compaction: the leading system message is request chrome, never cut (fix the no-tools request)

Owner report (OpenRouter logs, 2026-10-05): the post-compaction request
arrived with NO system prompt and NO tool definitions — everything
before the cut replaced by the compaction message.

Root cause: pi-agent-core's Agent seeds a SystemMessage carrying the
system prompt AND the tool declarations at state.messages[0]
(createInitialSystemMessage — 'messages declare the provider-visible
loadout'). The record never persists it (ui-stream's settleWith filters
the role), but convertToLlm DOES receive it — and the cut projection
sliced from firstKeptMessageId, dropping [0] from the wire: no prompt,
no tools.

Fix (pi's own law — verified against pi-agent-core + pi's coding-agent):
the projection now carries the leading system message through AHEAD of
the compaction head, exactly as pi's prepareRequest re-applies
context.systemPrompt + context.tools around its compaction projection.
The cut slices the RECORD's history; the chrome is never compactable
payload. Loop start skips [0] when chrome is present (no duplicate);
record-path callers are unchanged.

Pinned: chrome-first-through-cut, exactly-once without a cut,
record-path head-first.

src/core/native-messages.ts

@@ -491,8 +491,23 @@ export function toLlmMessages(messages: readonly AgentMessage[]): Message[] {
 			};
 		}
 	}
-	const out: Message[] = head ? [head] : [];
-	for (let i = start; i < messages.length; i++) {
+	// THE LEADING SYSTEM MESSAGE IS REQUEST CHROME, NEVER COMPACTABLE
+	// PAYLOAD (the OpenRouter no-tools incident, owner 2026-10-05):
+	// pi-agent-core's Agent seeds a SystemMessage carrying the system
+	// prompt AND the tool declarations at state.messages[0]
+	// (createInitialSystemMessage — "messages declare the provider-visible
+	// loadout"). The record never persists it (ui-stream's settleWith
+	// filters the role), so RECORD-path callers never see it — but the
+	// Agent's convertToLlm DOES. The cut slices the RECORD's history;
+	// when [0] is the chrome it must carry through AHEAD of the
+	// compaction head, exactly as pi's own prepareRequest re-applies
+	// context.systemPrompt + context.tools around its projection.
+	const leading =
+		(messages[0] as { role?: string } | undefined)?.role === "system" ? (messages[0] as Message) : null;
+	const out: Message[] = [];
+	if (leading) out.push(leading);
+	if (head) out.push(head);
+	for (let i = leading ? Math.max(start, 1) : start; i < messages.length; i++) {
 		const m = messages[i]!;
 		const role = (m as { role?: string }).role;
 		if (role === "custom") {

src/server/compaction.ts

@@ -143,7 +143,11 @@ export function effectiveThresholdTokens(settingTokens: number | undefined, cont
 // ─── the estimate over the ACTIVE projection ────────────────────────────────
 
 /** The projected context estimate: what the next LLM call would carry —
- *  toLlmMessages output (cut honored) + the system prompt. chars/4. */
+ *  toLlmMessages output (cut honored) + the system prompt. The record
+ *  path carries no leading system message (settleWith filters it), so
+ *  the chrome rides as the additive term instead: prompt text here,
+ *  tool declarations absorbed by the 16k reserve (the declarations are
+ *  a few k and stable per session). chars/4. */
 export function projectedContextTokens(messages: readonly LhMessage[], systemPromptTokens: number): number {
 	return estimateTokens(toLlmMessages(messages as readonly AgentMessage[]) as unknown as readonly LhMessage[]) + systemPromptTokens;
 }

tests/compaction.test.ts

@@ -283,3 +283,63 @@ describe("projectView compaction dividers", () => {
 		assert.ok(view.indexOf(moment!) > keptIdx);
 	});
 });
+
+// ---------------------------------------------------------------------------
+// THE CHROME LAW (the OpenRouter no-tools incident, owner 2026-10-05):
+// pi-agent-core seeds a leading SystemMessage (prompt + tool
+// declarations) at state.messages[0]; the record never persists it. The
+// cut slices the RECORD's history — the chrome carries through ahead of
+// the compaction head, exactly as pi's prepareRequest re-applies
+// context.systemPrompt + context.tools around its projection.
+// ---------------------------------------------------------------------------
+describe("toLlmMessages carries the leading system message (request chrome)", () => {
+	const chrome = {
+		id: "sys",
+		role: "system",
+		content: "SYSTEM PROMPT + tool declarations",
+		toolsAdded: [{ name: "quiz" }, { name: "plan_init" }],
+		timestamp: 0,
+	};
+	const record = (): LhMessage[] => [
+		{ id: "old", role: "user", content: "dropped history", timestamp: 1 },
+		{ id: "kept", role: "user", content: "kept tail", timestamp: 2 },
+		newCompactionMarker("SUMMARY", {
+			firstKeptMessageId: "kept",
+			tokensBefore: 99,
+			at: new Date(0).toISOString(),
+		}) as unknown as LhMessage,
+	];
+
+	it("chrome FIRST, then the compaction head, then the kept tail — never dropped by the cut", () => {
+		const out = toLlmMessages([chrome, ...record()] as never);
+		assert.equal(out[0]!.role, "system");
+		assert.equal((out[0] as { toolsAdded?: unknown[] }).toolsAdded?.length, 2);
+		assert.equal(out[1]!.role, "user");
+		assert.ok((out[1]!.content as { text: string }[])[0]!.text.includes("SUMMARY"));
+		const textOf = (m: (typeof out)[number]): string =>
+			typeof m.content === "string"
+				? m.content
+				: ((m.content as { text?: string }[])[0]?.text ?? "");
+		assert.ok(out.slice(2).some((m) => m.role === "user" && textOf(m) === "kept tail"));
+		assert.ok(!out.some((m) => m.role === "user" && textOf(m) === "dropped history"));
+	});
+
+	it("without a cut the chrome renders EXACTLY ONCE (no duplicate)", () => {
+		const plain = [
+			{ id: "u1", role: "user", content: "hello", timestamp: 1 },
+		] as unknown as LhMessage[];
+		const out = toLlmMessages([chrome, ...plain] as never);
+		assert.equal(out.filter((m) => m.role === "system").length, 1);
+		assert.equal(out[0]!.role, "system");
+	});
+
+	it("record-path callers (no chrome in the record) are unchanged: head first", () => {
+		const out = toLlmMessages(record());
+		assert.notEqual(out[0]!.role, "system");
+		const headText =
+			typeof out[0]!.content === "string"
+				? out[0]!.content
+				: ((out[0]!.content as { text?: string }[])[0]?.text ?? "");
+		assert.ok(headText.includes("SUMMARY"));
+	});
+});