feat: add conversation storage

2026-06-16 20:41:18 +01:00 · 2026-06-16 20:10:55 +01:00
parent 95f6c99f19
commit f1f81e0b7c
23 changed files with 3457 additions and 396 deletions
--- a/apps/freya-backend/drizzle/0001_misty_white_tiger.sql
+++ b/apps/freya-backend/drizzle/0001_misty_white_tiger.sql
@@ -1 +1,49 @@
-CREATE INDEX "user_sources_user_id_enabled_idx" ON "user_sources" USING btree ("user_id","enabled");
+CREATE INDEX "user_sources_user_id_enabled_idx" ON "user_sources" USING btree ("user_id","enabled");--> statement-breakpoint
+CREATE TABLE "conversation_entries" (
+	"id" uuid PRIMARY KEY DEFAULT gen_random_uuid() NOT NULL,
+	"conversation_id" uuid NOT NULL,
+	"sequence" integer NOT NULL,
+	"kind" text NOT NULL,
+	"visibility" text DEFAULT 'internal' NOT NULL,
+	"file_id" uuid,
+	"payload" jsonb NOT NULL,
+	"metadata" jsonb DEFAULT '{}'::jsonb NOT NULL,
+	"created_at" timestamp DEFAULT now() NOT NULL,
+	CONSTRAINT "conversation_entries_conversation_id_sequence_unique" UNIQUE("conversation_id","sequence")
+);
+--> statement-breakpoint
+CREATE TABLE "conversations" (
+	"id" uuid PRIMARY KEY DEFAULT gen_random_uuid() NOT NULL,
+	"user_id" text NOT NULL,
+	"created_at" timestamp DEFAULT now() NOT NULL,
+	"updated_at" timestamp DEFAULT now() NOT NULL
+);
+--> statement-breakpoint
+CREATE TABLE "files" (
+	"id" uuid PRIMARY KEY DEFAULT gen_random_uuid() NOT NULL,
+	"user_id" text NOT NULL,
+	"storage_key" text NOT NULL,
+	"original_name" text,
+	"mime_type" text NOT NULL,
+	"size_bytes" integer NOT NULL,
+	"metadata" jsonb DEFAULT '{}'::jsonb NOT NULL,
+	"created_at" timestamp DEFAULT now() NOT NULL,
+	CONSTRAINT "files_storage_key_unique" UNIQUE("storage_key")
+);
+--> statement-breakpoint
+ALTER TABLE "session" ADD COLUMN "impersonated_by" text;--> statement-breakpoint
+ALTER TABLE "user" ADD COLUMN "role" text;--> statement-breakpoint
+ALTER TABLE "user" ADD COLUMN "banned" boolean DEFAULT false;--> statement-breakpoint
+ALTER TABLE "user" ADD COLUMN "ban_reason" text;--> statement-breakpoint
+ALTER TABLE "user" ADD COLUMN "ban_expires" timestamp;--> statement-breakpoint
+ALTER TABLE "conversation_entries" ADD CONSTRAINT "conversation_entries_conversation_id_conversations_id_fk" FOREIGN KEY ("conversation_id") REFERENCES "public"."conversations"("id") ON DELETE cascade ON UPDATE no action;--> statement-breakpoint
+ALTER TABLE "conversation_entries" ADD CONSTRAINT "conversation_entries_file_id_files_id_fk" FOREIGN KEY ("file_id") REFERENCES "public"."files"("id") ON DELETE restrict ON UPDATE no action;--> statement-breakpoint
+ALTER TABLE "conversation_entries" ADD CONSTRAINT "conversation_entries_attachment_file_id_check" CHECK (("conversation_entries"."kind" = 'attachment' and "conversation_entries"."file_id" is not null) or ("conversation_entries"."kind" <> 'attachment' and "conversation_entries"."file_id" is null));--> statement-breakpoint
+ALTER TABLE "conversations" ADD CONSTRAINT "conversations_user_id_user_id_fk" FOREIGN KEY ("user_id") REFERENCES "public"."user"("id") ON DELETE cascade ON UPDATE no action;--> statement-breakpoint
+ALTER TABLE "files" ADD CONSTRAINT "files_user_id_user_id_fk" FOREIGN KEY ("user_id") REFERENCES "public"."user"("id") ON DELETE cascade ON UPDATE no action;--> statement-breakpoint
+CREATE INDEX "conversation_entries_conversation_id_sequence_idx" ON "conversation_entries" USING btree ("conversation_id","sequence");--> statement-breakpoint
+CREATE INDEX "conversation_entries_conversation_id_visibility_sequence_idx" ON "conversation_entries" USING btree ("conversation_id","visibility","sequence");--> statement-breakpoint
+CREATE INDEX "conversation_entries_kind_idx" ON "conversation_entries" USING btree ("kind");--> statement-breakpoint
+CREATE INDEX "conversation_entries_file_id_idx" ON "conversation_entries" USING btree ("file_id");--> statement-breakpoint
+CREATE INDEX "conversations_user_id_updated_at_idx" ON "conversations" USING btree ("user_id","updated_at");--> statement-breakpoint
+CREATE INDEX "files_user_id_created_at_idx" ON "files" USING btree ("user_id","created_at");
--- a/apps/freya-backend/drizzle/meta/0001_snapshot.json
+++ b/apps/freya-backend/drizzle/meta/0001_snapshot.json
--- a/apps/freya-backend/src/admin/http.test.ts
+++ b/apps/freya-backend/src/admin/http.test.ts
@@ -44,6 +44,20 @@ mock.module("../sources/user-sources.ts", () => ({
 	}),
 }))

+mock.module("../conversations/storage.ts", () => ({
+	conversations: (_db: Database, userId: string) => ({
+		async getOrCreateConversation() {
+			return { id: `conversation-${userId}` }
+		},
+		async listEntries() {
+			return []
+		},
+		async appendEntry() {
+			return { id: "entry-1", sequence: 1 }
+		},
+	}),
+}))
+
 function createStubSource(id: string): FeedSource {
 	return {
 		id,
--- a/apps/freya-backend/src/agent/conversation-recording-query-agent.test.ts
+++ b/apps/freya-backend/src/agent/conversation-recording-query-agent.test.ts
@@ -0,0 +1,347 @@
+import { describe, expect, test } from "bun:test"
+
+import type { AppendConversationEntryInput } from "../conversations/storage.ts"
+import type {
+	ConversationStorage,
+	ConversationStorageEntry,
+} from "./conversation-recording-query-agent.ts"
+
+import { ConversationEntryKind } from "../conversations/types.ts"
+import { ConversationRecordingQueryAgent } from "./conversation-recording-query-agent.ts"
+import {
+	createQueryAgentEventListeners,
+	QueryAgentEvent,
+	type QueryAgent,
+	type QueryAgentAsk,
+	type QueryAgentCompactionEvent,
+	type QueryAgentEventListeners,
+	type QueryAgentEventListener,
+	type QueryAgentEventMap,
+	type QueryAgentStreamEvent,
+} from "./query-agent.ts"
+
+interface RecordedEntry {
+	conversationId: string
+	input: AppendConversationEntryInput
+}
+
+class FakeQueryAgent implements QueryAgent {
+	readonly inputs: QueryAgentAsk[] = []
+	private readonly events: QueryAgentStreamEvent[]
+	private readonly eventListeners = createQueryAgentEventListeners()
+
+	constructor(events: QueryAgentStreamEvent[]) {
+		this.events = events
+	}
+
+	async *ask(input: QueryAgentAsk): AsyncIterable<QueryAgentStreamEvent> {
+		this.inputs.push(input)
+		for (const event of this.events) {
+			yield event
+		}
+	}
+
+	addEventListener<T extends QueryAgentEvent>(
+		type: T,
+		listener: QueryAgentEventListener<T>,
+	): () => void {
+		const listeners = this.listenersFor(type)
+		listeners.add(listener)
+		return () => {
+			listeners.delete(listener)
+		}
+	}
+
+	async emitCompaction(event: QueryAgentCompactionEvent): Promise<void> {
+		await this.emitEvent(event)
+	}
+
+	private async emitEvent<T extends QueryAgentEvent>(event: QueryAgentEventMap[T]): Promise<void> {
+		const listeners = this.listenersFor(event.type)
+		for (const listener of listeners) {
+			await listener(event)
+		}
+	}
+
+	private listenersFor<T extends QueryAgentEvent>(type: T): QueryAgentEventListeners[T] {
+		return this.eventListeners[type]
+	}
+
+	dispose(): void {}
+}
+
+class FakeConversationStorage implements ConversationStorage {
+	getOrCreateCount = 0
+	readonly entries: RecordedEntry[] = []
+	conversationId = "conversation-1"
+
+	async getOrCreateConversation(): Promise<{ id: string }> {
+		this.getOrCreateCount += 1
+		return { id: this.conversationId }
+	}
+
+	async appendEntry(
+		conversationId: string,
+		input: AppendConversationEntryInput,
+	): Promise<ConversationStorageEntry> {
+		this.entries.push({ conversationId, input })
+		return {
+			id: `entry-${this.entries.length}`,
+			sequence: this.entries.length,
+			kind: input.kind,
+			payload: input.payload,
+			metadata: input.metadata ?? {},
+			createdAt: new Date("2026-06-15T00:00:00.000Z"),
+		}
+	}
+
+	async listEntries(_conversationId: string): Promise<ConversationStorageEntry[]> {
+		return this.entries.map((entry, index) => ({
+			id: `entry-${index + 1}`,
+			sequence: index + 1,
+			kind: entry.input.kind,
+			payload: entry.input.payload,
+			metadata: entry.input.metadata ?? {},
+			createdAt: new Date("2026-06-15T00:00:00.000Z"),
+		}))
+	}
+}
+
+describe("ConversationRecordingQueryAgent", () => {
+	test("records user and assistant messages in the conversation timeline", async () => {
+		const queryAgent = new FakeQueryAgent([
+			{ type: "text_delta", text: "Hello " },
+			{ type: "text_delta", text: "there." },
+			{ type: "done" },
+		])
+		const storage = new FakeConversationStorage()
+		const agent = new ConversationRecordingQueryAgent({
+			agent: queryAgent,
+			storage,
+			modelProvider: "openrouter",
+			modelId: "test-model",
+		})
+
+		const events = await collectEvents(
+			agent.ask({
+				message: "hi",
+			}),
+		)
+
+		expect(events[0]).toEqual({ type: "conversation", conversationId: "conversation-1" })
+		expect(queryAgent.inputs[0]?.conversationId).toBe("conversation-1")
+		expect(storage.getOrCreateCount).toBe(1)
+		expect(storage.entries).toHaveLength(2)
+
+		const userEntry = storage.entries[0]!.input
+		if (userEntry.kind !== ConversationEntryKind.UserMessage) {
+			throw new Error("Expected user message entry")
+		}
+		expect(userEntry.payload.parts).toEqual([{ type: "text", text: "hi" }])
+
+		const assistantEntry = storage.entries[1]!.input
+		if (assistantEntry.kind !== ConversationEntryKind.AssistantMessage) {
+			throw new Error("Expected assistant message entry")
+		}
+		expect(assistantEntry.payload.parts).toEqual([{ type: "text", text: "Hello there." }])
+		expect(assistantEntry.metadata?.modelRun?.provider).toBe("openrouter")
+		expect(assistantEntry.metadata?.modelRun?.model).toBe("test-model")
+	})
+
+	test("uses a provided conversation id without creating a default conversation", async () => {
+		const queryAgent = new FakeQueryAgent([{ type: "done" }])
+		const storage = new FakeConversationStorage()
+		const agent = new ConversationRecordingQueryAgent({
+			agent: queryAgent,
+			storage,
+			modelProvider: "openrouter",
+			modelId: "test-model",
+		})
+
+		const events = await collectEvents(
+			agent.ask({
+				conversationId: "conversation-existing",
+				message: "continue",
+			}),
+		)
+
+		expect(events[0]).toEqual({
+			type: "conversation",
+			conversationId: "conversation-existing",
+		})
+		expect(storage.getOrCreateCount).toBe(0)
+		expect(storage.entries[0]?.conversationId).toBe("conversation-existing")
+		expect(queryAgent.inputs[0]?.conversationId).toBe("conversation-existing")
+	})
+
+	test("uses the eager default conversation id without reading storage on ask", async () => {
+		const queryAgent = new FakeQueryAgent([{ type: "done" }])
+		const storage = new FakeConversationStorage()
+		const agent = new ConversationRecordingQueryAgent({
+			agent: queryAgent,
+			storage,
+			defaultConversationId: "conversation-eager",
+			modelProvider: "openrouter",
+			modelId: "test-model",
+		})
+
+		const events = await collectEvents(
+			agent.ask({
+				message: "continue",
+			}),
+		)
+
+		expect(events[0]).toEqual({
+			type: "conversation",
+			conversationId: "conversation-eager",
+		})
+		expect(storage.getOrCreateCount).toBe(0)
+		expect(storage.entries[0]?.conversationId).toBe("conversation-eager")
+		expect(queryAgent.inputs[0]?.conversationId).toBe("conversation-eager")
+	})
+
+	test("rejects switching away from the eager default conversation", async () => {
+		const queryAgent = new FakeQueryAgent([{ type: "done" }])
+		const storage = new FakeConversationStorage()
+		const agent = new ConversationRecordingQueryAgent({
+			agent: queryAgent,
+			storage,
+			defaultConversationId: "conversation-eager",
+			modelProvider: "openrouter",
+			modelId: "test-model",
+		})
+
+		const events = await collectEvents(
+			agent.ask({
+				conversationId: "conversation-other",
+				message: "continue",
+			}),
+		)
+
+		expect(events).toEqual([
+			{
+				type: "error",
+				message: "Conversation switching is not supported for this session",
+			},
+		])
+		expect(storage.entries).toHaveLength(0)
+		expect(queryAgent.inputs).toHaveLength(0)
+	})
+
+	test("records tool activity and agent errors as internal entries", async () => {
+		const queryAgent = new FakeQueryAgent([
+			{ type: "tool_start", toolName: "freya_get_feed" },
+			{ type: "tool_end", toolName: "freya_get_feed", ok: true },
+			{ type: "error", message: "model unavailable" },
+		])
+		const storage = new FakeConversationStorage()
+		const agent = new ConversationRecordingQueryAgent({
+			agent: queryAgent,
+			storage,
+			modelProvider: "openrouter",
+			modelId: "test-model",
+		})
+
+		await collectEvents(
+			agent.ask({
+				message: "what now?",
+			}),
+		)
+
+		expect(storage.entries.map((entry) => entry.input.kind)).toEqual([
+			ConversationEntryKind.UserMessage,
+			ConversationEntryKind.ToolCall,
+			ConversationEntryKind.ToolResult,
+			ConversationEntryKind.SystemNote,
+		])
+
+		const toolCall = storage.entries[1]!.input
+		if (toolCall.kind !== ConversationEntryKind.ToolCall) {
+			throw new Error("Expected tool call entry")
+		}
+		expect(toolCall.payload.toolName).toBe("freya_get_feed")
+
+		const toolResult = storage.entries[2]!.input
+		if (toolResult.kind !== ConversationEntryKind.ToolResult) {
+			throw new Error("Expected tool result entry")
+		}
+		expect(toolResult.payload.ok).toBe(true)
+
+		const systemNote = storage.entries[3]!.input
+		if (systemNote.kind !== ConversationEntryKind.SystemNote) {
+			throw new Error("Expected system note entry")
+		}
+		expect(systemNote.payload).toMatchObject({
+			type: "agent_error",
+			message: "model unavailable",
+		})
+	})
+
+	test("records compaction events as context summaries", async () => {
+		const queryAgent = new FakeQueryAgent([
+			{ type: "text_delta", text: "Kept answer." },
+			{ type: "done" },
+		])
+		const storage = new FakeConversationStorage()
+		const agent = new ConversationRecordingQueryAgent({
+			agent: queryAgent,
+			storage,
+			defaultConversationId: "conversation-1",
+			modelProvider: "openrouter",
+			modelId: "test-model",
+		})
+		const forwardedCompactions: QueryAgentCompactionEvent[] = []
+		agent.addEventListener(QueryAgentEvent.Compaction, (event) => {
+			forwardedCompactions.push(event)
+		})
+
+		await collectEvents(
+			agent.ask({
+				message: "remember this",
+			}),
+		)
+
+		await queryAgent.emitCompaction({
+			type: QueryAgentEvent.Compaction,
+			conversationId: "conversation-1",
+			summary: "The user prefers compact summaries.",
+			firstKeptEntryId: "pi-entry-7",
+			compactedEntryRange: {
+				startSequence: 1,
+				endSequence: 1,
+			},
+			tokensBefore: 1234,
+			details: { reason: "threshold" },
+			fromExtension: false,
+		})
+
+		const summaryEntry = storage.entries.at(-1)?.input
+		if (summaryEntry?.kind !== ConversationEntryKind.ContextSummary) {
+			throw new Error("Expected context summary entry")
+		}
+		expect(summaryEntry.payload.covers).toEqual({
+			startSequence: 1,
+			endSequence: 1,
+		})
+		expect(summaryEntry.payload.summary.importantDetails).toEqual([
+			"The user prefers compact summaries.",
+		])
+		expect(summaryEntry.metadata?.piCompaction).toMatchObject({
+			firstKeptEntryId: "pi-entry-7",
+			tokensBefore: 1234,
+			fromExtension: false,
+			details: { reason: "threshold" },
+		})
+		expect(forwardedCompactions).toHaveLength(1)
+	})
+})
+
+async function collectEvents(
+	events: AsyncIterable<QueryAgentStreamEvent>,
+): Promise<QueryAgentStreamEvent[]> {
+	const result: QueryAgentStreamEvent[] = []
+	for await (const event of events) {
+		result.push(event)
+	}
+	return result
+}
--- a/apps/freya-backend/src/agent/conversation-recording-query-agent.ts
+++ b/apps/freya-backend/src/agent/conversation-recording-query-agent.ts
@@ -0,0 +1,252 @@
+import { randomUUID } from "node:crypto"
+
+import type {
+	AppendConversationEntryInput,
+	ConversationEntryRow,
+} from "../conversations/storage.ts"
+import type { ConversationEntryMetadata } from "../conversations/types.ts"
+
+import { ConversationEntryKind } from "../conversations/types.ts"
+import {
+	createQueryAgentEventListeners,
+	QueryAgentEvent,
+	type QueryAgent,
+	type QueryAgentAsk,
+	type QueryAgentCompactionEvent,
+	type QueryAgentEventListeners,
+	type QueryAgentEventListener,
+	type QueryAgentEventMap,
+	type QueryAgentStreamEvent,
+} from "./query-agent.ts"
+
+export interface ConversationStorage {
+	getOrCreateConversation(): Promise<{ id: string }>
+	appendEntry(
+		conversationId: string,
+		input: AppendConversationEntryInput,
+	): Promise<ConversationStorageEntry>
+	listEntries(conversationId: string): Promise<ConversationStorageEntry[]>
+}
+
+export type ConversationStorageEntry = Pick<
+	ConversationEntryRow,
+	"id" | "sequence" | "kind" | "payload" | "metadata" | "createdAt"
+>
+
+export interface ConversationRecordingQueryAgentConfig {
+	agent: QueryAgent
+	storage: ConversationStorage
+	defaultConversationId?: string
+	route?: string
+	modelProvider: string
+	modelId: string
+}
+
+const DefaultRoute = "agent_query"
+
+export class ConversationRecordingQueryAgent implements QueryAgent {
+	private readonly agent: QueryAgent
+	private readonly storage: ConversationStorage
+	private readonly defaultConversationId: string | undefined
+	private readonly route: string
+	private readonly modelProvider: string
+	private readonly modelId: string
+	private readonly eventListeners = createQueryAgentEventListeners()
+	private readonly removeAgentCompactionListener: () => void
+
+	constructor(config: ConversationRecordingQueryAgentConfig) {
+		this.agent = config.agent
+		this.storage = config.storage
+		this.defaultConversationId = config.defaultConversationId
+		this.route = config.route ?? DefaultRoute
+		this.modelProvider = config.modelProvider
+		this.modelId = config.modelId
+		this.removeAgentCompactionListener = this.agent.addEventListener(
+			QueryAgentEvent.Compaction,
+			async (event) => {
+				await this.appendCompactionSummary(event)
+				await this.emitEvent(event)
+			},
+		)
+	}
+
+	async *ask(input: QueryAgentAsk): AsyncIterable<QueryAgentStreamEvent> {
+		if (
+			this.defaultConversationId &&
+			input.conversationId &&
+			input.conversationId !== this.defaultConversationId
+		) {
+			yield {
+				type: "error",
+				message: "Conversation switching is not supported for this session",
+			}
+			return
+		}
+
+		const conversationId =
+			input.conversationId ??
+			this.defaultConversationId ??
+			(await this.storage.getOrCreateConversation()).id
+		const runId = randomUUID()
+
+		const userEntry = await this.storage.appendEntry(conversationId, {
+			kind: ConversationEntryKind.UserMessage,
+			payload: {
+				role: "user",
+				parts: [{ type: "text", text: input.message }],
+			},
+			metadata: { runId },
+		})
+
+		yield { type: "conversation", conversationId }
+
+		const assistantText: string[] = []
+		for await (const event of this.agent.ask({
+			...input,
+			conversationId,
+			userMessageEntry: {
+				id: userEntry.id,
+				sequence: userEntry.sequence,
+			},
+		})) {
+			switch (event.type) {
+				case "conversation":
+					break
+				case "text_delta":
+					assistantText.push(event.text)
+					yield event
+					break
+				case "tool_start":
+					await this.storage.appendEntry(conversationId, {
+						kind: ConversationEntryKind.ToolCall,
+						payload: {
+							toolName: event.toolName,
+							runId,
+						},
+						metadata: { runId },
+					})
+					yield event
+					break
+				case "tool_end":
+					await this.storage.appendEntry(conversationId, {
+						kind: ConversationEntryKind.ToolResult,
+						payload: {
+							toolName: event.toolName,
+							ok: event.ok,
+							runId,
+						},
+						metadata: { runId },
+					})
+					yield event
+					break
+				case "error":
+					await this.storage.appendEntry(conversationId, {
+						kind: ConversationEntryKind.SystemNote,
+						payload: {
+							type: "agent_error",
+							message: event.message,
+							runId,
+						},
+						metadata: { runId },
+					})
+					yield event
+					return
+				case "done":
+					await this.appendAssistantMessage(conversationId, assistantText, runId)
+					yield event
+					return
+			}
+		}
+
+		await this.appendAssistantMessage(conversationId, assistantText, runId)
+	}
+
+	dispose(): void {
+		this.removeAgentCompactionListener()
+		this.clearEventListeners()
+		this.agent.dispose()
+	}
+
+	addEventListener<T extends QueryAgentEvent>(
+		type: T,
+		listener: QueryAgentEventListener<T>,
+	): () => void {
+		const listeners = this.listenersFor(type)
+		listeners.add(listener)
+		return () => {
+			listeners.delete(listener)
+		}
+	}
+
+	private async appendAssistantMessage(
+		conversationId: string,
+		assistantText: string[],
+		runId: string,
+	): Promise<void> {
+		const text = assistantText.join("")
+		if (text.length === 0) return
+
+		await this.storage.appendEntry(conversationId, {
+			kind: ConversationEntryKind.AssistantMessage,
+			payload: {
+				role: "assistant",
+				parts: [{ type: "text", text }],
+			},
+			metadata: this.modelRunMetadata(runId),
+		})
+	}
+
+	private modelRunMetadata(runId: string): ConversationEntryMetadata {
+		const metadata: ConversationEntryMetadata = { runId }
+		metadata.modelRun = {
+			route: this.route,
+			provider: this.modelProvider,
+			model: this.modelId,
+		}
+		return metadata
+	}
+
+	private async appendCompactionSummary(event: QueryAgentCompactionEvent): Promise<void> {
+		if (event.compactedEntryRange === null) return
+
+		await this.storage.appendEntry(event.conversationId, {
+			kind: ConversationEntryKind.ContextSummary,
+			payload: {
+				covers: event.compactedEntryRange,
+				summary: {
+					durableFacts: [],
+					preferences: [],
+					decisions: [],
+					openTasks: [],
+					importantDetails: [event.summary],
+				},
+				promptVersion: "pi-sdk-compaction-v1",
+			},
+			metadata: {
+				piCompaction: {
+					firstKeptEntryId: event.firstKeptEntryId,
+					tokensBefore: event.tokensBefore,
+					fromExtension: event.fromExtension,
+					details: event.details,
+				},
+			},
+		})
+	}
+
+	private async emitEvent<T extends QueryAgentEvent>(event: QueryAgentEventMap[T]): Promise<void> {
+		const listeners = this.listenersFor(event.type)
+		for (const listener of listeners) {
+			await listener(event)
+		}
+	}
+
+	private listenersFor<T extends QueryAgentEvent>(type: T): QueryAgentEventListeners[T] {
+		return this.eventListeners[type]
+	}
+
+	private clearEventListeners(): void {
+		for (const listeners of Object.values(this.eventListeners)) {
+			listeners.clear()
+		}
+	}
+}
--- a/apps/freya-backend/src/agent/http.test.ts
+++ b/apps/freya-backend/src/agent/http.test.ts
@@ -3,7 +3,13 @@ import { Hono } from "hono"

 import type { UserSessionManager } from "../session/index.ts"
 import type { QueryDebugTools, QueryDebugToolDefinition } from "./debug-tools.ts"
-import type { QueryAgent, QueryAgentAsk, QueryAgentEvent } from "./query-agent.ts"
+import type {
+	QueryAgent,
+	QueryAgentAsk,
+	QueryAgentEventListener,
+	QueryAgentStreamEvent,
+	QueryAgentEvent,
+} from "./query-agent.ts"

 import { mockAuthSessionMiddleware } from "../auth/session-middleware.ts"
 import { registerAgentHttpHandlers, registerDebugAgentHttpHandlers } from "./http.ts"
@@ -12,19 +18,26 @@ const MockUserId = "k7Gx2mPqRvNwYs9TdLfA4bHcJeUo1iZn"

 class FakeQueryAgent implements QueryAgent {
 	readonly inputs: QueryAgentAsk[] = []
-	private readonly events: QueryAgentEvent[]
+	private readonly events: QueryAgentStreamEvent[]

-	constructor(events: QueryAgentEvent[]) {
+	constructor(events: QueryAgentStreamEvent[]) {
 		this.events = events
 	}

-	async *ask(input: QueryAgentAsk): AsyncIterable<QueryAgentEvent> {
+	async *ask(input: QueryAgentAsk): AsyncIterable<QueryAgentStreamEvent> {
 		this.inputs.push(input)
 		for (const event of this.events) {
 			yield event
 		}
 	}

+	addEventListener<T extends QueryAgentEvent>(
+		_type: T,
+		_listener: QueryAgentEventListener<T>,
+	): () => void {
+		return () => {}
+	}
+
 	dispose(): void {}
 }

@@ -110,6 +123,27 @@ describe("POST /api/agent", () => {
 		expect(body.message).toBe("You should leave at 8:30.")
 	})

+	test("passes conversation id to the query agent", async () => {
+		const agent = new FakeQueryAgent([
+			{ type: "conversation", conversationId: "conversation-1" },
+			{ type: "done" },
+		])
+		const app = buildTestApp(agent, "user-1")
+
+		const res = await app.request("/api/agent", {
+			method: "POST",
+			body: JSON.stringify({
+				message: "Continue this chat.",
+				conversationId: "conversation-1",
+			}),
+		})
+
+		expect(res.status).toBe(200)
+		expect(agent.inputs[0]?.conversationId).toBe("conversation-1")
+		const body = (await res.json()) as { conversationId?: string }
+		expect(body.conversationId).toBe("conversation-1")
+	})
+
 	test("returns 400 for invalid body", async () => {
 		const app = buildTestApp(new FakeQueryAgent([]), "user-1")

--- a/apps/freya-backend/src/agent/http.ts
+++ b/apps/freya-backend/src/agent/http.ts
@@ -35,6 +35,7 @@ interface AgentDebugHttpHandlersDeps {
 const AgentAskRequestBody = type({
 	"+": "reject",
 	message: "string",
+	"conversationId?": "string",
 })

 export function registerAgentHttpHandlers(
@@ -82,6 +83,7 @@ async function handleAgentAsk(c: Context<Env>) {
 		const session = await sessionManager.getOrCreate(user.id)
 		const response = await collectQueryAgentResponse(session.agent, {
 			message: parsed.message,
+			conversationId: parsed.conversationId,
 		})
 		return c.json(response)
 	} catch (err) {
--- a/apps/freya-backend/src/agent/in-memory-resource-loader.ts
+++ b/apps/freya-backend/src/agent/in-memory-resource-loader.ts
@@ -1,43 +0,0 @@
-import { createExtensionRuntime, type ResourceLoader } from "@earendil-works/pi-coding-agent"
-
-export class InMemoryResourceLoader implements ResourceLoader {
-	private readonly extensions: ReturnType<ResourceLoader["getExtensions"]> = {
-		extensions: [],
-		errors: [],
-		runtime: createExtensionRuntime(),
-	}
-
-	constructor(private readonly systemPrompt: string) {}
-
-	getExtensions(): ReturnType<ResourceLoader["getExtensions"]> {
-		return this.extensions
-	}
-
-	getSkills(): ReturnType<ResourceLoader["getSkills"]> {
-		return { skills: [], diagnostics: [] }
-	}
-
-	getPrompts(): ReturnType<ResourceLoader["getPrompts"]> {
-		return { prompts: [], diagnostics: [] }
-	}
-
-	getThemes(): ReturnType<ResourceLoader["getThemes"]> {
-		return { themes: [], diagnostics: [] }
-	}
-
-	getAgentsFiles(): ReturnType<ResourceLoader["getAgentsFiles"]> {
-		return { agentsFiles: [] }
-	}
-
-	getSystemPrompt(): string {
-		return this.systemPrompt
-	}
-
-	getAppendSystemPrompt(): string[] {
-		return []
-	}
-
-	extendResources(_paths: Parameters<ResourceLoader["extendResources"]>[0]): void {}
-
-	async reload(_options?: Parameters<ResourceLoader["reload"]>[0]): Promise<void> {}
-}
--- a/apps/freya-backend/src/agent/pi-query-agent.test.ts
+++ b/apps/freya-backend/src/agent/pi-query-agent.test.ts
@@ -1,7 +1,10 @@
 import { beforeEach, describe, expect, mock, test } from "bun:test"

 import type { QueryAgentToolbox } from "./query-agent-toolbox.ts"
-import type { QueryAgentEvent } from "./query-agent.ts"
+import type { QueryAgentStreamEvent } from "./query-agent.ts"
+
+import { ConversationEntryKind } from "../conversations/types.ts"
+import { QueryAgentEvent } from "./query-agent.ts"

 interface FakePiSession {
 	subscribe(listener: (event: unknown) => void): () => void
@@ -9,6 +12,61 @@ interface FakePiSession {
 	dispose(): void
 }

+type CapturedExtensionHandler = (event: unknown) => Promise<unknown> | unknown
+
+interface CapturedExtensionApi {
+	on(event: string, handler: CapturedExtensionHandler): void
+}
+
+type CapturedExtensionFactory = (pi: CapturedExtensionApi) => Promise<void> | void
+
+interface CapturedExtension {
+	handlers: Map<string, CapturedExtensionHandler[]>
+}
+
+interface CapturedResourceLoader {
+	getExtensions(): unknown
+}
+
+interface CapturedDefaultResourceLoaderOptions {
+	extensionFactories?: CapturedExtensionFactory[]
+}
+
+class FakeDefaultResourceLoader implements CapturedResourceLoader {
+	private readonly extensionFactories: CapturedExtensionFactory[]
+	private extensionsResult: { extensions: CapturedExtension[] }
+
+	constructor(options: unknown) {
+		this.extensionFactories = isDefaultResourceLoaderOptions(options)
+			? (options.extensionFactories ?? [])
+			: []
+		this.extensionsResult = { extensions: [] }
+	}
+
+	async reload(): Promise<void> {
+		const handlers: CapturedExtension["handlers"] = new Map()
+		const api: CapturedExtensionApi = {
+			on(event: string, handler: CapturedExtensionHandler): void {
+				const existing = handlers.get(event) ?? []
+				existing.push(handler)
+				handlers.set(event, existing)
+			},
+		}
+
+		for (const factory of this.extensionFactories) {
+			await factory(api)
+		}
+
+		this.extensionsResult = {
+			extensions: [{ handlers }],
+		}
+	}
+
+	getExtensions(): unknown {
+		return this.extensionsResult
+	}
+}
+
 let createAgentSessionCalls = 0
 let createAgentSessionOptions: unknown
 let runtimeApiKeyCalls: Array<{ provider: string; apiKey: string }> = []
@@ -51,6 +109,44 @@ const fakeSession: FakePiSession = {
 	dispose(): void {},
 }

+class FakeSessionManager {
+	private messages: unknown[] = []
+	private compaction: { summary: string; tokensBefore: number; timestamp: number } | null = null
+
+	appendMessage(message: unknown): string {
+		this.messages.push(message)
+		return `message-${this.messages.length}`
+	}
+
+	appendCompaction(summary: string, _firstKeptEntryId: string, tokensBefore: number): string {
+		this.compaction = {
+			summary,
+			tokensBefore,
+			timestamp: Date.now(),
+		}
+		this.messages = []
+		return "compaction-1"
+	}
+
+	buildSessionContext(): unknown {
+		const messages = [...this.messages]
+		if (this.compaction) {
+			messages.unshift({
+				role: "compactionSummary",
+				summary: this.compaction.summary,
+				tokensBefore: this.compaction.tokensBefore,
+				timestamp: this.compaction.timestamp,
+			})
+		}
+
+		return {
+			messages,
+			thinkingLevel: "off",
+			model: modelFromMessages(messages),
+		}
+	}
+}
+
 mock.module("@earendil-works/pi-coding-agent", () => ({
 	AuthStorage: {
 		inMemory() {
@@ -71,6 +167,7 @@ mock.module("@earendil-works/pi-coding-agent", () => ({
 	createExtensionRuntime() {
 		return {}
 	},
+	DefaultResourceLoader: FakeDefaultResourceLoader,
 	defineTool(tool: unknown): unknown {
 		return tool
 	},
@@ -86,7 +183,7 @@ mock.module("@earendil-works/pi-coding-agent", () => ({
 	},
 	SessionManager: {
 		inMemory(_cwd: string): unknown {
-			return {}
+			return new FakeSessionManager()
 		},
 	},
 	SettingsManager: {
@@ -131,7 +228,6 @@ describe("PiQueryAgent", () => {
 	test("rejects a concurrent first query while the Pi session is being created", async () => {
 		const { PiQueryAgent } = await import("./pi-query-agent.ts")
 		const agent = new PiQueryAgent({
-			userId: "user-1",
 			toolbox: createStubToolbox(),
 			apiKey: "test-api-key",
 			cwd: "/tmp/freya-pi-query-agent-test",
@@ -155,7 +251,7 @@ describe("PiQueryAgent", () => {
 		expect(secondEvents).toEqual([
 			{
 				type: "error",
-				message: "A query is already running for this user",
+				message: "A query is already running",
 			},
 		])
 		expect(createAgentSessionCalls).toBe(1)
@@ -175,6 +271,228 @@ describe("PiQueryAgent", () => {
 		}
 		expect("agentDir" in createAgentSessionOptions).toBe(false)
 		expect(createAgentSessionOptions.resourceLoader).toBeDefined()
+		expect(typeof sessionCompactHandlerFromCapturedOptions()).toBe("function")
+
+		agent.dispose()
+	})
+
+	test("hydrates initial entries into the Pi session manager", async () => {
+		const { PiQueryAgent } = await import("./pi-query-agent.ts")
+		const agent = new PiQueryAgent({
+			toolbox: createStubToolbox(),
+			cwd: "/tmp/freya-pi-query-agent-test",
+			systemPrompt: "test",
+			initialEntries: [
+				{
+					id: "entry-1",
+					sequence: 1,
+					kind: ConversationEntryKind.UserMessage,
+					payload: {
+						role: "user",
+						parts: [{ type: "text", text: "stored hello" }],
+					},
+					metadata: {},
+					createdAt: new Date("2026-06-15T00:00:00.000Z"),
+				},
+				{
+					id: "entry-2",
+					sequence: 2,
+					kind: ConversationEntryKind.AssistantMessage,
+					payload: {
+						role: "assistant",
+						parts: [{ type: "text", text: "stored reply" }],
+					},
+					metadata: {},
+					createdAt: new Date("2026-06-15T00:00:01.000Z"),
+				},
+			],
+		})
+
+		const events = collectEvents(
+			agent.ask({
+				message: "hello",
+			}),
+		)
+
+		await sessionCreationStarted
+		if (!isRecord(createAgentSessionOptions)) {
+			throw new Error("createAgentSession options were not captured")
+		}
+		const sessionManager = createAgentSessionOptions.sessionManager
+		if (!(sessionManager instanceof FakeSessionManager)) {
+			throw new Error("session manager was not hydrated by PiQueryAgent")
+		}
+		const context = sessionManager.buildSessionContext()
+		if (!isRecord(context) || !Array.isArray(context.messages)) {
+			throw new Error("session context messages were not captured")
+		}
+		expect(context.messages[0]).toEqual({
+			role: "user",
+			content: "stored hello",
+			timestamp: new Date("2026-06-15T00:00:00.000Z").getTime(),
+		})
+		expect(context.messages[1]).toMatchObject({
+			role: "assistant",
+			provider: "openrouter",
+			model: "z-ai/glm-4.7-flash",
+			stopReason: "stop",
+			timestamp: new Date("2026-06-15T00:00:01.000Z").getTime(),
+		})
+
+		releaseSessionCreation()
+		await promptStarted
+		releasePrompt()
+
+		expect(await events).toEqual([{ type: "done" }])
+
+		agent.dispose()
+	})
+
+	test("emits Pi compaction events for the active conversation", async () => {
+		const recordedCompactions: unknown[] = []
+		const { PiQueryAgent } = await import("./pi-query-agent.ts")
+		const agent = new PiQueryAgent({
+			toolbox: createStubToolbox(),
+			cwd: "/tmp/freya-pi-query-agent-test",
+			systemPrompt: "test",
+		})
+		agent.addEventListener(QueryAgentEvent.Compaction, (event) => {
+			recordedCompactions.push(event)
+		})
+
+		const events = collectEvents(
+			agent.ask({
+				conversationId: "conversation-1",
+				message: "hello",
+			}),
+		)
+
+		await sessionCreationStarted
+		releaseSessionCreation()
+		await promptStarted
+
+		const handler = sessionCompactHandlerFromCapturedOptions()
+		await handler({
+			type: "session_compact",
+			fromExtension: false,
+			compactionEntry: {
+				type: "compaction",
+				id: "pi-compaction-1",
+				timestamp: "2026-06-15T00:00:00.000Z",
+				summary: "The user prefers concise updates.",
+				firstKeptEntryId: "pi-entry-7",
+				tokensBefore: 1234,
+				details: { reason: "threshold" },
+			},
+		})
+
+		expect(recordedCompactions).toEqual([
+			{
+				type: QueryAgentEvent.Compaction,
+				conversationId: "conversation-1",
+				summary: "The user prefers concise updates.",
+				firstKeptEntryId: "pi-entry-7",
+				compactedEntryRange: null,
+				tokensBefore: 1234,
+				details: { reason: "threshold" },
+				fromExtension: false,
+			},
+		])
+
+		releasePrompt()
+
+		expect(await events).toEqual([{ type: "done" }])
+		expect(unsubscribeCalls).toBe(1)
+
+		agent.dispose()
+	})
+
+	test("emits Freya coverage through the entry before Pi's kept boundary", async () => {
+		const recordedCompactions: unknown[] = []
+		const { PiQueryAgent } = await import("./pi-query-agent.ts")
+		const agent = new PiQueryAgent({
+			toolbox: createStubToolbox(),
+			cwd: "/tmp/freya-pi-query-agent-test",
+			systemPrompt: "test",
+			initialEntries: [
+				{
+					id: "entry-1",
+					sequence: 1,
+					kind: ConversationEntryKind.UserMessage,
+					payload: {
+						role: "user",
+						parts: [{ type: "text", text: "old hello" }],
+					},
+					metadata: {},
+					createdAt: new Date("2026-06-15T00:00:00.000Z"),
+				},
+				{
+					id: "entry-2",
+					sequence: 2,
+					kind: ConversationEntryKind.AssistantMessage,
+					payload: {
+						role: "assistant",
+						parts: [{ type: "text", text: "kept reply" }],
+					},
+					metadata: {},
+					createdAt: new Date("2026-06-15T00:00:01.000Z"),
+				},
+			],
+		})
+		agent.addEventListener(QueryAgentEvent.Compaction, (event) => {
+			recordedCompactions.push(event)
+		})
+
+		const events = collectEvents(
+			agent.ask({
+				conversationId: "conversation-1",
+				message: "hello",
+			}),
+		)
+
+		await sessionCreationStarted
+
+		await extensionHandlerFromCapturedOptions("session_before_compact")({
+			type: "session_before_compact",
+			preparation: {
+				firstKeptEntryId: "message-2",
+			},
+			branchEntries: [{ id: "message-1" }, { id: "message-2" }],
+		})
+		await extensionHandlerFromCapturedOptions("session_compact")({
+			type: "session_compact",
+			fromExtension: false,
+			compactionEntry: {
+				type: "compaction",
+				id: "pi-compaction-1",
+				timestamp: "2026-06-15T00:00:00.000Z",
+				summary: "Old hello was discussed.",
+				firstKeptEntryId: "message-2",
+				tokensBefore: 1234,
+			},
+		})
+
+		expect(recordedCompactions).toEqual([
+			{
+				type: QueryAgentEvent.Compaction,
+				conversationId: "conversation-1",
+				summary: "Old hello was discussed.",
+				firstKeptEntryId: "message-2",
+				compactedEntryRange: {
+					startSequence: 1,
+					endSequence: 1,
+				},
+				tokensBefore: 1234,
+				details: undefined,
+				fromExtension: false,
+			},
+		])
+
+		releaseSessionCreation()
+		await promptStarted
+		releasePrompt()
+
+		expect(await events).toEqual([{ type: "done" }])

 		agent.dispose()
 	})
@@ -182,7 +500,6 @@ describe("PiQueryAgent", () => {
 	test("surfaces Pi message_end provider errors instead of done", async () => {
 		const { PiQueryAgent } = await import("./pi-query-agent.ts")
 		const agent = new PiQueryAgent({
-			userId: "user-1",
 			toolbox: createStubToolbox(),
 			cwd: "/tmp/freya-pi-query-agent-test",
 			systemPrompt: "test",
@@ -219,7 +536,6 @@ describe("PiQueryAgent", () => {
 	test("surfaces Pi agent_end provider errors instead of done", async () => {
 		const { PiQueryAgent } = await import("./pi-query-agent.ts")
 		const agent = new PiQueryAgent({
-			userId: "user-1",
 			toolbox: createStubToolbox(),
 			cwd: "/tmp/freya-pi-query-agent-test",
 			systemPrompt: "test",
@@ -256,8 +572,10 @@ describe("PiQueryAgent", () => {
 	})
 })

-async function collectEvents(events: AsyncIterable<QueryAgentEvent>): Promise<QueryAgentEvent[]> {
-	const result: QueryAgentEvent[] = []
+async function collectEvents(
+	events: AsyncIterable<QueryAgentStreamEvent>,
+): Promise<QueryAgentStreamEvent[]> {
+	const result: QueryAgentStreamEvent[] = []
 	for await (const event of events) {
 		result.push(event)
 	}
@@ -290,6 +608,79 @@ function createStubToolbox(): QueryAgentToolbox {
 	}
 }

+function sessionCompactHandlerFromCapturedOptions(): CapturedExtensionHandler {
+	return extensionHandlerFromCapturedOptions("session_compact")
+}
+
+function extensionHandlerFromCapturedOptions(eventName: string): CapturedExtensionHandler {
+	if (!isRecord(createAgentSessionOptions)) {
+		throw new Error("createAgentSession options were not captured")
+	}
+
+	const resourceLoader = createAgentSessionOptions.resourceLoader
+	if (!isCapturedResourceLoader(resourceLoader)) {
+		throw new Error("resourceLoader was not captured")
+	}
+
+	const extensionsResult = resourceLoader.getExtensions()
+	if (!isRecord(extensionsResult) || !Array.isArray(extensionsResult.extensions)) {
+		throw new Error("extensions were not captured")
+	}
+
+	const extension = extensionsResult.extensions[0]
+	if (!isCapturedExtension(extension)) {
+		throw new Error("compaction extension was not captured")
+	}
+
+	const handlers = extension.handlers.get(eventName)
+	const handler = handlers?.[0]
+	if (!handler) {
+		throw new Error(`${eventName} handler was not captured`)
+	}
+
+	return handler
+}
+
+function isCapturedResourceLoader(value: unknown): value is CapturedResourceLoader {
+	return isRecord(value) && typeof value.getExtensions === "function"
+}
+
+function isCapturedExtension(value: unknown): value is CapturedExtension {
+	return isRecord(value) && value.handlers instanceof Map
+}
+
+function isDefaultResourceLoaderOptions(
+	value: unknown,
+): value is CapturedDefaultResourceLoaderOptions {
+	return (
+		isRecord(value) &&
+		(value.extensionFactories === undefined ||
+			(Array.isArray(value.extensionFactories) &&
+				value.extensionFactories.every(isCapturedExtensionFactory)))
+	)
+}
+
+function isCapturedExtensionFactory(value: unknown): value is CapturedExtensionFactory {
+	return typeof value === "function"
+}
+
+function modelFromMessages(messages: unknown[]): { provider: string; modelId: string } | null {
+	let model: { provider: string; modelId: string } | null = null
+
+	for (const message of messages) {
+		if (!isRecord(message)) continue
+		if (message.role !== "assistant") continue
+		if (typeof message.provider !== "string" || typeof message.model !== "string") continue
+
+		model = {
+			provider: message.provider,
+			modelId: message.model,
+		}
+	}
+
+	return model
+}
+
 function isRecord(value: unknown): value is Record<string, unknown> {
 	return typeof value === "object" && value !== null
 }
--- a/apps/freya-backend/src/agent/pi-query-agent.ts
+++ b/apps/freya-backend/src/agent/pi-query-agent.ts
@@ -1,73 +1,119 @@
-import type { AgentSessionEvent } from "@earendil-works/pi-coding-agent"
+import type {
+	AgentSessionEvent,
+	ExtensionFactory,
+	SessionEntry,
+} from "@earendil-works/pi-coding-agent"

 import {
 	AuthStorage,
 	createAgentSession,
+	DefaultResourceLoader,
 	ModelRegistry,
-	SessionManager,
 	SettingsManager,
 } from "@earendil-works/pi-coding-agent"
 import { tmpdir } from "node:os"

+import type { ConversationStorageEntry } from "./conversation-recording-query-agent.ts"
 import type { QueryAgentToolbox } from "./query-agent-toolbox.ts"
-import type { QueryAgent, QueryAgentAsk, QueryAgentEvent } from "./query-agent.ts"

-import { InMemoryResourceLoader } from "./in-memory-resource-loader.ts"
 import defaultSystemPrompt from "./prompts/system.txt"
+import {
+	createQueryAgentEventListeners,
+	QueryAgentEvent,
+	type QueryAgent,
+	type QueryAgentAsk,
+	type QueryAgentCompactedEntryRange,
+	type QueryAgentCompactionEvent,
+	type QueryAgentConversationEntryRef,
+	type QueryAgentEventListeners,
+	type QueryAgentEventListener,
+	type QueryAgentEventMap,
+	type QueryAgentStreamEvent,
+} from "./query-agent.ts"
+import { createSessionManager } from "./session-manager.ts"
 import { createFreyaAgentTools, FREYA_AGENT_TOOL_NAMES } from "./tools.ts"

 type PiSession = Awaited<ReturnType<typeof createAgentSession>>["session"]
 type PiMessageEndEvent = Extract<AgentSessionEvent, { type: "message_end" }>
 type PiAgentMessage = PiMessageEndEvent["message"]
 type PiAgentEndEvent = Extract<AgentSessionEvent, { type: "agent_end" }>
+type PiSessionManager = ReturnType<typeof createSessionManager>
+type PiSessionMessage = Parameters<PiSessionManager["appendMessage"]>[0]

 export interface PiQueryAgentConfig {
-	userId: string
 	toolbox: QueryAgentToolbox
 	apiKey?: string
 	cwd?: string
 	systemPrompt?: string
+	initialEntries?: ConversationStorageEntry[]
 }

-const MODEL_PROVIDER = "openrouter"
-const MODEL_ID = "z-ai/glm-4.7-flash"
+export const PI_MODEL_PROVIDER = "openrouter"
+export const PI_MODEL_ID = "z-ai/glm-4.7-flash"

 export class PiQueryAgent implements QueryAgent {
-	private readonly userId: string
 	private readonly toolbox: QueryAgentToolbox
 	private readonly cwd: string
 	private readonly systemPrompt: string
 	private readonly apiKey: string | undefined
+	private readonly initialEntries: ConversationStorageEntry[]
+	private readonly eventListeners = createQueryAgentEventListeners()
 	private session: PiSession | null = null
 	private pendingSession: Promise<PiSession> | null = null
-	private activeRun: symbol | null = null
+	/**
+	 * Conversation currently receiving Pi events for an active ask().
+	 *
+	 * Pi's compaction hook fires from the SDK session rather than from our
+	 * QueryAgent call stack, so the hook reads this value to attach the
+	 * compaction summary to the right Freya conversation. null means no active
+	 * run; "" means a run is active but no Freya conversation id was supplied.
+	 */
+	private activeConversationId: string | null = null
+	/**
+	 * Freya entry for the user message currently being handed to Pi.
+	 *
+	 * ConversationRecordingQueryAgent appends the user message before calling
+	 * PiQueryAgent. Pi later persists its own copy of that user message into its
+	 * SessionManager, and this one-shot reference lets us map Pi's generated
+	 * session entry id back to the Freya sequence.
+	 */
+	private activeUserMessageEntry: QueryAgentConversationEntryRef | null = null
+	/**
+	 * Maps Pi SessionManager entry ids to Freya conversation sequences.
+	 *
+	 * Pi compaction reports boundaries with Pi entry ids, while our DB replay
+	 * logic uses monotonically increasing Freya sequences. This map is the bridge
+	 * that lets us translate Pi's firstKeptEntryId into a compacted entry range.
+	 */
+	private readonly piEntryConversationSequences = new Map<string, number>()
 	private disposed = false

 	constructor(config: PiQueryAgentConfig) {
-		this.userId = config.userId
 		this.toolbox = config.toolbox
 		this.apiKey = config.apiKey
 		this.cwd = config.cwd ?? tmpdir()
 		this.systemPrompt = config.systemPrompt ?? defaultSystemPrompt
+		this.initialEntries = config.initialEntries ?? []
 	}

-	async *ask(input: QueryAgentAsk): AsyncIterable<QueryAgentEvent> {
-		if (this.activeRun) {
+	async *ask(input: QueryAgentAsk): AsyncIterable<QueryAgentStreamEvent> {
+		if (this.activeConversationId !== null) {
 			yield {
 				type: "error",
-				message: "A query is already running for this user",
+				message: "A query is already running",
 			}
 			return
 		}

-		const run = Symbol(this.userId)
-		this.activeRun = run
+		this.activeConversationId = input.conversationId ?? ""
+		this.activeUserMessageEntry = input.userMessageEntry ?? null

 		let session: PiSession
 		try {
 			session = await this.getOrCreateSession()
 		} catch (err) {
-			this.clearActiveRun(run)
+			this.activeConversationId = null
+			this.activeUserMessageEntry = null
 			yield {
 				type: "error",
 				message: `Failed to create query session: ${errorMessage(err)}`,
@@ -75,11 +121,11 @@ export class PiQueryAgent implements QueryAgent {
 			return
 		}

-		const events: QueryAgentEvent[] = []
+		const events: QueryAgentStreamEvent[] = []
 		let closed = false
 		let wake: (() => void) | null = null

-		function push(event: QueryAgentEvent): void {
+		function push(event: QueryAgentStreamEvent): void {
 			events.push(event)
 			if (wake) {
 				wake()
@@ -88,7 +134,7 @@ export class PiQueryAgent implements QueryAgent {
 		}

 		let runFailed = false
-		function pushRunEvent(event: QueryAgentEvent): void {
+		function pushRunEvent(event: QueryAgentStreamEvent): void {
 			if (event.type === "error") {
 				if (runFailed) return
 				runFailed = true
@@ -108,7 +154,8 @@ export class PiQueryAgent implements QueryAgent {
 			this.handlePiEvent(event, pushRunEvent)
 		})

-		void this.runPrompt(session, input)
+		session
+			.prompt(input.message)
 			.then(() => {
 				if (runFailed) return
 				pushRunEvent({ type: "done" })
@@ -118,7 +165,8 @@ export class PiQueryAgent implements QueryAgent {
 			})
 			.finally(() => {
 				unsubscribe()
-				this.clearActiveRun(run)
+				this.activeConversationId = null
+				this.activeUserMessageEntry = null
 				close()
 			})

@@ -140,12 +188,19 @@ export class PiQueryAgent implements QueryAgent {
 		this.session?.dispose()
 		this.session = null
 		this.pendingSession = null
-		this.activeRun = null
+		this.activeConversationId = null
+		this.activeUserMessageEntry = null
+		this.clearEventListeners()
 	}

-	private clearActiveRun(run: symbol): void {
-		if (this.activeRun === run) {
-			this.activeRun = null
+	addEventListener<T extends QueryAgentEvent>(
+		type: T,
+		listener: QueryAgentEventListener<T>,
+	): () => void {
+		const listeners = this.listenersFor(type)
+		listeners.add(listener)
+		return () => {
+			listeners.delete(listener)
 		}
 	}

@@ -184,38 +239,200 @@ export class PiQueryAgent implements QueryAgent {
 		})
 		const authStorage = AuthStorage.inMemory()
 		if (this.apiKey) {
-			authStorage.setRuntimeApiKey(MODEL_PROVIDER, this.apiKey)
+			authStorage.setRuntimeApiKey(PI_MODEL_PROVIDER, this.apiKey)
 		}

 		const modelRegistry = ModelRegistry.inMemory(authStorage)
-		const model = modelRegistry.find(MODEL_PROVIDER, MODEL_ID)
+		const model = modelRegistry.find(PI_MODEL_PROVIDER, PI_MODEL_ID)
 		if (!model) {
-			throw new Error(`Pi model not found: ${MODEL_PROVIDER}/${MODEL_ID}`)
+			throw new Error(`Pi model not found: ${PI_MODEL_PROVIDER}/${PI_MODEL_ID}`)
 		}

+		const resourceLoader = new DefaultResourceLoader({
+			cwd: this.cwd,
+			agentDir: this.cwd,
+			settingsManager,
+			systemPrompt: this.systemPrompt,
+			extensionFactories: [this.createCompactionExtension()],
+			noExtensions: true,
+			noSkills: true,
+			noPromptTemplates: true,
+			noThemes: true,
+			noContextFiles: true,
+		})
+		await resourceLoader.reload()
+
+		const sessionManager = this.createMappedSessionManager()
+
 		const { session } = await createAgentSession({
 			cwd: this.cwd,
 			authStorage,
 			modelRegistry,
 			model,
-			resourceLoader: new InMemoryResourceLoader(this.systemPrompt),
+			resourceLoader,
 			settingsManager,
-			sessionManager: SessionManager.inMemory(this.cwd),
+			sessionManager,
 			noTools: "builtin",
 			customTools: createFreyaAgentTools({
 				toolbox: this.toolbox,
 			}),
-			tools: [...FREYA_AGENT_TOOL_NAMES],
+			tools: FREYA_AGENT_TOOL_NAMES,
 		})

 		return session
 	}

-	private async runPrompt(session: PiSession, input: QueryAgentAsk): Promise<void> {
-		await session.prompt(input.message)
+	/**
+	 * Creates Pi's SessionManager and records Pi-id -> Freya-sequence mappings.
+	 *
+	 * Hydrated DB messages are mapped through createSessionManager's callback.
+	 * Live user messages are mapped by wrapping appendMessage(), because Pi owns
+	 * the generated session entry id for messages written during prompt handling.
+	 */
+	private createMappedSessionManager(): PiSessionManager {
+		this.piEntryConversationSequences.clear()
+		const sessionManager = createSessionManager({
+			cwd: this.cwd,
+			entries: this.initialEntries,
+			modelProvider: PI_MODEL_PROVIDER,
+			modelId: PI_MODEL_ID,
+			onMessageEntryAppended: (piEntryId, entry) => {
+				this.piEntryConversationSequences.set(piEntryId, entry.sequence)
+			},
+		})
+		const appendMessage = sessionManager.appendMessage.bind(sessionManager)
+
+		sessionManager.appendMessage = (message: PiSessionMessage): string => {
+			const piEntryId = appendMessage(message)
+			const sequence = this.liveConversationSequenceForMessage(message)
+			if (sequence !== null) {
+				this.piEntryConversationSequences.set(piEntryId, sequence)
+			}
+			return piEntryId
+		}
+
+		return sessionManager
 	}

-	private handlePiEvent(event: AgentSessionEvent, push: (event: QueryAgentEvent) => void): void {
+	/**
+	 * Returns the Freya sequence for Pi's persisted live user message.
+	 *
+	 * We only map user messages here because they are the messages Freya writes
+	 * before invoking Pi. Assistant/tool entries are recorded from the stream
+	 * outside Pi's SessionManager and do not have a stable live Pi id available
+	 * at the storage boundary.
+	 */
+	private liveConversationSequenceForMessage(message: PiSessionMessage): number | null {
+		if (message.role !== "user") return null
+
+		const entry = this.activeUserMessageEntry
+		this.activeUserMessageEntry = null
+		if (!entry) return null
+
+		return entry.sequence
+	}
+
+	/**
+	 * Installs the minimal Pi extension used to observe compaction.
+	 *
+	 * session_before_compact gives us the full branch plus firstKeptEntryId, so
+	 * we translate that boundary before Pi writes the compaction entry. The later
+	 * session_compact event carries the saved summary, which we forward with the
+	 * cached Freya compacted entry range.
+	 */
+	private createCompactionExtension(): ExtensionFactory {
+		return (pi) => {
+			/**
+			 * Temporary handoff between Pi's before/after compaction hooks.
+			 *
+			 * session_compact receives the saved compaction entry, not the original
+			 * branch entries needed for boundary translation.
+			 */
+			let pendingCompactedEntryRange: QueryAgentCompactedEntryRange | null = null
+
+			pi.on("session_before_compact", async (event) => {
+				pendingCompactedEntryRange = this.compactedEntryRangeBeforePiEntry(
+					event.branchEntries,
+					event.preparation.firstKeptEntryId,
+				)
+			})
+
+			pi.on("session_compact", async (event) => {
+				const conversationId = this.activeConversationId
+				if (!conversationId) return
+
+				const entry = event.compactionEntry
+				const compactedEntryRange = pendingCompactedEntryRange
+				pendingCompactedEntryRange = null
+				const compactionEvent: QueryAgentCompactionEvent = {
+					type: QueryAgentEvent.Compaction,
+					conversationId,
+					summary: entry.summary,
+					firstKeptEntryId: entry.firstKeptEntryId,
+					compactedEntryRange,
+					tokensBefore: entry.tokensBefore,
+					details: entry.details,
+					fromExtension: event.fromExtension,
+				}
+
+				await this.emitEvent(compactionEvent)
+			})
+		}
+	}
+
+	/**
+	 * Returns the Freya entry range compacted before a Pi session entry.
+	 *
+	 * Pi keeps firstKeptEntryId and everything after it as raw context. Therefore
+	 * the summary covers only mapped entries before that Pi entry. If none of
+	 * those entries map back to Freya, we return null so storage can avoid
+	 * recording a summary with an unsafe coverage range.
+	 */
+	private compactedEntryRangeBeforePiEntry(
+		branchEntries: SessionEntry[],
+		piEntryId: string,
+	): QueryAgentCompactedEntryRange | null {
+		let endSequence: number | null = null
+		for (const entry of branchEntries) {
+			if (entry.id === piEntryId) {
+				if (endSequence === null) return null
+
+				return {
+					startSequence: 1,
+					endSequence,
+				}
+			}
+
+			const sequence = this.piEntryConversationSequences.get(entry.id)
+			if (typeof sequence === "number") {
+				endSequence = sequence
+			}
+		}
+
+		return null
+	}
+
+	private async emitEvent<T extends QueryAgentEvent>(event: QueryAgentEventMap[T]): Promise<void> {
+		const listeners = this.listenersFor(event.type)
+		for (const listener of listeners) {
+			await listener(event)
+		}
+	}
+
+	private listenersFor<T extends QueryAgentEvent>(type: T): QueryAgentEventListeners[T] {
+		return this.eventListeners[type]
+	}
+
+	private clearEventListeners(): void {
+		for (const listeners of Object.values(this.eventListeners)) {
+			listeners.clear()
+		}
+	}
+
+	private handlePiEvent(
+		event: AgentSessionEvent,
+		push: (event: QueryAgentStreamEvent) => void,
+	): void {
 		switch (event.type) {
 			case "message_end": {
 				const message = piAssistantMessageError(event.message)
@@ -283,7 +500,6 @@ function piAssistantMessageError(message: PiAgentMessage): string | null {
 				case "toolUse":
 					return null
 			}
-			return null
 		default:
 			return null
 	}
--- a/apps/freya-backend/src/agent/query-agent.ts
+++ b/apps/freya-backend/src/agent/query-agent.ts
@@ -1,21 +1,74 @@
 export interface QueryAgentAsk {
 	message: string
+	conversationId?: string
+	userMessageEntry?: QueryAgentConversationEntryRef
 }

-export type QueryAgentEvent =
+export type QueryAgentStreamEvent =
+	| { type: "conversation"; conversationId: string }
 	| { type: "text_delta"; text: string }
 	| { type: "tool_start"; toolName: string }
 	| { type: "tool_end"; toolName: string; ok: boolean }
 	| { type: "done" }
 	| { type: "error"; message: string }

+export const QueryAgentEvent = {
+	Compaction: "compaction",
+} as const
+
+export type QueryAgentEvent = (typeof QueryAgentEvent)[keyof typeof QueryAgentEvent]
+
+export interface QueryAgentConversationEntryRef {
+	id: string
+	sequence: number
+}
+
+export interface QueryAgentCompactedEntryRange {
+	startSequence: number
+	endSequence: number
+}
+
+export interface QueryAgentCompactionEvent {
+	type: typeof QueryAgentEvent.Compaction
+	conversationId: string
+	summary: string
+	firstKeptEntryId: string
+	compactedEntryRange: QueryAgentCompactedEntryRange | null
+	tokensBefore: number
+	details?: unknown
+	fromExtension: boolean
+}
+
+export interface QueryAgentEventMap {
+	[QueryAgentEvent.Compaction]: QueryAgentCompactionEvent
+}
+
+export type QueryAgentEventListener<T extends QueryAgentEvent> = (
+	event: QueryAgentEventMap[T],
+) => void | Promise<void>
+
+export type QueryAgentEventListeners = {
+	[T in QueryAgentEvent]: Set<QueryAgentEventListener<T>>
+}
+
+export function createQueryAgentEventListeners(): QueryAgentEventListeners {
+	return {
+		[QueryAgentEvent.Compaction]: new Set(),
+	}
+}
+
 export interface QueryAgent {
-	ask(input: QueryAgentAsk): AsyncIterable<QueryAgentEvent>
+	ask(input: QueryAgentAsk): AsyncIterable<QueryAgentStreamEvent>
+	addEventListener<T extends QueryAgentEvent>(
+		type: T,
+		listener: QueryAgentEventListener<T>,
+	): () => void
 	dispose(): void
 }

 export interface QueryAgentResponse {
 	message: string
+	conversationId?: string
 }

 export class QueryAgentError extends Error {
@@ -30,9 +83,13 @@ export async function collectQueryAgentResponse(
 	input: QueryAgentAsk,
 ): Promise<QueryAgentResponse> {
 	let message = ""
+	let conversationId: string | undefined

 	for await (const event of agent.ask(input)) {
 		switch (event.type) {
+			case "conversation":
+				conversationId = event.conversationId
+				break
 			case "text_delta":
 				message += event.text
 				break
@@ -45,5 +102,5 @@ export async function collectQueryAgentResponse(
 		}
 	}

-	return { message }
+	return { message, conversationId }
 }
--- a/apps/freya-backend/src/agent/session-manager.test.ts
+++ b/apps/freya-backend/src/agent/session-manager.test.ts
@@ -0,0 +1,156 @@
+import { describe, expect, test } from "bun:test"
+
+import type { ConversationStorageEntry } from "./conversation-recording-query-agent.ts"
+
+import { ConversationEntryKind } from "../conversations/types.ts"
+import { createSessionManager } from "./session-manager.ts"
+
+describe("createSessionManager", () => {
+	test("hydrates user and assistant entries into Pi session context", () => {
+		const sessionManager = createSessionManager({
+			entries: [
+				entry({
+					id: "entry-1",
+					sequence: 1,
+					kind: ConversationEntryKind.UserMessage,
+					payload: {
+						role: "user",
+						parts: [{ type: "text", text: "hello" }],
+					},
+				}),
+				entry({
+					id: "entry-2",
+					sequence: 2,
+					kind: ConversationEntryKind.AssistantMessage,
+					payload: {
+						role: "assistant",
+						parts: [{ type: "text", text: "hi there" }],
+					},
+					metadata: {
+						modelRun: {
+							route: "agent_query",
+							provider: "openrouter",
+							model: "stored-model",
+						},
+					},
+				}),
+			],
+			modelProvider: "openrouter",
+			modelId: "fallback-model",
+		})
+
+		const context = sessionManager.buildSessionContext()
+
+		expect(context.messages.map(roleOf)).toEqual(["user", "assistant"])
+		expect(textFromMessage(context.messages[0])).toBe("hello")
+		expect(textFromMessage(context.messages[1])).toBe("hi there")
+		expect(context.model).toEqual({
+			provider: "openrouter",
+			modelId: "stored-model",
+		})
+	})
+
+	test("uses the latest context summary and replays only uncovered raw entries", () => {
+		const sessionManager = createSessionManager({
+			entries: [
+				entry({
+					id: "entry-1",
+					sequence: 1,
+					kind: ConversationEntryKind.UserMessage,
+					payload: {
+						role: "user",
+						parts: [{ type: "text", text: "old question" }],
+					},
+				}),
+				entry({
+					id: "entry-2",
+					sequence: 2,
+					kind: ConversationEntryKind.AssistantMessage,
+					payload: {
+						role: "assistant",
+						parts: [{ type: "text", text: "old answer" }],
+					},
+				}),
+				entry({
+					id: "entry-3",
+					sequence: 3,
+					kind: ConversationEntryKind.ContextSummary,
+					payload: {
+						covers: {
+							startSequence: 1,
+							endSequence: 2,
+						},
+						summary: {
+							durableFacts: ["The user is designing conversation storage."],
+							preferences: [],
+							decisions: ["Context compaction is stored as a conversation entry."],
+							openTasks: [],
+							importantDetails: [],
+						},
+						promptVersion: "test-v1",
+					},
+				}),
+				entry({
+					id: "entry-4",
+					sequence: 4,
+					kind: ConversationEntryKind.UserMessage,
+					payload: {
+						role: "user",
+						parts: [{ type: "text", text: "new question" }],
+					},
+				}),
+			],
+			modelProvider: "openrouter",
+			modelId: "fallback-model",
+		})
+
+		const context = sessionManager.buildSessionContext()
+
+		expect(context.messages.map(roleOf)).toEqual(["compactionSummary", "user"])
+		expect(textFromMessage(context.messages[0])).toContain(
+			"The user is designing conversation storage.",
+		)
+		expect(textFromMessage(context.messages[0])).toContain(
+			"Context compaction is stored as a conversation entry.",
+		)
+		expect(textFromMessage(context.messages[1])).toBe("new question")
+	})
+})
+
+function entry(
+	input: Omit<ConversationStorageEntry, "createdAt" | "metadata"> & {
+		createdAt?: Date
+		metadata?: ConversationStorageEntry["metadata"]
+	},
+): ConversationStorageEntry {
+	return {
+		...input,
+		metadata: input.metadata ?? {},
+		createdAt: input.createdAt ?? new Date("2026-06-15T00:00:00.000Z"),
+	}
+}
+
+function roleOf(message: unknown): string | undefined {
+	if (!isRecord(message)) return undefined
+	return typeof message.role === "string" ? message.role : undefined
+}
+
+function textFromMessage(message: unknown): string {
+	if (!isRecord(message)) return ""
+	if (typeof message.summary === "string") return message.summary
+
+	const content = message.content
+	if (typeof content === "string") return content
+	if (!Array.isArray(content)) return ""
+
+	return content.map(textFromContentPart).join("")
+}
+
+function textFromContentPart(part: unknown): string {
+	if (!isRecord(part)) return ""
+	return typeof part.text === "string" ? part.text : ""
+}
+
+function isRecord(value: unknown): value is Record<string, unknown> {
+	return typeof value === "object" && value !== null
+}
--- a/apps/freya-backend/src/agent/session-manager.ts
+++ b/apps/freya-backend/src/agent/session-manager.ts
@@ -0,0 +1,188 @@
+import { SessionManager } from "@earendil-works/pi-coding-agent"
+import { tmpdir } from "node:os"
+
+import type { ConversationStorageEntry } from "./conversation-recording-query-agent.ts"
+
+import {
+	AssistantMessagePayload,
+	ContextSummaryPayload,
+	ConversationEntryKind,
+	UserMessagePayload,
+} from "../conversations/types.ts"
+
+type PiMessage = Parameters<SessionManager["appendMessage"]>[0]
+type PiAssistantMessage = Extract<PiMessage, { role: "assistant" }>
+
+export interface CreateSessionManagerInput {
+	cwd?: string
+	entries: ConversationStorageEntry[]
+	modelProvider: string
+	modelId: string
+	onMessageEntryAppended?: (piEntryId: string, entry: ConversationStorageEntry) => void
+}
+
+export function createSessionManager(input: CreateSessionManagerInput): SessionManager {
+	const sessionManager = SessionManager.inMemory(input.cwd ?? tmpdir())
+	const context = buildContextFromEntries(input.entries)
+
+	if (context.summary) {
+		sessionManager.appendCompaction(
+			context.summary.text,
+			"freya-db-context-start",
+			0,
+			{
+				conversationEntryId: context.summary.entry.id,
+				covers: context.summary.covers,
+			},
+			true,
+		)
+	}
+
+	for (const entry of context.entries) {
+		const message = messageForEntry(entry, input.modelProvider, input.modelId)
+		if (message) {
+			const piEntryId = sessionManager.appendMessage(message)
+			input.onMessageEntryAppended?.(piEntryId, entry)
+		}
+	}
+
+	return sessionManager
+}
+
+function buildContextFromEntries(entries: ConversationStorageEntry[]): {
+	summary?: { entry: ConversationStorageEntry; text: string; covers: unknown }
+	entries: ConversationStorageEntry[]
+} {
+	const orderedEntries = [...entries].sort((left, right) => left.sequence - right.sequence)
+	const summaryEntry = latestContextSummaryEntry(orderedEntries)
+	if (!summaryEntry || summaryEntry.kind !== ConversationEntryKind.ContextSummary) {
+		return { entries: orderedEntries }
+	}
+
+	const payload = ContextSummaryPayload.assert(summaryEntry.payload)
+	const text = contextSummaryText(payload.summary)
+	const rawStartSequence = payload.covers.endSequence + 1
+
+	return {
+		summary: {
+			entry: summaryEntry,
+			text,
+			covers: payload.covers,
+		},
+		entries: orderedEntries.filter((entry) => entry.sequence >= rawStartSequence),
+	}
+}
+
+function latestContextSummaryEntry(
+	entries: ConversationStorageEntry[],
+): ConversationStorageEntry | undefined {
+	let latest: ConversationStorageEntry | undefined
+
+	for (const entry of entries) {
+		if (entry.kind !== ConversationEntryKind.ContextSummary) continue
+		if (!latest || entry.sequence > latest.sequence) {
+			latest = entry
+		}
+	}
+
+	return latest
+}
+
+function messageForEntry(
+	entry: ConversationStorageEntry,
+	modelProvider: string,
+	modelId: string,
+): PiMessage | null {
+	switch (entry.kind) {
+		case ConversationEntryKind.UserMessage: {
+			const payload = UserMessagePayload.assert(entry.payload)
+			return {
+				role: "user",
+				content: messagePartsText(payload.parts),
+				timestamp: entry.createdAt.getTime(),
+			}
+		}
+		case ConversationEntryKind.AssistantMessage: {
+			const payload = AssistantMessagePayload.assert(entry.payload)
+			return {
+				role: "assistant",
+				content: [{ type: "text", text: messagePartsText(payload.parts) }],
+				api: "anthropic-messages",
+				provider: entry.metadata.modelRun?.provider ?? modelProvider,
+				model: entry.metadata.modelRun?.model ?? modelId,
+				usage: zeroUsage(),
+				stopReason: "stop",
+				timestamp: entry.createdAt.getTime(),
+			} satisfies PiAssistantMessage
+		}
+		case ConversationEntryKind.Attachment:
+		case ConversationEntryKind.ContextSummary:
+		case ConversationEntryKind.SystemNote:
+		case ConversationEntryKind.ToolCall:
+		case ConversationEntryKind.ToolResult:
+			return null
+	}
+}
+
+function messagePartsText(
+	parts: Array<{ type: "text"; text: string } | { type: "json"; value: unknown }>,
+): string {
+	return parts.map(messagePartText).join("\n")
+}
+
+function messagePartText(
+	part: { type: "text"; text: string } | { type: "json"; value: unknown },
+): string {
+	switch (part.type) {
+		case "text":
+			return part.text
+		case "json":
+			return stringifyJson(part.value)
+	}
+}
+
+function contextSummaryText(summary: {
+	userIntent?: string
+	durableFacts: string[]
+	preferences: string[]
+	decisions: string[]
+	openTasks: string[]
+	importantDetails: string[]
+}): string {
+	const sections: string[] = []
+	pushSection(sections, "User intent", summary.userIntent ? [summary.userIntent] : [])
+	pushSection(sections, "Durable facts", summary.durableFacts)
+	pushSection(sections, "Preferences", summary.preferences)
+	pushSection(sections, "Decisions", summary.decisions)
+	pushSection(sections, "Open tasks", summary.openTasks)
+	pushSection(sections, "Important details", summary.importantDetails)
+	return sections.join("\n\n")
+}
+
+function pushSection(sections: string[], title: string, values: string[]): void {
+	const trimmedValues = values.map((value) => value.trim()).filter(Boolean)
+	if (trimmedValues.length === 0) return
+
+	sections.push(`${title}:\n${trimmedValues.map((value) => `- ${value}`).join("\n")}`)
+}
+
+function stringifyJson(value: unknown): string {
+	return JSON.stringify(value, null, 2) ?? String(value)
+}
+
+function zeroUsage(): PiAssistantMessage["usage"] {
+	return {
+		input: 0,
+		output: 0,
+		cacheRead: 0,
+		cacheWrite: 0,
+		totalTokens: 0,
+		cost: {
+			input: 0,
+			output: 0,
+			cacheRead: 0,
+			cacheWrite: 0,
+			total: 0,
+		},
+	}
+}
--- a/apps/freya-backend/src/conversations/storage.ts
+++ b/apps/freya-backend/src/conversations/storage.ts
@@ -0,0 +1,373 @@
+import { and, asc, desc, eq } from "drizzle-orm"
+
+import type { Database } from "../db/index.ts"
+import type {
+	AssistantMessagePayload,
+	AttachmentPayload,
+	ContextSummaryPayload,
+	ConversationEntryKind as ConversationEntryKindType,
+	ConversationEntryMetadata,
+	ConversationEntryPayload,
+	ConversationEntryVisibility as ConversationEntryVisibilityType,
+	GenericObjectPayload,
+	UserMessagePayload,
+} from "./types.ts"
+
+import {
+	conversationEntries,
+	conversations as conversationsTable,
+	files,
+	user,
+} from "../db/schema.ts"
+import {
+	ConversationEntryMetadata as ConversationEntryMetadataSchema,
+	AssistantMessagePayload as AssistantMessagePayloadSchema,
+	AttachmentPayload as AttachmentPayloadSchema,
+	ConversationEntryKind,
+	ConversationEntryKindInput,
+	ConversationEntryVisibility,
+	ConversationEntryVisibilityInput,
+	ContextSummaryPayload as ContextSummaryPayloadSchema,
+	GenericObjectPayload as GenericObjectPayloadSchema,
+	UserMessagePayload as UserMessagePayloadSchema,
+} from "./types.ts"
+
+export type ConversationRow = typeof conversationsTable.$inferSelect
+export type ConversationEntryRow = typeof conversationEntries.$inferSelect
+export type FileRow = typeof files.$inferSelect
+
+export interface CreateFileInput {
+	storageKey: string
+	originalName?: string
+	mimeType: string
+	sizeBytes: number
+	metadata?: Record<string, unknown>
+}
+
+export interface AppendAttachmentEntryInput {
+	file: CreateFileInput
+	payload: AttachmentPayload
+	visibility?: ConversationEntryVisibilityType
+	metadata?: ConversationEntryMetadata
+}
+
+export interface AppendAttachmentEntryResult {
+	file: FileRow
+	entry: ConversationEntryRow
+}
+
+interface AppendConversationEntryBase {
+	visibility?: ConversationEntryVisibilityType
+	metadata?: ConversationEntryMetadata
+}
+
+export type AppendConversationEntryInput =
+	| (AppendConversationEntryBase & {
+			kind: typeof ConversationEntryKind.UserMessage
+			payload: UserMessagePayload
+			fileId?: never
+	  })
+	| (AppendConversationEntryBase & {
+			kind: typeof ConversationEntryKind.AssistantMessage
+			payload: AssistantMessagePayload
+			fileId?: never
+	  })
+	| (AppendConversationEntryBase & {
+			kind: typeof ConversationEntryKind.Attachment
+			payload: AttachmentPayload
+			fileId: string
+	  })
+	| (AppendConversationEntryBase & {
+			kind: typeof ConversationEntryKind.ContextSummary
+			payload: ContextSummaryPayload
+			fileId?: never
+	  })
+	| (AppendConversationEntryBase & {
+			kind:
+				| typeof ConversationEntryKind.ToolCall
+				| typeof ConversationEntryKind.ToolResult
+				| typeof ConversationEntryKind.SystemNote
+			payload: GenericObjectPayload
+			fileId?: never
+	  })
+
+export interface ListConversationEntriesParams {
+	visibility?: ConversationEntryVisibilityType
+}
+
+export function conversations(db: Database, userId: string) {
+	return {
+		async createConversation(): Promise<ConversationRow> {
+			return insertConversation(db, userId)
+		},
+
+		async getOrCreateConversation(): Promise<ConversationRow> {
+			return db.transaction(async (tx) => {
+				await requireUserForUpdate(tx, userId)
+				const existing = await latestConversation(tx, userId)
+				if (existing) return existing
+
+				return insertConversation(tx, userId)
+			})
+		},
+
+		async createFile(input: CreateFileInput): Promise<FileRow> {
+			return insertFile(db, userId, input)
+		},
+
+		async appendEntry(
+			conversationId: string,
+			input: AppendConversationEntryInput,
+		): Promise<ConversationEntryRow> {
+			const kind = ConversationEntryKindInput.assert(input.kind)
+			const visibility = ConversationEntryVisibilityInput.assert(
+				input.visibility ?? defaultVisibilityForKind(kind),
+			)
+			const payload = payloadForKind(kind, input.payload)
+			const metadata = ConversationEntryMetadataSchema.assert(input.metadata ?? {})
+			let fileId: string | null = null
+
+			if (input.kind === ConversationEntryKind.Attachment) {
+				fileId = input.fileId
+				await requireFile(db, userId, fileId)
+			}
+
+			const rows = await db.transaction(async (tx) => {
+				await requireConversationForUpdate(tx, userId, conversationId)
+				const sequence = await nextSequence(tx, conversationId)
+
+				const rows = await tx
+					.insert(conversationEntries)
+					.values({
+						conversationId,
+						sequence,
+						kind,
+						visibility,
+						fileId,
+						payload,
+						metadata,
+					})
+					.returning()
+
+				await touchConversation(tx, userId, conversationId)
+				return rows
+			})
+
+			return requireRow(rows)
+		},
+
+		async appendAttachmentEntry(
+			conversationId: string,
+			input: AppendAttachmentEntryInput,
+		): Promise<AppendAttachmentEntryResult> {
+			const payload = AttachmentPayloadSchema.assert(input.payload)
+			const visibility = ConversationEntryVisibilityInput.assert(
+				input.visibility ?? defaultVisibilityForKind(ConversationEntryKind.Attachment),
+			)
+			const metadata = ConversationEntryMetadataSchema.assert(input.metadata ?? {})
+
+			return db.transaction(async (tx) => {
+				await requireConversationForUpdate(tx, userId, conversationId)
+
+				const file = await insertFile(tx, userId, input.file)
+				const sequence = await nextSequence(tx, conversationId)
+				const rows = await tx
+					.insert(conversationEntries)
+					.values({
+						conversationId,
+						sequence,
+						kind: ConversationEntryKind.Attachment,
+						visibility,
+						fileId: file.id,
+						payload,
+						metadata,
+					})
+					.returning()
+
+				await touchConversation(tx, userId, conversationId)
+				return {
+					file,
+					entry: requireRow(rows),
+				}
+			})
+		},
+
+		async listEntries(
+			conversationId: string,
+			params: ListConversationEntriesParams = {},
+		): Promise<ConversationEntryRow[]> {
+			await requireConversation(db, userId, conversationId)
+
+			if (params.visibility) {
+				return db
+					.select()
+					.from(conversationEntries)
+					.where(
+						and(
+							eq(conversationEntries.conversationId, conversationId),
+							eq(conversationEntries.visibility, params.visibility),
+						),
+					)
+					.orderBy(asc(conversationEntries.sequence))
+			}
+
+			return db
+				.select()
+				.from(conversationEntries)
+				.where(eq(conversationEntries.conversationId, conversationId))
+				.orderBy(asc(conversationEntries.sequence))
+		},
+	}
+}
+
+function payloadForKind(
+	kind: ConversationEntryKindType,
+	payload: AppendConversationEntryInput["payload"],
+): ConversationEntryPayload {
+	switch (kind) {
+		case ConversationEntryKind.UserMessage:
+			return UserMessagePayloadSchema.assert(payload)
+		case ConversationEntryKind.AssistantMessage:
+			return AssistantMessagePayloadSchema.assert(payload)
+		case ConversationEntryKind.Attachment:
+			return AttachmentPayloadSchema.assert(payload)
+		case ConversationEntryKind.ContextSummary:
+			return ContextSummaryPayloadSchema.assert(payload)
+		case ConversationEntryKind.ToolCall:
+		case ConversationEntryKind.ToolResult:
+		case ConversationEntryKind.SystemNote:
+			return GenericObjectPayloadSchema.assert(payload)
+	}
+}
+
+async function requireUserForUpdate(db: Database, userId: string): Promise<void> {
+	const rows = await db
+		.select({ id: user.id })
+		.from(user)
+		.where(eq(user.id, userId))
+		.limit(1)
+		.for("update")
+
+	requireRow(rows, `User not found: ${userId}`)
+}
+
+async function requireConversation(
+	db: Database,
+	userId: string,
+	conversationId: string,
+): Promise<ConversationRow> {
+	const rows = await db
+		.select()
+		.from(conversationsTable)
+		.where(and(eq(conversationsTable.id, conversationId), eq(conversationsTable.userId, userId)))
+		.limit(1)
+
+	return requireRow(rows, `Conversation not found: ${conversationId}`)
+}
+
+async function requireConversationForUpdate(
+	db: Database,
+	userId: string,
+	conversationId: string,
+): Promise<ConversationRow> {
+	const rows = await db
+		.select()
+		.from(conversationsTable)
+		.where(and(eq(conversationsTable.id, conversationId), eq(conversationsTable.userId, userId)))
+		.limit(1)
+		.for("update")
+
+	return requireRow(rows, `Conversation not found: ${conversationId}`)
+}
+
+async function latestConversation(db: Database, userId: string): Promise<ConversationRow | null> {
+	const rows = await db
+		.select()
+		.from(conversationsTable)
+		.where(eq(conversationsTable.userId, userId))
+		.orderBy(desc(conversationsTable.updatedAt), desc(conversationsTable.createdAt))
+		.limit(1)
+
+	return rows[0] ?? null
+}
+
+async function insertConversation(db: Database, userId: string): Promise<ConversationRow> {
+	const rows = await db
+		.insert(conversationsTable)
+		.values({
+			userId,
+		})
+		.returning()
+
+	return requireRow(rows)
+}
+
+async function requireFile(db: Database, userId: string, fileId: string): Promise<FileRow> {
+	const rows = await db
+		.select()
+		.from(files)
+		.where(and(eq(files.id, fileId), eq(files.userId, userId)))
+		.limit(1)
+
+	return requireRow(rows, `File not found: ${fileId}`)
+}
+
+async function insertFile(db: Database, userId: string, input: CreateFileInput): Promise<FileRow> {
+	const rows = await db
+		.insert(files)
+		.values({
+			userId,
+			storageKey: input.storageKey,
+			originalName: input.originalName ?? null,
+			mimeType: input.mimeType,
+			sizeBytes: input.sizeBytes,
+			metadata: input.metadata ?? {},
+		})
+		.returning()
+
+	return requireRow(rows)
+}
+
+async function touchConversation(
+	db: Database,
+	userId: string,
+	conversationId: string,
+): Promise<void> {
+	await db
+		.update(conversationsTable)
+		.set({ updatedAt: new Date() })
+		.where(and(eq(conversationsTable.id, conversationId), eq(conversationsTable.userId, userId)))
+}
+
+async function nextSequence(db: Database, conversationId: string): Promise<number> {
+	const rows = await db
+		.select({ sequence: conversationEntries.sequence })
+		.from(conversationEntries)
+		.where(eq(conversationEntries.conversationId, conversationId))
+		.orderBy(desc(conversationEntries.sequence))
+		.limit(1)
+
+	return (rows[0]?.sequence ?? 0) + 1
+}
+
+function requireRow<T>(rows: T[], message = "Expected database row"): T {
+	const row = rows[0]
+	if (!row) throw new Error(message)
+	return row
+}
+
+function defaultVisibilityForKind(
+	kind: ConversationEntryKindType,
+): ConversationEntryVisibilityType {
+	switch (kind) {
+		case ConversationEntryKind.UserMessage:
+		case ConversationEntryKind.AssistantMessage:
+		case ConversationEntryKind.Attachment:
+			return ConversationEntryVisibility.UserVisible
+		case ConversationEntryKind.ToolCall:
+		case ConversationEntryKind.ToolResult:
+		case ConversationEntryKind.ContextSummary:
+		case ConversationEntryKind.SystemNote:
+			return ConversationEntryVisibility.Internal
+	}
+}
--- a/apps/freya-backend/src/conversations/types.test.ts
+++ b/apps/freya-backend/src/conversations/types.test.ts
@@ -0,0 +1,146 @@
+import { describe, expect, test } from "bun:test"
+
+import {
+	AttachmentType,
+	AttachmentPayload,
+	ContextSummaryPayload,
+	ConversationEntryMetadata,
+	GenericObjectPayload,
+	UserMessagePayload,
+} from "./types.ts"
+
+describe("conversation entry schemas", () => {
+	test("parses valid user message payloads", () => {
+		const payload = UserMessagePayload.assert({
+			role: "user",
+			parts: [{ type: "text", text: "hello" }],
+		})
+
+		expect(payload).toEqual({
+			role: "user",
+			parts: [{ type: "text", text: "hello" }],
+		})
+	})
+
+	test("rejects user message payloads with the wrong role", () => {
+		expect(() =>
+			UserMessagePayload.assert({
+				role: "assistant",
+				parts: [{ type: "text", text: "hello" }],
+			}),
+		).toThrow()
+	})
+
+	test("rejects user message payloads with no parts", () => {
+		expect(() =>
+			UserMessagePayload.assert({
+				role: "user",
+				parts: [],
+			}),
+		).toThrow()
+	})
+
+	test("parses valid attachment payloads", () => {
+		const payload = AttachmentPayload.assert({
+			role: "user",
+			name: "whiteboard.png",
+			mimeType: "image/png",
+			attachmentType: AttachmentType.Image,
+			caption: "whiteboard sketch",
+		})
+
+		expect(payload).toEqual({
+			role: "user",
+			name: "whiteboard.png",
+			mimeType: "image/png",
+			attachmentType: AttachmentType.Image,
+			caption: "whiteboard sketch",
+		})
+	})
+
+	test("rejects extra fields on structured payloads", () => {
+		expect(() =>
+			AttachmentPayload.assert({
+				role: "user",
+				name: "whiteboard.png",
+				mimeType: "image/png",
+				attachmentType: AttachmentType.Image,
+				fileId: "file-1",
+			}),
+		).toThrow()
+	})
+
+	test("parses context summary payloads", () => {
+		const payload = ContextSummaryPayload.assert({
+			covers: {
+				startSequence: 1,
+				endSequence: 12,
+			},
+			summary: {
+				userIntent: "Design message storage.",
+				durableFacts: [],
+				preferences: ["Keep the schema simple."],
+				decisions: ["Use conversation_entries as the timeline."],
+				openTasks: [],
+				importantDetails: [],
+			},
+			promptVersion: "conversation-summary-v1",
+			sourceEntryIds: ["entry-1", "entry-2"],
+		})
+
+		expect(payload).toMatchObject({
+			covers: {
+				startSequence: 1,
+				endSequence: 12,
+			},
+			promptVersion: "conversation-summary-v1",
+		})
+	})
+
+	test("allows generic object payloads for tool entries", () => {
+		const payload = GenericObjectPayload.assert({
+			toolCallId: "call-1",
+			toolName: "calendar.search",
+			input: { date: "2026-06-15" },
+		})
+
+		expect(payload).toEqual({
+			toolCallId: "call-1",
+			toolName: "calendar.search",
+			input: { date: "2026-06-15" },
+		})
+	})
+
+	test("rejects non-object generic payloads", () => {
+		expect(() => GenericObjectPayload.assert("done")).toThrow()
+	})
+
+	test("parses model run metadata and allows extra top-level metadata", () => {
+		const metadata = ConversationEntryMetadata.assert({
+			modelRun: {
+				route: "default-chat",
+				provider: "pi",
+				model: "pi-model",
+				inputTokens: 120,
+				outputTokens: 24,
+			},
+			traceId: "trace-1",
+		})
+
+		expect(metadata.modelRun?.model).toBe("pi-model")
+		expect(metadata.traceId).toBe("trace-1")
+	})
+
+	test("rejects invalid model run metadata", () => {
+		expect(() =>
+			ConversationEntryMetadata.assert({
+				modelRun: {
+					route: "default-chat",
+					provider: "pi",
+					model: "pi-model",
+					inputTokens: -1,
+				},
+			}),
+		).toThrow()
+	})
+})
--- a/apps/freya-backend/src/conversations/types.ts
+++ b/apps/freya-backend/src/conversations/types.ts
@@ -0,0 +1,136 @@
+import { type } from "arktype"
+
+export const ConversationEntryKind = {
+	UserMessage: "user_message",
+	AssistantMessage: "assistant_message",
+	Attachment: "attachment",
+	ToolCall: "tool_call",
+	ToolResult: "tool_result",
+	ContextSummary: "context_summary",
+	SystemNote: "system_note",
+} as const
+
+export type ConversationEntryKind =
+	(typeof ConversationEntryKind)[keyof typeof ConversationEntryKind]
+
+export const ConversationEntryVisibility = {
+	UserVisible: "user_visible",
+	Internal: "internal",
+} as const
+
+export type ConversationEntryVisibility =
+	(typeof ConversationEntryVisibility)[keyof typeof ConversationEntryVisibility]
+
+export const AttachmentType = {
+	Image: "image",
+	Audio: "audio",
+	Video: "video",
+	Document: "document",
+	Other: "other",
+} as const
+
+export type AttachmentType = (typeof AttachmentType)[keyof typeof AttachmentType]
+
+export const ConversationEntryKindInput = type.enumerated(...Object.values(ConversationEntryKind))
+export const ConversationEntryVisibilityInput = type.enumerated(
+	...Object.values(ConversationEntryVisibility),
+)
+export const AttachmentTypeInput = type.enumerated(...Object.values(AttachmentType))
+
+const TextMessagePart = type({
+	"+": "reject",
+	type: "'text'",
+	text: "string",
+})
+
+const JsonMessagePart = type({
+	"+": "reject",
+	type: "'json'",
+	value: "unknown",
+})
+
+export const MessagePart = type.or(TextMessagePart, JsonMessagePart)
+export type MessagePart = typeof MessagePart.infer
+
+export const UserMessagePayload = type({
+	"+": "reject",
+	role: "'user'",
+	parts: MessagePart.array().atLeastLength(1),
+})
+
+export type UserMessagePayload = typeof UserMessagePayload.infer
+
+export const AssistantMessagePayload = type({
+	"+": "reject",
+	role: "'assistant'",
+	parts: MessagePart.array().atLeastLength(1),
+})
+
+export type AssistantMessagePayload = typeof AssistantMessagePayload.infer
+
+export const AttachmentPayload = type({
+	"+": "reject",
+	role: type.enumerated("user", "assistant"),
+	name: "string",
+	mimeType: "string",
+	attachmentType: AttachmentTypeInput,
+	"caption?": "string",
+})
+
+export type AttachmentPayload = typeof AttachmentPayload.infer
+
+const ContextSummary = type({
+	"+": "reject",
+	"userIntent?": "string",
+	durableFacts: type.string.array(),
+	preferences: type.string.array(),
+	decisions: type.string.array(),
+	openTasks: type.string.array(),
+	importantDetails: type.string.array(),
+})
+
+export const ContextSummaryPayload = type({
+	"+": "reject",
+	covers: type({
+		"+": "reject",
+		startSequence: "number.integer >= 1",
+		endSequence: "number.integer >= 1",
+	}),
+	summary: ContextSummary,
+	promptVersion: "string",
+	"sourceEntryIds?": type.string.array(),
+})
+
+export type ContextSummaryPayload = typeof ContextSummaryPayload.infer
+
+export const ModelRunMetadata = type({
+	"+": "reject",
+	route: "string",
+	provider: "string",
+	model: "string",
+	"contextSummaryEntryId?": "string",
+	"rawEntriesStartSequence?": "number.integer >= 1",
+	"rawEntriesEndSequence?": "number.integer >= 1",
+	"inputTokens?": "number.integer >= 0",
+	"outputTokens?": "number.integer >= 0",
+	"providerRequestId?": "string",
+})
+
+export type ModelRunMetadata = typeof ModelRunMetadata.infer
+
+export const ConversationEntryMetadata = type({
+	"modelRun?": ModelRunMetadata,
+	"[string]": "unknown",
+})
+
+export type ConversationEntryMetadata = typeof ConversationEntryMetadata.infer
+
+export const GenericObjectPayload = type("Record<string, unknown>")
+export type GenericObjectPayload = typeof GenericObjectPayload.infer
+
+export type ConversationEntryPayload =
+	| UserMessagePayload
+	| AssistantMessagePayload
+	| AttachmentPayload
+	| ContextSummaryPayload
+	| GenericObjectPayload
--- a/apps/freya-backend/src/db/schema.ts
+++ b/apps/freya-backend/src/db/schema.ts
@@ -1,6 +1,9 @@
+import { sql } from "drizzle-orm"
 import {
 	boolean,
+	check,
 	customType,
+	integer,
 	index,
 	jsonb,
 	pgTable,
@@ -10,6 +13,14 @@ import {
 	uuid,
 } from "drizzle-orm/pg-core"

+import {
+	ConversationEntryVisibility,
+	type ConversationEntryKind,
+	type ConversationEntryMetadata,
+	type ConversationEntryPayload,
+	type ConversationEntryVisibility as ConversationEntryVisibilityType,
+} from "../conversations/types.ts"
+
 // ---------------------------------------------------------------------------
 // Better Auth core tables
 // Re-exported from CLI-generated schema.
@@ -61,6 +72,81 @@ export const userSources = pgTable(
 	],
 )

+// ---------------------------------------------------------------------------
+// FREYA — conversations
+// ---------------------------------------------------------------------------
+
+export const conversations = pgTable(
+	"conversations",
+	{
+		id: uuid("id").primaryKey().defaultRandom(),
+		userId: text("user_id")
+			.notNull()
+			.references(() => user.id, { onDelete: "cascade" }),
+		createdAt: timestamp("created_at").notNull().defaultNow(),
+		updatedAt: timestamp("updated_at")
+			.notNull()
+			.defaultNow()
+			.$onUpdate(() => new Date()),
+	},
+	(t) => [index("conversations_user_id_updated_at_idx").on(t.userId, t.updatedAt)],
+)
+
+export const files = pgTable(
+	"files",
+	{
+		id: uuid("id").primaryKey().defaultRandom(),
+		userId: text("user_id")
+			.notNull()
+			.references(() => user.id, { onDelete: "cascade" }),
+		storageKey: text("storage_key").notNull(),
+		originalName: text("original_name"),
+		mimeType: text("mime_type").notNull(),
+		sizeBytes: integer("size_bytes").notNull(),
+		metadata: jsonb("metadata").$type<Record<string, unknown>>().notNull().default({}),
+		createdAt: timestamp("created_at").notNull().defaultNow(),
+	},
+	(t) => [
+		unique("files_storage_key_unique").on(t.storageKey),
+		index("files_user_id_created_at_idx").on(t.userId, t.createdAt),
+	],
+)
+
+export const conversationEntries = pgTable(
+	"conversation_entries",
+	{
+		id: uuid("id").primaryKey().defaultRandom(),
+		conversationId: uuid("conversation_id")
+			.notNull()
+			.references(() => conversations.id, { onDelete: "cascade" }),
+		sequence: integer("sequence").notNull(),
+		kind: text("kind").$type<ConversationEntryKind>().notNull(),
+		visibility: text("visibility")
+			.$type<ConversationEntryVisibilityType>()
+			.notNull()
+			.default(ConversationEntryVisibility.Internal),
+		fileId: uuid("file_id").references(() => files.id, { onDelete: "restrict" }),
+		payload: jsonb("payload").$type<ConversationEntryPayload>().notNull(),
+		metadata: jsonb("metadata").$type<ConversationEntryMetadata>().notNull().default({}),
+		createdAt: timestamp("created_at").notNull().defaultNow(),
+	},
+	(t) => [
+		unique("conversation_entries_conversation_id_sequence_unique").on(t.conversationId, t.sequence),
+		index("conversation_entries_conversation_id_sequence_idx").on(t.conversationId, t.sequence),
+		index("conversation_entries_conversation_id_visibility_sequence_idx").on(
+			t.conversationId,
+			t.visibility,
+			t.sequence,
+		),
+		index("conversation_entries_kind_idx").on(t.kind),
+		index("conversation_entries_file_id_idx").on(t.fileId),
+		check(
+			"conversation_entries_attachment_file_id_check",
+			sql`(${t.kind} = 'attachment' and ${t.fileId} is not null) or (${t.kind} <> 'attachment' and ${t.fileId} is null)`,
+		),
+	],
+)
+
 // ---------------------------------------------------------------------------
 // FREYA — reminders source storage
 // ---------------------------------------------------------------------------
--- a/apps/freya-backend/src/engine/http.test.ts
+++ b/apps/freya-backend/src/engine/http.test.ts
@@ -85,6 +85,20 @@ mock.module("../sources/user-sources.ts", () => ({
 	}),
 }))

+mock.module("../conversations/storage.ts", () => ({
+	conversations: (_db: Database, userId: string) => ({
+		async getOrCreateConversation() {
+			return { id: `conversation-${userId}` }
+		},
+		async listEntries() {
+			return []
+		},
+		async appendEntry() {
+			return { id: "entry-1", sequence: 1 }
+		},
+	}),
+}))
+
 const fakeDb = {} as Database

 describe("GET /api/feed", () => {
--- a/apps/freya-backend/src/session/user-session-manager.test.ts
+++ b/apps/freya-backend/src/session/user-session-manager.test.ts
@@ -4,9 +4,12 @@ import { LocationSource } from "@freya/source-location"
 import { WeatherSource } from "@freya/source-weatherkit"
 import { beforeEach, describe, expect, mock, spyOn, test } from "bun:test"

+import type { ConversationStorageEntry } from "../agent/conversation-recording-query-agent.ts"
+import type { AppendConversationEntryInput } from "../conversations/storage.ts"
 import type { Database } from "../db/index.ts"
 import type { FeedSourceProvider } from "./feed-source-provider.ts"

+import { ConversationEntryKind } from "../conversations/types.ts"
 import { CredentialEncryptor } from "../lib/crypto.ts"
 import {
 	CredentialStorageUnavailableError,
@@ -21,6 +24,8 @@ import { UserSessionManager } from "./user-session-manager.ts"
 * Key = userId (or "*" for a default), value = array of enabled sourceIds.
 */
 const enabledByUser = new Map<string, string[]>()
+const conversationEntriesByUser = new Map<string, ConversationStorageEntry[]>()
+const mockConversationCalls: Array<{ type: "getOrCreate" | "listEntries"; userId: string }> = []

 /** Set which sourceIds are enabled for all users. */
 function setEnabledSources(sourceIds: string[]) {
@@ -37,6 +42,10 @@ function getEnabledSourceIds(userId: string): string[] {
 	return enabledByUser.get(userId) ?? enabledByUser.get("*") ?? []
 }

+function setConversationEntriesForUser(userId: string, entries: ConversationStorageEntry[]) {
+	conversationEntriesByUser.set(userId, entries)
+}
+
 /**
 * Controls what `find()` returns in the mock. When `undefined` (the default),
 * `find()` returns a standard enabled row. Set to a specific value (including
@@ -111,6 +120,35 @@ mock.module("../sources/user-sources.ts", () => ({
 	}),
 }))

+mock.module("../conversations/storage.ts", () => ({
+	conversations: (_db: Database, userId: string) => ({
+		async getOrCreateConversation(): Promise<{ id: string }> {
+			mockConversationCalls.push({ type: "getOrCreate", userId })
+			return { id: `conversation-${userId}` }
+		},
+		async listEntries(_conversationId: string): Promise<ConversationStorageEntry[]> {
+			mockConversationCalls.push({ type: "listEntries", userId })
+			return conversationEntriesByUser.get(userId) ?? []
+		},
+		async appendEntry(
+			_conversationId: string,
+			input: AppendConversationEntryInput,
+		): Promise<ConversationStorageEntry> {
+			const entries = conversationEntriesByUser.get(userId) ?? []
+			const row: ConversationStorageEntry = {
+				id: `entry-${entries.length + 1}`,
+				sequence: entries.length + 1,
+				kind: input.kind,
+				payload: input.payload,
+				metadata: input.metadata ?? {},
+				createdAt: new Date("2026-06-15T00:00:00.000Z"),
+			}
+			conversationEntriesByUser.set(userId, [...entries, row])
+			return row
+		},
+	}),
+}))
+
 const fakeDb = {
 	transaction: <T>(fn: (tx: unknown) => Promise<T>) => fn(fakeDb),
 } as unknown as Database
@@ -160,6 +198,8 @@ const weatherProvider: FeedSourceProvider = {

 beforeEach(() => {
 	enabledByUser.clear()
+	conversationEntriesByUser.clear()
+	mockConversationCalls.length = 0
 	mockFindResult = undefined
 	mockUpdateCredentialsCalls.length = 0
 	mockUpdateCredentialsError = null
@@ -176,6 +216,31 @@ describe("UserSessionManager", () => {
 		expect(session.engine).toBeDefined()
 	})

+	test("getOrCreate eagerly loads conversation entries for the user session", async () => {
+		setEnabledSources([])
+		setConversationEntriesForUser("user-1", [
+			{
+				id: "entry-1",
+				sequence: 1,
+				kind: ConversationEntryKind.UserMessage,
+				payload: {
+					role: "user",
+					parts: [{ type: "text", text: "stored hello" }],
+				},
+				metadata: {},
+				createdAt: new Date("2026-06-15T00:00:00.000Z"),
+			},
+		])
+		const manager = new UserSessionManager({ db: fakeDb, providers: [] })
+
+		await manager.getOrCreate("user-1")
+
+		expect(mockConversationCalls).toEqual([
+			{ type: "getOrCreate", userId: "user-1" },
+			{ type: "listEntries", userId: "user-1" },
+		])
+	})
+
 	test("getOrCreate returns same session for same user", async () => {
 		setEnabledSources(["freya.location"])
 		const manager = new UserSessionManager({ db: fakeDb, providers: [locationProvider] })
--- a/apps/freya-backend/src/session/user-session-manager.ts
+++ b/apps/freya-backend/src/session/user-session-manager.ts
@@ -8,6 +8,7 @@ import type { FeedEnhancer } from "../enhancement/enhance-feed.ts"
 import type { CredentialEncryptor } from "../lib/crypto.ts"
 import type { FeedSourceProvider } from "./feed-source-provider.ts"

+import { conversations } from "../conversations/storage.ts"
 import {
 	CredentialStorageUnavailableError,
 	InvalidSourceConfigError,
@@ -362,6 +363,7 @@ export class UserSessionManager {

 	private async createSession(userId: string): Promise<UserSession> {
 		const enabledRows = await sources(this.db, userId).enabled()
+		const agentConfig = this.queryAgentConfigForUser(userId)

 		const promises: Promise<FeedSource>[] = []
 		for (const row of enabledRows) {
@@ -373,7 +375,7 @@ export class UserSessionManager {
 		}

 		if (promises.length === 0) {
-			return new UserSession(userId, [], this.feedEnhancer, this.queryAgentConfig)
+			return this.initializedSession(userId, [], agentConfig)
 		}

 		const results = await Promise.allSettled(promises)
@@ -397,7 +399,29 @@ export class UserSessionManager {
 			console.error("[UserSessionManager] Feed source provider failed:", error)
 		}

-		return new UserSession(userId, feedSources, this.feedEnhancer, this.queryAgentConfig)
+		return this.initializedSession(userId, feedSources, agentConfig)
+	}
+
+	private queryAgentConfigForUser(userId: string): UserSessionAgentConfig {
+		return {
+			...(this.queryAgentConfig ?? {}),
+			conversationStorage: conversations(this.db, userId),
+		}
+	}
+
+	private async initializedSession(
+		userId: string,
+		sources: FeedSource[],
+		agentConfig: UserSessionAgentConfig,
+	): Promise<UserSession> {
+		const session = new UserSession(userId, sources, this.feedEnhancer, agentConfig)
+		try {
+			await session.initialize()
+			return session
+		} catch (err) {
+			session.destroy()
+			throw err
+		}
 	}

 	/**
--- a/apps/freya-backend/src/session/user-session.test.ts
+++ b/apps/freya-backend/src/session/user-session.test.ts
@@ -3,6 +3,13 @@ import type { ActionDefinition, ContextEntry, FeedItem, FeedSource } from "@frey
 import { LocationSource } from "@freya/source-location"
 import { describe, expect, spyOn, test } from "bun:test"

+import type {
+	ConversationStorage,
+	ConversationStorageEntry,
+} from "../agent/conversation-recording-query-agent.ts"
+import type { AppendConversationEntryInput } from "../conversations/storage.ts"
+
+import { ConversationEntryKind } from "../conversations/types.ts"
 import { UserSession } from "./user-session.ts"

 function createStubSource(id: string, items: FeedItem[] = []): FeedSource {
@@ -23,6 +30,40 @@ function createStubSource(id: string, items: FeedItem[] = []): FeedSource {
 	}
 }

+class FakeConversationStorage implements ConversationStorage {
+	readonly calls: string[] = []
+	private readonly entries: ConversationStorageEntry[]
+
+	constructor(entries: ConversationStorageEntry[] = []) {
+		this.entries = entries
+	}
+
+	async getOrCreateConversation(): Promise<{ id: string }> {
+		this.calls.push("getOrCreateConversation")
+		return { id: "conversation-1" }
+	}
+
+	async appendEntry(
+		_conversationId: string,
+		input: AppendConversationEntryInput,
+	): Promise<ConversationStorageEntry> {
+		this.calls.push("appendEntry")
+		return {
+			id: "entry-appended",
+			sequence: 1,
+			kind: input.kind,
+			payload: input.payload,
+			metadata: input.metadata ?? {},
+			createdAt: new Date("2026-06-15T00:00:00.000Z"),
+		}
+	}
+
+	async listEntries(_conversationId: string): Promise<ConversationStorageEntry[]> {
+		this.calls.push("listEntries")
+		return this.entries
+	}
+}
+
 describe("UserSession", () => {
 	test("registers sources and starts engine", async () => {
 		const session = new UserSession("test-user", [
@@ -67,6 +108,32 @@ describe("UserSession", () => {
 		expect(disposeSpy).toHaveBeenCalled()
 	})

+	test("initialize loads conversation entries before exposing stored agent", async () => {
+		const storage = new FakeConversationStorage([
+			{
+				id: "entry-1",
+				sequence: 1,
+				kind: ConversationEntryKind.UserMessage,
+				payload: {
+					role: "user",
+					parts: [{ type: "text", text: "stored hello" }],
+				},
+				metadata: {},
+				createdAt: new Date("2026-06-15T00:00:00.000Z"),
+			},
+		])
+		const session = new UserSession("test-user", [createStubSource("test")], null, {
+			conversationStorage: storage,
+		})
+
+		expect(() => session.agent).toThrow("UserSession has not been initialized")
+
+		await session.initialize()
+
+		expect(storage.calls).toEqual(["getOrCreateConversation", "listEntries"])
+		expect(session.agent).toBeDefined()
+	})
+
 	test("engine.executeAction routes to correct source", async () => {
 		const location = new LocationSource()
 		const session = new UserSession("test-user", [location])
--- a/apps/freya-backend/src/session/user-session.ts
+++ b/apps/freya-backend/src/session/user-session.ts
@@ -10,22 +10,30 @@ import type { QueryAgentToolbox } from "../agent/query-agent-toolbox.ts"
 import type { QueryAgent } from "../agent/query-agent.ts"
 import type { FeedEnhancer } from "../enhancement/enhance-feed.ts"

-import { PiQueryAgent } from "../agent/pi-query-agent.ts"
+import {
+	ConversationRecordingQueryAgent,
+	type ConversationStorage,
+} from "../agent/conversation-recording-query-agent.ts"
+import { PiQueryAgent, PI_MODEL_ID, PI_MODEL_PROVIDER } from "../agent/pi-query-agent.ts"
 import { UserSessionQueryAgentToolbox } from "../agent/user-session-query-agent-toolbox.ts"

 export interface UserSessionAgentConfig {
 	apiKey?: string
 	cwd?: string
 	systemPrompt?: string
+	conversationStorage?: ConversationStorage
 }

 export class UserSession {
 	readonly userId: string
 	readonly engine: FeedEngine
 	readonly toolbox: QueryAgentToolbox
-	readonly agent: QueryAgent
 	private sources = new Map<string, FeedSource>()
 	private readonly enhancer: FeedEnhancer | null
+	private readonly agentConfig: UserSessionAgentConfig | undefined
+	private queryAgent: QueryAgent | null = null
+	private initializePromise: Promise<void> | null = null
+	private initialized = false
 	private enhancedItems: FeedItem[] | null = null
 	/** The FeedResult that enhancedItems was derived from. */
 	private enhancedSource: FeedResult | null = null
@@ -41,6 +49,7 @@ export class UserSession {
 		this.userId = userId
 		this.engine = new FeedEngine()
 		this.enhancer = enhancer ?? null
+		this.agentConfig = agentConfig
 		for (const source of sources) {
 			this.sources.set(source.id, source)
 			this.engine.register(source)
@@ -54,17 +63,43 @@ export class UserSession {
 		}

 		this.toolbox = new UserSessionQueryAgentToolbox(this)
-		this.agent = new PiQueryAgent({
-			userId: this.userId,
-			toolbox: this.toolbox,
-			apiKey: agentConfig?.apiKey,
-			cwd: agentConfig?.cwd,
-			systemPrompt: agentConfig?.systemPrompt,
-		})
+		if (!agentConfig?.conversationStorage) {
+			this.queryAgent = new PiQueryAgent({
+				toolbox: this.toolbox,
+				apiKey: this.agentConfig?.apiKey,
+				cwd: this.agentConfig?.cwd,
+				systemPrompt: this.agentConfig?.systemPrompt,
+			})
+			this.initialized = true
+		}

 		this.engine.start()
 	}

+	get agent(): QueryAgent {
+		if (!this.queryAgent) {
+			throw new Error("UserSession has not been initialized")
+		}
+		return this.queryAgent
+	}
+
+	async initialize(): Promise<void> {
+		if (this.initialized) return
+		if (this.initializePromise) return this.initializePromise
+
+		const promise = this.initializeAgent()
+		this.initializePromise = promise
+
+		try {
+			await promise
+			this.initialized = true
+		} finally {
+			if (this.initializePromise === promise) {
+				this.initializePromise = null
+			}
+		}
+	}
+
 	/**
 	 * Returns the current feed, refreshing if the engine cache expired.
 	 * Enhancement runs eagerly on engine updates; this method awaits
@@ -201,7 +236,8 @@ export class UserSession {
 	}

 	destroy(): void {
-		this.agent.dispose()
+		this.queryAgent?.dispose()
+		this.queryAgent = null
 		this.unsubscribe?.()
 		this.unsubscribe = null
 		this.engine.stop()
@@ -210,6 +246,38 @@ export class UserSession {
 		this.enhancingPromise = null
 	}

+	private async initializeAgent(): Promise<void> {
+		if (this.queryAgent) return
+
+		const conversationStorage = this.agentConfig?.conversationStorage
+		if (!conversationStorage) {
+			this.queryAgent = new PiQueryAgent({
+				toolbox: this.toolbox,
+				apiKey: this.agentConfig?.apiKey,
+				cwd: this.agentConfig?.cwd,
+				systemPrompt: this.agentConfig?.systemPrompt,
+			})
+			return
+		}
+
+		const conversation = await conversationStorage.getOrCreateConversation()
+		const entries = await conversationStorage.listEntries(conversation.id)
+
+		this.queryAgent = new ConversationRecordingQueryAgent({
+			agent: new PiQueryAgent({
+				toolbox: this.toolbox,
+				apiKey: this.agentConfig?.apiKey,
+				cwd: this.agentConfig?.cwd,
+				systemPrompt: this.agentConfig?.systemPrompt,
+				initialEntries: entries,
+			}),
+			storage: conversationStorage,
+			defaultConversationId: conversation.id,
+			modelProvider: PI_MODEL_PROVIDER,
+			modelId: PI_MODEL_ID,
+		})
+	}
+
 	private invalidateEnhancement(): void {
 		this.enhancedItems = null
 		this.enhancedSource = null
--- a/apps/freya-backend/src/sources/http.test.ts
+++ b/apps/freya-backend/src/sources/http.test.ts
@@ -128,6 +128,20 @@ mock.module("../sources/user-sources.ts", () => ({
 	},
 }))

+mock.module("../conversations/storage.ts", () => ({
+	conversations: (_db: Database, userId: string) => ({
+		async getOrCreateConversation() {
+			return { id: `conversation-${userId}` }
+		},
+		async listEntries() {
+			return []
+		},
+		async appendEntry() {
+			return { id: "entry-1", sequence: 1 }
+		},
+	}),
+}))
+
 const fakeDb = {
 	transaction: <T>(fn: (tx: unknown) => Promise<T>) => fn(fakeDb),
 } as unknown as Database