Usually means: Switching to different software version.
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We found 3 dictionaries that define the word crossgrade:

General (2 matching dictionaries)
  1. crossgrade: Wordnik
  2. crossgrade: Wiktionary

Slang (1 matching dictionary)
  1. crossgrade: Urban Dictionary

Definitions from Wiktionary (crossgrade)

verb:  (computing, transitive) To upgrade (a software application) so that it is able to run on a different platform.
verb:  (business, transitive) To switch from an existing subscription to one at the same price or service level.
noun:  (computing) An upgrade of a software application that enables it to run on a different platform.
noun:  (business) A switch from an existing subscription to one at the same price or service level.

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