Iterating

What it does

When your agent uses it

• Users request work that spans multiple sessions (research
• Feature development)
• Need to build on past progress
• Explicitly mention iterative work

Example prompts

• “/iterating”

Workflow steps

5 steps, taken from the first numbered list in SKILL.md.

1. 1Create/Update WorkLog → Output for user → STOP
2. 2User saves WorkLog to project knowledge (survives conversation limits)
3. 3User says "continue" (same or new conversation)
4. 4Make incremental progress on ONE item → Update WorkLog → STOP
5. 5Repeat

What it can do on your machine

Read from SKILL.md and the folder at commit 6fc82b8. It shows what the files ask for, not the result of running them.

• Tool permissions

  Pre-approves nothing: there is no allowed-tools line, so your agent's usual permission prompts apply.

  From allowed-tools in the SKILL.md frontmatter.

• Runs code

  No scripts in the folder and no shell commands in SKILL.md (its code samples are markdown and bash).

  From the folder's file list and the shell code blocks in SKILL.md.

• Network

  No URLs in SKILL.md.

  From URLs in SKILL.md, links to its own repository left out.

• Credentials

  Names no API keys, tokens, secrets or passwords.

  From names ending in _API_KEY, _TOKEN, _SECRET, _KEY or _PASSWORD in SKILL.md.

Context cost

Iterating loads about 1.8k tokens when it runs, and up to ~4.8k if it reads all its reference files. Until then it costs about 85 tokens; SKILL.md has 602 words of instructions outside code blocks.

Always · name and description, kept in context so the agent knows when to use it

~85

When it runs · the whole SKILL.md, loaded when a task matches

~1.8k

With references · SKILL.md plus every file in references/, read only if the agent opens them

~4.8k

Estimates: characters ÷ 4, the usual rule of thumb; real counts depend on the model's tokenizer. Scripts and assets cost tokens only if the agent reads them.

Safety

Automated static check — not a guarantee. Review scripts before installing. It scans the text of SKILL.md for risky patterns (piping downloads into a shell, reading credential files, hidden Unicode, destructive commands); files beside SKILL.md are not scanned.

SKILL.md

The full file from oaustegard/claude-skills at commit 6fc82b8, republished under its MIT licence (© oaustegard). 602 words, ~1,776 tokens.

name

iterating

description

Multi-conversation methodology for iterative stateful work with context accumulation. Use when users request work that spans multiple sessions (research, debugging, refactoring, feature development), need to build on past progress, explicitly mention iterative work, work logs, project knowledge, or cross-conversation learning.

metadata.version

1.2.0

if [ "$CLAUDE_CODE_REMOTE" = "true" ]; then
  # Claude Code on the Web (CCotw) - writes to GitHub
  # Read: references/ccotw-environment.md
elif [ -n "$CLAUDE_CODE_REMOTE" ]; then
  # Claude Code CLI - writes to local filesystem
  # Read: references/codecli-environment.md
elif [ -x "$(command -v osascript)" ] && [ -d "/Applications/Claude.app" ]; then
  # Claude Desktop - may write to disk OR output for download
  # Read: references/desktop-environment.md
else
  # Claude.ai (web/chat/native app) - outputs for download
  # Read: references/chat-environment.md
fi

---
version: v1
status: in_progress
---

# [Project Name] Work Log

## v1 | YYYY-MM-DD HH:MM | Title

**Prev:** [previous context OR "Starting new work"]
**Now:** [current goal]

**Progress:** [X% complete OR milestone status]

**Files:**
- `path/to/file.ext` (Why this file matters)
  - L45-67: [What to examine/change here]
  - L123-145: [Another area, specific issue]

**Work:**
+: [additions with file:line]
~: [changes with file:line]
!: [fixes with file:line]

**Decisions:**
- [what]: [why] (vs [alternatives])

**Works:** [effective approaches]
**Fails:** [ineffective approaches, why]

**Blockers:** [None OR specific blocker with owner/ETA]

**Next:**
- [HIGH] [Critical action item]
- [MED] [Important but not urgent]
- [LOW] [Nice to have]

**Open:** [questions needing answers]

**Files:**
- `src/auth/oauth.ts` (OAuth implementation needs refactoring)
  - L45-67: Current token validation logic
  - L123-145: Refresh token handling (race condition on L134)

**Progress:** 60% complete

**Progress:** Phase 2/3 | Auth ✅ | Payments 50% 🔄 | UI ⏳

© oaustegard, MIT. Rendered from Markdown: HTML in the file is shown as text, images as links, and headings moved down two levels. Raw file

Files

SKILL.md and 7 other files (references) in iterating of oaustegard/claude-skills.

• SKILL.md
• CHANGELOG.md
• README.md
• references/advanced-patterns.md
• references/ccotw-environment.md
• references/chat-environment.md
• references/codecli-environment.md
• references/desktop-environment.md

Open the folder on GitHubat commit 6fc82b8