KB5044277: Windows Server 2019 Security Update (October 2024)

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Download KB5044277

Get the official update for KB5044277. The download and file size for each supported product are on the Microsoft Update Catalog page.

Update summary

Senserva AI Opinion for KB5044277

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

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.

Exploitation and severity

Fixes 79 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.

What to do

Treat as urgent: it is being exploited in the wild (CISA KEV), so patch ahead of items that are not. Senserva flags whether KB5044277 is missing on your devices.

Check if KB5044277 is installed

Copy-paste PowerShell: one machine, or your whole fleet in one pass. No output means the update is not installed.

Get-HotFix covers Windows updates. Office, SharePoint, and Exchange server updates show under installed updates in Programs and Features, or check the Update Catalog history.

Known issues, from Microsoft

Quoted from Microsoft's support article for KB5044277 (checked 2026-07-22). 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 .

Writing about KB5044277? Cite this page

Copy-paste for a blog post, forum answer, or internal doc. The link always carries the current risk data.

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.

Affected products

• Windows Server 2019
• Windows Server 2019 (Server Core installation)
• Windows Server 2022

Also released in October 2024

The highest-risk updates from the same release:

The full month, summarized: Microsoft Patch Tuesday.

How to install KB5044277

Any of these paths delivers KB5044277; most organizations already have one of the first three running:

• Intune update rings (Windows Update for Business): the update flows on each ring's deferral schedule. For this update, consider an expedite policy: it bypasses deferrals for exactly this fix-now case.
• Windows Autopatch: rings, rollout, and pause or rollback are managed for you; exploited updates can be expedited.
• WSUS / Configuration Manager: approve KB5044277 for your device groups and set a deadline (deadline, not just approval, for an exploited fix).
• Manual: download from the Update Catalog above and install; fine for a handful of machines, unmanageable at any real scale.

After the rollout, verify rather than assume: update compliance reporting in Intune or Autopatch shows which devices actually installed it, and Siemserva reads Intune, Defender, Autopatch, and Azure Update Manager together to show the devices still missing KB5044277, ranked by exploitation.

Common questions about KB5044277

Does KB5044277 have known issues?

Yes. Microsoft's support article documents known issues for KB5044277 (checked 2026-07-22). The Known issues section on this page quotes it; verify against the article before acting.

Is KB5044277 urgent?

Yes. KB5044277 fixes at least one vulnerability in the CISA Known Exploited Vulnerabilities catalog, meaning attackers are using it in the wild. Deploy it first.

How do I download KB5044277?

From the Microsoft Update Catalog (linked on this page), or let Intune, Windows Update for Business, Windows Autopatch, or WSUS deliver it. The catalog page lists the download for each supported product.

How do I deploy KB5044277 with Intune?

Assign a Windows Update ring (quality update policy) to the device groups and the update flows on the ring's deferral schedule. Because KB5044277 fixes an actively exploited CVE, an Intune expedite policy is the right tool: it bypasses configured deferrals and pushes the update as soon as devices check in. Verify the rollout with update compliance reporting rather than assuming delivery.

Can I ask my own AI about KB5044277?

Yes. This page includes a free, ready-to-paste AI prompt containing KB5044277's key facts: severity, CVE count, exploitation status, and the download link. Copy it into Claude, ChatGPT, or Copilot for a rollout plan; the data is refreshed three times a day (5 AM, 12:30 PM, and 7 PM US Central).

Authoritative references