Open-Source Security · silverhack

monkey365

Monkey365 is an open-source PowerShell module that audits Microsoft 365, Azure, and Entra ID for security misconfigurations and compliance gaps. It bundles all dependencies, requires no external Microsoft tools, and generates HTML, JSON, and CSV reports against CIS benchmarks.

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Source: GitHub — github.com/silverhack/monkey365

1.3k

GitHub stars

139

Forks

PowerShell

Primary language

Apache-2.0

License (OSI-approved)

Key facts

Objective fields from the source. Values we can't verify are shown as “Unknown” rather than guessed.

Field	Value
Repository	silverhack/monkey365
Owner	silverhack
Primary language	PowerShell
License	Apache-2.0 — OSI-approved
Stars	1.3k
Forks	139
Open issues	15
Latest release	v0.98 (2026-05-18)
Last updated	2026-05-18
Source	https://github.com/silverhack/monkey365

What monkey365 is

Self-contained PowerShell security assessment framework with collector-based architecture supporting multiple authentication methods (interactive, MFA, service principals, certificates, tokens). Covers Exchange Online, SharePoint, Teams, Purview, and Fabric with built-in CIS benchmark checks and multi-cloud environment support (Public, China, Government).

Quickstart

Get the monkey365 source

Clone the repository and explore it locally.

terminalbash

1git clone https://github.com/silverhack/monkey365.git2cd monkey3653# follow the project's README for install & configuration

Need it deployed, integrated, or customized instead? DEV.co ships production installs.

Best use cases

Security posture assessments for Microsoft 365 tenants

Organizations conducting routine or incident-driven security reviews of Microsoft 365, Azure, and Entra ID can deploy Monkey365 to identify configuration weaknesses, access control gaps, and deviations from CIS benchmarks without learning multiple Microsoft APIs or management portals.

Automated compliance and hardening validation

Security teams can integrate Monkey365 into CI/CD pipelines or scheduled automation to continuously validate tenant hardening against CIS standards, generate structured reports for compliance audits, and track security posture over time.

Consultant and MSP rapid assessment workflows

External security consultants and managed service providers can quickly assess customer tenants using a single bundled module with zero external dependency overhead, then deliver findings via HTML, JSON, or CSV for reporting and remediation planning.

Implementation considerations

Requires PowerShell execution policy configured appropriately; test in non-production first, especially for automation scenarios.
Authentication must be configured before assessment—choose method (interactive, service principal, certificate) based on deployment context (workstation, CI/CD, automation account).
Assessments require appropriate API permissions on the target tenant (scope varies by workload: Exchange, SharePoint, Teams, Entra ID); verify service principal or user account has necessary roles.
Report output format (HTML, JSON, CSV) should align with downstream compliance/SOAR tooling; validate export structure before production automation.
Bundled dependencies simplify deployment but may lag behind latest Microsoft API changes; plan for periodic module updates to maintain assessment accuracy.

When to avoid it — and what to weigh

Require real-time threat detection or monitoring — Monkey365 is a point-in-time assessment tool, not a SIEM, EDR, or continuous monitoring solution. It does not provide alert ingestion, forensic analysis, or live threat hunting.
Need support for non-Microsoft cloud environments — Monkey365 is Microsoft-cloud specific (Azure, Microsoft 365, Entra ID). AWS, GCP, or on-premises environments are out of scope.
Expect vendor support or SLA guarantees — This is a community open-source project. No commercial support, SLAs, or guaranteed response times are offered through GitHub.
Require graphical UI or no PowerShell knowledge — Monkey365 is PowerShell-based and requires command-line comfort. No web dashboard or point-and-click interface is provided.

License & commercial use

Licensed under Apache License 2.0 (Apache-2.0), a permissive OSI-approved license allowing use, modification, and distribution for any purpose.

Apache 2.0 permits commercial use, modification, and redistribution. However, this is a community open-source project with no vendor backing, commercial support, or warranty. Organizations using it in production should allocate internal resources for monitoring, testing, and maintenance. Review license terms in detail; consult legal counsel if integrating into commercial products or services.

DEV.co evaluation signals

Editorial assessment — not user reviews. Directional, with an explicit confidence level.

Signal	Assessment
Maintenance	Active
Documentation	Strong
License clarity	Clear
Deployment complexity	Low
DEV.co fit	Strong
Assessment confidence	High

Security considerations

Monkey365 runs in the context of the authenticated principal and exercises granted API permissions. Access controls depend on the service principal, user account, or token used. Secure credential handling in automation (use managed identities, certificate stores, secure vaults, not hardcoded secrets). Output reports may contain sensitive configuration data; restrict access. No explicit code audit, vulnerability scanning results, or security certifications are provided in the data. Users should review code and threat model integration before production deployment in sensitive environments.

Alternatives to consider

Microsoft Defender for Cloud

Microsoft's native Azure and multi-cloud security posture assessment service with real-time monitoring, threat detection, and compliance frameworks. Requires licensing; vendor-supported SLA.

ScubaScan (CISA)

Government-backed PowerShell security scanner for Microsoft 365 with CISA Secure Configuration Baseline checks. Community project; no commercial support.

CloudMapper (Duo Security)

Multi-cloud security posture assessment tool supporting Azure, AWS, GCP. Commercial offering with vendor support; requires licensing.

Software development agency

Build on monkey365 with DEV.co software developers

Deploy Monkey365 in minutes. Generate CIS-aligned security reports across Microsoft 365, Azure, and Entra ID. Zero external module dependencies. Start your assessment now.

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monkey365 FAQ

Do I need to install Microsoft PowerShell modules (Az, ExchangeOnlineManagement, Microsoft Graph SDK)?

No. Monkey365 bundles its own dependencies and is self-contained. This reduces setup friction and dependency management.

Can I run assessments automatically on a schedule or in CI/CD?

Yes. Monkey365 supports service principal and certificate authentication, making it suitable for Azure Automation, GitHub Actions, and other CI/CD platforms. Results can be exported as JSON/CSV for downstream processing.

What permissions does my service principal or user need?

Permissions vary by workload (Exchange, SharePoint, Teams, Entra ID). Consult the documentation and test in a non-production tenant first. Monkey365 will report missing permissions during execution.

Is Monkey365 production-ready?

Yes, it is widely used by consultants, security teams, and organizations for assessments. As community open-source, it has no commercial SLA. Allocate internal resources for testing, monitoring, and updates.

Custom software development services

Need help beyond evaluating monkey365? DEV.co is a software development agency offering software development services and web development for teams of every size. Our software developers and web developers build custom software, web applications, APIs, and open-source security integrations — and maintain them long-term.

Assess Your Microsoft Cloud Security Posture

Deploy Monkey365 in minutes. Generate CIS-aligned security reports across Microsoft 365, Azure, and Entra ID. Zero external module dependencies. Start your assessment now.

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