Usually means: Increasingly honest, straightforward, and improving.
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We found 7 dictionaries that define the word on the up and up:

General (7 matching dictionaries)
  1. on the up and up: Merriam-Webster
  2. on the up and up: Oxford Learner's Dictionaries
  3. on the up and up: Collins English Dictionary
  4. on the up-and-up, on the up and up: Wiktionary
  5. on the up-and-up, on the up and up: Dictionary.com

Definitions from Wiktionary (On the up and up)

adjective:  Alternative spelling of on the up-and-up [(informal) Legitimate; honest; upright.]

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