clementine-agent 1.18.193 → 1.18.194

package/dist/agent/bg-planner.js

@@ -44,7 +44,7 @@ import fs from 'node:fs';
 import path from 'node:path';
 import { randomUUID } from 'node:crypto';
 import pino from 'pino';
-import { BASE_DIR, MODELS, applyOneMillionContextRecovery, claudeCodeSystemPrompt, looksLikeClaudeOneMillionContextError, normalizeClaudeSdkOptionsForOneMillionContext } from '../config.js';
+import { BASE_DIR, MODELS, applyOneMillionContextRecovery, claudeCodeSubprocessEnv, claudeCodeSystemPrompt, looksLikeClaudeOneMillionContextError, normalizeClaudeSdkOptionsForOneMillionContext } from '../config.js';
 const logger = pino({ name: 'clementine.bg-planner' });
 // ── Persistence ──────────────────────────────────────────────────────
 /**
@@ -287,6 +287,10 @@ async function runPlannerLlm(userPrompt, systemPrompt, model) {
             // from knowing the working directory + git status so it can decompose
             // accurately. See claudeCodeSystemPrompt() in config.ts.
             systemPrompt: claudeCodeSystemPrompt(systemPrompt),
+            // 1.18.194 — pass OAuth token to the SDK subprocess. Without this,
+            // process.env doesn't have CLAUDE_CODE_OAUTH_TOKEN (config.ts keeps
+            // secrets out of process.env) and the SDK fails with "Not logged in".
+            env: claudeCodeSubprocessEnv(),
         }),
     });
     for await (const msg of stream) {

package/dist/agent/daily-planner.js

@@ -8,7 +8,7 @@
 import { existsSync, mkdirSync, readFileSync, readdirSync, writeFileSync } from 'node:fs';
 import path from 'node:path';
 import pino from 'pino';
-import { BASE_DIR, CRON_REFLECTIONS_DIR, TASKS_FILE, INBOX_DIR, MODELS, applyOneMillionContextRecovery, claudeCodeSystemPrompt, looksLikeClaudeOneMillionContextError, normalizeClaudeSdkOptionsForOneMillionContext, } from '../config.js';
+import { BASE_DIR, CRON_REFLECTIONS_DIR, TASKS_FILE, INBOX_DIR, MODELS, applyOneMillionContextRecovery, claudeCodeSubprocessEnv, claudeCodeSystemPrompt, looksLikeClaudeOneMillionContextError, normalizeClaudeSdkOptionsForOneMillionContext, } from '../config.js';
 import { listAllGoals } from '../tools/shared.js';
 const logger = pino({ name: 'clementine.daily-planner' });
 const PLANS_DIR = path.join(BASE_DIR, 'plans', 'daily');
@@ -259,6 +259,8 @@ Rules:
                     // 1.18.192 — preset form so SDK uses Claude Code subscription auth
                     // (raw string → API-key auth → "Not logged in" failure for Max users).
                     systemPrompt: claudeCodeSystemPrompt('You are a planning assistant. Analyze the context and produce a prioritized daily plan as JSON. Return only valid JSON, no markdown fencing.', { minimal: true }),
+                    // 1.18.194 — propagate OAuth token to SDK subprocess.
+                    env: claudeCodeSubprocessEnv(),
                 }),
             });
             for await (const msg of stream) {

package/dist/agent/mcp-bridge.js

@@ -10,7 +10,7 @@ import { existsSync, readFileSync, readdirSync, writeFileSync } from 'node:fs';
 import os from 'node:os';
 import path from 'node:path';
 import pino from 'pino';
-import { BASE_DIR, applyOneMillionContextRecovery, claudeCodeSystemPrompt, looksLikeClaudeOneMillionContextError, normalizeClaudeSdkOptionsForOneMillionContext, } from '../config.js';
+import { BASE_DIR, applyOneMillionContextRecovery, claudeCodeSubprocessEnv, claudeCodeSystemPrompt, looksLikeClaudeOneMillionContextError, normalizeClaudeSdkOptionsForOneMillionContext, } from '../config.js';
 const logger = pino({ name: 'clementine.mcp-bridge' });
 const MCP_SERVERS_FILE = path.join(BASE_DIR, 'mcp-servers.json');
 const INTEGRATIONS_FILE = path.join(BASE_DIR, 'claude-integrations.json');
@@ -453,6 +453,8 @@ export async function probeAvailableTools(force = false) {
             options: normalizeClaudeSdkOptionsForOneMillionContext({
                 // 1.18.192 — preset form for Claude Code subscription auth.
                 systemPrompt: claudeCodeSystemPrompt('Reply ok.', { minimal: true }),
+                // 1.18.194 — propagate OAuth token to SDK subprocess.
+                env: claudeCodeSubprocessEnv(),
                 model: 'claude-haiku-4-5',
                 permissionMode: 'dontAsk',
                 mcpServers: externalMcpServers,

package/dist/agent/run-agent-context.js

@@ -123,7 +123,14 @@ const BEHAVIORAL_POSTURE = `## How you operate
 
 **Discovering new projects.** If the owner mentions a project by name that isn't in your registry, don't free-float — call \`project_discover\` with the name. It searches common locations (~/Downloads, ~/Desktop, ~/Projects, ~/Documents) and returns ranked candidates. Confirm the right one with the owner, then call \`project_link\` to register it. Future turns will then resolve it automatically.
 
-**Verification posture for disputed claims.** If you see "Dispute mode" in the turn context, the owner is reporting that prior work FAILED. Past \`done\` claims in memory are NOT authoritative — your recall is biased. Before defending any past success, re-verify against reality: curl URLs, check file existence, run status commands. Saying "but my memory says it's live" without re-checking is a hallucination, not a defense.`;
+**Verification posture for disputed claims.** If you see "Dispute mode" in the turn context, the owner is reporting that prior work FAILED. Past \`done\` claims in memory are NOT authoritative — your recall is biased. Before defending any past success, re-verify against reality: curl URLs, check file existence, run status commands. Saying "but my memory says it's live" without re-checking is a hallucination, not a defense.
+
+**Fan-out posture (1.18.194).** When the owner asks for 3+ similar operations — send N emails, pull N records, enrich N contacts, summarize N pages — dispatch subagents in PARALLEL via the Agent tool. One subagent per item. Don't loop in your own turn; that's slow, serializes I/O that should be concurrent, and burns context linearly. Available subagents (see Agent tool descriptions for the canonical list):
+- \`researcher\` (Haiku, parallel, read-only) — per-item investigation
+- \`planner\` (Opus, 1-turn, no tools) — decomposition before write/send batches
+- Hired agents (Ross, Nora, etc.) — cross-delegation when relevant
+
+A 25-contact enrichment that fans out to 25 \`researcher\` calls finishes in ~30s. The same work done serially in your own turn takes 10+ minutes AND fills your context window with tool outputs. Default to fan-out for batch work.`;
 /**
  * Read the long-term memory block for an autonomous run (cron, team-task).
  * Returns the agent-specific MEMORY.md when a hired agent is active, the

package/dist/agent/strategic-planner.js

@@ -12,7 +12,7 @@
 import { existsSync, mkdirSync, readFileSync, readdirSync, writeFileSync } from 'node:fs';
 import path from 'node:path';
 import pino from 'pino';
-import { BASE_DIR, GOALS_DIR, MODELS, applyOneMillionContextRecovery, claudeCodeSystemPrompt, looksLikeClaudeOneMillionContextError, normalizeClaudeSdkOptionsForOneMillionContext, } from '../config.js';
+import { BASE_DIR, GOALS_DIR, MODELS, applyOneMillionContextRecovery, claudeCodeSubprocessEnv, claudeCodeSystemPrompt, looksLikeClaudeOneMillionContextError, normalizeClaudeSdkOptionsForOneMillionContext, } from '../config.js';
 import { listAllGoals } from '../tools/shared.js';
 const logger = pino({ name: 'clementine.strategic-planner' });
 const DAILY_PLANS_DIR = path.join(BASE_DIR, 'plans', 'daily');
@@ -31,6 +31,8 @@ async function llmJsonCall(prompt, systemPrompt) {
             // failures on Max-only installs. Logs confirmed weekly review was
             // silently falling through to the fallback path here since the bug landed.
             systemPrompt: claudeCodeSystemPrompt(systemPrompt, { minimal: true }),
+            // 1.18.194 — propagate OAuth token to SDK subprocess.
+            env: claudeCodeSubprocessEnv(),
         }),
     });
     for await (const msg of stream) {

package/dist/brain/adapters/pdf.js

@@ -14,7 +14,7 @@ import { readFileSync } from 'node:fs';
 import path from 'node:path';
 import pdfParse from 'pdf-parse';
 import { contentHash } from './common.js';
-import { MODELS, applyOneMillionContextRecovery, claudeCodeSystemPrompt, looksLikeClaudeOneMillionContextError, normalizeClaudeSdkOptionsForOneMillionContext, } from '../../config.js';
+import { MODELS, applyOneMillionContextRecovery, claudeCodeSubprocessEnv, claudeCodeSystemPrompt, looksLikeClaudeOneMillionContextError, normalizeClaudeSdkOptionsForOneMillionContext, } from '../../config.js';
 export async function* parsePdf(filePath) {
     let buf;
     try {
@@ -98,6 +98,8 @@ async function ocrPdfViaClaude(filePath) {
                 // Without this, every scanned-PDF ingest hit "Not logged in" and
                 // silently fell back to empty OCR output.
                 systemPrompt: claudeCodeSystemPrompt('You are a faithful OCR transcriber. Copy text exactly as written. When the PDF has images or scans, read the text from them using vision. Never invent content.', { minimal: true }),
+                // 1.18.194 — propagate OAuth token to SDK subprocess.
+                env: claudeCodeSubprocessEnv(),
                 // Claude Code's built-in Read tool handles PDFs (text + vision)
                 tools: ['Read'],
                 allowedTools: ['Read'],

package/dist/cli/dashboard.js

@@ -19,7 +19,7 @@ import { TunnelManager } from './tunnel.js';
 import { AgentManager } from '../agent/agent-manager.js';
 import { discoverMcpServers, getClaudeIntegrations, KNOWN_MCP_DESCRIPTIONS } from '../agent/mcp-bridge.js';
 import { buildBuilderEnrichedMessage, builderSessionKey } from '../dashboard/builder/prompt.js';
-import { AGENTS_DIR, MEMORY_FILE, MODELS, SESSIONS_FILE, TIMEZONE, applyOneMillionContextRecovery, claudeCodeSystemPrompt, currentTimeZone, looksLikeClaudeOneMillionContextError, normalizeClaudeSdkOptionsForOneMillionContext, setEnvOverride, } from '../config.js';
+import { AGENTS_DIR, MEMORY_FILE, MODELS, SESSIONS_FILE, TIMEZONE, applyOneMillionContextRecovery, claudeCodeSubprocessEnv, claudeCodeSystemPrompt, currentTimeZone, looksLikeClaudeOneMillionContextError, normalizeClaudeSdkOptionsForOneMillionContext, setEnvOverride, } from '../config.js';
 import { parseTasks } from '../tools/shared.js';
 // 1.18.160 — also pull parseCronJobs + parseAgentCronJobs so getCronJobs()
 // returns the same merged set the runtime fires (CRON.md + agent CRON +
@@ -6401,6 +6401,8 @@ If the tool returns nothing or errors, return an empty array \`[]\`.`,
                     maxTurns: 3,
                     // 1.18.192 — preset form for Claude Code subscription auth.
                     systemPrompt: claudeCodeSystemPrompt('You are a data enumerator. You call the given tool once, extract the items from its response, and emit a strict JSON array. No commentary.', { minimal: true }),
+                    // 1.18.194 — propagate OAuth token to SDK subprocess.
+                    env: claudeCodeSubprocessEnv(),
                     allowedTools: [tool],
                     mcpServers,
                     permissionMode: 'dontAsk',
@@ -9728,6 +9730,8 @@ If the tool returns nothing or errors, return an empty array \`[]\`.`,
                             maxTurns: 1,
                             // 1.18.192 — preset form for Claude Code subscription auth.
                             systemPrompt: claudeCodeSystemPrompt('You are a memory consolidation assistant. Extract only facts directly evidenced by the corpus. Be terse. Output exactly the requested format.', { minimal: true }),
+                            // 1.18.194 — propagate OAuth token to SDK subprocess.
+                            env: claudeCodeSubprocessEnv(),
                         }),
                     });
                     for await (const msg of stream) {

package/dist/config.d.ts

@@ -63,6 +63,31 @@ export declare function claudeCodeSystemPrompt(append: string, opts?: {
     append: string;
     excludeDynamicSections?: boolean;
 };
+/**
+ * 1.18.194 — Build the env Record for a direct SDK `query()` call so the
+ * Claude Code OAuth token reaches the SDK subprocess.
+ *
+ * Why this matters: `getSecret('CLAUDE_CODE_OAUTH_TOKEN')` reads
+ * ~/.clementine/.env and stores the value in the in-memory constant
+ * `CLAUDE_CODE_OAUTH_TOKEN` — it intentionally does NOT write to
+ * process.env (config.ts:478 keeps secrets out of process.env to prevent
+ * leakage). When a direct `query()` call omits `env:`, the SDK defaults
+ * to `process.env` — which doesn't have the token — and authentication
+ * silently falls back to API-key mode and fails with "Not logged in".
+ *
+ * 1.18.192 fixed the systemPrompt shape (preset vs raw string) but missed
+ * this env-propagation half of the same auth bug. Daily-planner, weekly
+ * review, bg-planner, and several other Haiku utility paths were still
+ * silently failing AFTER 1.18.192 because env: wasn't being passed.
+ *
+ * Use this alongside `claudeCodeSystemPrompt()` for every direct `query()`
+ * call. The runAgent path already builds its own env via buildRunAgentEnv;
+ * the assistant.ts auto-memory + verifier already use SAFE_ENV (same
+ * pattern). This helper exists for the lightweight utility callers.
+ *
+ * Priority order matches buildRunAgentEnv: OAuth > ANTHROPIC_AUTH_TOKEN > API key.
+ */
+export declare function claudeCodeSubprocessEnv(): Record<string, string>;
 export declare function normalizeClaudeModelForOneMillionContext(model: string, mode?: OneMillionContextMode): string;
 export declare function usesOneMillionContext(model: string | null | undefined, mode?: OneMillionContextMode, plan?: ClaudePlan): boolean;
 /**

package/dist/config.js

@@ -225,6 +225,51 @@ export function claudeCodeSystemPrompt(append, opts) {
         ...(opts?.minimal ? { excludeDynamicSections: true } : {}),
     };
 }
+/**
+ * 1.18.194 — Build the env Record for a direct SDK `query()` call so the
+ * Claude Code OAuth token reaches the SDK subprocess.
+ *
+ * Why this matters: `getSecret('CLAUDE_CODE_OAUTH_TOKEN')` reads
+ * ~/.clementine/.env and stores the value in the in-memory constant
+ * `CLAUDE_CODE_OAUTH_TOKEN` — it intentionally does NOT write to
+ * process.env (config.ts:478 keeps secrets out of process.env to prevent
+ * leakage). When a direct `query()` call omits `env:`, the SDK defaults
+ * to `process.env` — which doesn't have the token — and authentication
+ * silently falls back to API-key mode and fails with "Not logged in".
+ *
+ * 1.18.192 fixed the systemPrompt shape (preset vs raw string) but missed
+ * this env-propagation half of the same auth bug. Daily-planner, weekly
+ * review, bg-planner, and several other Haiku utility paths were still
+ * silently failing AFTER 1.18.192 because env: wasn't being passed.
+ *
+ * Use this alongside `claudeCodeSystemPrompt()` for every direct `query()`
+ * call. The runAgent path already builds its own env via buildRunAgentEnv;
+ * the assistant.ts auto-memory + verifier already use SAFE_ENV (same
+ * pattern). This helper exists for the lightweight utility callers.
+ *
+ * Priority order matches buildRunAgentEnv: OAuth > ANTHROPIC_AUTH_TOKEN > API key.
+ */
+export function claudeCodeSubprocessEnv() {
+    const env = {
+        PATH: process.env.PATH ?? '',
+        HOME: process.env.HOME ?? '',
+        LANG: process.env.LANG ?? 'en_US.UTF-8',
+        TERM: process.env.TERM ?? 'xterm-256color',
+        USER: process.env.USER ?? '',
+        SHELL: process.env.SHELL ?? '',
+        CLEMENTINE_HOME: BASE_DIR,
+    };
+    const oauthTok = CLAUDE_CODE_OAUTH_TOKEN || process.env.CLAUDE_CODE_OAUTH_TOKEN;
+    const authTok = process.env.ANTHROPIC_AUTH_TOKEN;
+    const apiKey = ANTHROPIC_API_KEY || process.env.ANTHROPIC_API_KEY;
+    if (oauthTok)
+        env.CLAUDE_CODE_OAUTH_TOKEN = oauthTok;
+    else if (authTok)
+        env.ANTHROPIC_AUTH_TOKEN = authTok;
+    else if (apiKey)
+        env.ANTHROPIC_API_KEY = apiKey;
+    return env;
+}
 export function normalizeClaudeModelForOneMillionContext(model, mode = currentOneMillionContextMode()) {
     const family = modelFamily(model);
     if (mode === 'on')

package/dist/gateway/router.d.ts

@@ -87,7 +87,6 @@ export declare class Gateway {
     private createBackgroundOffer;
     private queueBackgroundOffer;
     private formatBackgroundQueuedResponse;
-    private queueBackgroundTaskAfterContextOverflow;
     /**
      * 1.18.191 — chat-side plan mode state machine.
      *

package/dist/gateway/router.js

@@ -49,15 +49,13 @@ const CHAT_TIMEOUT_MS = 10 * 60 * 1000;
  *  Safety net so no session runs forever, even if active.
  *  Primary guardrail is cost budget (maxBudgetUsd), not this timer. */
 const CHAT_MAX_WALL_MS = 30 * 60 * 1000;
-// 1.18.189 — tightened from 6_000 / 16_000 because the recovery prompt
-// was eating ~22KB of the bg-task worker's context window before any
-// real work started. On 2026-05-12 the worker autocompact-thrashed while
-// reading project files; the new tighter caps give it ~10KB more headroom
-// to do actual tool calls. The dropped content (older memory recall,
-// less-relevant bg-task headlines) is recoverable via memory_search if
-// the model actually needs it.
+// 1.18.189 — tightened cap on retry-recovery context. 1.18.194 — only
+// CHAT_CONTEXT_RETRY_CONTEXT_MAX_CHARS still has a caller (the legacy
+// buildContextOverflowRetryPrompt, exported for an existing unit test
+// but no longer invoked from the chat path). The system-prompt-cap was
+// removed when we deleted the in-line retry loop in favor of trusting
+// the SDK's own autocompact.
 const CHAT_CONTEXT_RETRY_CONTEXT_MAX_CHARS = 3_000;
-const CHAT_CONTEXT_RETRY_SYSTEM_MAX_CHARS = 8_000;
 const BACKGROUND_TASK_ID_RE = /\bbg-[a-z0-9]+-[a-f0-9]{6}\b/i;
 function collectRunToolNames(runId) {
     if (!runId)
@@ -429,46 +427,12 @@ export class Gateway {
             `Use \`status ${task.id}\` or check the dashboard Background Tasks panel for progress.`,
         ].join('\n');
     }
-    queueBackgroundTaskAfterContextOverflow(sessionKey, prompt) {
-        // 1.18.190 — the chat-overflow recovery path is now the canonical
-        // entry to the planner-orchestrator chain. Instead of queuing a
-        // monolithic bg-task that tries to do everything in one worker
-        // (which thrashed when the worker's context filled), we queue a
-        // planner task. The planner is a tiny Sonnet LLM call that
-        // decomposes the user's request into 3-7 PlanSteps; the
-        // orchestrator then dispatches one step at a time, each with
-        // its own fresh 200K worker window. See agent/bg-planner.ts +
-        // agent/bg-orchestrator.ts for the full pattern.
-        //
-        // The legacy `detectComplexTaskForBackground` heuristic is no
-        // longer used here — the planner itself decides how to decompose,
-        // and per-step maxMinutes is governed by orchestrator settings.
-        // Planner tasks get a tight 5-minute cap; total chain wall-clock
-        // is the sum of each step's own maxMinutes.
-        const task = createBackgroundTask({
-            fromAgent: this.backgroundAgentForSession(sessionKey),
-            prompt,
-            maxMinutes: 5, // planner needs minutes, not hours
-            sessionKey,
-            kind: 'planner',
-        });
-        logger.warn({
-            taskId: task.id,
-            sessionKey,
-            fromAgent: task.fromAgent,
-            kind: 'planner',
-        }, 'Queued planner task after repeated chat context overflow');
-        return {
-            task,
-            response: [
-                `The live chat context hit the limit, so I'm decomposing your request into chained steps via background task **${task.id}**.`,
-                '',
-                `Step 1: a Sonnet planner reads the request and emits a plan (~30 seconds).`,
-                `Then each step runs as its own fresh task — you'll see step-by-step updates rather than one big "done" at the end.`,
-                `Use \`status ${task.id}\` or the dashboard Background Tasks panel for progress.`,
-            ].join('\n'),
-        };
-    }
+    // 1.18.194 — `queueBackgroundTaskAfterContextOverflow` removed.
+    // The chat-overflow path no longer auto-fires the planner. Instead
+    // the chat-error handler surfaces a clean "rephrase or `/plan`"
+    // message and trusts the SDK's own autocompact. The planner +
+    // orchestrator stay available as the implementation behind explicit
+    // `/plan` (see `_maybeHandlePlanMode`).
     /**
      * 1.18.191 — chat-side plan mode state machine.
      *
@@ -2350,7 +2314,6 @@ export class Gateway {
                     // Interrupt flag was set but no useful partial text — just clear it.
                     delete sessState.pendingInterrupt;
                 }
-                let contextOverflowRecoveryPrompt = '';
                 try {
                     // ── Canonical SDK chat path (Phase 5) ────────────────────────
                     // runAgent() owns chat. No legacy fallback — errors propagate
@@ -2493,7 +2456,6 @@ export class Gateway {
                     const chatSystemAppend = resolvedSkills && resolvedSkills.promptBlock
                         ? (baseSystemAppend ? `${baseSystemAppend}\n\n${resolvedSkills.promptBlock}` : resolvedSkills.promptBlock)
                         : baseSystemAppend;
-                    const retrySystemAppend = trimContextRecoveryText(chatSystemAppend, CHAT_CONTEXT_RETRY_SYSTEM_MAX_CHARS);
                     // Per-turn context (recall + persistent learnings + silent
                     // blocks + security/toolset directives) — real chat only.
                     // Builder doesn't need recall of unrelated transcripts.
@@ -2638,34 +2600,12 @@ export class Gateway {
                         },
                         abortSignal: chatAc.signal,
                     });
-                    let didContextOverflowRetry = false;
-                    const contextOverflowAfterRetryError = () => new Error('rapid_refill_breaker after context overflow retry');
-                    const retryAfterContextOverflow = async () => {
-                        if (didContextOverflowRetry)
-                            throw contextOverflowAfterRetryError();
-                        didContextOverflowRetry = true;
-                        const retryPrompt = buildContextOverflowRetryPrompt({
-                            chatPrompt,
-                            turnContextPrefix,
-                            project: sess?.project ?? null,
-                        });
-                        contextOverflowRecoveryPrompt = retryPrompt;
-                        logger.info({
-                            sessionKey: effectiveSessionKey,
-                            hadResume: !!priorSdkSessionId,
-                            promptChars: finalPrompt.length,
-                            retryPromptChars: retryPrompt.length,
-                            systemAppendChars: chatSystemAppend.length,
-                            retrySystemAppendChars: retrySystemAppend.length,
-                        }, 'Context overflow — retrying current message in fresh SDK session');
-                        if (onProgress) {
-                            await onProgress('refreshing conversation context...').catch(() => { });
-                        }
-                        this.assistant.clearSession(effectiveSessionKey);
-                        return runAgent(retryPrompt, buildRunAgentChatOptions({
-                            ...(retrySystemAppend ? { systemPromptAppend: retrySystemAppend } : {}),
-                        }));
-                    };
+                    // 1.18.194 — single SDK call. The SDK does its own autocompact
+                    // internally; we don't layer our own compress-and-retry on top.
+                    // If the SDK returns context_overflow (either thrown or as a
+                    // result with terminalReason), we surface a clean "rephrase or
+                    // /plan" message via the `case 'context_overflow':` handler
+                    // below. No more "Planning failed" half-finished chains.
                     let runAgentResult;
                     try {
                         runAgentResult = await runAgent(finalPrompt, buildRunAgentChatOptions({
@@ -2677,34 +2617,18 @@ export class Gateway {
                         if (chatAc.signal.aborted || classifyChatError(err) !== 'context_overflow') {
                             throw err;
                         }
-                        runAgentResult = await retryAfterContextOverflow();
+                        // Re-throw so the outer catch's classifyChatError gets it
+                        // and routes to the 'context_overflow' case.
+                        throw err;
                     }
                     if (!chatAc.signal.aborted && runAgentResultIndicatesContextOverflow(runAgentResult)) {
-                        if (didContextOverflowRetry) {
-                            logger.info({
-                                sessionKey: effectiveSessionKey,
-                                subtype: runAgentResult.subtype,
-                                terminalReason: runAgentResult.terminalReason,
-                                textPreview: runAgentResult.text?.slice(0, 240),
-                            }, 'Context overflow result after retry — queueing background task');
-                            throw contextOverflowAfterRetryError();
-                        }
                         logger.info({
                             sessionKey: effectiveSessionKey,
                             subtype: runAgentResult.subtype,
                             terminalReason: runAgentResult.terminalReason,
                             textPreview: runAgentResult.text?.slice(0, 240),
-                        }, 'Context overflow result — retrying current message in fresh SDK session');
-                        runAgentResult = await retryAfterContextOverflow();
-                        if (runAgentResultIndicatesContextOverflow(runAgentResult)) {
-                            logger.info({
-                                sessionKey: effectiveSessionKey,
-                                subtype: runAgentResult.subtype,
-                                terminalReason: runAgentResult.terminalReason,
-                                textPreview: runAgentResult.text?.slice(0, 240),
-                            }, 'Context overflow result after retry — queueing background task');
-                            throw contextOverflowAfterRetryError();
-                        }
+                        }, 'Context overflow result — autocompact ceiling reached, surfacing recovery message');
+                        throw new Error('context_overflow_after_autocompact');
                     }
                     if (ledgerRunMetadata) {
                         ledgerRunMetadata.runId = runAgentResult.runId;
@@ -2789,19 +2713,31 @@ export class Gateway {
                             applyOneMillionContextRecovery();
                             this.clearSession(effectiveSessionKey);
                             return oneMillionContextRecoveryMessage();
-                        case 'context_overflow':
-                            logger.info({ sessionKey }, 'Context overflow after retry — queueing background task');
+                        case 'context_overflow': {
+                            // 1.18.194 — trust the SDK. By the time we see context_overflow
+                            // here, the SDK has ALREADY tried autocompact (it's built-in).
+                            // Our previous behavior was to compress + retry + queue a
+                            // separate planner background task. That layered our own
+                            // retry on top of the SDK's, and when any step in the planner
+                            // pipeline failed (auth, planning, chain dispatch), users saw
+                            // a confusing "Planning failed" message — that's what bit
+                            // Zach. SDK best practice: when autocompact + retry have both
+                            // failed, that's a real context ceiling. Surface a clean
+                            // message that gives the owner two recovery options, clear
+                            // the session pointer, and trust them to resend smaller or
+                            // opt in to explicit plan mode.
+                            logger.info({ sessionKey }, 'Context overflow — autocompact ceiling reached, resetting');
                             this.assistant.clearSession(effectiveSessionKey);
-                            {
-                                const promptForBackground = contextOverflowRecoveryPrompt || chatPrompt;
-                                const { response, task } = this.queueBackgroundTaskAfterContextOverflow(sessionKey, promptForBackground);
-                                if (ledgerRunMetadata) {
-                                    ledgerRunMetadata.executionMode = 'background_queued';
-                                    ledgerRunMetadata.backgroundTaskId = task.id;
-                                }
-                                this.mirrorChatExchange(sessionKey, originalText, response, { model: 'chat-control' });
-                                return response;
-                            }
+                            const response = [
+                                "That work pushed past the context limit even with autocompact.",
+                                "I've reset our conversation. Two ways forward:",
+                                "",
+                                "1. Rephrase the task in smaller scope (e.g. 'just the first 10' instead of 'all 100')",
+                                "2. Use `/plan` to have me decompose it into chained workers before running",
+                            ].join('\n');
+                            this.mirrorChatExchange(sessionKey, originalText, response, { model: 'chat-control' });
+                            return response;
+                        }
                         case 'auth':
                             this.recordAuthFailure();
                             return "I'm temporarily offline due to an authentication issue. The owner needs to re-authenticate — I'll recover automatically once it's resolved.";

package/dist/index.js

@@ -638,6 +638,8 @@ async function asyncMain() {
                             // 1.18.192 — preset form so SDK uses Claude Code subscription
                             // auth (raw string → API-key path → "Not logged in" for Max users).
                             systemPrompt: config.claudeCodeSystemPrompt('You are a memory consolidation assistant. Be concise.', { minimal: true }),
+                            // 1.18.194 — propagate OAuth token to SDK subprocess.
+                            env: config.claudeCodeSubprocessEnv(),
                         }),
                     });
                     for await (const msg of stream) {

package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "clementine-agent",
-  "version": "1.18.193",
+  "version": "1.18.194",
   "description": "Clementine — Personal AI Assistant (TypeScript)",
   "type": "module",
   "main": "dist/index.js",