The 2027 IT end-of-life calendar
Every major end-of-support date landing in 2027, from Windows Server 2016 in January to SAP ECC in December. Star the products you run, export the dates to your calendar, and check what a paid extension will cost before you commit to one.
Three windows carry most of the 2027 risk
If your 2027 budget covers only three projects, cover these.
January 11–12
Windows Server 2016, the System Center 2016 suite and Windows 10 Enterprise LTSC 2021 all lose support. Paid ESU covers most of it.
May 2–31
PAN-OS 11.1, FortiOS 7.4, RHEL 9 full support and Ubuntu 22.04 standard support end within four weeks, right at your network edge.
October 11–12
vSphere 8 and SQL Server 2017 end with no announced ESU, Windows 11 24H2 Enterprise stops servicing, and Windows 10 ESU jumps to $244 per device.
Every 2027 deadline, searchable
Open any row for a plain-language explanation and your 12, 6 and 3-month checkpoints.
Calendar files include reminders 12, 6 and 3 months before each date. Your starred products are saved in this browser only.
What will ESU cost you?
Microsoft charges ESU cumulatively, so a late start means paying for the years you skipped. Compare the bridge cost with replacement before you sign.
Windows 10 PCs
Windows Server 2016 hosts (Azure Arc ESU)
Uses Microsoft's published list prices as of October 2026: Windows 10 ESU at $61, $122 and $244 per device for Years 1 to 3, and Azure Arc meters of $5.21 (Standard) or $29.98 (Datacenter) per core per month. Server pricing assumes physical-host licensing with a 16-core minimum per host. Your agreement may differ.
Why auditors care: the rules that turn end-of-life into a finding
- PCI DSS v4.0.1 Requirement 12.3.4, mandatory since March 31, 2025, requires an annual review confirming every technology still gets vendor security fixes, plus a management-approved plan for anything with an announced end of life.
- PCI DSS Requirement 6.3.3 requires critical and high-security patches within one month of release. Unsupported software cannot meet it.
- CISA BOD 26-02, issued February 5, 2026, orders federal civilian agencies to remove end-of-support edge devices. Already-unsupported devices go first (around February 2027), and replacement of every identified device follows (around August 2027). CISA, the FBI and the UK NCSC urge every organization to follow it.
- CISA's Bad Practices list names unsupported or end-of-life software in critical infrastructure as dangerous, and especially so when it is reachable from the internet.
Frequently asked questions
Short answers to what IT leaders ask most about 2027 end-of-support dates.
What is the difference between end of mainstream support and end of extended support?
End of mainstream support stops new features and non-security fixes, but security patches keep shipping. End of extended support stops security patches too. For many Microsoft products, paid Extended Security Updates (ESU) can buy up to three more years of patches.
Which 2027 deadlines have no paid extension?
SQL Server 2017 (October 12), Azure Front Door classic and Cloud Services extended support (March 31), Windows 11 24H2 Enterprise (October 12), Visual Studio 2017 (April 13), the final SQL Server 2014 ESU year (July 12) and upstream Kubernetes 1.35 and 1.36. Plan full migrations for these, because buying more time is not an option.
How much does Windows 10 ESU cost in 2027?
Commercial ESU costs $61 per device for Year 1, $122 for Year 2 and $244 for Year 3, which runs from October 13, 2027 to October 10, 2028. Pricing is cumulative, so a device that enrolls late pays for the years it skipped. Windows 365 Cloud PC access includes ESU at no extra cost.
What happens to vSphere 8 after October 11, 2027?
Broadcom stops shipping patches and updates for ESXi 8, vCenter 8 and vSAN 8, and self-help technical guidance continues to October 11, 2029. vSphere 9 is sold only as a subscription inside VMware Cloud Foundation, so perpetual-license holders must choose between subscribing, migrating to another hypervisor or running unpatched. Confirm dates and any paid extension with Broadcom in writing.
Is paying for ESU worth it?
ESU works as a short bridge for named systems with a firm exit date, such as an application waiting on a vendor upgrade. It is a poor long-term plan, because Windows 10 ESU doubles every year and SQL Server 2017 has no ESU at all. Use the calculator above to compare the bridge with the cost of replacement.
How do I build an end-of-life inventory?
Pull versions from three sources and reconcile them: endpoint management such as Intune or Configuration Manager, your hypervisor inventory, and network discovery for firmware. Record version, edition, core count, owner, internet exposure and extension status for every system. Review it quarterly, because vendors move dates.
Replacing something on this list? TechnologyMatch matches IT teams with vendors based on actual requirements, so you can evaluate options without a cold-call queue.
Tell us what you needDates checked against vendor lifecycle pages in October 2026. Ubuntu 22.04, vSphere 8 and PAN-OS Extended Support+ dates come from conflicting or secondary sources, so confirm them with the vendor before you budget. Network hardware from Cisco, Juniper, HPE Aruba, SonicWall and Meraki carries per-model dates; check your vendor's bulletins. Risk reflects internet exposure and blast radius.
Get your calendar file
Fill in a few details and your calendar file downloads as soon as you submit. Each date comes with reminders 12, 6 and 3 months ahead. You only need to do this once.
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