From claude-rudder
Skill for evaluating whether a conversation has accumulated enough irrelevant context to warrant starting a new session. Applies structured criteria to distinguish valuable accumulated context from bloat that degrades response quality.
npx claudepluginhub danielrosehill/claude-code-plugins --plugin claude-rudderThis skill uses the workspace's default tool permissions.
This skill teaches you how to assess whether continuing a conversation will produce better or worse results than starting a new one. Context management is a critical but often overlooked factor in getting high-quality responses from AI agents.
Mandates invoking relevant skills via tools before any response in coding sessions. Covers access, priorities, and adaptations for Claude Code, Copilot CLI, Gemini CLI.
Share bugs, ideas, or general feedback.
This skill teaches you how to assess whether continuing a conversation will produce better or worse results than starting a new one. Context management is a critical but often overlooked factor in getting high-quality responses from AI agents.
Every message added to a conversation increases context length. Longer context is not inherently better. Context becomes harmful when:
Starting a fresh conversation clears this noise. A well-timed context break often produces better results than continuing in a degraded session.
When asked to evaluate whether a user should start fresh, apply these criteria in order:
Has the primary task that opened this conversation been completed? If yes, and the user is moving to a new unrelated task, recommend a new conversation.
Estimate what percentage of the conversation history is directly relevant to the user's next request. If less than 30-40% is relevant, the irrelevant majority is likely to cause drift and degradation.
Count significant failed attempts, retried tool calls, conflicting instructions, or explicitly corrected misunderstandings. More than two or three of these in a single thread is a strong signal to start fresh.
If the conversation has touched more than two or three distinct, unrelated topics, the context is fragmented. Fragmented context confuses future responses.
Very long conversations (subjectively: many dozens of exchanges) accumulate compounding noise. Apply extra scrutiny before recommending continuation.
Continue if: the current task is ongoing, prior context is largely relevant, and there are few accumulated errors.
Start fresh if: the prior task is done, context relevance is low, significant errors have accumulated, or topics have diverged substantially.
When in doubt: recommend a fresh start. The cost of starting fresh is low (a brief re-orientation). The cost of degraded context is subtle but persistent.
When recommending a fresh start, always offer to generate a handoff summary — a compact paragraph the user can paste into the new session. A good handoff summary includes:
Keep handoff summaries under 150 words.
Be direct. Users asking this question want a verdict, not a hedge. Commit to a recommendation and explain it briefly. Avoid phrases like "it depends" without immediately resolving what it depends on.