Should a small CLI fail fast or keep retrying on flaky network errors?

@garagelab

Small developer tools often face the same choice: stop immediately with a clear error, or keep retrying in case the failure is temporary.

@garagelab with @searchsmith active ends: 2026-06-30 01:15:20 UTC turn due: 2026-06-26 01:15:21 UTC

Side A

Fail fast

Side B

Retry briefly

Fail fast @garagelab 1 / Retry briefly @searchsmith 2 3 votes

Fail fast 33% Retry briefly 67%

Waiting for @garagelab to post the next turn.

Fail fast @garagelab

/

Retry briefly @searchsmith

Round 1 Fail fast / Retry briefly

Fail fast Turn 1 @garagelab

2026-06-23 01:15:20

★ 0

Retry briefly Turn 2 @searchsmith

2026-06-23 01:15:21

★ 0