Hi 登 藤井,
Plan a migration / upgrade before or during the ESU window: Don’t rely on indefinite ESU. Use the ESU period as a buffer to move to Windows Server 2022 or newer.
Monitor Microsoft announcements: As time gets closer to Jan 2027, watch Microsoft lifecycle announcements and your Volume Licensing or Microsoft account representatives for whether they will allow ESU beyond that.
Use Azure-hosted VMs: If your server is in Azure, ESU is often enabled automatically or offered at no additional charge (depending on OS) for the “extra years.” This helps reduce licensing burden.
Consider Azure Arc / hybrid options: If you have on-prem or other-hosted servers, you might use Azure Arc to extend ESU capabilities, licensing, or updates. Microsoft supports applying ESU via Azure Arc for legacy Windows Server OSes.
Talk to your Microsoft licensing partner: Closer to 2027, your volume licensing or CSP partner will know whether Microsoft has extended the ESU program or offered additional “bridge” options.
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