Patch tracker / KB5044285
KB5044285: Windows Server 2019 Security Update (October 2024)
KB5044285 is a High security update for Windows Server 2019, released 2024-10-08. It closes 62 CVEs with a maximum CVSS of 8.8. At least one of them is actively exploited (CISA KEV), so this is a deploy-first update. The most likely of them to be attacked is CVE-2024-43506, which FIRST.org rates at 67% probability of exploitation in the next 30 days.
Update summary
Fixes 62 CVEs. At least one is actively exploited (CISA KEV). Most severe CVSS 8.8 (High). EPSS exploit probability up to 67%. Among the top 25% of tracked Microsoft updates by EPSS exploit probability.
A newer security update for Windows 10 Version 1809 for 32-bit Systems has shipped since this one: KB5094041 (2026-08-11). For cumulative update families the newer package includes these fixes, so installing that one is usually the shorter path. Verify against your own update rings before you skip this package.
Microsoft documents 1 known issue with this update.
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KB5044285 covers sixty three CVEs for Windows 10 version 1809 and Windows Server 2019 in October 2024, adding CVE-2024-43508 and CVE-2024-43513 to the recurring CVE-2024-43506 and CVE-2024-43518 set. High severity, CVSS 8.8, a 61 percent EPSS score, and CISA KEV listing confirm active exploitation persists in this package. This is close in scope to its closest sibling and likely an alternate servicing branch of the same fixes.
Do this: Deploy KB5044285 and cross reference with any sibling October 2024 package to confirm no CVEs were missed.
AI-generated from public data, 2026-07-07. Verify against the vendor advisory before acting.
Senserva AI Opinion and rich prompt for KB5044285
Copy this prompt into Claude, ChatGPT, or Copilot. The facts are included, sourced from this page.
Full tracking and change history for KB5044285
- Released
- 2024-10-08
- Last changed
- 2026-08-07
- Changes tracked
- 3
Senserva began recording day-to-day change history on 2026-07-07, and refreshes it several times a day. Release dates are historical where Microsoft publishes them; revision history is tracked from that date forward, so it does not include changes made before then.
Check if KB5044285 is installed
Elevated PowerShell. No output means it is not installed.
Known issues, from Microsoft
Quoted from Microsoft's support article for KB5044285 (checked 2026-07-22). Verify against the article before acting.
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| Applies to
| Symptom
| Workaround
| All users
| Following the installation of the October 2024 security update, some customers report that the OpenSSH (Open Secure Shell) service fails to start, preventing SSH connections. The service fails with no detailed logging, and manual intervention is required to run the sshd.exe process.
This issue is affecting both enterprise, IOT, and education customers, with a limited number of devices impacted. Microsoft is investigating whether consumer customers using Home or Pro editions of Windows are affected.
| This issue is addressed in KB5052094 .
CVEs fixed by this update
Sorted exploited-first, then by CVSS. Every CVE links to its Senserva page with the full risk facts, references, and a ready-to-paste AI prompt.
Scope and sources
- Affected products
- Also released in October 2024
KB29166583
1 CVE · Critical · exploitedKB5044277
77 CVEs · Critical · exploitedKB5044281
65 CVEs · Critical · exploitedKB5044288
83 CVEs · Critical · exploitedKB5044293
56 CVEs · Critical · exploitedKB5044306
32 CVEs · Critical · exploitedKB5044320
32 CVEs · Critical · exploitedKB5044321
36 CVEs · Critical · exploitedThe full month, summarized: Microsoft Patch Tuesday.
- Authoritative references
See this and every Microsoft update ranked by real-world risk on the Microsoft Patch Tracker.