context-surfing

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Monitors context window health throughout a session and rides peak context quality for maximum output fidelity. Activates automatically after plan-interview and intent-framed-agent. Stays active through execution and hands off cleanly to simplify-and-harden and self-improvement when the wave completes naturally or exits via handoff. Use this skill whenever a multi-step agent task is underway and session continuity or context drift is a concern. Especially important for long-running tasks, complex refactors, or any work where degraded context would silently corrupt the output. Trigger even if the user doesn't say "context surfing" — if an agent task is running across multiple steps with intent and a plan already established, this skill is live.

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Sourcepskoett/pskoett-ai-skills
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NPX Install

npx skill4agent add pskoett/pskoett-ai-skills context-surfing

Tags

Translated version includes tags in frontmatter
context-surfingagent-context-managementcontext-drift-detectionsession-continuityai-agent-workflow

SKILL.md Content

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Context Surfing

Install

bash
npx skills add pskoett/pskoett-ai-skills/skills/context-surfing
The agent rides the wave of peak context. When the wave crests, it commits. When it detects drift, it pulls out cleanly — saving state, handing off, and letting the next session catch the next wave.
No wipeouts. No zombie sessions. Only intentional, high-fidelity execution.

Mental Model

Think of context like an ocean wave:
  • Paddling in = loading the intent frame, plan, and initial context. Energy is building.
  • The peak = full context coherence. The agent knows exactly what it's doing and why. This is when to execute.
  • The shoulder = context starting to flatten. Still rideable, but output density is dropping.
  • The close-out = drift. Contradiction, hedging, second-guessing, or hallucinated details. Wipe-out territory.
The skill's job: ride as long as the wave is good, exit before it closes out.

Lifecycle Position

[plan-interview] → [intent-framed-agent] → [context-surfing ACTIVE] → [simplify-and-harden] → [self-improvement]
Context Surfing is the execution layer. It wraps all work between intent capture and post-completion review. Simplify-and-harden and self-improvement are the next steps in the pipeline — they run after context-surfing completes, not as conditions that end it.

Relationship with intent-framed-agent

Both skills are live during execution. They monitor different failure modes:
  • intent-framed-agent monitors scope drift — am I doing the right thing? It fires structured Intent Checks when work moves outside the stated outcome.
  • context-surfing monitors context quality drift — am I still capable of doing it well? It fires when the agent's own coherence degrades (hallucination, contradiction, hedging).
They are complementary, not redundant. An agent can be perfectly on-scope while its context quality degrades (e.g., it's doing the right thing but starting to hallucinate details). Conversely, scope drift can happen with perfect context quality (the agent deliberately chases a tangent). Intent-framed-agent's Intent Checks continue firing alongside context-surfing's wave monitoring.
Precedence rule: If both skills fire simultaneously (an Intent Check and a drift exit at the same time), context-surfing's exit takes precedence. Degraded context makes scope checks unreliable — resolve the context issue first, then resume scope monitoring in the next session.

When to Use the Full Pipeline

Not every task needs all five skills. Match pipeline depth to task complexity:
Task TypeSkills to Use
Trivial (rename, typo fix)None — just do it
Small (isolated bug fix, single-file change)
simplify-and-harden
only
Medium (feature in known area, multi-file)
intent-framed-agent
+ 
simplify-and-harden
Large (complex refactor, new architecture, unfamiliar codebase)Full pipeline
Long-running (multi-session, high context pressure)Full pipeline with 
context-surfing
as the critical skill
When in doubt, start light. Add skills if you notice drift or quality issues mid-task.

Activation

This skill is live the moment the intent frame and plan are established. No explicit invocation needed.
At activation, load and confirm:
  1. The intent frame (from intent-framed-agent output)
  2. The plan (from plan-interview output)
  3. The current session state from the Entire CLI (if available)
  4. All project context files (see below)

Entire CLI Integration

Entire CLI (github.com/entireio/cli) provides persistent session state that serves as external ground truth for drift checks and handoff files.
At activation, detect Entire:
bash
entire status 2>/dev/null
  • If it succeeds, use Entire as the session state backend. Log completions, in-progress items, and scope notes to it as work progresses.
  • If unavailable or failing, continue without it. Use the intent frame and plan file as the wave anchor instead. Track progress via structured comments in your output rather than Entire CLI commands. Do not block execution and do not nag about installation.
The wave anchor is not held mentally. It is the intent-framed-agent output combined with Entire CLI session state (when available) or the plan file (when Entire is unavailable). Both are external, persistent artifacts. Every drift check reads from them directly — never from reconstructed memory.

Project Context Files

Before executing anything, scan the project for 
.md
files that carry standing context. These are not documentation to skim — they are constraints, decisions, and architectural truth that must stay in the wave at all times.

Always load at activation

  • CLAUDE.md
    — agent configuration, conventions, constraints
  • AGENTS.md
    — multi-agent setup, role definitions
  • README.md
    — project intent and structure
  • Any 
    .md
    in the project root

Load on demand (when relevant to the current task)

  • .md
    files in 
    skills/
    , 
    docs/
    , 
    .learnings/
    , or similar directories
  • SKILL.md
    files for any skill being invoked alongside this one

Rules for context files

  1. They are always part of the wave anchor. If output contradicts a project 
    .md
    file, that is a drift signal — treat it as a strong one.
  2. Re-read them if the task changes domain or scope. Don't assume you remembered correctly 20 steps in.
  3. Include their key constraints in the handoff file. The next session needs to reload them too — note which files were active and whether any were updated during the session.
  4. If a 
    .md
    file is modified during the session    , flag it explicitly in the handoff under a "Modified Context Files" section so the next session re-reads it fresh rather than relying on the handoff summary.

Drift Detection

Continuously monitor for these signals. Any single strong signal, or two weak ones together, means the wave is closing out.

Strong signals (exit immediately)

  • The agent contradicts a decision it already made and committed to
  • A detail appears in the output that was never in the original context (hallucination)
  • The agent re-opens a scope question that was explicitly resolved in the plan
  • Output starts re-explaining the task rather than executing it

Weak signals (watch closely)

  • Responses are getting longer without getting more useful
  • Hedging language increases: "it depends", "could be", "might want to consider"
  • The agent switches approaches mid-task without explicit user direction
  • References to the original intent become vague or paraphrased instead of precise
  • The agent asks a clarifying question it should already know the answer to

Not drift

  • Normal iteration and refinement within scope
  • Asking about genuinely new information not in the original context
  • Simplifying a previous output (that's the wave working, not breaking)

The Monitoring Paradox

An agent with degraded context is the least likely to detect its own degradation. The strong signals (hallucination, contradiction) are exactly the ones a compromised agent will miss — because it no longer has the context to recognize the contradiction.
This is an inherent limitation of self-monitoring. Mitigate it with external grounding:
  1. Re-read the intent frame verbatim before each major step. Don't rely on your memory of it. Open the artifact and read it. If what you're about to do doesn't match what you read, stop.
  2. Cross-check against the plan file. Before starting a new work unit, re-read the relevant plan section. Compare it to what you're actually doing.
  3. Use Entire CLI logs as external memory. If Entire is available, read back your own session log before non-trivial decisions. Your logged state is more reliable than your recalled state.
  4. Treat the user as a drift sensor. If the user expresses confusion, asks "why are you doing that?", or redirects you — treat it as a strong signal regardless of your own assessment.
The weak signals (hedging, verbosity) are more reliably self-detectable precisely because they're behavioral, not factual. Watch for those as early warnings.

Riding the Wave

While context is healthy:
  1. Execute with commitment. No hedge, no re-litigating decisions already made. The plan is the plan.
  2. Check the wave anchor before non-trivial decisions. Re-read the intent-framed-agent output. If the decision aligns, proceed. If it doesn't, stop.
  3. Track completions. Log what's done, what's in progress, what's pending as work progresses — not at exit. If Entire CLI is available, use it as the session log. If not, maintain a running status in your output. This feeds the handoff if needed.
  4. Resist scope creep. If something interesting but out-of-scope appears, note it (in Entire CLI or in your output) — don't chase it.

Exit Protocol (Wave Close-Out)

When drift is detected, execute a clean exit. Do not try to push through.

Step 1: Stop executing

Immediately pause task execution. Do not produce more output that may be corrupted by the degraded context.

Step 2: Write the handoff file

Create a file named 
.context-surfing/handoff-[slug]-[timestamp].md
(create the 
.context-surfing/
directory if it doesn't exist). Add 
.context-surfing/
to 
.gitignore
— handoff files are session artifacts, not project history.
Structure:
markdown
# Context Surf Handoff

## Session Info
- Task: [task name / slug]
- Started: [timestamp]
- Ended: [timestamp]
- Exit reason: [what drift signal was detected]

## Intent Frame (from intent-framed-agent output — read verbatim, do not reconstruct)
[copy directly from the intent-framed-agent artifact]

## Plan (from plan-interview output — read verbatim, do not reconstruct)
[copy directly from the plan-interview artifact]

## Completed Work (from Entire CLI session state or running output log)
[pull directly from CLI log or structured output — do not reconstruct from memory]

## In Progress at Exit (from Entire CLI session state or running output log)
[what the session log shows as active at the moment of exit]
[include any partial outputs if useful]

## Pending Work (from plan-interview output — cross-reference session log to confirm what's genuinely not done)
[remaining tasks from the plan, in order]

## Drift Notes
[what specifically triggered the exit — be precise, this helps the next session replan intelligently]

## Active Context Files
[list all .md files loaded during this session — root level and any skill/docs files consulted]

## Modified Context Files
[any .md files that were changed during this session — next session must re-read these, not trust the handoff summary]

## Scope Notes (Out-of-Band)
[anything interesting discovered that's outside scope — flagged for the next session to decide on]

## Recommended Re-entry Point
[where the next session should pick up, and any replanning it should do before continuing]

Step 3: Notify the user

Briefly and clearly:
"Context wave is done. I've saved the session state to 
.context-surfing/[filename]
. The next session should load that file, run plan-interview to replan from [re-entry point], and catch the next wave. Here's what triggered the exit: [one sentence on drift signal]."
Do not over-explain. The handoff file has the details.

Handoff to Next Session

The next session should:
  1. Read the handoff file completely before doing anything else
  2. Run plan-interview using the handoff as input context
  3. Re-establish the intent frame via intent-framed-agent
  4. Pick up context-surfing again from the recommended re-entry point
This is not failure. This is the system working correctly. Clean exits produce better total output than zombie sessions that limp to the finish line.

Session Close (Natural Completion)

When the task completes within a healthy wave (no drift exit needed):
  1. Confirm all plan items are done
  2. Note session end in a brief summary (optional, not a full handoff file)
  3. Signal readiness for simplify-and-harden — the next skill in the pipeline picks up from here
No handoff file needed for clean completions — just the outputs and a one-liner status.

Interoperability with Other Skills

What this skill consumes

  • From plan-interview: The plan file (
    docs/plans/plan-NNN-<slug>.md
    ). Used as part of the wave anchor and copied verbatim into handoff files.
  • From intent-framed-agent: The intent frame artifact. Used as part of the wave anchor and copied verbatim into handoff files.
  • From Entire CLI (optional): Session state for progress tracking and external memory.

What this skill produces

  • For simplify-and-harden: A "ready" signal on natural completion. Simplify-and-harden picks up from the completed work.
  • For the next session (on drift exit): A handoff file in 
    .context-surfing/
    with full state for session resumption.
  • For self-improvement: Drift patterns observed during the session can be logged as learnings if they recur.

Pipeline position

  1. plan-interview
    (optional, for requirement shaping)
  2. intent-framed-agent
    (execution contract + scope drift monitoring)
  3. context-surfing
    (context quality monitoring — runs concurrently with intent-framed-agent during execution)
  4. simplify-and-harden
    (post-completion quality/security pass)
  5. self-improvement
    (capture recurring patterns and promote durable rules)

Hook Integration

Enable automatic handoff detection at session start. This ensures handoff files from previous context exits are never silently ignored.

Setup (Claude Code / Codex)

Add to 
.claude/settings.json
:
json
{
  "hooks": {
    "UserPromptSubmit": [{
      "matcher": "",
      "hooks": [{
        "type": "command",
        "command": "./skills/context-surfing/scripts/handoff-checker.sh"
      }]
    }]
  }
}
This checks for unread handoff files in 
.context-surfing/
on every prompt. If found, it reminds the agent to read the handoff before starting new work (~100 tokens overhead, skips silently when no handoff exists).

Copilot / Chat Fallback

For agents without hook support, manually check at session start:
bash
ls .context-surfing/handoff-*.md 2>/dev/null

Principles

Ride the peak, not the whole ocean. A shorter session with high fidelity beats a long session with gradual corruption.
Exit is not failure. The wave close-out is a feature. Detecting it early is the skill.
The handoff file is the continuity. It's not documentation overhead — it's what makes the next session as sharp as this one started.
Never hide the exit. Always be explicit with the user that a context exit happened and why. Silently continuing in degraded context is the worst outcome.