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
- 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.
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