#28 in Build & DeploymentUpdated 2026-08

Chocolatey

by Chocolatey · Package manager and software deployment automation for Windows

45.3 — BenchRank score out of 100

Homepage
Pricing page

Visit website See full Build & Deployment ranking

Overview

Chocolatey is a package manager for Windows that wraps installers, executables, zips and scripts into compiled packages. The free open-source edition creates packages, installs and upgrades software from the command line and can use a self-hosted repository. Paid editions add package building, internalisation for offline use, auditing and a Central Management web console.

Best for: Windows sysadmins automating software packaging, deployment and updates across servers and desktops.
Pricing: Open-source edition is free; Pro is $96/year for up to 8 personal machines; Chocolatey for Business starts at $18.00 per node/year with a 100-node minimum ($1,800/year).
Runs on: WindowsCLI

Strengths and trade-offs

Strengths

Free open-source edition with no limit on managed machines
Package Internalizer recompiles 7,500+ packages for offline use
Central Management web console with PDF and Excel reporting
Integrates with SCCM, Puppet, Chef and PowerShell scripts

Trade-offs

Windows only; no macOS or Linux support is stated
Business edition has a 100-node minimum, so a $1,800/year floor
Central Management, audit and internalizer are paid editions only
Support is listed as included only with 100+ licenses

Pricing

Published plans from Chocolatey’s own pricing page, in USD. Usage charges and add-ons may apply on top.

Chocolatey pricing tiers, monthly and annual rates in USD
Plan	Monthly	Annual (per month)	Includes
Open Source	—per machine	—	Free, with no limit on machines Create packages and host your own repository Package shims and 30+ built-in PowerShell functions Upgrade all software with one command
Pro (Individual)	—per named individual, billed $96/year for up to 8 machines	$8	All open-source features Package Reducer and Package Throttle Runtime malware/virus protection and download CDN cache Student pricing available
Business (C4B)	—per node, billed $18.00/node/year with a 100-node minimum	$1.5	All Pro features plus Central Management Self-service install management and full package synchronisation Package Internalizer and Package Audit Support with 100+ licences; perpetual pricing available

How this score is made up

Each dimension is scored out of 100 and combined into the headline score using fixed weights.

MCP support: 0 out of 100
API quality: 20 out of 100
Documentation: 80 out of 100
Agent friendliness: 45 out of 100
Pricing transparency: 85 out of 100
Customer sentiment: 79 out of 100
Changelog: 0 out of 100
Marketing site structure: 80 out of 100
Operational trust: 40 out of 100

Measured, but not part of the score

Useful to know, but not a mark for or against the product — so these do not affect the ranking.

Openness: 85 out of 100
Maintenance: 100 out of 100

This doesn’t look right — report a problem with Chocolatey’s score

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