shouldiuse.io

VERDICT

Should I use Chocolatey Software?

Chocolatey is software management automation for Windows that wraps installers, executables, zips, and scripts into compiled packages. Chocolatey integrates w/SCCM, Puppet, Chef, etc. - chocolatey.org

Depends. Buy if you run a Windows fleet or dev team — the free CLI is solid and Business is cheap per seat. Skip if you just install a few apps on one PC; winget or Ninite covers that free.

Confidence

Medium. Based on ~30 public sources; review snippets truncated, so no rating numbers were available.

Ratings

  • Value for money
  • Ease of use
  • Feature depth
  • Support qualityNo support evidence in sources
  • Security posture

Pricing

Free

Open Source

ModelNot disclosed
Monthly feesNot disclosed
HardwareNot disclosed
Free tierYes
Chocolatey for Business$17.60/license/year

Best for

  • Windows-heavy IT fleets
  • DevOps automating installs
  • Shops already on SCCM/Puppet/Chef
  • PowerShell-comfortable admins

Not for

  • Home users with a handful of PCs
  • Non-technical teams avoiding command lines
  • Mac/Linux-only shops
  • Offices without any dedicated IT staff

Gotchas - check before you buy

medium

Business pricing is per license per year — costs scale with every machine you add

medium

Community repo packages aren't written or vetted by Chocolatey staff — review before broad deployment

medium

Users have questioned how fast CVE fixes land in the CLI

low

Microsoft's free winget now overlaps much of the core use case

Pros and cons

Pros

  • Free open-source CLI with a large community package catalog
  • Business tier cheap at $17.60 per license yearly
  • Integrates with SCCM, Puppet, and Chef pipelines
  • Central Management and self-service GUI for org deployments
  • Published security docs and trust guidance for the binary

Cons

  • Community packages maintained by volunteers, not Chocolatey staff
  • History of CVEs in CLI and Boxstarter components
  • Malware and phishing campaigns have abused the tool
  • New users report small post-install complaints

Sources & method

Analyzed 9/20/2026 - 15 sources - Mature security docs; historical CVEs patched; third parties abused the installer flow in 2022 campaigns, not a product breach.

official x6review x4security x3news x2
  • CVE-2020-15264 — Boxstarter privilege vulnerability, CERT VU#208577 disclosed a privilege issue in the Chocolatey Boxstarter installer.
  • CVE-2017-17969 — CLI vulnerability, Fixed and listed in official CLI release notes.
  • Third-party malware/phishing campaigns abused Chocolatey, Serpent campaign and a French phishing run used Chocolatey; vendor says users were unaffected — abuse, not a product CVE.

Key stats

  • Value for money: 5/5

    Rating

  • Free

    Starting price

  • 15

    Sources

  • Analyzed

  • Value for money: 5/5. Free core; $17.60/license/year business tier
  • Ease of use: 4/5. CLI-first; Reddit users report minor annoyances
  • Feature depth: 4/5. Central Management, self-service, SCCM/Puppet/Chef integration
  • Support quality. No support evidence in sources
  • Security posture: 3/5. Past CVEs patched; abused in third-party campaigns
  • $17.60 Business price per license, per year
  • Yes Free tier Open Source edition + community packages
  • ~15 people Company size per aspnetzero customer story
  • SCCM, Puppet, Chef Integrations named on product page

Pricing

Open Source

Free

  • Full CLI package manager
  • Community package gallery

Chocolatey for Business

$17.60/license/year

  • Central Management
  • Self-service GUI
  • SCCM/Puppet/Chef integration

Security

Mature security docs; historical CVEs patched; third parties abused the installer flow in 2022 campaigns, not a product breach.

  • CVE-2020-15264 — Boxstarter privilege vulnerabilityCERT VU#208577 disclosed a privilege issue in the Chocolatey Boxstarter installer.⁵
  • CVE-2017-17969 — CLI vulnerabilityFixed and listed in official CLI release notes.⁶
  • Third-party malware/phishing campaigns abused ChocolateySerpent campaign and a French phishing run used Chocolatey; vendor says users were unaffected — abuse, not a product CVE.

What users say

Reddit users generally like Chocolatey but note packages are community-maintained and there are minor rough edges.

“I used chocolatey a bit a few years back and liked it”
Reddit, r/chocolatey

Alternatives

Compare Chocolatey Software with each alternative.

  • Winget

    Microsoft's free built-in Windows package manager; enough for most needs

  • Ninite

    One-click installer/updater for common Windows apps, no CLI

  • PDQ Deploy & Inventory

    GUI-first Windows software deployment, popular with small IT teams

  • JFrog

    Artifact repository better suited to dev pipeline package storage

Companies that use it

Full analysis

Based on ~30 public sources; review snippets truncated, so no rating numbers were available.

Free Windows package manager for IT fleets and devs; overkill for home PCs — winget or Ninite suffice.

Methodology

Based on ~30 public sources; review snippets truncated, so no rating numbers were available.

Sources

  1. Chocolatey Pricingchocolatey.org
    official
  2. Chocolatey for Businesschocolatey.org
    official
  3. Community package repositorycommunity.chocolatey.org
    official
  4. Chocolatey Security docsdocs.chocolatey.org
    security
  5. VU#208577 Boxstarter privilege vulnerabilitykb.cert.org
    security
  6. Chocolatey CLI release notesdocs.chocolatey.org
    security
  7. Serpent malware campaign abuses Chocolateybleepingcomputer.com
    news
  8. Reddit: How safe and secure is Chocolateyreddit.com
    review
  9. Reddit: Recently installed Chocolatey complaintsreddit.com
    review
  10. G2 Chocolatey reviewsg2.com
    review
  11. Facebook Windows management case studychocolatey.org
    official
  12. Puppet Group Policy case studychocolatey.org
    official
  13. ASP.NET Zero customer storyaspnetzero.com
    review
  14. Chocolatey vs Winget comparisonflowdevs.io
    news
  15. Chocolatey vs Ninite docsdocs.chocolatey.org
    official

Rate this review

Anonymous. You can change your vote.

Loading votes…

Comments

One queue. No nested comments. Give a display name first. Limit: 200 words per comment and 7 comments per day. You can edit or delete yours.

Save a name to write a comment.

0 / 200 words

No comments yet.