fix(compaction): honor /clear reset boundary in prepareCompaction

prepareCompaction walked the branch from the last compaction and ignored reset_boundary markers, so /compact (and auto-compaction) resurrected pre-/clear turns into the summary even though buildSessionContext already starts the model context after the boundary.

Model reset_boundary as a first-class agent-core session entry and start the summarization window after the latest boundary, dropping the superseded pre-reset compaction summary. A boundary before the last compaction stays superseded by it.

Fixes #8718

packages/agent/CHANGELOG.md

@@ -2,6 +2,10 @@
 
 ## [Unreleased]
 
+### Fixed
+
+- Fixed `/compact` (and automatic compaction) resurrecting pre-`/clear` conversation turns: `prepareCompaction` now honors the latest `reset_boundary`, so a compaction after an in-place `/clear` only summarizes messages created after the reset ([#8718](https://github.com/can1357/oh-my-pi/issues/8718)).
+
 ## [17.3.5] - 2026-08-16
 
 ### Added

packages/agent/src/compaction/compaction.ts

@@ -1271,7 +1271,26 @@ export function prepareCompaction(
 		prevCompactionIndex = i;
 		break;
 	}
-	const boundaryStart = prevCompactionIndex + 1;
+
+	// Honor the latest `/clear` reset boundary. `/clear` records a
+	// `reset_boundary` marker and reports the model context empty, so compaction
+	// must not resurrect the dropped pre-clear turns into its summary — matching
+	// how buildSessionContext starts the model-context rebuild after the boundary.
+	// A boundary after the last reusable compaction supersedes it: the pre-reset
+	// summary was cleared too, so drop the previous-compaction reuse and start
+	// fresh after the boundary. A boundary at or before that compaction is already
+	// superseded by it, so only scan newer entries.
+	let resetBoundaryIndex = -1;
+	for (let i = pathEntries.length - 1; i > prevCompactionIndex; i--) {
+		if (pathEntries[i].type === "reset_boundary") {
+			resetBoundaryIndex = i;
+			break;
+		}
+	}
+	if (resetBoundaryIndex > prevCompactionIndex) {
+		prevCompactionIndex = -1;
+	}
+	const boundaryStart = Math.max(prevCompactionIndex, resetBoundaryIndex) + 1;
 	const boundaryEnd = pathEntries.length;
 
 	const lastUsage = getLastAssistantUsage(pathEntries);

packages/agent/src/compaction/entries.ts

@@ -117,6 +117,16 @@ export interface ModeChangeEntry extends SessionEntryBase {
 	data?: Record<string, unknown>;
 }
 
+/**
+ * Durable context-reset marker recorded by an in-place `/clear`. It carries no
+ * payload — its presence on the branch means every entry before it was dropped
+ * from the model context, so context assembly and compaction start after the
+ * latest one. The full pre-reset history stays on disk for transcript export.
+ */
+export interface ResetBoundaryEntry extends SessionEntryBase {
+	type: "reset_boundary";
+}
+
 export interface CustomCompactionSessionEntries {}
 
 export type SessionEntry =
@@ -133,6 +143,7 @@ export type SessionEntry =
 	| TtsrInjectionEntry
 	| SessionInitEntry
 	| ModeChangeEntry
+	| ResetBoundaryEntry
 	| CustomCompactionSessionEntries[keyof CustomCompactionSessionEntries];
 
 export interface ReadonlySessionManager {

packages/agent/test/compact-reset-boundary.test.ts

@@ -0,0 +1,102 @@
+import { describe, expect, test } from "bun:test";
+import {
+	type CompactionEntry,
+	DEFAULT_COMPACTION_SETTINGS,
+	prepareCompaction,
+	type SessionEntry,
+} from "@oh-my-pi/pi-agent-core/compaction";
+import { createAssistantMessage, createUserMessage } from "./helpers";
+
+let seq = 0;
+function base(type: string) {
+	const id = `e${seq++}`;
+	return { id, parentId: null, timestamp: new Date().toISOString(), type };
+}
+function userEntry(text: string): SessionEntry {
+	return { ...base("message"), type: "message", message: createUserMessage(text) };
+}
+function assistantEntry(text: string): SessionEntry {
+	return {
+		...base("message"),
+		type: "message",
+		message: createAssistantMessage([{ type: "text", text }]),
+	};
+}
+function resetBoundary(): SessionEntry {
+	return { ...base("reset_boundary"), type: "reset_boundary" };
+}
+function compaction(summary: string, firstKeptEntryId: string): SessionEntry {
+	const entry: CompactionEntry = {
+		...base("compaction"),
+		type: "compaction",
+		summary,
+		firstKeptEntryId,
+		tokensBefore: 0,
+	};
+	return entry;
+}
+
+describe("prepareCompaction reset boundary", () => {
+	test("does not resurrect pre-clear turns into the summary", () => {
+		const entries: SessionEntry[] = [
+			userEntry("PRECLEAR user request"),
+			assistantEntry("PRECLEAR assistant answer"),
+			resetBoundary(),
+			userEntry("POSTCLEAR first request"),
+			assistantEntry("POSTCLEAR first answer"),
+			userEntry("POSTCLEAR second request"),
+			assistantEntry("POSTCLEAR second answer"),
+		];
+		const prep = prepareCompaction(entries, { ...DEFAULT_COMPACTION_SETTINGS, keepRecentTokens: 1 });
+		expect(prep).toBeDefined();
+		const summarized = JSON.stringify(prep?.messagesToSummarize ?? []);
+		const kept = JSON.stringify([...(prep?.turnPrefixMessages ?? []), ...(prep?.recentMessages ?? [])]);
+		expect(summarized).not.toContain("PRECLEAR");
+		expect(kept).not.toContain("PRECLEAR");
+		expect(summarized).toContain("POSTCLEAR first");
+	});
+
+	test("a reset boundary after the last compaction drops that compaction's summary reuse", () => {
+		const entries: SessionEntry[] = [
+			userEntry("OLD user"),
+			assistantEntry("OLD assistant"),
+			compaction("OLD SUMMARY", "kept-old"),
+			userEntry("MIDCLEAR user"),
+			assistantEntry("MIDCLEAR assistant"),
+			resetBoundary(),
+			userEntry("POST first"),
+			assistantEntry("POST first answer"),
+			userEntry("POST second"),
+			assistantEntry("POST second answer"),
+		];
+		const prep = prepareCompaction(entries, { ...DEFAULT_COMPACTION_SETTINGS, keepRecentTokens: 1 });
+		expect(prep).toBeDefined();
+		// The cleared compaction is not reused as previous context.
+		expect(prep?.previousSummary).toBeUndefined();
+		const summarized = JSON.stringify(prep?.messagesToSummarize ?? []);
+		expect(summarized).not.toContain("MIDCLEAR");
+		expect(summarized).not.toContain("OLD");
+		expect(summarized).toContain("POST first");
+	});
+
+	test("a reset boundary before the last compaction is superseded by it", () => {
+		const entries: SessionEntry[] = [
+			userEntry("PRE user"),
+			resetBoundary(),
+			userEntry("MID user"),
+			assistantEntry("MID assistant"),
+			compaction("KEEP SUMMARY", "kept-mid"),
+			userEntry("TAIL one"),
+			assistantEntry("TAIL one answer"),
+			userEntry("TAIL two"),
+			assistantEntry("TAIL two answer"),
+		];
+		const prep = prepareCompaction(entries, { ...DEFAULT_COMPACTION_SETTINGS, keepRecentTokens: 1 });
+		expect(prep).toBeDefined();
+		// Compaction after the boundary wins: its summary is still reused.
+		expect(prep?.previousSummary).toBe("KEEP SUMMARY");
+		const summarized = JSON.stringify(prep?.messagesToSummarize ?? []);
+		expect(summarized).toContain("TAIL one");
+		expect(summarized).not.toContain("MID");
+	});
+});

packages/coding-agent/src/session/session-entries.ts

@@ -171,7 +171,6 @@ declare module "@oh-my-pi/pi-agent-core/compaction/entries" {
 	interface CustomCompactionSessionEntries {
 		titleChange: TitleChangeEntry;
 		credentialPin: CredentialPinEntry;
-		resetBoundary: ResetBoundaryEntry;
 	}
 }