Pentesting JumpCloud vs Active Directory (AD) vs Azure ADDS

Insights

1. Architecture and Deployment

• JumpCloud operates as a SaaS model with no domain controllers or local servers to manage.

• Traditional AD is an on-premises system requiring domain controllers and infrastructure management.

• Azure AD DS provides traditional AD features as a managed Azure service, eliminating the need to administer domain controllers but retaining AD protocols.

2. User Management and Authentication

• JumpCloud: Web and API-driven user management with SSO and MFA.

• AD: Uses Group Policy and local policies with Kerberos/NTLM authentication.

• Azure AD DS: Supports traditional AD protocols and group policies within a cloud-managed environment.

3. Privilege Escalation

• JumpCloud: Focus on API role abuse and token mismanagement.

• AD: Exploitation of Kerberos tickets, group membership, and domain trusts.

• Azure AD DS: Combination of traditional AD attack vectors plus Azure role misconfigurations.

4. Integration and Attack Surface

• JumpCloud: APIs and multi-cloud service integrations.

• AD: Network services, trusts, Group Policies.

• Azure AD DS: Cloud management APIs plus classic AD services on Azure.

5. Security Controls and Compliance

• JumpCloud: Vendor-managed cloud security and compliance.

• AD: Traditional network hardening and internal compliance.

• Azure AD DS: Azure’s cloud security plus organizational policies and shared responsibilities.

6. Logging, Monitoring, and Incident Response

• JumpCloud: Centralized logs through vendor portal; managed incident response.

• AD: Extensive event logs with SIEM integration; in-house IR.

• Azure AD DS: Combines Azure Monitor and Sentinel with traditional AD logs; includes shared incident response model.

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Aspect	JumpCloud	Active Directory (AD)	Azure ADDS (Cloud-native AD)
Architecture	Cloud-based SaaS, no domain controllers	On-premises infrastructure with domain controllers	Managed cloud domain service offering traditional AD protocols
Deployment	Fully managed by JumpCloud	Self-hosted, requires on-premises infrastructure	Fully managed by Microsoft in Azure, no domain controllers to deploy
User Management	Centralized via cloud portal and APIs	Managed via Group Policy and local policies	Managed using Azure portal, supports GPOs and LDAP
Authentication	SSO, MFA, password policies via cloud platform	Kerberos, NTLM, LDAP	Kerberos, NTLM, LDAP authentication as in traditional AD
Privilege Escalation	Misuse of API tokens and user roles	Ticket-based attacks, group membership abuse	Similar to traditional AD exploits + Azure role/configuration risks
Integration	Multi-cloud integrations (AWS, G Suite, etc.)	On-premises and cloud system integrations	Deep Microsoft ecosystem integration, hybrid/on-prem connectivity
Attack Surface	API endpoints, integrations	Network services, GPOs, domain trusts	Cloud management APIs + traditional AD protocols exposed
Security Controls	Cloud provider-managed security practices	Firewalls, network segmentation, on-prem controls	Azure cloud security controls + traditional AD policies
Logging & Monitoring	Centralized JumpCloud logs	Event logs, SIEM integration	Azure Monitor, Azure Sentinel, and traditional AD event logs
User Roles/Permissions	Role-Based Access Control (RBAC)	Group-based roles and GPOs	Combination of Azure RBAC and AD group-based roles
Data Storage	Cloud-hosted user and device data	Stored on local domain controllers and servers	Cloud-hosted user and domain data managed by Azure
Network Security	Relies on cloud provider's network security	Firewalls, VPNs, network segmentation	Secured via Azure infrastructure with network controls
Compliance	Built-in cloud compliance (GDPR, HIPAA, etc.)	Dependent on organizational policies	Azure compliance certifications plus organizational controls
Incident Response	Managed by vendor	Handled by internal IR teams	Shared responsibility: Microsoft provides infra-level security, customer manages access and config
Vulnerability Management	Focus on API/cloud vulnerabilities	Focus on network/system vulnerabilities	Vulnerabilities in cloud platform, APIs + traditional AD

Summary

Pentesting JumpCloud, traditional Active Directory, and Azure ADDS requires tailored approaches grounded in the architecture and operation of each platform:

• JumpCloud challenges focus on cloud-native API security, RBAC, and third-party integrations, with the cloud provider managing most infrastructure security.

• Traditional AD pentests revolve around network-level controls, protocol abuses such as Kerberos and NTLM exploitation, and domain trust attacks within an on-premises setting.

• Azure AD DS offers a hybrid model whereby classic AD attacks are blended with cloud-specific vulnerabilities involving Azure RBAC, management APIs, and identity federation, requiring pentesters to combine traditional AD knowledge with cloud security expertise.