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We've had several reports (since before the release of Windows 10) that the "jump lists" UI feature (Pinned/Recent Sessions available from the taskbar button) doesn't work on Windows 10. The list is present, but selecting an item from it reportedly launches the PuTTY configuration dialog rather than the desired session.
We've applied a workaround discovered by a correspondent to the post-0.65 development snapshots, but we don't know why this works.
We don't currently have access to Windows 10 to debug this ourselves.