So if I buy KIS 2015 (3 years), by the the time KIS 2018 releases, would I still be using KIS 2015 or am I entitled to free upgrade every year (sounds unlikely).
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You should be able to upgrade, i have upgraded my KIS in the past with a key from the previous version.
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Yes, You can upgrade your existing Kaspersky to future updates until your license get expired.
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It will upgrade automatically when updates comes, until your license is active.