shouldiuse.io

VERDICT

Should I use Askwoody?

Not disclosed - askwoody.com

Depends. If you manage Windows PCs and dread Patch Tuesday, the free site or cheap Plus membership is a no-brainer. If you expected software that patches or automates anything, look elsewhere — this is editorial content and forums.

Confidence

Medium. Based on ~20 public sources; no third-party ratings or published pricing figures found.

Ratings

  • Value for money
  • Ease of useNo usability evidence in sources.
  • Feature depth
  • Support quality
  • Security posture

Pricing

$0

Free

ModelNot disclosed
Monthly feesNot disclosed
HardwareNot disclosed
Free tierYes
AskWoody PlusNot listed in reviewed sources

Best for

  • Windows sysadmins tracking Patch Tuesday
  • Patch-cautious home users
  • MSPs advising clients on updates
  • Fans of MS-DEFCON risk ratings

Not for

  • Anyone wanting software that does something — this is advice only
  • Mac, Linux, or ChromeOS shops
  • Teams needing automated patch deployment
  • Buyers expecting support SLAs or a vendor contract

Gotchas - check before you buy

medium

Best analysis and early newsletters are Plus-members-only; free tier is teasers plus ads.

medium

Site logins lack 2FA; members have publicly requested it.

medium

Runs on donations and ads, not a company with SLAs; continuity risk after founder's death.

low

Plus pricing is not visible in public sources; verify cost before subscribing.

Pros and cons

Pros

  • Independent Patch Tuesday risk ratings via the MS-DEFCON system.
  • Free newsletters, forums, and articles funded by ads and donations.
  • Trusted by security press; Krebs on Security calls it 'the excellent AskWoody'.
  • Active forums where named experts reply to member questions.
  • Fast coverage of zero-days and regressions, e.g. RegreSSHion.

Cons

  • Not software — nothing installs, patches, or automates.
  • In-depth and early content reserved for paid Plus members.
  • Ad-supported site with dated forum software.
  • Community reports founder Woody Leonhard died in 2025.
  • Windows-only focus; no value outside Microsoft ecosystems.

Sources & method

Analyzed 9/20/2026 - 10 sources - No known vulnerabilities found in the sources reviewed.

official x4review x2security x2news x2
  • 2FA requested for site logins, Forum members ask AskWoody to add two-factor authentication; none is evident.

Key stats

  • Value for money: 4/5

    Rating

  • $0

    Starting price

  • 10

    Sources

  • Analyzed

  • Value for money: 4/5. Large free tier; Plus is optional and donation-funded.
  • Ease of use. No usability evidence in sources.
  • Feature depth: 4/5. Deep Patch Tuesday analysis, MS-DEFCON risk system, active forums.
  • Support quality: 4/5. Experts like Susan Bradley answer directly in forums.
  • Security posture: 3/5. No public vulns found; users request 2FA for logins.
  • Yes Free tier Free newsletters, forums, articles
  • 2005 Earliest site content Askwoody archive article
  • 889 Facebook followers @WoodyOnWindows page
  • Plus membership Paid tier Price not shown in public sources

Pricing

Free

$0

  • Newsletters, forums, patch analysis
  • Ad- and donation-supported

AskWoody Plus

Not listed in reviewed sources

  • Members-only extras and early newsletters
  • Supports the site financially

Security

No known vulnerabilities found in the sources reviewed.

  • 2FA requested for site loginsForum members ask AskWoody to add two-factor authentication; none is evident.⁹

What users say

Reddit sysadmins cite AskWoody as a go-to source for Microsoft patch reliability reviews, and Krebs on Security endorses it.

“Reliable website for Microsoft patch reviews”
Reddit, r/msp (thread title)
Full analysis

Based on ~20 public sources; no third-party ratings or published pricing figures found.

Not a tool — a trusted Windows patch-advice site. Great if you track Patch Tuesday; useless if you need software.

Methodology

Based on ~20 public sources; no third-party ratings or published pricing figures found.

Sources

  1. AskWoody homepageaskwoody.com
    official
  2. MS-DEFCON Systemaskwoody.com
    official
  3. Plus Membershipaskwoody.com
    official
  4. Free edition newsletteraskwoody.com
    official
  5. Reddit r/msp — reliable patch review sitesreddit.com
    review
  6. ghacks — AskWoody, Tech Sites We Loveghacks.net
    review
  7. Krebs on Security — Patch Tuesday editionkrebsonsecurity.com
    news
  8. Reddit — RIP Woody Leonhardreddit.com
    news
  9. Forum — AW login security / 2FA requestaskwoody.com
    security
  10. Forum — RegreSSHion vulnerability discussionaskwoody.com
    security

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