnerability in the networking stack could allow attackers to execute unauthorized code within the firmware environment, potentially affecting other critical services on the device. In tightly integrated systems, these failures can propagate beyond a single component, increasing overall risk. Constraining failures with hardware-enforced isolation CHERIoT-Ibex enables hardware-enforced isolation between these components, helping ensure that even if the networking stack is compromised, its ability to impact system initialization or telemetry functions remains constrained. By limiting the blast radius of software failures, CHERIoT-Ibex supports a system-level approach to security rather than relying on individual components to defend themselves in isolation. Advancing memory-safe infrastructure by design CHERIoT-Ibex’s certification by the CHERI Alliance marks an important milestone for open-source memory-safe solutions. It validates that strong security guarantees can coexist with efficiency and transparency, reflecting Microsoft’s broader silicon-to-systems strategy of embedding security into the foundational hardware infrastructure. Explore and engage with the open-source CHERIoT ecosystem by visiting the CHERIoT Platform and the CHERIoT-Ibex GitHub repository (microsoft/cheriot-ibex). The repositories enable developers and researchers to experiment with, contribute to, and build on memory-safe hardware and software foundations.
Deploying Azure Redis Enterprise with Geo-Replication Using Terraform
This post walks through a production‑proven pattern for running stateful services across Azure regions using Terraform. We’ll cover a primary–replica Redis architecture, regional isolation with Key Vault and networking, and a clean Terraform parameterization strategy that scales from development to production without duplication. Why Multi‑Region State Is Hard Running applications globally is easy when everything is stateless—if something fails, you redeploy. But stateful services tell a different story. Caches, message brokers, and data stores can’t be treated as disposable. They hold business‑critical data, and downtime or inconsistency quickly becomes customer‑visible. In real‑world systems, common requirements include: Low‑latency reads from multiple regions Automatic recovery when a region becomes unavailable Predictable data consistency Repeatable infrastructure from dev through production Manually configuring this per region doesn’t scale. Drift sets in. Failover is unclear. Backups get forgotten. That’s where Terraform + Azure Managed Redis geo‑replication shines. Github Link : https://github.com/vsakash5/Managed-redis.git High‑Level Architecture We use a primary–replica Redis Enterprise model: Primary Redis Single write endpoint Highly available inside its region Source of truth Replica Redis Read‑only Asynchronously synced from primary Can be promoted during disaster recovery Each region is fully isolated: Separate subnets Separate Key Vaults Private Endpoints only (no public exposure) This prevents shared failure domains and allows each region to operate independently if needed. The Terraform Design Principle Instead of maintaining separate Terraform stacks per region, the key idea is: One reusable module, one tfvars file per environment, multiple regions inside it. The module is written once. Regional differences are supplied via parameter suffixes like: _replica _secondary _tertiary This keeps logic centralized and environments consistent. Core Parameter Layers 1. Environment Identity (Shared) Terraform environment = "dev" # dev | staging | prod context_prefix = "app" Show more lines These values are reused everywhere—names, tags, and identifiers. 2. Primary Region Terraform location = "eastus2" resource_group_name = "rg-app-dev-primary" Show more lines 3. Replica Region Terraform location_replica = "uksouth" resource_group_name_replica = "rg-app-dev-replica" The symmetry is intentional. Terraform can now apply the same module twice without branching logic. Regional Isolation: Networking and Secrets Why isolation matters Geo‑replication copies data, not dependencies. If both Redis instances depend on: the same subnet the same Key Vault then a failure in one region can cascade into the other. Networking (One Subnet per Region) Benefits: Independent NSGs Independent routing Independent capacity planning Key Vault (One per Region) Why this matters: Redis credentials are not replicated Each region stores its own secrets A Key Vault outage doesn’t take both regions down Redis Configuration Primary Redis (Writes Enabled) The geo‑replication group name must match. That’s the logical binding Azure uses to link instances. Private Endpoint‑Only Access No Redis instance is exposed publicly. Each region uses: A private endpoint A workload subnet Internal DNS resolution This means: No public IPs No inbound attack surface Traffic stays on the Azure backbone Linking Primary and Replica Terraform explicitly defines the relationship: Terraform managed_redis_geo_replication_config = { primary_to_replica = { primary_redis_key = "primary" replica_keys = ["replica"] } } Terraform ensures: Primary is created first Replica is deployed second Geo‑replication is established last Environment Scaling: Dev → Staging → Prod The infrastructure pattern never changes. Only values do. Environment Group Name Dev dev-grp Staging stg-grp Prod prod-grp This is how you avoid “snowflake” environments. Disaster Recovery Strategy If the primary region fails: Applications fail over to the replica read endpoint Terraform configuration is updated to: Remove geo‑replication Promote replica config to primary Traffic is fully restored Once the original region recovers, roles can be re‑established cleanly. No click‑ops. No guesswork. Key Lessons Learned 1. Naming is Infrastructure Predictable names enable automation, discovery, and auditing. 2. Key Vault Isolation Beats Availability A shared Key Vault is a shared outage. 3. Parameterization Beats Copy‑Paste Fix once → benefit everywhere. 4. Geo‑Replication Is a Contract Matching replication group names is non‑negotiable. 5. The tfvars File Is the Source of Truth If it’s not in Terraform, it’s not real. Final Thoughts Running stateful services in multiple regions doesn’t require magic— it requires discipline: Isolate aggressively Parameterize consistently Automate everything Test failure often With this approach, adding a new region becomes configuration—not redesign. That’s how infrastructure scales.
How AI Agents Are Turning Threat Intelligence Into Validated Detections
The promise of AI-assisted cybersecurity has long been hampered by a fundamental measurement problem: how do organizations validate whether an AI agent can actually perform the complex, multi-step work that security analysts do every day? Traditional benchmarks test whether models can recall MITRE ATT&CK techniques or classify threat actor tactics, but they miss the harder question—can an agent translate raw threat intelligence into production-ready detection rules that find real attacks?microsoft Microsoft Research has addressed this gap with CTI-REALM (Cyber Threat Intelligence Real World Evaluation and LLM Benchmarking), an open-source benchmark that evaluates AI agents on end-to-end detection engineering workflows. Released in March 2026, CTI-REALM measures whether agents can read threat intelligence reports, explore telemetry schemas, iteratively refine KQL queries, and produce validated Sigma rules and KQL detection logic—exactly the workflow security analysts follow when building detections for platforms like Microsoft Sentinel.microsoft Why Traditional Benchmarks Fall Short Existing cybersecurity AI benchmarks primarily test parametric knowledge—can a model name the technique behind a log entry, or correctly label a tactic from a threat report? While useful, these assessments evaluate isolated skills rather than the operational capability security teams actually need: translating narrative threat intelligence into working detection logic that identifies attacks in production environments.microsoft CTI-REALM fills this gap by measuring three critical dimensions that earlier benchmarks overlook:microsoft Operationalization over recall: Agents must produce working Sigma rules and KQL queries validated against real attack telemetry, not just answer multiple-choice questions about threat actors. Complete workflow evaluation: The benchmark scores intermediate decision quality—CTI report selection, MITRE technique mapping, data source identification, and iterative query refinement—not just final output. Realistic tooling: Agents use the same tools security analysts rely on: CTI repositories, schema explorers, Kusto query engines, and MITRE ATT&CK databases. This granular, checkpoint-based scoring reveals precisely where AI agents struggle in the detection pipeline, helping security leaders understand whether performance gaps stem from comprehension failures, query construction issues, or detection specificity problems.microsoft The Benchmark: Real Threat Intelligence, Real Azure Environments Microsoft curated 37 CTI reports from public sources including Microsoft Security, Datadog Security Labs, Palo Alto Networks, and Splunk, selecting scenarios that could be faithfully simulated in sandboxed environments with telemetry suitable for detection development.microsoft The benchmark spans three Azure-relevant platforms: Linux endpoints: Traditional host-based detection scenarios Azure Kubernetes Service (AKS): Container and orchestration layer attacks Azure cloud infrastructure: Multi-source, APT-style attack chains requiring correlation across identity, resource, and network logs Ground-truth scoring validates detection rules at every workflow stage, from technique identification through final KQL query accuracy.microsoft Key Findings: What Works, What Doesn't Microsoft evaluated multiple frontier AI models on CTI-REALM-50, a subset spanning all three platforms. The results reveal both promise and clear limitations:microsoft Performance drops sharply across platform complexity: Linux endpoint detections scored 0.585, AKS scenarios dropped to 0.517, and Azure cloud infrastructure plummeted to 0.282. This reflects the reality that multi-source correlation across identity logs, Azure Activity, and resource-specific telemetry remains exceptionally difficult for AI agents—precisely the scenario SOC teams working in Microsoft Sentinel face when investigating sophisticated, multi-stage cloud attacks.microsoft More reasoning isn't always better: Within model families, medium reasoning configurations consistently outperformed high reasoning modes, suggesting that overthinking hurts performance in tool-rich, iterative agentic environments.microsoft Structured guidance closes performance gaps: Providing smaller models with human-authored workflow guidance improved threat technique identification and closed approximately one-third of the performance gap to much larger models.microsoft What This Means for Azure Security Operations For security architects and SOC teams working with Microsoft Sentinel, CTI-REALM's findings have immediate practical implications: Traditional Detection Engineering AI-Assisted Detection Engineering Analyst reads threat report manually AI agent parses CTI report and extracts techniques Analyst identifies relevant MITRE techniques Agent maps techniques to data sources automatically Analyst explores schema, writes KQL queries Agent iterates on KQL queries using schema tools Analyst validates detection against test data Agent generates Sigma rule + KQL validated against telemetry Process takes hours to days per report Process completes in minutes with human validation The benchmark demonstrates that AI agents can meaningfully accelerate detection development, particularly for Linux and AKS scenarios where success rates exceed 50%. However, the 28% success rate for Azure cloud infrastructure detections underscores a critical reality: human expertise remains essential for validating complex, multi-source detections before operational deployment.microsoft+1 Security teams should view AI agents as analyst augmentation tools rather than replacements. The checkpoint-based scoring in CTI-REALM helps organizations identify where human review is most critical—typically in cloud correlation logic, detection specificity tuning, and false positive reduction. Responsible Adoption: Human-in-the-Loop Remains Non-Negotiable Microsoft's research reinforces that AI-generated detection rules require validation before production use. Organizations adopting AI-assisted detection workflows should implement structured governance:microsoft Validate AI-generated KQL queries against test datasets before enabling in Sentinel analytics rules Require peer review for detections targeting cloud infrastructure, where AI performance is weakest Benchmark models using CTI-REALM before considering downstream operational use Maintain detection metadata tracking whether rules originated from AI or human analysts to support incident response context The benchmark's open-source availability on the Inspect AI repository enables security teams to test models against their own operational requirements before adoption.microsoft The Path Forward CTI-REALM represents a foundational shift in how the security industry evaluates AI capabilities—moving from knowledge recall to operational competence. For Azure practitioners, this matters because the benchmark's platforms (Linux, AKS, Azure cloud) and output formats (Sigma rules, KQL queries) directly mirror working with Microsoft Sentinel's analytics engine.microsoft As Microsoft continues integrating AI capabilities into Security Copilot and the broader unified SIEM+XDR vision, benchmarks like CTI-REALM provide the measurement framework security leaders need to adopt AI responsibly—understanding both capabilities and limitations before operationalizing agent-assisted workflows. The benchmark is freely available to model developers and security teams. Organizations interested in contributing, benchmarking, or exploring partnership opportunities can access the repository and contact Microsoft Research at msecaimrbenchmarking@microsoft.com.microsoft About the Research: CTI-REALM was developed by Microsoft Research and announced March 20, 2026. The full technical paper is available at CTI-REALM: A new benchmark for end-to-end detection rule generation with AI agents | Microsoft Security Blog
Entra ID Login via Azure Bastion Fails After VM Recreation
However, you may encounter a confusing scenario where: An Entra ID user attempts to sign in to a Windows VM through Azure Bastion The connection appears to succeed in the backend logs The session is disconnected within a second Bastion returns a generic sign-in error to the user At first glance, everything looks correctly configured. Terraform applies cleanly, permissions are in place, and Bastion access is allowed. This blog walks through a real-world troubleshooting journey that exposes a non-obvious Entra ID device registration issue, explains the root cause, and provides a clean resolution. Scenario We manage Azure infrastructure using Terraform, with Entra ID login enabled via the AADLoginForWindows VM extension. Azure Bastion is used to provide secure, inbound‑port‑free access to Windows VMs. After deleting and recreating a Windows VM with the same hostname, Entra ID login through Bastion started failing. Traditional local admin login worked, but Entra ID–based access did not. Key Terraform Configuration The VM was deployed with Entra ID login enabled using Infrastructure as Code: AADLoginForWindows extension Role assignments: Virtual Machine Administrator Login or Virtual Machine User Login Bastion configured for Entra ID authentication From an IaC perspective, nothing was misconfigured. Symptoms Observed The issue manifested in multiple subtle ways: Bastion login using Entra ID fails with a generic error message Backend logs show authentication success Session disconnects immediately after connection establishment Running the following on the VM: dsregcmd /status shows: IsDeviceJoined: NO This explains why Entra ID authentication succeeds initially but instantly fails during session creation. Root Cause Explained When a Windows VM is joined to Microsoft Entra ID, a device object is created in Entra ID, keyed to the VM’s Windows hostname. If the VM is later deleted without removing the device object, and a new VM is recreated using the same hostname, the Entra ID join process fails silently due to a hostname collision. Key points: The old Entra ID device object still exists The new VM cannot complete Entra ID registration Bastion authentication succeeds, but authorization fails immediately The VM therefore disconnects the session This is why backend logs look “successful” even though the user experience is not. Resolution Steps Identify the Stale Device Object Navigate to: Azure Portal → Microsoft Entra ID → Devices → All devices Search for the VM hostname (for example, VM01) Open the device object and note the Object ID Confirm it matches the Object ID referenced in the extension logs. Delete the Stale Device This does not delete the VM or any Azure resources. Only the Entra ID registration is removed. You can delete the device using either method: Azure Portal Select the device Choose Delete Azure CLI az ad device delete --id <ObjectId> Retry the Entra ID Join Restart the VM or restart the AADLoginForWindows extension Wait for the extension to re‑execute Verify the join status: dsregcmd /status Expected output: IsDeviceJoined: YES Retry Bastion login using Entra ID The session should now remain connected and function normally Why This Issue Is Easy to Miss Azure VM deletion does not automatically clean up Entra ID device objects Terraform recreations with identical hostnames are common in non‑prod environments Bastion logs are not explicit about device join failures Authentication succeeds, but authorization fails post‑connection Key Takeaways Deleting a device from Microsoft Entra ID does not impact the VM itself Always check for stale Entra ID device objects when reusing hostnames dsregcmd /status is the fastest way to validate join state AADLoginForWindows extension logs are critical for root cause analysis Bastion disconnections immediately after login often indicate identity‑level issues, not networking problems References Troubleshoot Microsoft Entra ID device registration issues Manage and delete stale Entra ID devices AADLoginForWindows extension documentationEnterprise UAMI Design in Azure: Trust Boundaries and Blast Radius
As organizations move toward secretless authentication models in Azure, Managed Identity has become the preferred approach for enabling secure communication between services. User Assigned Managed Identity (UAMI) in particular offers flexibility that allows identity reuse across multiple compute resources such as: Azure App Service Azure Function Apps Virtual Machines Azure Kubernetes Service While this flexibility is beneficial from an operational perspective, it also introduces architectural considerations that are often overlooked during initial implementation. In enterprise environments where shared infrastructure patterns are common, the way UAMI is designed and assigned can directly influence the effective trust boundary of the deployment. Understanding Identity Scope in Azure Unlike System Assigned Managed Identity, a UAMI exists independently of the compute resource lifecycle and can be attached to multiple services across: Resource Groups Subscriptions Environments This capability allows a single identity to be reused across development, testing, or production services when required. However, identity reuse across multiple logical environments can expand the operational trust boundary of that identity. Any permission granted to the identity is implicitly inherited by all services to which the identity is attached. From an architectural standpoint, this creates a shared authentication surface across isolated deployment environments. High-Level Architecture: Shared Identity Pattern In many enterprise Azure deployments, it is common to observe patterns where: A single UAMI is assigned to multiple App Services The same identity is reused across automation workloads Identities are provisioned centrally and attached dynamically While this simplifies management and avoids identity sprawl, it may also introduce unintended privilege propagation across services. For example: In this architecture: Multiple App Services across environments share the same managed identity. Each compute instance requests an access token from Microsoft Entra ID using Azure Instance Metadata Service (IMDS). The issued token is then used to authenticate against downstream platform services such as: Azure SQL Database Azure Key Vault Azure Storage Because RBAC permissions are assigned to the shared identity rather than the compute instance itself, the effective authentication boundary becomes identity‑scoped instead of environment‑scoped. As a result, any compromised lower‑tier environment such as DEV may obtain an access token capable of accessing production‑level resources if those permissions are assigned to the shared identity. This expands the operational trust boundary across environments and increases the potential blast radius in the event of identity misuse. Blast Radius Considerations Blast radius refers to the potential impact scope of a security or configuration compromise. When a shared UAMI is used across multiple services, the following conditions may increase the blast radius: Design Pattern Potential Risk Single UAMI across environments Cross‑environment access Subscription‑wide RBAC assignment Broad privilege scope Identity used for automation pipelines Lateral movement Shared identity across teams Ownership ambiguity Because Managed Identity authentication relies on Azure Instance Metadata Service (IMDS), any compromised compute resource with access to IMDS may request an access token using the attached identity. This token can then be used to authenticate with downstream Azure services for which the identity has RBAC permissions. Enterprise Design Recommendations: Environment‑Isolated Identity Model To reduce identity blast radius in enterprise deployments, the following architectural principles may be considered: Environment‑Scoped Identity Provision separate UAMIs per environment: UAMI‑DEV UAMI‑UAT UAMI‑PROD Avoid reusing the same identity across isolated lifecycle stages. Resource‑Level RBAC Assignment Prefer assigning RBAC permissions at: Resource Resource Group instead of Subscription scope wherever feasible. Identity Ownership Model Ensure ownership clarity for identities assigned across shared workloads. Identity lifecycle should be aligned with: Application ownership Service ownership Deployment boundary Least Privilege Assignment Assign roles such as: Key Vault Secrets User Storage Blob Data Reader instead of broader roles such as: Contributor Owner Recommended High‑Level Architecture In this architecture: Each App Service instance is attached to an environment‑specific managed identity. RBAC assignments are scoped at the resource or resource group level. Microsoft Entra ID issues tokens independently for each identity. Trust boundaries remain aligned with deployment environments. A compromised DEV compute instance can only obtain a token associated with UAMI‑DEV. Because UAMI‑DEV does not have RBAC permissions for production resources, lateral access to PROD dependencies is prevented. Blast Radius Containment: This design significantly reduces the potential blast radius by ensuring that: Identity compromise remains environment‑scoped. Token issuance does not grant unintended cross‑environment privileges. RBAC permissions align with application ownership boundaries. Authentication trust boundaries match deployment lifecycle boundaries. Conclusion User Assigned Managed Identity offers significant advantages for secretless authentication in Azure environments. However, architectural considerations related to identity reuse and scope of assignment must be evaluated carefully in enterprise deployments. By aligning identity design with trust boundaries and minimizing the blast radius through scoped RBAC and environment isolation, organizations can implement Managed Identity in a way that balances operational efficiency with security governance.Private DNS and Hub–Spoke Networking for Enterprise AI Workloads on Azure
Introduction As organizations deploy enterprise AI platforms on Azure, security requirements increasingly drive the adoption of private-first architectures. Private networking only Centralized firewalls or NVAs Hub–and–spoke virtual network architectures Private Endpoints for all PaaS services While these patterns are well understood individually, their interaction often exposes hidden failure modes, particularly around DNS and name resolution. During a recent production deployment of a private, enterprise-grade AI workload on Azure, several issues surfaced that initially appeared to be platform or service instability. Closer analysis revealed the real cause: gaps in network and DNS design. This post shares a real-world technical walkthrough of the problem, root causes, resolution steps, and key lessons that now form a reusable blueprint for running AI workloads reliably in private Azure environments. Problem Statement The platform was deployed with the following characteristics: Hub and spoke network topology Custom DNS servers running in the hub Firewall / NVA enforcing strict egress controls AI, data, and platform services exposed through Private Endpoints Azure Container Apps using internal load balancer mode Centralized monitoring, secrets, and identity services Despite successful infrastructure deployment, the environment exhibited non-deterministic production issues, including: Container Apps intermittently failing to start or scale AI platform endpoints becoming unreachable from workload subnets Authentication and secret access failures DNS resolution working in some environments but failing in others Terraform deployments stalling or failing unexpectedly Because the symptoms varied across subnets and environments, root cause identification was initially non-trivial. Root Cause Analysis After end-to-end isolation, the issue was not AI services, authentication, or application logic. The core problem was DNS resolution in a private Azure environment. 1. Custom DNS servers were not Azure-aware The hub DNS servers correctly resolved: Corporate domains On‑premises records However, they could not resolve Azure platform names or Private Endpoint FQDNs by default. Azure relies on an internal recursive resolver (168.63.129.16) that must be explicitly integrated when using custom DNS. 2. Missing conditional forwarders for private DNS zones Many Azure services depend on service-specific private DNS zones, such as: privatelink.cognitiveservices.azure.com privatelink.openai.azure.com privatelink.vaultcore.azure.net privatelink.search.windows.net privatelink.blob.core.windows.net Without conditional forwarders pointing to Azure’s internal DNS, queries either: Failed silently, or Resolved to public endpoints that were blocked by firewall rules 3. Container Apps internal DNS requirements were overlooked When Azure Container Apps are deployed with: internal_load_balancer_enabled = true Azure does not automatically create supporting DNS records. The environment generates: A default domain .internal subdomains for internal FQDNs Without explicitly creating: A private DNS zone matching the default domain *, @, and *.internal wildcard records internal service-to-service communication fails. 4. Private DNS zones were not consistently linked Even when DNS zones existed, they were: Spread across multiple subscriptions Linked to some VNets but not others Missing links to DNS server VNets or shared services VNets As a result, name resolution succeeded in one subnet and failed in another, depending on the lookup path. Resolution No application changes were required. Stability was achieved entirely through architectural corrections. ✅ Step 1: Make custom DNS Azure-aware On all custom DNS servers (or NVAs acting as DNS proxies): Configure conditional forwarders for all Azure private DNS zones Forward those queries to: 168.63.129.16 This IP is Azure’s internal recursive resolver and is mandatory for Private Endpoint resolution. ✅ Step 2: Centralize and link private DNS zones A centralized private DNS model was adopted: All private DNS zones hosted in a shared subscription Linked to: Hub VNet All spoke VNets DNS server VNet Any operational or virtual desktop VNets This ensured consistent resolution regardless of workload location. ✅ Step 3: Explicitly handle Container Apps DNS For Container Apps using internal ingress: Create a private DNS zone matching the environment’s default domain Add: * wildcard record @ apex record *.internal wildcard record Point all records to the Container Apps Environment static IP Add a conditional forwarder for the default domain if using custom DNS This step alone resolved multiple internal connectivity issues. ✅ Step 4: Align routing, NSGs, and service tags Firewall, NSG, and route table rules were aligned to: Allow DNS traffic (TCP/UDP 53) Allow Azure service tags such as: AzureCloud CognitiveServices AzureActiveDirectory Storage AzureMonitor Ensure certain subnets (e.g., Container Apps, Application Gateway) retained direct internet access where required by Azure platform services Key Learnings 1. DNS is a Tier‑0 dependency for AI platforms Many AI “service issues” are DNS failures in disguise. DNS must be treated as foundational platform infrastructure. 2. Private Endpoints require Azure DNS integration If you use: Custom DNS ✅ Private Endpoints ✅ Then forwarding to 168.63.129.16 is non‑negotiable. 3. Container Apps internal ingress has hidden DNS requirements Internal Container Apps environments will not function correctly without manually created DNS zones and .internal records. 4. Centralized DNS prevents environment drift Decentralized or subscription-local DNS zones lead to fragile, inconsistent environments. Centralization improves reliability and operability. 5. Validate networking first, then the platform Before escalating issues to service teams: Validate DNS resolution Verify routing Check Private Endpoint connectivity In many cases, the perceived “platform issue” disappears. Quick Production Validation Checklist Before go-live, always validate: ✅ Private FQDNs resolve to private IPs from all required VNets ✅ UDR/NSG rules allow required Azure service traffic ✅ Managed identities can access all dependent resources ✅ AI portal user workflows succeed (evaluations, agents, etc.) ✅ terraform plan shows only intended changes Conclusion Running private, enterprise-grade AI workloads on Azure is absolutely achievable—but it requires intentional DNS and networking design. By: Making custom DNS Azure-aware Centralizing private DNS zones Explicitly handling Container Apps DNS Aligning routing and firewall rules an unstable environment was transformed into a repeatable, production-ready platform pattern. If you are building AI solutions on Azure with Private Endpoints and hub–spoke networking, getting DNS right early will save weeks of troubleshooting later.Guardrails for Generative AI: Securing Developer Workflows
Generative AI is revolutionizing software development that accelerates delivery but introduces compliance and security risks if unchecked. Tools like GitHub Copilot empower developers to write code faster, automate repetitive tasks, and even generate tests and documentation. But speed without safeguards introduces risk. Unchecked AI‑assisted development can lead to security vulnerabilities, data leakage, compliance violations, and ethical concerns. In regulated or enterprise environments, this risk multiplies rapidly as AI scales across teams. The solution? Guardrails—a structured approach to ensure AI-assisted development remains secure, responsible, and enterprise-ready. In this blog, we explore how to embed responsible AI guardrails directly into developer workflows using: Azure AI Content Safety GitHub Copilot enterprise controls Copilot Studio governance Azure AI Foundry CI/CD and ALM integration The goal: maximize developer productivity without compromising trust, security, or compliance. Key Points: Why Guardrails Matter: AI-generated code may include insecure patterns or violate organizational policies. Azure AI Content Safety: Provides APIs to detect harmful or sensitive content in prompts and outputs, ensuring compliance with ethical and legal standards. Copilot Studio Governance: Enables environment strategies, Data Loss Prevention (DLP), and role-based access to control how AI agents interact with enterprise data. Azure AI Foundry: Acts as the control plane for Generative AI turning Responsible AI from policy into operational reality. Integration with GitHub Workflows: Guardrails can be enforced in IDE, Copilot Chat, and CI/CD pipelines using GitHub Actions for automated checks. Outcome: Developers maintain productivity while ensuring secure, compliant, and auditable AI-assisted development. Why Guardrails Are Non-Negotiable AI‑generated code and prompts can unintentionally introduce: Security flaws — injection vulnerabilities, unsafe defaults, insecure patterns Compliance risks — exposure of PII, secrets, or regulated data Policy violations — copyrighted content, restricted logic, or non‑compliant libraries Harmful or biased outputs — especially in user‑facing or regulated scenarios Without guardrails, organizations risk shipping insecure code, violating governance policies, and losing customer trust. Guardrails enable teams to move fast—without breaking trust. The Three Pillars of AI Guardrails Enterprise‑grade AI guardrails operate across three core layers of the developer experience. These pillars are centrally governed and enforced through Azure AI Foundry, which provides lifecycle, evaluation, and observability controls across all three. 1. GitHub Copilot Controls (Developer‑First Safety) GitHub Copilot goes beyond autocomplete and includes built‑in safety mechanisms designed for enterprise use: Duplicate Detection: Filters code that closely matches public repositories. Custom Instructions: Enhance coding standards via .github/copilot-instructions.md. Copilot Chat: Provides contextual help for debugging and secure coding practices. Pro Tip: Use Copilot Enterprise controls to enforce consistent policies across repositories and teams. 2. Azure AI Content Safety (Prompt & Output Protection) This service adds a critical protection layer across prompts and AI outputs: Prompt Injection Detection: Blocks malicious attempts to override instructions or manipulate model behaviour. Groundedness Checks: Ensures outputs align with trusted sources and expected context. Protected Material Detection: Flags copyrighted or sensitive content. Custom Categories: Tailor filters for industry-specific or regulatory requirements. Example: A financial services app can block outputs containing PII or regulatory violations using custom safety categories. 3. Copilot Studio Governance (Enterprise‑Scale Control) For organizations building custom copilots, governance is non‑negotiable. Copilot Studio enables: Data Loss Prevention (DLP): Prevent sensitive data leaks from flowing through risky connectors or channels. Role-Based Access (RBAC): Control who can create, test, approve, deploy and publish copilots. Environment Strategy: Separate dev, test, and production environments. Testing Kits: Validate prompts, responses, and behavior before production rollout. Why it matters: Governance ensures copilots scale safely across teams and geographies without compromising compliance. Azure AI Foundry: The Platform That Operationalizes the Three Pillars While the three pillars define where guardrails are applied, Azure AI Foundry defines how they are governed, evaluated, and enforced at scale. Azure AI Foundry acts as the control plane for Generative AI—turning Responsible AI from policy into operational reality. What Azure AI Foundry Adds Centralized Guardrail Enforcement: Define guardrails once and apply them consistently across: Models, Agents, Tool calls and Outputs. Guardrails specify: Risk types (PII, prompt injection, protected material) Intervention points (input, tool call, tool response, output) Enforcement actions (annotate or block) Built‑In Evaluation & Red‑Teaming: Azure AI Foundry embeds continuous evaluation into the GenAIOps lifecycle: Pre‑deployment testing for safety, groundedness, and task adherence Adversarial testing to detect jailbreaks and misuse Post‑deployment monitoring using built‑in and custom evaluators Guardrails are measured and validated, not assumed. Observability & Auditability: Foundry integrates with Azure Monitor and Application Insights to provide: Token usage and cost visibility Latency and error tracking Safety and quality signals Trace‑level debugging for agent actions Every interaction is logged, traceable, and auditable—supporting compliance reviews and incident investigations. Identity‑First Security for AI Agents: Each AI agent operates as a first‑class identity backed by Microsoft Entra ID: No secrets embedded in prompts or code Least‑privilege access via Azure RBAC Full auditability and revocation Policy‑Driven Platform Governance: Azure AI Foundry aligns with the Azure Cloud Adoption Framework, enabling: Azure Policy enforcement for approved models and regions Cost and quota controls Integration with Microsoft Purview for compliance tracking How to Implement Guardrails in Developer Workflows Shift-Left Security Embed guardrails directly into the IDE using GitHub Copilot and Azure AI Content Safety APIs—catch issues early, when they’re cheapest to fix. Automate Compliance in CI/CD Integrate automated checks into GitHub Actions to enforce policies at pull‑request and build stages. Monitor Continuously Use Azure AI Foundry and governance dashboards to track usage, violations, and policy drift. Educate Developers Conduct readiness sessions and share best practices so developers understand why guardrails exist—not just how they’re enforced. Implementing DLP Policies in Copilot Studio Access Power Platform Admin Center Navigate to Power Platform Admin Centre Ensure you have Tenant Admin or Environment Admin role Create a DLP Policy Go to Data Policies → New Policy. Define data groups: Business (trusted connectors) Non-business Blocked (e.g., HTTP, social channels) Configure Enforcement for Copilot Studio Enable DLP enforcement for copilots using PowerShell Set-PowerVirtualAgentsDlpEnforcement ` -TenantId <tenant-id> ` -Mode Enabled Modes: Disabled (default, no enforcement) SoftEnabled (blocks updates) Enabled (full enforcement) Apply Policy to Environments Choose scope: All environments, specific environments, or exclude certain environments. Block channels (e.g., Direct Line, Teams, Omnichannel) and connectors that pose risk. Validate & Monitor Use Microsoft Purview audit logs for compliance tracking. Configure user-friendly DLP error messages with admin contact and “Learn More” links for makers. Implementing ALM Workflows in Copilot Studio Environment Strategy Use Managed Environments for structured development. Separate Dev, Test, and Prod clearly. Assign roles for makers and approvers. Application Lifecycle Management (ALM) Configure solution-aware agents for packaging and deployment. Use Power Platform pipelines for automated movement across environments. Govern Publishing Require admin approval before publishing copilots to organizational catalog. Enforce role-based access and connector governance. Integrate Compliance Controls Apply Microsoft Purview sensitivity labels and enforce retention policies. Monitor telemetry and usage analytics for policy alignment. Key Takeaways Guardrails are essential for safe, compliant AI‑assisted development. Combine GitHub Copilot productivity with Azure AI Content Safety for robust protection. Govern agents and data using Copilot Studio. Azure AI Foundry operationalizes Responsible AI across the full GenAIOps lifecycle. Responsible AI is not a blocker—it’s an enabler of scale, trust, and long‑term innovation.🚀 Securing Enterprise AI: From Red Teaming to Risk Cards and Azure Guardrails
AI is no longer experimental—it’s deeply embedded into critical business workflows. From copilots to decision intelligence systems, organizations are rapidly adopting large language models (LLMs). But here’s the reality: AI is not just another application layer—it’s a new attack surface. 🧠 Why Traditional Security Thinking Fails for AI In traditional systems: You secure APIs You validate inputs You control access In AI systems: The input is language The behavior is probabilistic The attack surface is conversational 👉 Which means: You don’t just secure infrastructure—you must secure behavior 🔍 How AI Systems Actually Break (Red Teaming) To secure AI, we first need to understand how it fails. 👉 Red Teaming = intentionally trying to break your AI system using prompts 🧩 Common Attack Patterns 🪤 Jailbreaking “Ignore all previous instructions…” → Attempts to override system rules 🎭 Role Playing “You are a fictional villain…” → AI behaves differently under alternate identities 🔀 Prompt Injection Hidden instructions inside documents or inputs → Critical risk in RAG systems 🔁 Iterative Attacks Repeatedly refining prompts until the model breaks 💡 Key Insight AI attacks are not deterministic—they are creative, iterative, and human-driven 📊 From Attacks to Understanding Risk (Risk Cards) Knowing how AI breaks is only half the story. 👉 You need a structured way to define and communicate risk 🧠 What are Risk Cards? A Risk Card helps answer: What can go wrong? (Hazard) What is the impact? (Harm) How likely is it? (Risk) 🧪 Example: Prompt Injection Risk: External input overrides system behavior Harm: Data leakage, loss of control Affected: Organization, users Mitigation: Input sanitization + prompt isolation 🧪 Example: Hallucination Risk: Incorrect or fabricated output Harm: Wrong business decisions Mitigation: Grounding using trusted data (RAG) 💡 Critical Insight AI risk is not model-specific—it is context-dependent 🏢 Designing Secure AI Systems in Azure Now let’s translate all of this into real-world enterprise architecture 🔷 Secure AI Reference Architecture 🧱 Architecture Layers 1. User Layer Applications / APIs Azure Front Door + WAF 2. Security Layer (First Line of Defense) Azure AI Content Safety Input validation Prompt filtering 3. Orchestration Layer Azure Functions / AKS Prompt templates Context builders 4. Model Layer Azure OpenAI Locked system prompts 5. Grounding Layer (RAG) Azure AI Search Trusted enterprise data 6. Output Control Layer Response filtering Sensitive data masking 7. Monitoring & Governance Azure Monitor Defender for Cloud 🔐 Core Security Principles ❌ Never trust user input ✅ Validate both input and output ✅ Separate system and user instructions ✅ Ground responses in trusted data ✅ Monitor everything ⚠️ Real-World Risk Scenarios 🚨 Prompt Injection via Documents Malicious instructions hidden in uploaded files 👉 Mitigation: Document sanitization + prompt isolation 🚨 Data Leakage AI exposes sensitive or cross-user data 👉 Mitigation: RBAC + tenant isolation 🚨 Tool Misuse (AI Agents) AI triggers unintended real-world actions 👉 Mitigation: Approval workflows + least privilege 🚨 Gradual Jailbreak User bypasses safeguards over multiple interactions 👉 Mitigation: Session monitoring + context reset 📊 Operationalizing AI Security: Risk Register To move from theory to execution, organizations should maintain a Risk Register 🧠 Example Risk Impact Likelihood Score Prompt Injection 5 4 20 Hallucination 5 4 20 Bias 5 3 15 👉 This enables: Prioritization Governance Executive visibility 🚀 Bringing It All Together Let’s simplify everything: 👉 Red Teaming shows how AI breaks 👉 Risk Cards define what can go wrong 👉 Architecture determines whether you are secure 💡 One Line for Leaders “Deploying AI without guardrails is like exposing an API to the internet—understanding attack patterns and implementing layered defenses is essential for safe enterprise adoption.” 🙌 Final Thought AI is powerful—but power without control is risk The organizations that succeed will not just build AI systems… They will build: Secure, governed, and resilient AI platformsDefending the cloud: Azure neutralized a record-breaking 15 Tbps DDoS attack
On October 24, 2025, Azure DDOS Protection automatically detected and mitigated a multi-vector DDoS attack measuring 15.72 Tbps and nearly 3.64 billion packets per second (pps). This was the largest DDoS attack ever observed in the cloud and it targeted a single endpoint in Australia. By utilizing Azure’s globally distributed DDoS Protection infrastructure and continuous detection capabilities, mitigation measures were initiated. Malicious traffic was effectively filtered and redirected, maintaining uninterrupted service availability for customer workloads. The attack originated from Aisuru botnet. Aisuru is a Turbo Mirai-class IoT botnet that frequently causes record-breaking DDoS attacks by exploiting compromised home routers and cameras, mainly in residential ISPs in the United States and other countries. The attack involved extremely high-rate UDP floods targeting a specific public IP address, launched from over 500,000 source IPs across various regions. These sudden UDP bursts had minimal source spoofing and used random source ports, which helped simplify traceback and facilitated provider enforcement. Attackers are scaling with the internet itself. As fiber-to-the-home speeds rise and IoT devices get more powerful, the baseline for attack size keeps climbing. As we approach the upcoming holiday season, it is essential to confirm that all internet-facing applications and workloads are adequately protected against DDOS attacks. Additionally, do not wait for an actual attack to assess your defensive capabilities or operational readiness—conduct regular simulations to identify and address potential issues proactively. Learn more about Azure DDOS Protection at Azure DDoS Protection Overview | Microsoft Learn
