@alfe.ai/openclaw-memory-cloud 0.0.25 → 0.0.26

package/.turbo/turbo-build.log

@@ -1,4 +1,4 @@
 
-> @alfe.ai/openclaw-memory-cloud@0.0.25 build /home/runner/work/alfe/alfe/packages/openclaw-memory-cloud
+> @alfe.ai/openclaw-memory-cloud@0.0.26 build /home/runner/work/alfe/alfe/packages/openclaw-memory-cloud
 > tsc
 

package/CHANGELOG.md

@@ -1,5 +1,24 @@
 # @alfe.ai/openclaw-memory-cloud
 
+## 0.0.26
+
+### Patch Changes
+
+- 0f90085: One-time backfill of existing chat history when memory is first installed. On
+  startup, if the server-side `sessionsBackfillSyncedAt` flag is unset, the plugin
+  reads the openclaw-chat session files (`~/.alfe/sessions/chat/*.json`), takes the
+  most recent `backfillMaxSessions` (default 50) sessions, and ingests messages
+  through the existing `/agent/memory/ingest` pipeline. Duplicate-safe by
+  construction: a timestamp cutoff excludes anything already captured live (agents
+  that had memory before this release only backfill pre-install messages), and the
+  ingest consumer's per-session `lastProcessedIndex` high-water mark makes retries
+  free. New plugin config: `backfillSessions` (default true), `backfillMaxSessions`
+  (default 50). agent-api-client: `memoryBootstrapStatus()` now also returns
+  `sessionsBackfillSynced`/`sessionsBackfillSyncedAt`, and
+  `memoryBootstrapStatusMark()` accepts an optional `scope` ("files" | "sessions").
+- Updated dependencies [0f90085]
+  - @alfe.ai/agent-api-client@0.6.0
+
 ## 0.0.25
 
 ### Patch Changes

package/dist/index.d.ts.map

@@ -1 +1 @@
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package/dist/index.js

@@ -18,6 +18,7 @@ import { AgentApiClient } from "@alfe.ai/agent-api-client";
 import { AutoCapture } from "./auto-capture.js";
 import { AutoRecall } from "./auto-recall.js";
 import { formatSearchResults } from "./formatter.js";
+import { runSessionsBackfill } from "./session-backfill.js";
 import { createRequire } from 'node:module';
 const require = createRequire(import.meta.url);
 const pkg = require('../package.json');
@@ -26,6 +27,8 @@ const DEFAULT_CONFIG = {
     autoRecall: true,
     captureMaxChars: 500,
     idleFlushSeconds: 60,
+    backfillSessions: true,
+    backfillMaxSessions: 50,
 };
 function resolvePluginConfig(pluginConfig) {
     return {
@@ -33,6 +36,10 @@ function resolvePluginConfig(pluginConfig) {
         autoRecall: typeof pluginConfig?.autoRecall === "boolean" ? pluginConfig.autoRecall : DEFAULT_CONFIG.autoRecall,
         captureMaxChars: typeof pluginConfig?.captureMaxChars === "number" ? pluginConfig.captureMaxChars : DEFAULT_CONFIG.captureMaxChars,
         idleFlushSeconds: typeof pluginConfig?.idleFlushSeconds === "number" ? pluginConfig.idleFlushSeconds : DEFAULT_CONFIG.idleFlushSeconds,
+        backfillSessions: typeof pluginConfig?.backfillSessions === "boolean" ? pluginConfig.backfillSessions : DEFAULT_CONFIG.backfillSessions,
+        backfillMaxSessions: typeof pluginConfig?.backfillMaxSessions === "number" && Number.isFinite(pluginConfig.backfillMaxSessions) && pluginConfig.backfillMaxSessions > 0
+            ? Math.floor(pluginConfig.backfillMaxSessions)
+            : DEFAULT_CONFIG.backfillMaxSessions,
     };
 }
 export default {
@@ -280,16 +287,20 @@ export default {
                 await autoCapture.onAgentEnd();
             }
         });
-        // Fire-and-forget first-run sync: if MEMORY.md / memory/*.md exist
-        // in the workspace, ingest them once into cloud memory. Idempotent
-        // via PalaceMetadata.bootstrapSyncedAt.
-        void runBootstrap(client, logger).catch((err) => {
-            logger.warn("memory bootstrap failed; will retry on next startup", { err: String(err) });
+        // Fire-and-forget first-run sync: workspace files (MEMORY.md / memory/*.md)
+        // and pre-existing chat sessions, each idempotent via its own
+        // PalaceMetadata flag (bootstrapSyncedAt / sessionsBackfillSyncedAt).
+        void runStartupSync(client, config, logger).catch((err) => {
+            logger.warn("memory startup sync failed; will retry on next startup", { err: String(err) });
         });
         logger.info("memory-cloud extension registered", { autoCapture: config.autoCapture, autoRecall: config.autoRecall });
     },
 };
-async function runBootstrap(client, logger) {
+async function runStartupSync(client, config, logger) {
+    // Fetch status ONCE, before the file bootstrap runs: the sessions backfill
+    // computes its dedup cutoff from the pre-bootstrap `syncedAt` (an agent
+    // that already had memory installed captured everything after that moment
+    // live, so backfilling past it would duplicate memories).
     let status;
     try {
         status = await client.memoryBootstrapStatus();
@@ -298,10 +309,29 @@ async function runBootstrap(client, logger) {
         logger.debug("memory bootstrap status check failed; skipping", { err: String(err) });
         return;
     }
+    const startupMs = Date.now();
     if (status.synced) {
         logger.debug("memory bootstrap: already synced, skipping");
-        return;
     }
+    else {
+        try {
+            await runBootstrap(client, logger);
+        }
+        catch (err) {
+            logger.warn("memory bootstrap failed; will retry on next startup", { err: String(err) });
+        }
+    }
+    // Strict `=== false` on purpose: an old server (deployed before the
+    // sessions-backfill release) omits the field entirely, and its mark
+    // endpoint would clobber `bootstrapSyncedAt` — corrupting the cutoff
+    // anchor. Defer until the service is deployed and reports the flag.
+    if (config.backfillSessions && status.sessionsBackfillSynced === false) {
+        const installedAtMs = status.syncedAt ? Date.parse(status.syncedAt) : Number.POSITIVE_INFINITY;
+        const cutoffMs = Math.min(startupMs, Number.isNaN(installedAtMs) ? Number.POSITIVE_INFINITY : installedAtMs);
+        await runSessionsBackfill(client, config, logger, { cutoffMs });
+    }
+}
+async function runBootstrap(client, logger) {
     const cwd = process.cwd();
     const filesToSync = [];
     try {

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package/dist/session-backfill.d.ts

@@ -0,0 +1,54 @@
+/**
+ * Session backfill — one-time ingestion of pre-existing chat history into
+ * cloud memory, run fire-and-forget at plugin startup (see index.ts).
+ *
+ * Reads the openclaw-chat plugin's on-disk session files directly:
+ *   ~/.alfe/sessions/chat/{sessionId}.json
+ * The write side is packages/openclaw-chat/src/session-store.ts — that path
+ * and file shape are a read contract; keep the two in sync. The chat plugin
+ * is not a package dependency because its session-store functions aren't
+ * part of its public entry and the plugin isn't guaranteed to be installed
+ * alongside memory. Like the session store itself, this assumes one agent
+ * per machine (`alfe remove` deletes ~/.alfe, so files never outlive the
+ * agent they belong to).
+ *
+ * No-re-sync guarantees (in concert with services/memory):
+ * 1. Runs only while the server-side `sessionsBackfillSyncedAt` flag is
+ *    unset; the flag survives integration uninstall/reinstall.
+ * 2. Only messages with timestamp < cutoffMs are ingested — for agents that
+ *    already had memory installed, everything after `bootstrapSyncedAt` was
+ *    already captured live by AutoCapture.
+ * 3. sessionKey = file sessionId and index = file array position, so the
+ *    ingest consumer's per-session `lastProcessedIndex` high-water mark makes
+ *    a crash-and-retry replay free (filtered server-side before any cost).
+ *
+ * Each session is sent as exactly ONE memoryIngest call (one SQS message,
+ * windowed to the most recent messages that fit the caps below). Splitting a
+ * session across multiple SQS messages would race the shared per-session
+ * high-water mark on the standard (non-FIFO) ingest queue: a transiently
+ * failed early chunk redelivered after a later chunk succeeds gets filtered
+ * out and silently lost.
+ */
+import type { MemoryCloudConfig, MemoryMessage, SessionMetadata } from "./types.js";
+interface BackfillApi {
+    memoryIngest(sessionKey: string, messages: MemoryMessage[], metadata?: SessionMetadata): Promise<{
+        queued: boolean;
+        messageCount: number;
+    }>;
+    memoryBootstrapStatusMark(scope?: "files" | "sessions"): Promise<{
+        synced: true;
+        syncedAt: string;
+    }>;
+}
+interface BackfillLogger {
+    info: (msg: string, ctx?: Record<string, unknown>) => void;
+    debug: (msg: string, ctx?: Record<string, unknown>) => void;
+    warn: (msg: string, ctx?: Record<string, unknown>) => void;
+}
+export interface SessionsBackfillOptions {
+    cutoffMs: number;
+    sessionsDir?: string;
+}
+export declare function runSessionsBackfill(client: BackfillApi, config: MemoryCloudConfig, logger: BackfillLogger, opts: SessionsBackfillOptions): Promise<void>;
+export {};
+//# sourceMappingURL=session-backfill.d.ts.map

package/dist/session-backfill.d.ts.map

@@ -0,0 +1 @@
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package/dist/session-backfill.js

@@ -0,0 +1,192 @@
+/**
+ * Session backfill — one-time ingestion of pre-existing chat history into
+ * cloud memory, run fire-and-forget at plugin startup (see index.ts).
+ *
+ * Reads the openclaw-chat plugin's on-disk session files directly:
+ *   ~/.alfe/sessions/chat/{sessionId}.json
+ * The write side is packages/openclaw-chat/src/session-store.ts — that path
+ * and file shape are a read contract; keep the two in sync. The chat plugin
+ * is not a package dependency because its session-store functions aren't
+ * part of its public entry and the plugin isn't guaranteed to be installed
+ * alongside memory. Like the session store itself, this assumes one agent
+ * per machine (`alfe remove` deletes ~/.alfe, so files never outlive the
+ * agent they belong to).
+ *
+ * No-re-sync guarantees (in concert with services/memory):
+ * 1. Runs only while the server-side `sessionsBackfillSyncedAt` flag is
+ *    unset; the flag survives integration uninstall/reinstall.
+ * 2. Only messages with timestamp < cutoffMs are ingested — for agents that
+ *    already had memory installed, everything after `bootstrapSyncedAt` was
+ *    already captured live by AutoCapture.
+ * 3. sessionKey = file sessionId and index = file array position, so the
+ *    ingest consumer's per-session `lastProcessedIndex` high-water mark makes
+ *    a crash-and-retry replay free (filtered server-side before any cost).
+ *
+ * Each session is sent as exactly ONE memoryIngest call (one SQS message,
+ * windowed to the most recent messages that fit the caps below). Splitting a
+ * session across multiple SQS messages would race the shared per-session
+ * high-water mark on the standard (non-FIFO) ingest queue: a transiently
+ * failed early chunk redelivered after a later chunk succeeds gets filtered
+ * out and silently lost.
+ */
+import { readdir, readFile } from "node:fs/promises";
+import { join } from "node:path";
+import { homedir } from "node:os";
+const DEFAULT_SESSIONS_DIR = join(homedir(), ".alfe", "sessions", "chat");
+// Server-side zod caps on /agent/memory/ingest (services/memory
+// api-agents/ingest/post.ts) — exceeding any of these is a deterministic 400,
+// which would put the startup retry loop into a permanent failure.
+const MAX_MESSAGES_PER_SESSION = 500;
+const MAX_SESSION_KEY_CHARS = 256;
+const MAX_MESSAGE_INDEX = 1_000_000;
+const MAX_CONTENT_CHARS = 100_000;
+/** One ingest call becomes one SQS SendMessage (256KB hard limit). */
+const MAX_BATCH_BYTES = 180_000;
+export async function runSessionsBackfill(client, config, logger, opts) {
+    const sessionsDir = opts.sessionsDir ?? DEFAULT_SESSIONS_DIR;
+    let fileNames;
+    try {
+        fileNames = (await readdir(sessionsDir)).filter((name) => name.endsWith(".json"));
+    }
+    catch (err) {
+        if (err.code === "ENOENT") {
+            // No sessions directory — nothing to backfill, ever.
+            logger.debug("sessions backfill: no sessions directory, marking complete");
+            try {
+                await client.memoryBootstrapStatusMark("sessions");
+            }
+            catch { /* retry next start */ }
+        }
+        else {
+            // Transient (EACCES/EMFILE/...) — don't forfeit the backfill.
+            logger.warn("sessions backfill: sessions directory unreadable; will retry on next startup", { err: String(err) });
+        }
+        return;
+    }
+    const sessions = [];
+    for (const name of fileNames) {
+        const parsed = await parseSessionFile(join(sessionsDir, name), config.captureMaxChars, opts.cutoffMs);
+        if (parsed)
+            sessions.push(parsed);
+    }
+    // Most recent non-empty sessions first, capped. Filter BEFORE capping:
+    // on a retrofit agent the newest sessions are often entirely post-install
+    // (emptied by the cutoff) and must not occupy the cap slots.
+    const eligible = sessions
+        .filter((s) => s.messages.length > 0)
+        .sort((a, b) => b.lastMessageMs - a.lastMessageMs)
+        .slice(0, config.backfillMaxSessions);
+    if (eligible.length === 0) {
+        logger.debug("sessions backfill: no eligible sessions, marking complete");
+        try {
+            await client.memoryBootstrapStatusMark("sessions");
+        }
+        catch { /* retry next start */ }
+        return;
+    }
+    logger.info("sessions backfill: ingesting sessions", {
+        sessionCount: eligible.length,
+        messageCount: eligible.reduce((n, s) => n + s.messages.length, 0),
+    });
+    for (const session of eligible) {
+        const metadata = {
+            ...(session.channel ? { channelId: session.channel } : {}),
+            ...(session.userId ? { userId: session.userId } : {}),
+        };
+        try {
+            await client.memoryIngest(session.sessionId, session.messages, metadata);
+        }
+        catch (err) {
+            // Abort without marking — next startup replays, and the server-side
+            // lastProcessedIndex filter discards already-processed sessions free.
+            logger.warn("sessions backfill: ingest failed; will retry on next startup", {
+                sessionId: session.sessionId,
+                err: String(err),
+            });
+            return;
+        }
+    }
+    try {
+        await client.memoryBootstrapStatusMark("sessions");
+        logger.info("sessions backfill: complete", { sessionCount: eligible.length });
+    }
+    catch (err) {
+        logger.warn("sessions backfill: mark failed; will retry on next startup", { err: String(err) });
+    }
+}
+/**
+ * Tolerant parse of a single session file. Returns null for corrupt or
+ * shape-mismatched files (skipped, never fatal). Message `index` is the
+ * original array position in the file — stable because the store is
+ * append-only — so retries resume idempotently server-side.
+ */
+async function parseSessionFile(filePath, captureMaxChars, cutoffMs) {
+    let raw;
+    try {
+        raw = JSON.parse(await readFile(filePath, "utf8"));
+    }
+    catch {
+        return null;
+    }
+    if (typeof raw !== "object" || raw === null)
+        return null;
+    const data = raw;
+    if (typeof data.sessionId !== "string" || data.sessionId.length === 0)
+        return null;
+    if (data.sessionId.length > MAX_SESSION_KEY_CHARS)
+        return null;
+    if (!Array.isArray(data.messages))
+        return null;
+    const maxContentChars = Math.min(captureMaxChars, MAX_CONTENT_CHARS);
+    let lastMessageMs = 0;
+    const filtered = [];
+    for (const [index, entry] of data.messages.entries()) {
+        if (index > MAX_MESSAGE_INDEX)
+            break;
+        if (typeof entry !== "object" || entry === null)
+            continue;
+        const msg = entry;
+        if (msg.role !== "user" && msg.role !== "assistant")
+            continue;
+        if (typeof msg.content !== "string" || msg.content.trim().length === 0)
+            continue;
+        if (typeof msg.timestamp !== "number")
+            continue;
+        lastMessageMs = Math.max(lastMessageMs, msg.timestamp);
+        if (msg.timestamp >= cutoffMs)
+            continue;
+        filtered.push({
+            role: msg.role,
+            content: msg.content.length > maxContentChars ? msg.content.slice(0, maxContentChars) : msg.content,
+            index,
+            timestamp: new Date(msg.timestamp).toISOString(),
+        });
+    }
+    return {
+        sessionId: data.sessionId,
+        channel: typeof data.channel === "string" ? data.channel : undefined,
+        userId: typeof data.userId === "string" ? data.userId : undefined,
+        messages: recentWindow(filtered),
+        lastMessageMs,
+    };
+}
+/**
+ * The most recent contiguous run of messages fitting both ingest caps
+ * (message count and serialized bytes). Walks backwards from the newest
+ * message and stops at the first one that would overflow the byte budget.
+ */
+function recentWindow(messages) {
+    const window = [];
+    let bytes = 0;
+    for (let i = messages.length - 1; i >= 0; i--) {
+        if (window.length >= MAX_MESSAGES_PER_SESSION)
+            break;
+        const msgBytes = Buffer.byteLength(JSON.stringify(messages[i])) + 1;
+        if (bytes + msgBytes > MAX_BATCH_BYTES)
+            break;
+        window.unshift(messages[i]);
+        bytes += msgBytes;
+    }
+    return window;
+}
+//# sourceMappingURL=session-backfill.js.map

package/dist/session-backfill.js.map

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package/dist/types.d.ts

@@ -3,6 +3,8 @@ export interface MemoryCloudConfig {
     autoRecall: boolean;
     captureMaxChars: number;
     idleFlushSeconds: number;
+    backfillSessions: boolean;
+    backfillMaxSessions: number;
 }
 export interface MemoryMessage {
     role: string;

package/dist/types.d.ts.map

@@ -1 +1 @@
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package/openclaw.plugin.json

@@ -43,6 +43,18 @@
         "minimum": 10,
         "maximum": 600,
         "description": "Flush memories after this many seconds of no messages"
+      },
+      "backfillSessions": {
+        "type": "boolean",
+        "default": true,
+        "description": "On first install, ingest the agent's existing chat sessions into memory (one-time, duplicate-safe)"
+      },
+      "backfillMaxSessions": {
+        "type": "number",
+        "default": 50,
+        "minimum": 1,
+        "maximum": 1000,
+        "description": "Maximum number of most-recent chat sessions to backfill"
       }
     }
   },
@@ -58,6 +70,14 @@
     "idleFlushSeconds": {
       "label": "Idle flush interval",
       "description": "Seconds of inactivity before flushing pending memories"
+    },
+    "backfillSessions": {
+      "label": "Backfill chat history",
+      "description": "Ingest existing chat sessions into memory on first install"
+    },
+    "backfillMaxSessions": {
+      "label": "Backfill session cap",
+      "description": "Maximum number of most-recent chat sessions to backfill"
     }
   }
 }

package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@alfe.ai/openclaw-memory-cloud",
-  "version": "0.0.25",
+  "version": "0.0.26",
   "description": "Cloud memory extension for OpenClaw — Turbopuffer vectors + DynamoDB knowledge graph",
   "type": "module",
   "main": "dist/index.js",
@@ -11,7 +11,7 @@
     ]
   },
   "dependencies": {
-    "@alfe.ai/agent-api-client": "0.5.0",
+    "@alfe.ai/agent-api-client": "0.6.0",
     "@alfe.ai/config": "0.3.0"
   },
   "license": "UNLICENSED",
@@ -27,6 +27,8 @@
   ],
   "scripts": {
     "build": "tsc",
+    "test": "vitest run --passWithNoTests",
+    "test:watch": "vitest",
     "typecheck": "tsc --noEmit",
     "lint": "eslint ."
   }

package/src/__tests__/session-backfill.test.ts

@@ -0,0 +1,289 @@
+import { describe, it, expect, vi, beforeEach, afterEach } from "vitest";
+import { mkdtemp, writeFile, rm, mkdir, chmod } from "node:fs/promises";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+import { runSessionsBackfill } from "../session-backfill.js";
+import type { MemoryCloudConfig, MemoryMessage, SessionMetadata } from "../types.js";
+
+const CONFIG: MemoryCloudConfig = {
+  autoCapture: true,
+  autoRecall: true,
+  captureMaxChars: 500,
+  idleFlushSeconds: 60,
+  backfillSessions: true,
+  backfillMaxSessions: 50,
+};
+
+const logger = { info: vi.fn(), debug: vi.fn(), warn: vi.fn() };
+
+function makeClient() {
+  return {
+    memoryIngest: vi.fn(async (sessionKey: string, messages: MemoryMessage[], metadata?: SessionMetadata) => {
+      void sessionKey;
+      void metadata;
+      return { queued: true, messageCount: messages.length };
+    }),
+    memoryBootstrapStatusMark: vi.fn(async (scope?: "files" | "sessions") => {
+      void scope;
+      return { synced: true as const, syncedAt: new Date().toISOString() };
+    }),
+  };
+}
+
+function sessionFile(sessionId: string, messages: { role: string; content: string; timestamp: number }[], extra?: Record<string, unknown>) {
+  return JSON.stringify({
+    sessionId,
+    agentId: "",
+    channel: "alfe",
+    createdAt: new Date(0).toISOString(),
+    updatedAt: new Date().toISOString(),
+    messages,
+    ...extra,
+  });
+}
+
+describe("runSessionsBackfill", () => {
+  let dir: string;
+
+  beforeEach(async () => {
+    dir = await mkdtemp(join(tmpdir(), "memory-backfill-"));
+    vi.clearAllMocks();
+  });
+
+  afterEach(async () => {
+    await rm(dir, { recursive: true, force: true });
+  });
+
+  it("marks complete immediately when the sessions directory is missing", async () => {
+    const client = makeClient();
+    await runSessionsBackfill(client, CONFIG, logger, { cutoffMs: Date.now(), sessionsDir: join(dir, "nope") });
+    expect(client.memoryIngest).not.toHaveBeenCalled();
+    expect(client.memoryBootstrapStatusMark).toHaveBeenCalledWith("sessions");
+  });
+
+  it("marks complete when no eligible sessions exist", async () => {
+    const client = makeClient();
+    await runSessionsBackfill(client, CONFIG, logger, { cutoffMs: Date.now(), sessionsDir: dir });
+    expect(client.memoryIngest).not.toHaveBeenCalled();
+    expect(client.memoryBootstrapStatusMark).toHaveBeenCalledWith("sessions");
+  });
+
+  it("skips corrupt and shape-mismatched files but ingests valid ones", async () => {
+    await writeFile(join(dir, "corrupt.json"), "{not json");
+    await writeFile(join(dir, "no-messages.json"), JSON.stringify({ sessionId: "x" }));
+    await writeFile(join(dir, "good.json"), sessionFile("alfe:dm:user1", [
+      { role: "user", content: "hello", timestamp: 1000 },
+      { role: "assistant", content: "hi there", timestamp: 2000 },
+    ]));
+
+    const client = makeClient();
+    await runSessionsBackfill(client, CONFIG, logger, { cutoffMs: Date.now(), sessionsDir: dir });
+
+    expect(client.memoryIngest).toHaveBeenCalledTimes(1);
+    const [sessionKey, messages] = client.memoryIngest.mock.calls[0];
+    expect(sessionKey).toBe("alfe:dm:user1");
+    expect(messages).toHaveLength(2);
+    expect(client.memoryBootstrapStatusMark).toHaveBeenCalledWith("sessions");
+  });
+
+  it("excludes messages at or after the cutoff (retrofit dedup)", async () => {
+    await writeFile(join(dir, "s.json"), sessionFile("alfe:dm:u", [
+      { role: "user", content: "before install", timestamp: 1000 },
+      { role: "user", content: "after install", timestamp: 5000 },
+    ]));
+
+    const client = makeClient();
+    await runSessionsBackfill(client, CONFIG, logger, { cutoffMs: 5000, sessionsDir: dir });
+
+    const [, messages] = client.memoryIngest.mock.calls[0];
+    expect(messages).toHaveLength(1);
+    expect((messages as MemoryMessage[])[0].content).toBe("before install");
+  });
+
+  it("preserves file-array positions as indexes and skips invalid entries without renumbering", async () => {
+    await writeFile(join(dir, "s.json"), sessionFile("alfe:dm:u", [
+      { role: "user", content: "first", timestamp: 1000 },
+      { role: "system", content: "not a chat role", timestamp: 1500 },
+      { role: "assistant", content: "second", timestamp: 2000 },
+    ]));
+
+    const client = makeClient();
+    await runSessionsBackfill(client, CONFIG, logger, { cutoffMs: Date.now(), sessionsDir: dir });
+
+    const [, messages] = client.memoryIngest.mock.calls[0] as [string, MemoryMessage[]];
+    expect(messages.map((m) => m.index)).toEqual([0, 2]);
+    expect(messages[0].timestamp).toBe(new Date(1000).toISOString());
+  });
+
+  it("truncates message content to captureMaxChars", async () => {
+    await writeFile(join(dir, "s.json"), sessionFile("alfe:dm:u", [
+      { role: "user", content: "x".repeat(2000), timestamp: 1000 },
+    ]));
+
+    const client = makeClient();
+    await runSessionsBackfill(client, CONFIG, logger, { cutoffMs: Date.now(), sessionsDir: dir });
+
+    const [, messages] = client.memoryIngest.mock.calls[0] as [string, MemoryMessage[]];
+    expect(messages[0].content).toHaveLength(500);
+  });
+
+  it("sends each session as exactly one ingest call (no cross-chunk race)", async () => {
+    const messages = Array.from({ length: 101 }, (_, i) => ({
+      role: "user",
+      content: `msg ${String(i)}`,
+      timestamp: 1000 + i,
+    }));
+    await writeFile(join(dir, "s.json"), sessionFile("alfe:dm:u", messages));
+
+    const client = makeClient();
+    await runSessionsBackfill(client, CONFIG, logger, { cutoffMs: Date.now(), sessionsDir: dir });
+
+    expect(client.memoryIngest).toHaveBeenCalledTimes(1);
+    expect(client.memoryIngest.mock.calls[0][1]).toHaveLength(101);
+  });
+
+  it("keeps only the most recent 500 messages of a session, preserving original indexes", async () => {
+    const messages = Array.from({ length: 600 }, (_, i) => ({
+      role: "user",
+      content: `msg ${String(i)}`,
+      timestamp: 1000 + i,
+    }));
+    await writeFile(join(dir, "s.json"), sessionFile("alfe:dm:u", messages));
+
+    const client = makeClient();
+    await runSessionsBackfill(client, CONFIG, logger, { cutoffMs: Date.now(), sessionsDir: dir });
+
+    expect(client.memoryIngest).toHaveBeenCalledTimes(1);
+    const sent = client.memoryIngest.mock.calls[0][1] as MemoryMessage[];
+    expect(sent).toHaveLength(500);
+    expect(sent[0].index).toBe(100);
+    expect(sent[sent.length - 1].index).toBe(599);
+  });
+
+  it("shrinks the window to the most recent messages when the byte budget would overflow", async () => {
+    // ~40KB of content per message → only 4 fit in the 180KB budget.
+    const messages = Array.from({ length: 10 }, (_, i) => ({
+      role: "user",
+      content: "x".repeat(40_000),
+      timestamp: 1000 + i,
+    }));
+    await writeFile(join(dir, "s.json"), sessionFile("alfe:dm:u", messages));
+
+    const client = makeClient();
+    await runSessionsBackfill(client, { ...CONFIG, captureMaxChars: 50_000 }, logger, { cutoffMs: Date.now(), sessionsDir: dir });
+
+    expect(client.memoryIngest).toHaveBeenCalledTimes(1);
+    const sent = client.memoryIngest.mock.calls[0][1] as MemoryMessage[];
+    expect(sent).toHaveLength(4);
+    expect(sent[sent.length - 1].index).toBe(9);
+  });
+
+  it("skips sessions whose sessionId exceeds the server's 256-char cap", async () => {
+    await writeFile(join(dir, "long.json"), sessionFile("x".repeat(300), [
+      { role: "user", content: "hello", timestamp: 1000 },
+    ]));
+
+    const client = makeClient();
+    await runSessionsBackfill(client, CONFIG, logger, { cutoffMs: Date.now(), sessionsDir: dir });
+
+    expect(client.memoryIngest).not.toHaveBeenCalled();
+    expect(client.memoryBootstrapStatusMark).toHaveBeenCalledWith("sessions");
+  });
+
+  it("does not let post-cutoff sessions starve pre-cutoff sessions out of the cap (retrofit)", async () => {
+    // Newest session is entirely post-install — emptied by the cutoff. It
+    // must not occupy the single cap slot.
+    await writeFile(join(dir, "post-install.json"), sessionFile("alfe:dm:recent", [
+      { role: "user", content: "captured live already", timestamp: 9000 },
+    ]));
+    await writeFile(join(dir, "pre-install.json"), sessionFile("alfe:dm:old", [
+      { role: "user", content: "history worth keeping", timestamp: 1000 },
+    ]));
+
+    const client = makeClient();
+    await runSessionsBackfill(client, { ...CONFIG, backfillMaxSessions: 1 }, logger, { cutoffMs: 5000, sessionsDir: dir });
+
+    expect(client.memoryIngest).toHaveBeenCalledTimes(1);
+    expect(client.memoryIngest.mock.calls[0][0]).toBe("alfe:dm:old");
+  });
+
+  it("caps at backfillMaxSessions, keeping the most recent sessions", async () => {
+    await writeFile(join(dir, "old.json"), sessionFile("alfe:dm:old", [
+      { role: "user", content: "old", timestamp: 1000 },
+    ]));
+    await writeFile(join(dir, "new.json"), sessionFile("alfe:dm:new", [
+      { role: "user", content: "new", timestamp: 9000 },
+    ]));
+
+    const client = makeClient();
+    await runSessionsBackfill(client, { ...CONFIG, backfillMaxSessions: 1 }, logger, { cutoffMs: Date.now(), sessionsDir: dir });
+
+    expect(client.memoryIngest).toHaveBeenCalledTimes(1);
+    expect(client.memoryIngest.mock.calls[0][0]).toBe("alfe:dm:new");
+  });
+
+  it("aborts without marking when an ingest call fails", async () => {
+    await writeFile(join(dir, "s.json"), sessionFile("alfe:dm:u", [
+      { role: "user", content: "hello", timestamp: 1000 },
+    ]));
+
+    const client = makeClient();
+    client.memoryIngest.mockRejectedValueOnce(new Error("boom"));
+    await runSessionsBackfill(client, CONFIG, logger, { cutoffMs: Date.now(), sessionsDir: dir });
+
+    expect(client.memoryBootstrapStatusMark).not.toHaveBeenCalled();
+    expect(logger.warn).toHaveBeenCalled();
+  });
+
+  it("passes session channel and userId as ingest metadata", async () => {
+    await writeFile(join(dir, "s.json"), sessionFile("alfe:dm:u", [
+      { role: "user", content: "hello", timestamp: 1000 },
+    ], { channel: "alfe", userId: "user_123" }));
+
+    const client = makeClient();
+    await runSessionsBackfill(client, CONFIG, logger, { cutoffMs: Date.now(), sessionsDir: dir });
+
+    const metadata = client.memoryIngest.mock.calls[0][2];
+    expect(metadata).toEqual({ channelId: "alfe", userId: "user_123" });
+  });
+
+  it("does not warn or fail when the mark call itself fails (retries next startup)", async () => {
+    await writeFile(join(dir, "s.json"), sessionFile("alfe:dm:u", [
+      { role: "user", content: "hello", timestamp: 1000 },
+    ]));
+
+    const client = makeClient();
+    client.memoryBootstrapStatusMark.mockRejectedValueOnce(new Error("mark failed"));
+    await expect(
+      runSessionsBackfill(client, CONFIG, logger, { cutoffMs: Date.now(), sessionsDir: dir }),
+    ).resolves.toBeUndefined();
+    expect(logger.warn).toHaveBeenCalledWith(
+      "sessions backfill: mark failed; will retry on next startup",
+      expect.anything(),
+    );
+  });
+
+  it("does not mark complete when the directory read fails for a non-ENOENT reason", async () => {
+    const locked = join(dir, "locked");
+    await mkdir(locked);
+    await chmod(locked, 0o000);
+    try {
+      const client = makeClient();
+      await runSessionsBackfill(client, CONFIG, logger, { cutoffMs: Date.now(), sessionsDir: locked });
+      expect(client.memoryIngest).not.toHaveBeenCalled();
+      expect(client.memoryBootstrapStatusMark).not.toHaveBeenCalled();
+      expect(logger.warn).toHaveBeenCalled();
+    } finally {
+      await chmod(locked, 0o755);
+    }
+  });
+
+  it("ignores non-json files and nested directories", async () => {
+    await writeFile(join(dir, "notes.txt"), "not a session");
+    await mkdir(join(dir, "sub.json.d"));
+    const client = makeClient();
+    await runSessionsBackfill(client, CONFIG, logger, { cutoffMs: Date.now(), sessionsDir: dir });
+    expect(client.memoryIngest).not.toHaveBeenCalled();
+    expect(client.memoryBootstrapStatusMark).toHaveBeenCalledWith("sessions");
+  });
+});

package/src/index.ts

@@ -19,6 +19,7 @@ import { AgentApiClient } from "@alfe.ai/agent-api-client";
 import { AutoCapture } from "./auto-capture.js";
 import { AutoRecall } from "./auto-recall.js";
 import { formatSearchResults } from "./formatter.js";
+import { runSessionsBackfill } from "./session-backfill.js";
 import type { MemoryCloudConfig } from "./types.js";
 import { createRequire } from 'node:module';
 const require = createRequire(import.meta.url);
@@ -63,6 +64,8 @@ const DEFAULT_CONFIG: MemoryCloudConfig = {
   autoRecall: true,
   captureMaxChars: 500,
   idleFlushSeconds: 60,
+  backfillSessions: true,
+  backfillMaxSessions: 50,
 };
 
 function resolvePluginConfig(pluginConfig?: Record<string, unknown>): MemoryCloudConfig {
@@ -71,6 +74,11 @@ function resolvePluginConfig(pluginConfig?: Record<string, unknown>): MemoryClou
     autoRecall: typeof pluginConfig?.autoRecall === "boolean" ? pluginConfig.autoRecall : DEFAULT_CONFIG.autoRecall,
     captureMaxChars: typeof pluginConfig?.captureMaxChars === "number" ? pluginConfig.captureMaxChars : DEFAULT_CONFIG.captureMaxChars,
     idleFlushSeconds: typeof pluginConfig?.idleFlushSeconds === "number" ? pluginConfig.idleFlushSeconds : DEFAULT_CONFIG.idleFlushSeconds,
+    backfillSessions: typeof pluginConfig?.backfillSessions === "boolean" ? pluginConfig.backfillSessions : DEFAULT_CONFIG.backfillSessions,
+    backfillMaxSessions:
+      typeof pluginConfig?.backfillMaxSessions === "number" && Number.isFinite(pluginConfig.backfillMaxSessions) && pluginConfig.backfillMaxSessions > 0
+        ? Math.floor(pluginConfig.backfillMaxSessions)
+        : DEFAULT_CONFIG.backfillMaxSessions,
   };
 }
 
@@ -341,33 +349,60 @@ export default {
       }
     });
 
-    // Fire-and-forget first-run sync: if MEMORY.md / memory/*.md exist
-    // in the workspace, ingest them once into cloud memory. Idempotent
-    // via PalaceMetadata.bootstrapSyncedAt.
-    void runBootstrap(client, logger).catch((err: unknown) => {
-      logger.warn("memory bootstrap failed; will retry on next startup", { err: String(err) });
+    // Fire-and-forget first-run sync: workspace files (MEMORY.md / memory/*.md)
+    // and pre-existing chat sessions, each idempotent via its own
+    // PalaceMetadata flag (bootstrapSyncedAt / sessionsBackfillSyncedAt).
+    void runStartupSync(client, config, logger).catch((err: unknown) => {
+      logger.warn("memory startup sync failed; will retry on next startup", { err: String(err) });
     });
 
     logger.info("memory-cloud extension registered", { autoCapture: config.autoCapture, autoRecall: config.autoRecall });
   },
 };
 
-async function runBootstrap(
+async function runStartupSync(
   client: AgentApiClient,
+  config: MemoryCloudConfig,
   logger: PluginApi["logger"],
 ): Promise<void> {
-  let status: { synced: boolean };
+  // Fetch status ONCE, before the file bootstrap runs: the sessions backfill
+  // computes its dedup cutoff from the pre-bootstrap `syncedAt` (an agent
+  // that already had memory installed captured everything after that moment
+  // live, so backfilling past it would duplicate memories).
+  let status: { synced: boolean; syncedAt?: string; sessionsBackfillSynced?: boolean };
   try {
     status = await client.memoryBootstrapStatus();
   } catch (err) {
     logger.debug("memory bootstrap status check failed; skipping", { err: String(err) });
     return;
   }
+  const startupMs = Date.now();
+
   if (status.synced) {
     logger.debug("memory bootstrap: already synced, skipping");
-    return;
+  } else {
+    try {
+      await runBootstrap(client, logger);
+    } catch (err) {
+      logger.warn("memory bootstrap failed; will retry on next startup", { err: String(err) });
+    }
   }
 
+  // Strict `=== false` on purpose: an old server (deployed before the
+  // sessions-backfill release) omits the field entirely, and its mark
+  // endpoint would clobber `bootstrapSyncedAt` — corrupting the cutoff
+  // anchor. Defer until the service is deployed and reports the flag.
+  if (config.backfillSessions && status.sessionsBackfillSynced === false) {
+    const installedAtMs = status.syncedAt ? Date.parse(status.syncedAt) : Number.POSITIVE_INFINITY;
+    const cutoffMs = Math.min(startupMs, Number.isNaN(installedAtMs) ? Number.POSITIVE_INFINITY : installedAtMs);
+    await runSessionsBackfill(client, config, logger, { cutoffMs });
+  }
+}
+
+async function runBootstrap(
+  client: AgentApiClient,
+  logger: PluginApi["logger"],
+): Promise<void> {
   const cwd = process.cwd();
   const filesToSync: string[] = [];
 

package/src/session-backfill.ts

@@ -0,0 +1,220 @@
+/**
+ * Session backfill — one-time ingestion of pre-existing chat history into
+ * cloud memory, run fire-and-forget at plugin startup (see index.ts).
+ *
+ * Reads the openclaw-chat plugin's on-disk session files directly:
+ *   ~/.alfe/sessions/chat/{sessionId}.json
+ * The write side is packages/openclaw-chat/src/session-store.ts — that path
+ * and file shape are a read contract; keep the two in sync. The chat plugin
+ * is not a package dependency because its session-store functions aren't
+ * part of its public entry and the plugin isn't guaranteed to be installed
+ * alongside memory. Like the session store itself, this assumes one agent
+ * per machine (`alfe remove` deletes ~/.alfe, so files never outlive the
+ * agent they belong to).
+ *
+ * No-re-sync guarantees (in concert with services/memory):
+ * 1. Runs only while the server-side `sessionsBackfillSyncedAt` flag is
+ *    unset; the flag survives integration uninstall/reinstall.
+ * 2. Only messages with timestamp < cutoffMs are ingested — for agents that
+ *    already had memory installed, everything after `bootstrapSyncedAt` was
+ *    already captured live by AutoCapture.
+ * 3. sessionKey = file sessionId and index = file array position, so the
+ *    ingest consumer's per-session `lastProcessedIndex` high-water mark makes
+ *    a crash-and-retry replay free (filtered server-side before any cost).
+ *
+ * Each session is sent as exactly ONE memoryIngest call (one SQS message,
+ * windowed to the most recent messages that fit the caps below). Splitting a
+ * session across multiple SQS messages would race the shared per-session
+ * high-water mark on the standard (non-FIFO) ingest queue: a transiently
+ * failed early chunk redelivered after a later chunk succeeds gets filtered
+ * out and silently lost.
+ */
+
+import { readdir, readFile } from "node:fs/promises";
+import { join } from "node:path";
+import { homedir } from "node:os";
+import type { MemoryCloudConfig, MemoryMessage, SessionMetadata } from "./types.js";
+
+const DEFAULT_SESSIONS_DIR = join(homedir(), ".alfe", "sessions", "chat");
+
+// Server-side zod caps on /agent/memory/ingest (services/memory
+// api-agents/ingest/post.ts) — exceeding any of these is a deterministic 400,
+// which would put the startup retry loop into a permanent failure.
+const MAX_MESSAGES_PER_SESSION = 500;
+const MAX_SESSION_KEY_CHARS = 256;
+const MAX_MESSAGE_INDEX = 1_000_000;
+const MAX_CONTENT_CHARS = 100_000;
+/** One ingest call becomes one SQS SendMessage (256KB hard limit). */
+const MAX_BATCH_BYTES = 180_000;
+
+interface BackfillApi {
+  memoryIngest(sessionKey: string, messages: MemoryMessage[], metadata?: SessionMetadata): Promise<{ queued: boolean; messageCount: number }>;
+  memoryBootstrapStatusMark(scope?: "files" | "sessions"): Promise<{ synced: true; syncedAt: string }>;
+}
+
+interface BackfillLogger {
+  info: (msg: string, ctx?: Record<string, unknown>) => void;
+  debug: (msg: string, ctx?: Record<string, unknown>) => void;
+  warn: (msg: string, ctx?: Record<string, unknown>) => void;
+}
+
+interface ParsedSession {
+  sessionId: string;
+  channel?: string;
+  userId?: string;
+  /** Recent-window messages carrying their original file-array position as `index`. */
+  messages: MemoryMessage[];
+  lastMessageMs: number;
+}
+
+export interface SessionsBackfillOptions {
+  cutoffMs: number;
+  sessionsDir?: string;
+}
+
+export async function runSessionsBackfill(
+  client: BackfillApi,
+  config: MemoryCloudConfig,
+  logger: BackfillLogger,
+  opts: SessionsBackfillOptions,
+): Promise<void> {
+  const sessionsDir = opts.sessionsDir ?? DEFAULT_SESSIONS_DIR;
+
+  let fileNames: string[];
+  try {
+    fileNames = (await readdir(sessionsDir)).filter((name) => name.endsWith(".json"));
+  } catch (err) {
+    if ((err as NodeJS.ErrnoException).code === "ENOENT") {
+      // No sessions directory — nothing to backfill, ever.
+      logger.debug("sessions backfill: no sessions directory, marking complete");
+      try { await client.memoryBootstrapStatusMark("sessions"); } catch { /* retry next start */ }
+    } else {
+      // Transient (EACCES/EMFILE/...) — don't forfeit the backfill.
+      logger.warn("sessions backfill: sessions directory unreadable; will retry on next startup", { err: String(err) });
+    }
+    return;
+  }
+
+  const sessions: ParsedSession[] = [];
+  for (const name of fileNames) {
+    const parsed = await parseSessionFile(join(sessionsDir, name), config.captureMaxChars, opts.cutoffMs);
+    if (parsed) sessions.push(parsed);
+  }
+
+  // Most recent non-empty sessions first, capped. Filter BEFORE capping:
+  // on a retrofit agent the newest sessions are often entirely post-install
+  // (emptied by the cutoff) and must not occupy the cap slots.
+  const eligible = sessions
+    .filter((s) => s.messages.length > 0)
+    .sort((a, b) => b.lastMessageMs - a.lastMessageMs)
+    .slice(0, config.backfillMaxSessions);
+
+  if (eligible.length === 0) {
+    logger.debug("sessions backfill: no eligible sessions, marking complete");
+    try { await client.memoryBootstrapStatusMark("sessions"); } catch { /* retry next start */ }
+    return;
+  }
+
+  logger.info("sessions backfill: ingesting sessions", {
+    sessionCount: eligible.length,
+    messageCount: eligible.reduce((n, s) => n + s.messages.length, 0),
+  });
+
+  for (const session of eligible) {
+    const metadata: SessionMetadata = {
+      ...(session.channel ? { channelId: session.channel } : {}),
+      ...(session.userId ? { userId: session.userId } : {}),
+    };
+    try {
+      await client.memoryIngest(session.sessionId, session.messages, metadata);
+    } catch (err) {
+      // Abort without marking — next startup replays, and the server-side
+      // lastProcessedIndex filter discards already-processed sessions free.
+      logger.warn("sessions backfill: ingest failed; will retry on next startup", {
+        sessionId: session.sessionId,
+        err: String(err),
+      });
+      return;
+    }
+  }
+
+  try {
+    await client.memoryBootstrapStatusMark("sessions");
+    logger.info("sessions backfill: complete", { sessionCount: eligible.length });
+  } catch (err) {
+    logger.warn("sessions backfill: mark failed; will retry on next startup", { err: String(err) });
+  }
+}
+
+/**
+ * Tolerant parse of a single session file. Returns null for corrupt or
+ * shape-mismatched files (skipped, never fatal). Message `index` is the
+ * original array position in the file — stable because the store is
+ * append-only — so retries resume idempotently server-side.
+ */
+async function parseSessionFile(
+  filePath: string,
+  captureMaxChars: number,
+  cutoffMs: number,
+): Promise<ParsedSession | null> {
+  let raw: unknown;
+  try {
+    raw = JSON.parse(await readFile(filePath, "utf8"));
+  } catch {
+    return null;
+  }
+  if (typeof raw !== "object" || raw === null) return null;
+
+  const data = raw as Record<string, unknown>;
+  if (typeof data.sessionId !== "string" || data.sessionId.length === 0) return null;
+  if (data.sessionId.length > MAX_SESSION_KEY_CHARS) return null;
+  if (!Array.isArray(data.messages)) return null;
+
+  const maxContentChars = Math.min(captureMaxChars, MAX_CONTENT_CHARS);
+  let lastMessageMs = 0;
+  const filtered: MemoryMessage[] = [];
+  for (const [index, entry] of data.messages.entries()) {
+    if (index > MAX_MESSAGE_INDEX) break;
+    if (typeof entry !== "object" || entry === null) continue;
+    const msg = entry as Record<string, unknown>;
+    if (msg.role !== "user" && msg.role !== "assistant") continue;
+    if (typeof msg.content !== "string" || msg.content.trim().length === 0) continue;
+    if (typeof msg.timestamp !== "number") continue;
+
+    lastMessageMs = Math.max(lastMessageMs, msg.timestamp);
+    if (msg.timestamp >= cutoffMs) continue;
+
+    filtered.push({
+      role: msg.role,
+      content: msg.content.length > maxContentChars ? msg.content.slice(0, maxContentChars) : msg.content,
+      index,
+      timestamp: new Date(msg.timestamp).toISOString(),
+    });
+  }
+
+  return {
+    sessionId: data.sessionId,
+    channel: typeof data.channel === "string" ? data.channel : undefined,
+    userId: typeof data.userId === "string" ? data.userId : undefined,
+    messages: recentWindow(filtered),
+    lastMessageMs,
+  };
+}
+
+/**
+ * The most recent contiguous run of messages fitting both ingest caps
+ * (message count and serialized bytes). Walks backwards from the newest
+ * message and stops at the first one that would overflow the byte budget.
+ */
+function recentWindow(messages: MemoryMessage[]): MemoryMessage[] {
+  const window: MemoryMessage[] = [];
+  let bytes = 0;
+  for (let i = messages.length - 1; i >= 0; i--) {
+    if (window.length >= MAX_MESSAGES_PER_SESSION) break;
+    const msgBytes = Buffer.byteLength(JSON.stringify(messages[i])) + 1;
+    if (bytes + msgBytes > MAX_BATCH_BYTES) break;
+    window.unshift(messages[i]);
+    bytes += msgBytes;
+  }
+  return window;
+}

package/src/types.ts

@@ -3,6 +3,8 @@ export interface MemoryCloudConfig {
   autoRecall: boolean;
   captureMaxChars: number;
   idleFlushSeconds: number;
+  backfillSessions: boolean;
+  backfillMaxSessions: number;
 }
 
 export interface MemoryMessage {

package/tsconfig.json

@@ -16,5 +16,5 @@
     "sourceMap": true
   },
   "include": ["src/**/*"],
-  "exclude": ["node_modules", "dist"]
+  "exclude": ["node_modules", "dist", "**/*.test.ts"]
 }