Usually means: Choose the safer, cautious option.
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We found 5 dictionaries that define the word err on the side of:

General (4 matching dictionaries)
  1. err on the side of: Merriam-Webster
  2. err on the side of: Oxford Learner's Dictionaries
  3. err on the side of: Wiktionary
  4. err on the side of: Dictionary.com

Miscellaneous (1 matching dictionary)
  1. err on the side of: Idioms

Definitions from Wiktionary (err on the side of)

verb:  (transitive, idiomatic) To behave in a manner which favours or which is biased toward.
verb:  To choose which mistake (err) will be perpetuated when all available options would result in different mistakes.

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