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ChatCLI implements an automatic context recovery system that handles three common failure types in long sessions: model context window overflow (“prompt too long”), corporate proxy/gateway payload limits (413 / WAF 403 / silent EOF), and output token limits. When the API rejects a request for any of these reasons, the system applies progressively more aggressive strategies to recover the session without losing the conversation.

Context Overflow Recovery

When the API returns a “context too long” error, ChatCLI applies up to 3 recovery levels before giving up. Every loop recovers, not only the agent/coder one: the chat REPL (the prefix and the turn-context message are rebuilt over the recovered history), RPC chat behind MCP/ACP/the gateway, one-shot (-p, notice on stderr so stdout stays pipeable) and each MoA participant (its own thread is compacted; the panel no longer fails on one overflow). The shared helper is bounded (CHATCLI_MAX_RECOVERY_ATTEMPTS, default 3) and gives the same guarantees as a planned compaction: memory flushed first, hooks told with the recovery trigger, dropped messages archived to CCR, the cache rebuild accounted for. The classifier that decides “this is an overflow” is shared by every loop and by the provider fallback chain, and covers each provider’s phrasing — OpenAI chat and Responses (“context window”, context_length_exceeded), Anthropic (“prompt is too long”), Gemini (“input token count … exceeds”), xAI (“maximum prompt length”), Mistral, Groq, Bedrock — plus a status-aware check on a 400/413 whose body pairs a token/length word with an excess word.
First attempt: halves the budget limits and cleans up misalignments.Actions:
  • Repairs tool result pairing (removes orphans, injects synthetics)
  • Applies 50% of DefaultTurnBudgetChars and DefaultPerResultMaxChars for this session only — the process-wide defaults are never mutated, so other sessions of a gateway or rpcserve process never observe halved limits
  • Applies budget enforcement with reduced limits
  • Truncates long assistant messages to 5,000 chars
The original limits are restored after application. Only the current history is affected by the reduction.

Error Detection — model overflow

The system recognizes multiple forms of overflow errors:

Corporate proxy / gateway recovery

Enterprise environments often sit behind a proxy or gateway that enforces a POST body size cap — typically 1-5 MB, completely independent of the model’s context window. You can be well within Anthropic’s 200K-token window (~800 KB) and still take a mysterious rejection from the proxy. Worse: many proxies don’t return a clean 413 — some send a WAF 403 (Cloudflare, Akamai, mod_security), 431 (header too large), or simply drop the TCP connection mid-POST, surfacing as EOF / connection reset on the client. ChatCLI detects all three patterns and funnels them through the same recovery flow as context overflow.

Error Detection — proxy/gateway

WAF detection is conservative — a 403 without firewall signals continues to be treated as an auth error (OAuth refresh + retry). Only when a 403 carries specific proxy/WAF signals is it reclassified as a recoverable payload failure. This prevents invalidating valid OAuth credentials when the real problem is on the network layer.
The corporate Bedrock case: when the proxy/WAF intercepts the POST to Bedrock Runtime and returns an HTML block page with status 403, the AWS SDK tries to parse the body as JSON and fails with "invalid character '<' looking for beginning of value" and an empty RequestID. That pattern is an unambiguous middlebox fingerprint (a real AWS 403 returns well-formed JSON) — ChatCLI reclassifies it as a recoverable payload failure and triggers the same recovery ladder.
EOF / connection-reset detection applies a history-size threshold (500 KB) before suspecting payload. Small requests that hit EOF keep being treated as transient network failures (normal retry). Only when the history is already suspiciously large is EOF reclassified as a probable body cap.

Pre-flight check

Every agent turn, history is measured before the request goes out. Two paths: With CHATCLI_MAX_PAYLOAD set: If history crosses 85% of the cap, BudgetRatio is forced to 0.40 up front — aggressive preventive compaction. The user sees:
Without a cap set: If history crosses 2.5 MB, a one-shot warning per session fires suggesting the env var. It will not re-trigger in the same run to avoid noise.

Adaptive learned cap

Bedrock providers annotate every transport error with the exact size of the request the middlebox rejected. When a payload rejection fires, ChatCLI derives the session cap directly from that observation — ¾ of the rejected size — instead of guessing:
This matters enormously in practice: real-world corporate gateways often cap bodies around 128 KB, where a guessed multi-megabyte cap would change nothing. The learned cap only ever tightens — if CHATCLI_MAX_PAYLOAD is already set below it, your value wins; a later, smaller rejection tightens it further. When the rejected size is unknown (providers without size annotation), the previous behavior remains as fallback: assume 4 MB for the rest of the session.

Floor diagnosis — when compaction cannot help

The system prompt (agent charter, personas, skills, MCP tool docs) is never compacted. When it alone reaches the size the gateway just rejected, no amount of history compaction can produce an acceptable request — retrying identical payloads would only burn recovery attempts. ChatCLI detects this and fails fast with an actionable message:
At ¾ of the rejected size a warning fires instead — the session continues, but you’re near the edge:
Three structural features shrink this floor: MCP tool descriptions are clamped to one line in the system-prompt index (full schema via @tools describe), injected skill bodies respect CHATCLI_SKILL_INJECT_BUDGET plus its 2× per-run cap, and mid-loop skill blocks age out to stubs after CHATCLI_SKILL_AGE_TURNS turns (recoverable via @recall). See MCP Integration and Skill Registry.

Content shrinking — Level 3 that actually works

Whole-message dropping is a no-op when the history is short — agent sessions often hold just a system prompt plus a handful of huge tool results, and MinKeepRecent keeps exactly the messages that carry the bulk. Emergency truncation therefore has a final pass: it shrinks the content of non-system messages, largest first, until the payload budget is met. System messages are never touched. When the compression layer is active, each message is archived verbatim in the CCR store before its first cut and the shrunk content carries a <<ccr:KEY>> marker — the model can recover the original at any time with @recall. Nuclear truncation (level 3 of the recovery ladder) additionally hard-caps every kept non-system message at 4,000 chars.

What every level guarantees

The same guarantees hold whichever loop compacts (chat, agent/coder, one-shot, /compact) and in overflow recovery:
  • Nothing the model asked to keep is touched. Messages flagged PreserveVerbatim (an @recall result the model explicitly requested in full) are excluded from the summarized segment and re-appended right after the summary at Level 2, kept whole at Level 3, and skipped by content shrinking. A verbatim native tool result re-appended without its owning tool call becomes a user-role message, so the tool-result pairing repair never deletes it. Verbatim messages may hold at most a quarter of the budget: past that, the oldest are archived to CCR again, stubbed with an @recall marker and lose the flag, so compaction always converges.
  • A compaction that changes nothing is not a compaction. A no-op, a rejected summary or a failure pops the undo snapshot (so /rewind compact never “restores” an identical history) and fires its paired PostCompact hook with outcome=skipped; restoring a /rewind checkpoint uses the same bookkeeping as /rewind compact (journal rewrite, expected cache rebuild, undo stack cleared).
  • Level 3 is no longer lossy. The messages it drops are archived to the CCR store first and the truncation notice carries an @recall marker for the whole segment — the same recoverability Levels 1 and 2 already had. Overflow recovery flushes pending memory, archives the messages it removes and appends the marker to the recovered history.
  • A bad summary never replaces the segment. A quality gate rejects refusals and answers too short for the segment (floor scales with its size, capped at 80 characters); the summarizer is retried once and, failing that, the pipeline falls to Level 3 with its archive.
  • The summarizer is not paid for nothing. When a summary does not bring the history under budget, the next two compactions skip Level 2 and go straight to Level 3 instead of paying a summarizer call per turn.
  • Hooks see every compaction. PreCompact/PostCompact fire with a trigger of auto, manual or recovery (hooks).
  • It is accounted. /cost shows the number of compactions, how many landed at Level 3 and what the summarizer cost; the counters persist with the session (cost tracking).
Guided /compact <instruction> follows the same rules: it uses the configured summarizer route (CHATCLI_COMPACT_MODEL) when there is one, gives the summary its own 10-minute allowance instead of the old 60-second command deadline, keeps PreserveVerbatim messages, archives the segment and runs the quality gate.

System notice injected in history

After a payload-limit-triggered recovery, ChatCLI injects a user message before the retry instructing the model to prefer smaller reads going forward. This breaks the model’s loop of trying to re-read the same huge file that caused the 413 in the first place. The notice is injected at most once per session — recovery detects an existing copy anywhere in the history (even folded into a compaction summary) and never stacks a second one, since every extra byte works against the very limit being recovered from:
This hint is intentionally injected in English. The AI follows English instructions much more faithfully even when the user is on pt-BR, and this message is never shown to the user — it only enters the history sent to the model.

Max Output Token Escalation

When the model stops generating because it hit the max_tokens limit, ChatCLI can automatically escalate:

Continuation Message

When the model is interrupted by a token limit, ChatCLI injects a continuation message:
The message instructs the model to continue from where it left off, avoiding repetition of already generated content.

Configuration

Live feedback during compaction

Since this release, the terminal never “freezes” during a long compaction anymore. HistoryCompactor emits status at each pipeline phase via SetStatusCallback:
Cancellation: the summarization LLM call now derives its context from the turn — Ctrl+C / ESC propagates correctly and aborts compaction without corrupting history (returns ctx.Err() instead of blindly falling through to emergency truncation).

Microcompact (pre-budget)

The budget check itself is payload-honest: it weighs message text plus native tool-call arguments, image payloads and system-part excess, so tool- or vision-heavy histories cross the threshold when the real request does — not after a proxy already rejected it. Before NeedsCompaction checks whether history exceeds budget, the agent loop applies ApplyMicrocompact — a pure-Go, no-LLM, no-network pass that progressively truncates/summarizes old tool results (2+ turns old → head+tail preview; 4+ turns old → one-line summary). In most cases this keeps history inside budget without triggering the (expensive) Level 2. The summarizer’s input is budgeted against the summarizer model’s own window (half of it, floor 20K chars) instead of a fixed head/tail cut per message: every message of the segment gets a fair allowance, a message that had already been folded into a <<ccr:KEY>> stub is restored from the CCR archive when the original fits, over-long messages keep head and tail in a 3:1 proportion, and native tool calls are named so the summary can list the commands executed. The same rendering serves /compact <instruction>. With the compression layer active, microcompact is lossless: the original tool result is archived in the CCR store before the cut and the preview/summary stub embeds a <<ccr:KEY>> marker. Markers carry forward across levels — when a truncated preview later degrades to a one-line summary, the marker survives on the summary — so the model can always expand the original with @recall.

Memory flush before compaction

The memory worker distills facts from the live history a couple of turns behind the conversation; compaction replaces the middle of that history with a summary, so anything the worker had not reached yet used to be distilled from the summary at best. Every compaction site (auto-compact in chat, agent and coder, explicit and guided /compact, one-shot) now hands the not-yet-extracted segment to the worker’s durable queue before the rewrite, so the original messages reach long-term memory verbatim regardless of what the summary keeps.

Repeated reads (pre-budget)

At the same turn boundary, DedupRepeatedReads removes the copies a coder session accumulates by reading the same file over and over: when a later @coder read of a path covers the same or a wider line range, every earlier read of that path is replaced by a one-line stub (archived in the CCR store first, so @recall can restore it) and the newest read stays verbatim. Narrower later reads never supersede a wider earlier one, @recall output is never touched, and each pass is reported in the turn line. The model keeps exactly one current view per file instead of five.
Configurable via env:

Aggressive Budget Ratio

At level 1, the tool result budget limits are multiplied by 0.5 (50%). This means:

Recovery Flow

After nuclear truncation (level 3), the model’s working context drops to the last 2 exchanges. With the compression layer active the dropped content stays recoverable — stubs carry <<ccr:KEY>> markers the model can expand with @recall — but proactive /compact remains the better experience: a structured summary beats a pile of recall markers.

Interaction with Other Systems

Context recovery works in conjunction with:

Tool Result Budget

The result budget is the first line of defense. Recovery activates when the budget was not sufficient.

Microcompaction

Progressive compaction reduces context growth over time.

Conversation Control

The /compact command is the proactive way to prevent overflow.

Cost Tracking

Monitor context usage to anticipate when /compact will be needed.

External context engine (MCP)

CHATCLI_CONTEXT_ENGINE=mcp:<server> hands the Level 2 summary to a configured MCP server exposing context_compact(segment, budget_chars, instruction): the rendered conversation segment (the same budgeted rendering the embedded summarizer receives), the character budget and, for guided /compact <instruction>, the user’s instruction. Its answer replaces the segment; the CCR archive, checkpoints and @recall keep working exactly as before. An error, a timeout (3 min) or an empty answer falls back to the embedded summarizer for that compaction. Shown in /config compression. CHATCLI_CONTEXT_ENGINE=provider adds the model’s own server-side context editing on top of the local pipeline. On Anthropic (API key or OAuth) every tool-loop request carries the context-management-2025-06-27 beta and a context_management block with one clear_tool_uses_20250919 edit: once the prompt passes 100 K input tokens the API clears the oldest tool results itself, keeping the five most recent tool uses and freeing at least 20 K tokens per edit, before those tokens are billed. The applied edits come back in the response and are mirrored locally: the oldest tool results the server cleared are stubbed in the local history (the originals archived to CCR, recoverable with @recall), the chars/token calibration skips that turn, the next cache write is booked as an expected rebuild and /context status shows how many edits, tool results and tokens the provider cleared. Local compaction, the CCR archive and /rewind compact keep working unchanged, so nothing is lost that was not already recoverable. Providers without a documented server-side equivalent ignore the setting.