gsd-pi 2.76.0 → 2.77.0-dev.2daa994b6

package/packages/pi-coding-agent/src/core/compaction/compaction.ts

@@ -16,6 +16,7 @@ import {
 	computeFileLists,
 	createFileOps,
 	createSummarizationMessage,
+	estimateSerializedTokens,
 	extractFileOpsFromMessage,
 	extractTextContent,
 	type FileOperations,
@@ -500,7 +501,13 @@ export function chunkMessages(messages: AgentMessage[], maxTokensPerChunk: numbe
 	let currentTokens = 0;
 
 	for (const msg of messages) {
-		const msgTokens = estimateTokens(msg);
+		// Use POST-truncation token estimate: serializeConversation caps every
+		// large content block to TOOL_RESULT_MAX_CHARS before sending to the LLM,
+		// so chunk sizing must reflect what the LLM will actually see. Using the
+		// pre-truncation `estimateTokens` here was the root cause of issue #4665:
+		// a single 400K-char tool result looked like 100K tokens but serialized
+		// to ~600 tokens, producing tens of tiny information-starved chunks.
+		const msgTokens = estimateSerializedTokens(msg);
 
 		if (currentChunk.length > 0 && currentTokens + msgTokens > maxTokensPerChunk) {
 			// Current chunk is full — start a new one
@@ -520,6 +527,39 @@ export function chunkMessages(messages: AgentMessage[], maxTokensPerChunk: numbe
 	return chunks;
 }
 
+// ============================================================================
+// Degenerate summary detection (issue #4665)
+// ============================================================================
+
+/**
+ * Heuristic: does this summary look like the "empty conversation" degenerate
+ * output that poisons the iterative UPDATE_SUMMARIZATION_PROMPT chain?
+ *
+ * The LLM occasionally returns short empty-sounding summaries when a chunk
+ * contains only truncated tool-call preambles without results. If the chain
+ * propagates this forward, every subsequent chunk is told to "PRESERVE all
+ * existing information" — which preserves the emptiness.
+ *
+ * Conservative match: an explicit substring hit OR length < 100 chars. We keep
+ * this deterministic (no fuzzy scoring) because fuzzy matching is where
+ * quality gates become flaky and hard to test.
+ *
+ * Exported for test access only.
+ */
+export function isDegenerateSummary(summary: string | undefined): boolean {
+	// undefined means "no summary was produced yet" (first chunk before any call)
+	// — not degenerate. Empty string IS degenerate: the LLM returned nothing.
+	if (summary === undefined) return false;
+	const lower = summary.toLowerCase();
+	if (lower.includes("empty conversation")) return true;
+	if (lower.includes("no conversation to summarize")) return true;
+	if (lower.includes("no messages to summarize")) return true;
+	// Length guard: any summary shorter than 100 chars is almost certainly
+	// degenerate for a multi-chunk pipeline.
+	if (summary.trim().length < 100) return true;
+	return false;
+}
+
 /** Type for the completion function, allowing injection for tests. */
 type CompleteFn = typeof completeSimple;
 
@@ -545,10 +585,12 @@ export async function generateSummary(
 ): Promise<string> {
 	const complete = _completeFn ?? completeSimple;
 
-	// Estimate total tokens for the messages to summarize
+	// Estimate total tokens using the POST-truncation serializer view (issue #4665).
+	// serializeConversation caps large content blocks to TOOL_RESULT_MAX_CHARS
+	// before sending, so asking "does this fit in one pass?" must reflect that.
 	let totalTokens = 0;
 	for (const msg of currentMessages) {
-		totalTokens += estimateTokens(msg);
+		totalTokens += estimateSerializedTokens(msg);
 	}
 
 	// Overhead for the prompt framing, system prompt, and response budget
@@ -561,12 +603,12 @@ export async function generateSummary(
 		return singlePassSummary(currentMessages, model, reserveTokens, apiKey, signal, customInstructions, previousSummary, complete);
 	}
 
-	// Chunked fallback: split messages and iteratively summarize
+	// Chunked fallback: split messages and iteratively summarize.
 	const chunks = chunkMessages(currentMessages, maxInputTokens);
 	let runningSummary = previousSummary;
 
 	for (let i = 0; i < chunks.length; i++) {
-		runningSummary = await singlePassSummary(
+		const chunkSummary = await singlePassSummary(
 			chunks[i],
 			model,
 			reserveTokens,
@@ -576,9 +618,83 @@ export async function generateSummary(
 			runningSummary,
 			complete,
 		);
+
+		// Degenerate-summary guard (issue #4665). UPDATE_SUMMARIZATION_PROMPT says
+		// "PRESERVE all existing information" — so if a chunk summary is empty or
+		// near-empty, propagating it forward actively reinforces the emptiness
+		// for every subsequent chunk.
+		//
+		// Strategy per chunk:
+		//   1. If degenerate, retry once. For the FIRST chunk with no prior
+		//      context, retry with the initial prompt (undefined previousSummary)
+		//      to break the poison chain at its source. For later chunks, retry
+		//      with the same prompt state (runningSummary preserved) since the
+		//      first failure may have been transient.
+		//   2. If the retry is also degenerate, warn and continue WITHOUT
+		//      updating runningSummary — losing that chunk's content is still
+		//      preferable to propagating emptiness forward, but the drop is now
+		//      observable in logs.
+		if (isDegenerateSummary(chunkSummary)) {
+			const retryPreviousSummary = i === 0 && runningSummary === undefined
+				? undefined
+				: runningSummary;
+			const retry = await singlePassSummary(
+				chunks[i],
+				model,
+				reserveTokens,
+				apiKey,
+				signal,
+				customInstructions,
+				retryPreviousSummary,
+				complete,
+			);
+			if (!isDegenerateSummary(retry)) {
+				runningSummary = retry;
+				continue;
+			}
+			// Both attempts degenerate — log and skip without poisoning the chain.
+			// Using process.stderr directly so this doesn't require the logger
+			// dependency graph. Visible to operators reviewing compaction health.
+			process.stderr.write(
+				`[compaction] WARN: chunk ${i + 1}/${chunks.length} produced a degenerate summary on both attempts; dropping chunk content from summary.\n`,
+			);
+			continue;
+		}
+
+		runningSummary = chunkSummary;
+	}
+
+	// R6 (issue #4665 follow-up): if every chunk was degenerate and we have no
+	// runningSummary, do NOT silently return "" — the caller would write an
+	// empty compaction entry, destroying all context with no signal. Fall back
+	// to the original previousSummary if available; otherwise throw a named
+	// error so the compaction pipeline can skip appending the entry.
+	if (runningSummary === undefined) {
+		if (previousSummary !== undefined) {
+			process.stderr.write(
+				"[compaction] WARN: every chunk produced a degenerate summary; falling back to existing previousSummary.\n",
+			);
+			return previousSummary;
+		}
+		throw new CompactionProducedNoSummaryError(
+			`Compaction produced no usable summary: all ${chunks.length} chunk(s) were degenerate and no previousSummary was available.`,
+		);
 	}
 
-	return runningSummary!;
+	return runningSummary;
+}
+
+/**
+ * Thrown when `generateSummary` could not produce any non-degenerate summary
+ * from the provided messages AND no previous summary was available to fall
+ * back to. Callers should catch this and skip writing a compaction entry
+ * rather than writing an empty string to the session history (issue #4665).
+ */
+export class CompactionProducedNoSummaryError extends Error {
+	constructor(message: string) {
+		super(message);
+		this.name = "CompactionProducedNoSummaryError";
+	}
 }
 
 /**

package/packages/pi-coding-agent/src/core/compaction/utils.ts

@@ -3,8 +3,14 @@
  */
 
 import type { AgentMessage } from "@gsd/pi-agent-core";
-import type { Message } from "@gsd/pi-ai";
+import type { AssistantMessage, Message } from "@gsd/pi-ai";
 import { TOOL_RESULT_MAX_CHARS } from "../constants.js";
+
+// Head/tail split for head+tail truncation. Keeps first half + last half up to
+// TOOL_RESULT_MAX_CHARS total. Tool results and other large blocks put their
+// information-dense content (exit codes, verdicts, commit hashes, pass/fail
+// counts) at the tail — pure head-slicing discards that signal. See issue #4665.
+const HEAD_TAIL_HALF = Math.floor(TOOL_RESULT_MAX_CHARS / 2);
 import {
 	createBranchSummaryMessage,
 	createCompactionSummaryMessage,
@@ -189,13 +195,20 @@ export function createSummarizationMessage(promptText: string): [{ role: "user";
 // TOOL_RESULT_MAX_CHARS imported from ../constants.js
 
 /**
- * Truncate text to a maximum character length for summarization.
- * Keeps the beginning and appends a truncation marker.
+ * Truncate text to a maximum character length for summarization, keeping both
+ * the head AND the tail. The tail is where information density lives for tool
+ * output (exit codes, verdicts, pass/fail counts, commit hashes), so pure
+ * head-slicing produced degenerate summaries (see issue #4665).
+ *
+ * Exported for test access only.
  */
-function truncateForSummary(text: string, maxChars: number): string {
+export function truncateForSummary(text: string, maxChars: number): string {
 	if (text.length <= maxChars) return text;
-	const truncatedChars = text.length - maxChars;
-	return `${text.slice(0, maxChars)}\n\n[... ${truncatedChars} more characters truncated]`;
+	const half = Math.floor(maxChars / 2);
+	const head = text.slice(0, half);
+	const tail = text.slice(text.length - half);
+	const truncatedChars = text.length - (head.length + tail.length);
+	return `${head}\n\n[... ${truncatedChars} more characters truncated ...]\n\n${tail}`;
 }
 
 /**
@@ -203,11 +216,15 @@ function truncateForSummary(text: string, maxChars: number): string {
  * This prevents the model from treating it as a conversation to continue.
  * Call convertToLlm() first to handle custom message types.
  *
- * Tool results are truncated to keep the summarization request within
- * reasonable token budgets. Full content is not needed for summarization.
+ * Every content block with a character count above TOOL_RESULT_MAX_CHARS is
+ * head+tail truncated. The issue #4665 fix broadened this from tool-results-
+ * only to every block type — large user pastes, assistant thinking, tool-call
+ * args, and bashExecution-derived blocks also bloat summarization input if
+ * uncapped.
  */
 export function serializeConversation(messages: Message[]): string {
 	const parts: string[] = [];
+	const cap = TOOL_RESULT_MAX_CHARS;
 
 	for (const msg of messages) {
 		if (msg.role === "user") {
@@ -218,7 +235,7 @@ export function serializeConversation(messages: Message[]): string {
 							.filter((c): c is { type: "text"; text: string } => c.type === "text")
 							.map((c) => c.text)
 							.join("");
-			if (content) parts.push(`**User said:** ${content}`);
+			if (content) parts.push(`**User said:** ${truncateForSummary(content, cap)}`);
 		} else if (msg.role === "assistant") {
 			const textParts: string[] = [];
 			const thinkingParts: string[] = [];
@@ -239,13 +256,13 @@ export function serializeConversation(messages: Message[]): string {
 			}
 
 			if (thinkingParts.length > 0) {
-				parts.push(`**Assistant thinking:** ${thinkingParts.join("\n")}`);
+				parts.push(`**Assistant thinking:** ${truncateForSummary(thinkingParts.join("\n"), cap)}`);
 			}
 			if (textParts.length > 0) {
-				parts.push(`**Assistant responded:** ${textParts.join("\n")}`);
+				parts.push(`**Assistant responded:** ${truncateForSummary(textParts.join("\n"), cap)}`);
 			}
 			if (toolCalls.length > 0) {
-				parts.push(`**Assistant tool calls:** ${toolCalls.join("; ")}`);
+				parts.push(`**Assistant tool calls:** ${truncateForSummary(toolCalls.join("; "), cap)}`);
 			}
 		} else if (msg.role === "toolResult") {
 			const content = msg.content
@@ -253,7 +270,7 @@ export function serializeConversation(messages: Message[]): string {
 				.map((c) => c.text)
 				.join("");
 			if (content) {
-				parts.push(`**Tool result:** ${truncateForSummary(content, TOOL_RESULT_MAX_CHARS)}`);
+				parts.push(`**Tool result:** ${truncateForSummary(content, cap)}`);
 			}
 		}
 	}
@@ -261,6 +278,87 @@ export function serializeConversation(messages: Message[]): string {
 	return parts.join("\n\n");
 }
 
+// ============================================================================
+// Token estimation for post-serialization size
+// ============================================================================
+
+/**
+ * Estimate tokens for a message AFTER the summarization serializer will have
+ * capped its large content blocks. Use this when deciding chunk sizes for
+ * summarization — NOT when deciding whether to compact in the first place
+ * (that needs the real in-memory content size via `estimateTokens`).
+ *
+ * See issue #4665: the old chunker used real content size but the serializer
+ * truncated tool results to 2000 chars, so a single 400K-char tool result
+ * looked like 100K tokens (triggering tens of unnecessary chunks) but actually
+ * serialized to ~600 tokens.
+ *
+ * Colocated with `truncateForSummary` / `serializeConversation` so the two
+ * stay in sync — if the serialization cap changes, both functions pick it up
+ * from `TOOL_RESULT_MAX_CHARS`.
+ */
+export function estimateSerializedTokens(message: AgentMessage): number {
+	const cap = TOOL_RESULT_MAX_CHARS;
+	const capLen = (len: number) => Math.min(len, cap);
+	let chars = 0;
+
+	switch (message.role) {
+		case "user": {
+			const content = (message as { content: string | Array<{ type: string; text?: string }> }).content;
+			if (typeof content === "string") {
+				chars = capLen(content.length);
+			} else if (Array.isArray(content)) {
+				let total = 0;
+				for (const block of content) {
+					if (block.type === "text" && block.text) total += block.text.length;
+				}
+				chars = capLen(total);
+			}
+			return Math.ceil(chars / 4);
+		}
+		case "assistant": {
+			const assistant = message as AssistantMessage;
+			let textLen = 0;
+			let thinkingLen = 0;
+			let toolCallsLen = 0;
+			for (const block of assistant.content) {
+				if (block.type === "text") textLen += block.text.length;
+				else if (block.type === "thinking") thinkingLen += block.thinking.length;
+				else if (block.type === "toolCall") toolCallsLen += block.name.length + JSON.stringify(block.arguments).length;
+			}
+			chars = capLen(textLen) + capLen(thinkingLen) + capLen(toolCallsLen);
+			return Math.ceil(chars / 4);
+		}
+		case "custom":
+		case "toolResult": {
+			if (typeof message.content === "string") {
+				chars = capLen(message.content.length);
+			} else {
+				let textLen = 0;
+				let imageChars = 0;
+				for (const block of message.content) {
+					if (block.type === "text" && block.text) textLen += block.text.length;
+					if (block.type === "image") imageChars += 4800;
+				}
+				chars = capLen(textLen) + imageChars;
+			}
+			return Math.ceil(chars / 4);
+		}
+		case "bashExecution": {
+			chars = capLen(message.command.length + message.output.length);
+			return Math.ceil(chars / 4);
+		}
+		case "branchSummary":
+		case "compactionSummary": {
+			// Summary messages are already concise; don't truncate them.
+			chars = message.summary.length;
+			return Math.ceil(chars / 4);
+		}
+	}
+
+	return 0;
+}
+
 // ============================================================================
 // Summarization System Prompt
 // ============================================================================

package/packages/pi-coding-agent/src/core/compaction-orchestrator.test.ts

@@ -0,0 +1,154 @@
+import assert from "node:assert/strict";
+import { mkdtempSync, rmSync } from "node:fs";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+import { describe, it, mock, type Mock } from "node:test";
+
+import type { Agent } from "@gsd/pi-agent-core";
+import type { Api, AssistantMessage, Model } from "@gsd/pi-ai";
+
+import { CompactionOrchestrator, type CompactionOrchestratorDeps } from "./compaction-orchestrator.js";
+import { SessionManager } from "./session-manager.js";
+
+function createMockModel(): Model<Api> {
+	return {
+		id: "claude-opus-4-6",
+		name: "Claude Opus 4.6",
+		api: "anthropic-messages" as Api,
+		provider: "anthropic",
+		baseUrl: "https://api.anthropic.com",
+		reasoning: false,
+		input: ["text"],
+		cost: { input: 0, output: 0, cacheRead: 0, cacheWrite: 0 },
+		contextWindow: 200_000,
+		maxTokens: 16_384,
+	} as Model<Api>;
+}
+
+function createAssistantMessage(
+	stopReason: AssistantMessage["stopReason"],
+	contentText: string,
+): AssistantMessage {
+	return {
+		role: "assistant",
+		content: [{ type: "text", text: contentText }],
+		api: "anthropic-messages",
+		provider: "anthropic",
+		model: "claude-opus-4-6",
+		usage: {
+			input: 100,
+			output: 100,
+			cacheRead: 0,
+			cacheWrite: 0,
+			totalTokens: 200,
+			cost: { input: 0, output: 0, cacheRead: 0, cacheWrite: 0, total: 0 },
+		},
+		stopReason,
+		timestamp: Date.now(),
+		errorMessage: stopReason === "error" ? contentText : undefined,
+	} as AssistantMessage;
+}
+
+function wait(ms: number): Promise<void> {
+	return new Promise((resolve) => setTimeout(resolve, ms));
+}
+
+function createHarness(overrides?: {
+	cancelResult?: boolean;
+	willRetry?: boolean;
+	hasQueuedMessages?: boolean;
+}) {
+	const dir = mkdtempSync(join(tmpdir(), "compaction-orchestrator-test-"));
+	const sessionManager = SessionManager.create(dir, dir);
+	sessionManager.appendMessage({ role: "user", content: "First user message" } as any);
+	sessionManager.appendMessage(createAssistantMessage("stop", "First assistant message"));
+	sessionManager.appendMessage({ role: "user", content: "Second user message" } as any);
+
+	const emittedEvents: Array<Record<string, unknown>> = [];
+	const continueFn = mock.fn(async () => {});
+	const replaceMessages = mock.fn((nextMessages: unknown[]) => {
+		(agent.state.messages as unknown[]) = nextMessages;
+	});
+	const agent = {
+		state: {
+			messages: [
+				{ role: "user", content: "queued follow-up" },
+				createAssistantMessage("error", "context overflow"),
+			],
+		},
+		continue: continueFn,
+		replaceMessages,
+		hasQueuedMessages: () => overrides?.hasQueuedMessages ?? false,
+	} as unknown as Agent;
+
+	const extensionRunner = {
+		hasHandlers: mock.fn(() => true),
+		emit: mock.fn(async () => ({ cancel: overrides?.cancelResult ?? true })),
+	};
+
+	const deps: CompactionOrchestratorDeps = {
+		agent,
+		sessionManager,
+		settingsManager: {
+			getCompactionSettings: () => ({
+				enabled: true,
+				reserveTokens: 16_384,
+				keepRecentTokens: 1,
+			}),
+		} as any,
+		modelRegistry: {
+			isProviderRequestReady: () => true,
+			getApiKey: async () => undefined,
+		} as any,
+		getModel: () => createMockModel(),
+		getSessionId: () => "test-session",
+		getExtensionRunner: () => extensionRunner as any,
+		emit: (event) => emittedEvents.push(event as unknown as Record<string, unknown>),
+		disconnectFromAgent: () => {},
+		reconnectToAgent: () => {},
+		abort: async () => {},
+	};
+
+	return {
+		dir,
+		agent,
+		continueFn,
+		replaceMessages,
+		emittedEvents,
+		extensionRunner,
+		orchestrator: new CompactionOrchestrator(deps),
+		cleanup: () => rmSync(dir, { recursive: true, force: true }),
+	};
+}
+
+describe("CompactionOrchestrator", () => {
+	it("overflow cancel keeps retry intent and resumes the agent (#3971)", async (t) => {
+		const harness = createHarness({ willRetry: true });
+		t.after(harness.cleanup);
+
+		await (harness.orchestrator as any)._runAutoCompaction("overflow", true);
+		await wait(150);
+
+		const endEvent = harness.emittedEvents.find((event) => event.type === "auto_compaction_end");
+		assert.ok(endEvent, "should emit auto_compaction_end");
+		assert.equal(endEvent?.aborted, true, "cancelled compaction should be marked aborted");
+		assert.equal(endEvent?.willRetry, true, "overflow cancel should preserve retry intent");
+		assert.equal(harness.continueFn.mock.callCount(), 1, "overflow cancel should resume the agent");
+		assert.equal(harness.replaceMessages.mock.callCount(), 1, "retry follow-up should trim the error message when present");
+	});
+
+	it("threshold cancel stays non-retrying when no queued messages exist", async (t) => {
+		const harness = createHarness({ willRetry: false, hasQueuedMessages: false });
+		t.after(harness.cleanup);
+
+		await (harness.orchestrator as any)._runAutoCompaction("threshold", false);
+		await wait(150);
+
+		const endEvent = harness.emittedEvents.find((event) => event.type === "auto_compaction_end");
+		assert.ok(endEvent, "should emit auto_compaction_end");
+		assert.equal(endEvent?.aborted, true, "cancelled compaction should be marked aborted");
+		assert.equal(endEvent?.willRetry, false, "threshold cancel should stay non-retrying");
+		assert.equal(harness.continueFn.mock.callCount(), 0, "threshold cancel should not resume the agent without queued work");
+		assert.equal(harness.replaceMessages.mock.callCount(), 0, "non-retry cancel should not trim messages");
+	});
+});

package/packages/pi-coding-agent/src/core/compaction-orchestrator.ts

@@ -14,6 +14,7 @@ import type { AssistantMessage, Model } from "@gsd/pi-ai";
 import { isContextOverflow } from "@gsd/pi-ai";
 import {
 	type CompactionResult,
+	CompactionProducedNoSummaryError,
 	calculateContextTokens,
 	compact,
 	estimateContextTokens,
@@ -332,8 +333,9 @@ export class CompactionOrchestrator {
 						type: "auto_compaction_end",
 						result: undefined,
 						aborted: true,
-						willRetry: false,
+						willRetry,
 					});
+					this._scheduleAutoCompactionFollowup(willRetry);
 					return;
 				}
 
@@ -391,24 +393,15 @@ export class CompactionOrchestrator {
 
 			const result: CompactionResult = { summary, firstKeptEntryId, tokensBefore, details };
 			this._deps.emit({ type: "auto_compaction_end", result, aborted: false, willRetry });
-
-			if (willRetry) {
-				const messages = this._deps.agent.state.messages;
-				const lastMsg = messages[messages.length - 1];
-				if (lastMsg?.role === "assistant" && (lastMsg as AssistantMessage).stopReason === "error") {
-					this._deps.agent.replaceMessages(messages.slice(0, -1));
-				}
-
-				setTimeout(() => {
-					this._deps.agent.continue().catch(() => {});
-				}, 100);
-			} else if (this._deps.agent.hasQueuedMessages()) {
-				setTimeout(() => {
-					this._deps.agent.continue().catch(() => {});
-				}, 100);
-			}
+			this._scheduleAutoCompactionFollowup(willRetry);
 		} catch (error) {
-			const errorMessage = getErrorMessage(error);
+			// Distinguish the "no usable summary" failure (issue #4665) so the UI
+			// can surface a clearer message than a generic compaction failure.
+			// Either way we drop the would-be compaction entry rather than writing
+			// an empty string to the session history.
+			const errorMessage = error instanceof CompactionProducedNoSummaryError
+				? `Compaction produced no usable summary — session history preserved as-is. (${error.message})`
+				: getErrorMessage(error);
 			this._deps.emit({
 				type: "auto_compaction_end",
 				result: undefined,
@@ -423,4 +416,25 @@ export class CompactionOrchestrator {
 			this._autoCompactionAbortController = undefined;
 		}
 	}
+
+	private _scheduleAutoCompactionFollowup(willRetry: boolean): void {
+		if (willRetry) {
+			const messages = this._deps.agent.state.messages;
+			const lastMsg = messages[messages.length - 1];
+			if (lastMsg?.role === "assistant" && (lastMsg as AssistantMessage).stopReason === "error") {
+				this._deps.agent.replaceMessages(messages.slice(0, -1));
+			}
+
+			setTimeout(() => {
+				this._deps.agent.continue().catch(() => {});
+			}, 100);
+			return;
+		}
+
+		if (this._deps.agent.hasQueuedMessages()) {
+			setTimeout(() => {
+				this._deps.agent.continue().catch(() => {});
+			}, 100);
+		}
+	}
 }

package/packages/pi-coding-agent/src/core/compaction-utils.test.ts

@@ -3,7 +3,7 @@ import test from "node:test";
 
 import type { Message } from "@gsd/pi-ai";
 
-import { serializeConversation } from "./compaction/index.js";
+import { serializeConversation, truncateForSummary } from "./compaction/index.js";
 
 test("serializeConversation uses narrative role markers instead of chat-style delimiters (#4054)", () => {
 	const messages: Message[] = [
@@ -48,3 +48,70 @@ test("serializeConversation uses narrative role markers instead of chat-style de
 	assert.ok(!serialized.includes("[Assistant]:"), "chat-style [Assistant]: markers should not remain");
 	assert.ok(!serialized.includes("[Tool result]:"), "chat-style [Tool result]: markers should not remain");
 });
+
+// ---------------------------------------------------------------------------
+// #4665 regression: head+tail truncation keeps verdicts/results
+// ---------------------------------------------------------------------------
+
+test("(#4665) truncateForSummary keeps both head AND tail — tail carries result/verdict text", () => {
+	// Construct a 10K-char fixture where the HEAD is "setup noise" and the TAIL
+	// contains a result line. The old head-only truncation would drop the tail
+	// and lose the result. The fix preserves both.
+	const head = "setup log line A\n".repeat(500); // ~8500 chars of setup
+	const tail = "RESULT: 258 passed, 0 failed. exit_code=0 commit=abc1234";
+	const input = head + tail;
+
+	const out = truncateForSummary(input, 2_000);
+
+	assert.ok(out.length < input.length, "must truncate when over cap");
+	assert.ok(out.includes("setup log line A"), "head content preserved");
+	assert.ok(out.includes("RESULT: 258 passed"), "tail content preserved (issue #4665)");
+	assert.match(out, /more characters truncated/, "emits an elision marker");
+});
+
+test("(#4665) truncateForSummary is a no-op when input is within the cap", () => {
+	const input = "short enough";
+	assert.equal(truncateForSummary(input, 2_000), input);
+});
+
+test("(#4665) serializeConversation caps large user content, not just tool results", () => {
+	// Pre-fix, only toolResult blocks were capped. A large user paste could
+	// still blow out the chunker's token math and the LLM's input budget.
+	const hugeUserText = "U".repeat(100_000);
+	const hugeAssistantText = "A".repeat(100_000);
+	const hugeToolResult = "T".repeat(100_000);
+
+	const messages: Message[] = [
+		{ role: "user", content: hugeUserText } as Message,
+		{
+			role: "assistant",
+			content: [{ type: "text", text: hugeAssistantText }],
+			api: "anthropic-messages",
+			provider: "anthropic",
+			model: "claude-sonnet-4-6",
+			usage: {
+				input: 0, output: 0, cacheRead: 0, cacheWrite: 0, totalTokens: 0,
+				cost: { input: 0, output: 0, cacheRead: 0, cacheWrite: 0, total: 0 },
+			},
+			stopReason: "stop",
+			timestamp: Date.now(),
+		} as Message,
+		{
+			role: "toolResult",
+			content: [{ type: "text", text: hugeToolResult }],
+			toolName: "Bash",
+			toolCallId: "tool-huge",
+		} as Message,
+	];
+
+	const serialized = serializeConversation(messages);
+
+	// Each block is truncated independently to TOOL_RESULT_MAX_CHARS plus the
+	// framing marker, so the serialized output should be a tiny fraction of
+	// the raw 300K chars of content.
+	assert.ok(
+		serialized.length < 10_000,
+		`serialized output should be small after capping all blocks, got ${serialized.length} chars`,
+	);
+	assert.match(serialized, /more characters truncated/, "truncation marker present");
+});