# silverhack/monkey365

Monkey365 is an open-source security assessment tool for Microsoft 365, Azure, and Microsoft Entra ID. It helps security professionals identify misconfigurations, review cloud security posture, and evaluate environments against industry security best practices and compliance standards.

Repository: https://github.com/silverhack/monkey365
Canonical: https://ross.abutalabs.com/products/monkey365
Homepage: https://silverhack.github.io/monkey365/
Language: PowerShell
License: Apache-2.0
License Family: permissive
Topics: azure, azuread, microsoft365, microsoft365-compliance, office365, powershell-module, security, security-tools, exchangeonline, purview, sharepoint-online, azure-security-audit, azuread-scanner, azuread-security, entraid, entraid-assessments, microsoft365-security, microsoft365-scanner, cis-benchmark
Last push: 2026-08-07T11:25:23+00:00

## Health v2 (maintenance only)
Score: 97/100 (v2, computed 2026-09-02T17:46:02.011165+00:00)
- activity 96, release rhythm 96, longevity 100
- inputs: {"age_days": 1594, "days_push": 26, "days_rel": 26, "gap_med": 27.5, "n_releases_24m": 19}
- flags: none
- formula: round(0.45*activity + 0.35*rhythm + 0.20*longevity); archived -> min(score, 10)

## Adoption (not part of the score)
Stars 1332, forks 141 (observed 2026-08-28T04:04:24.543478+00:00)

## What it is
Monkey365 is an open-source PowerShell-based security assessment framework for Microsoft 365, Azure, and Microsoft Entra ID. It collects tenant configuration data, evaluates it against security best practices and CIS benchmarks, and generates HTML, JSON, and CSV reports of misconfigurations.

## Use cases
- audit my Microsoft 365 tenant for security misconfigurations
- run a CIS benchmark compliance check on Azure subscriptions
- assess Entra ID security posture before an audit
- generate an HTML report of Exchange Online and SharePoint security issues
- review Microsoft Teams and Purview configuration against best practices
- automate cloud security posture assessments with JSON output
- check M365 tenant configuration as an incident responder

## When to choose
- you need a self-contained PowerShell tool with no dependency on Az, Microsoft Graph SDK, or ExchangeOnlineManagement modules
- you want consolidated M365, Azure, and Entra ID assessments in a single report
- you need CIS benchmark and compliance checks for Microsoft cloud workloads
- you support multiple authentication methods including service principals and certificates for unattended scans

## When to avoid
- you need security scanning for AWS, GCP, or non-Microsoft clouds
- you want continuous runtime monitoring or intrusion detection rather than point-in-time configuration reviews
- you need a GUI-driven vulnerability scanner rather than a PowerShell CLI
- your environment has no PowerShell availability (e.g., non-Windows without PowerShell Core installed)

## Facets
- artifact type: cli-tool
- maturity: active
- function: security, vulnerability-scanning, monitoring, developer-tools
- domain: security, cloud-computing, penetration-testing
- platform: windows, cross-platform, cli
- tags: microsoft-365, azure, entra-id, cloud-security-posture, cis-benchmark, compliance, powershell-module, security-assessment, exchange-online, sharepoint-online, microsoft-teams, purview, devops

## Member repositories
- silverhack/monkey365 (main) score 97

## Provenance
- Observed fields: from GitHub, fetched 2026-08-28T04:04:24.543478+00:00.
- Health v2: computed from the inputs above; adoption is never an input.
- Inferred fields (summary, facets, guidance): AI-extracted, prompt v1, taxonomy v1, on 2026-08-30T04:45:13.951517+00:00, confidence not recorded.
  - readme: https://github.com/silverhack/monkey365 (fetched 2026-08-28T04:04:24.543478+00:00, sha 1eb473b3b08a)
  - homepage: https://silverhack.github.io/monkey365/ (fetched 2026-08-29T12:04:15.289600+00:00, sha 9a42775cf7cc)
- Data as of 2026-08-30T08:39:29.467469+00:00.