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Add retries to flask ready-check #385

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Run time

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Job	Run time
type-check (3.13)	21s
lint-and-format	8s
type-check (3.11)	14s
type-check (3.12)	13s
test (3.12)	39s
test (3.13)	40s
test (3.11)	49s
	3m 4s