content-missing-stop-condition

Detect open-ended loop instructions (keep monitoring, poll, retry) without a stopping condition

Severity	warning (disabled)
Autofix	-
Since	v0.17.0
Category	Content Intelligence

Why

Agents follow instructions literally. "Keep monitoring the PR for feedback" with no bound tells an agent to loop forever — burning tokens, holding a session open, or polling an API until something external kills it. Frontier-model prompting guidance (e.g. OpenAI's GPT-5.6 prompting guide) lists stopping conditions and success criteria among the few things a prompt should always keep: define the destination, not just the activity.

The rule finds open-ended loop instructions — "keep monitoring", "keep checking", "poll for", "continuously check", "retry when" — and flags them when the surrounding paragraph contains no stopping condition: no "until", no "stop after N minutes", no "at most N attempts", no count, timeout, or exit criteria. Loop adverbs must sit next to a base-form activity verb in imperative position, so descriptive prose never fires: "the daemon continuously reconnects", "in-cluster pollers continuously check", and "the tool is run repeatedly" all describe behavior rather than order it. Also skipped: table rows ("Watch for crypto errors" is a matrix entry), headings ("### Poll for Bot Response" names a section), and colon-terminated captions directly above a code fence — when the loop is operationalized in the code block below, that code is where the bound lives.

This rule is opt-in (enabled: false by default): monitoring language is common in prose that never reaches an agent verbatim. Enable it for repositories whose instruction files drive autonomous agents.

Examples

Bad (unbounded loop):

After opening a PR, keep monitoring for reviewer feedback and address
comments as they arrive.

Good (bounded — same activity, explicit stop):

After opening a PR, keep monitoring for reviewer feedback and address
comments as they arrive. You may stop monitoring 20 minutes after the
last push.

Good (bounded retry):

Retry when the smoke-test job fails with a registry pull error; give
up after 3 attempts and page the infra channel instead.

How to fix

Add the bound in the same paragraph as the loop instruction. Any of these forms count:

• a condition: "until CI passes", "stop once the PR merges"
• a count: "at most 3 retries", "up to 5 times"
• a time budget: "for 20 minutes", "stop after 1 hour", "with a 10-minute timeout"

Tune the rule in .skillsaw.yaml:

rules:
  content-missing-stop-condition:
    enabled: true
    severity: warning
    extra-loop-patterns:          # project phrasing that starts a loop
      - '\bbabysit\b'
    extra-terminator-patterns:    # project phrasing that bounds one
      - '\bend\s+of\s+shift\b'

Configuration

rules:
  content-missing-stop-condition:
    enabled: false  # true | false | auto
    severity: warning

Parameter	Description	Default
extra-loop-patterns	Additional regex patterns that indicate open-ended looping activity (e.g. project-specific phrasing like 'babysit')	[]
extra-terminator-patterns	Additional regex patterns that count as a stopping condition when found in the same paragraph as a loop instruction	[]

Run skillsaw explain content-missing-stop-condition to see this documentation and the rule's effective configuration in your terminal.