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First, update to the latest patch release of your current major version, e.g., v1.6.0p2 → v1.6.0p30. Then, take the latest patch release of the next major version, e.g., v1.6.0p30 → v2.0.0p36. Then again latest patch release of the next major version until you get to the current version and its latest patch release, e.g., as of the time writing this, v2.0.0p36 → v2.1.0p28 → v2.2.0p7.
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Same as for software, first the latest minor version, then the latest minor version of the next major version, and so on. E.g., v1.3.20 → v1.4.19 → v1.5.5 → v1.6.4.
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