Patch tracker / KB5044277
KB5044277: Windows Server 2019 Security Update (October 2024)
KB5044277 is a Critical security update for Windows Server 2019, released 2024-10-08. It closes 77 CVEs with a maximum CVSS of 9.0. 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-2024-38261, which FIRST.org rates at 67% probability of exploitation in the next 30 days.
Update summary
Fixes 77 CVEs. At least one is actively exploited (CISA KEV). Most severe CVSS 9.0 (Critical). EPSS exploit probability up to 67%. Among the top 25% of tracked Microsoft updates by EPSS exploit probability.
A newer security update for Windows Server 2019 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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KB5044277 is the October 2024 rollup for Windows Server 2019 and 2022, addressing 79 CVEs including one already listed in the CISA Known Exploited Vulnerabilities catalog. The top-rated flaw carries a Critical rating at CVSS 9.0, and one CVE has a 67% EPSS score signaling high near-term exploitation probability, though none are currently tied to ransomware campaigns. Domain controllers and internet-facing servers running these editions are the primary exposure.
Do this: Deploy KB5044277 to your Windows Server 2019 and 2022 hosts this cycle, prioritizing domain controllers and externally reachable systems because of the KEV-listed CVE and 67% EPSS entry.
AI-generated from public data, 2026-07-21. Verify against the vendor advisory before acting.
Senserva AI Opinion and rich prompt for KB5044277
Copy this prompt into Claude, ChatGPT, or Copilot. The facts are included, sourced from this page.
Full tracking and change history for KB5044277
- 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.
The strongest signal is that on 2026-08-07 the CVE fix count for KB5044277 was revised down from 79 to 77. This is the only recorded movement, so there is no broader trend to weigh, just a single downward correction of two. For an IT admin today, treat this as a minor scope adjustment and confirm your patch inventory reflects 77.
- 2026-08-07 CVEs fixed 79 to 77
Recorded by Senserva on the dates shown, from the MSRC release feed. This is what moved and when, which neither the vendor advisory nor NVD publishes.
Check if KB5044277 is installed
Elevated PowerShell. No output means it is not installed.
Known issues, from Microsoft
Quoted from Microsoft's support article for KB5044277 (checked 2026-08-04). Verify against the article before acting.
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| Symptom
| Workaround
| 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 KB5053596 .
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 · exploitedKB5044281
65 CVEs · Critical · exploitedKB5044288
83 CVEs · Critical · exploitedKB5044293
56 CVEs · Critical · exploitedKB5044306
32 CVEs · Critical · exploitedKB5044320
32 CVEs · Critical · exploitedKB5044321
36 CVEs · Critical · exploitedKB5044342
46 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.