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PR #3847 hardened the prompt step's `timeout` guard against a huge-int value, but its twin in the shell step — the step the prompt one was mirrored from — still has the hole. `math.isfinite(10**400)` raises `OverflowError: int too large to convert to float`. A 400-digit YAML scalar is an `int` and is not a `bool`, so it clears every clause before `isfinite()` and raises there, escaping `_timeout_error()` as exactly the uncaught crash that helper exists to prevent: steps: - id: qa type: shell run: echo hi timeout: 1000...0 # 400 digits $ specify workflow run wf.yml Traceback (most recent call last): ... File "src/specify_cli/workflows/engine.py", line 361, in _validate_steps step_errors = step_impl.validate(step_config) File "src/specify_cli/workflows/steps/shell/__init__.py", line 127 or not math.isfinite(timeout) OverflowError: int too large to convert to float `workflow_run` calls `engine.validate()` before executing any step, so the OverflowError propagates out of `validate_workflow` and kills the command with a bare traceback that names neither the step nor the field, instead of the "Workflow validation failed" report. `execute()` shares the same helper, so an unvalidated run raises there too — and the engine re-raises anything a step throws, aborting the whole workflow after earlier steps have already run their side effects. The value is genuinely invalid rather than merely unrepresentable in the check: `subprocess.run(timeout=10**400)` raises the same OverflowError. Unlike the prompt step, the shell step checks `isfinite()` *before* `timeout <= 0`, so a negative huge int (`-(10**400)`) crashes as well rather than being caught by the sign check. Wrapped the condition in `try/except OverflowError` and treated the value as invalid, mirroring the prompt step's guard so both steps reject the same values with the same message. Now: Workflow validation failed: - Shell step 'qa': 'timeout' must be a positive number of seconds, got 1000...0. Valid int/float timeouts, non-finite floats, bools, strings and non-positive values are unaffected — the existing clauses are unchanged. Regression tests in `TestShellStep`: `validate()` rejects both signs of the huge int, `validate_workflow()` reports it end to end (pinning the path the CLI actually takes, not just the helper), and `execute()` fails only that step with `subprocess.run` patched to assert it is never reached. Test-the-test: reverting the source change fails all three with `OverflowError` and leaves the rest of `TestShellStep` passing. Assisted-by: Claude Code (model: claude-opus-5, under direct human supervision) Co-authored-by: Claude Opus 5 (1M context) <noreply@anthropic.com>