diff --git a/docs/channels/imessage.md b/docs/channels/imessage.md
index c21de4d19d9..c16ab0b6c33 100644
--- a/docs/channels/imessage.md
+++ b/docs/channels/imessage.md
@@ -442,6 +442,13 @@ See [ACP Agents](/tools/acp-agents) for shared ACP binding behavior.
     Each account can override fields such as `cliPath`, `dbPath`, `allowFrom`, `groupPolicy`, `mediaMaxMb`, history settings, and attachment root allowlists.
 
   </Accordion>
+
+  <Accordion title="Direct-message history">
+    Set `channels.imessage.dmHistoryLimit` to seed new direct-message sessions with recent decoded `imsg` history for that conversation. Use `channels.imessage.dms["<sender>"].historyLimit` for per-sender overrides, including `0` to disable history for a sender.
+
+    iMessage DM history is fetched on demand from `imsg`. Leaving `dmHistoryLimit` unset disables global DM history seeding, but a positive per-sender `channels.imessage.dms["<sender>"].historyLimit` still enables seeding for that sender.
+
+  </Accordion>
 </AccordionGroup>
 
 ## Media, chunking, and delivery targets
diff --git a/extensions/imessage/src/monitor/dm-history.test.ts b/extensions/imessage/src/monitor/dm-history.test.ts
new file mode 100644
index 00000000000..56f0a2e7ad3
--- /dev/null
+++ b/extensions/imessage/src/monitor/dm-history.test.ts
@@ -0,0 +1,102 @@
+import { resolveEnvelopeFormatOptions } from "openclaw/plugin-sdk/channel-inbound";
+import type { OpenClawConfig } from "openclaw/plugin-sdk/config-contracts";
+import { describe, expect, it, vi } from "vitest";
+import type { IMessageRpcClient } from "../client.js";
+import { resolveIMessageDmHistoryContext, resolveIMessageDmHistoryLimit } from "./dm-history.js";
+
+describe("resolveIMessageDmHistoryLimit", () => {
+  it("uses per-DM history overrides before the provider default", () => {
+    expect(
+      resolveIMessageDmHistoryLimit({
+        config: {
+          dmHistoryLimit: 5,
+          dms: {
+            "+15555550123": { historyLimit: 2 },
+          },
+        },
+        sender: "+1 (555) 555-0123",
+        senderNormalized: "+15555550123",
+      }),
+    ).toBe(2);
+  });
+
+  it("defaults to disabled when no iMessage DM history limit is configured", () => {
+    expect(resolveIMessageDmHistoryLimit({ config: {}, sender: "+15555550123" })).toBe(0);
+  });
+});
+
+describe("resolveIMessageDmHistoryContext", () => {
+  it("fetches decoded imsg history rows and excludes the current message", async () => {
+    const request = vi.fn(async () => ({
+      messages: [
+        {
+          id: 8,
+          guid: "previous-in",
+          chat_id: 44,
+          sender: "+15555550123",
+          is_from_me: false,
+          text: "earlier inbound",
+          created_at: "2026-05-25T12:00:00.000Z",
+          is_group: false,
+        },
+        {
+          id: 9,
+          guid: "previous-out",
+          chat_id: 44,
+          sender: null,
+          is_from_me: true,
+          text: "earlier outbound",
+          created_at: "2026-05-25T12:01:00.000Z",
+          is_group: false,
+        },
+        {
+          id: 10,
+          guid: "current",
+          chat_id: 44,
+          sender: "+15555550123",
+          is_from_me: false,
+          text: "current",
+          created_at: "2026-05-25T12:02:00.000Z",
+          is_group: false,
+        },
+      ],
+    }));
+
+    const context = await resolveIMessageDmHistoryContext({
+      client: { request } as unknown as IMessageRpcClient,
+      message: {
+        id: 10,
+        guid: "current",
+        chat_id: 44,
+        sender: "+15555550123",
+        text: "current",
+        is_from_me: false,
+        is_group: false,
+      },
+      senderNormalized: "+15555550123",
+      limit: 2,
+      envelopeOptions: resolveEnvelopeFormatOptions({} as OpenClawConfig),
+    });
+
+    expect(request).toHaveBeenCalledWith(
+      "messages.history",
+      { chat_id: 44, limit: 3, attachments: false },
+      { timeoutMs: 10_000 },
+    );
+    expect(context.inboundHistory).toEqual([
+      {
+        sender: "+15555550123",
+        body: "earlier inbound",
+        timestamp: Date.parse("2026-05-25T12:00:00.000Z"),
+      },
+      {
+        sender: "Me",
+        body: "earlier outbound",
+        timestamp: Date.parse("2026-05-25T12:01:00.000Z"),
+      },
+    ]);
+    expect(context.body).toContain("earlier inbound");
+    expect(context.body).toContain("earlier outbound");
+    expect(context.body).not.toContain("current");
+  });
+});
diff --git a/extensions/imessage/src/monitor/dm-history.ts b/extensions/imessage/src/monitor/dm-history.ts
new file mode 100644
index 00000000000..bcd044589c9
--- /dev/null
+++ b/extensions/imessage/src/monitor/dm-history.ts
@@ -0,0 +1,166 @@
+import {
+  formatInboundEnvelope,
+  type resolveEnvelopeFormatOptions,
+} from "openclaw/plugin-sdk/channel-inbound";
+import { normalizeOptionalString } from "openclaw/plugin-sdk/string-coerce-runtime";
+import type { IMessageRpcClient } from "../client.js";
+import { normalizeIMessageHandle } from "../targets.js";
+import { parseIMessageNotification } from "./parse-notification.js";
+import type { IMessagePayload } from "./types.js";
+
+const DM_HISTORY_RPC_TIMEOUT_MS = 10_000;
+
+type IMessageHistoryResult = {
+  messages?: unknown[];
+};
+
+type IMessageDmHistoryConfig = {
+  dmHistoryLimit?: number;
+  dms?: Record<string, { historyLimit?: number }>;
+};
+
+export type IMessageDmHistoryEntry = {
+  sender: string;
+  body: string;
+  timestamp?: number;
+};
+
+export type IMessageDmHistoryContext = {
+  body?: string;
+  inboundHistory?: IMessageDmHistoryEntry[];
+};
+
+export function resolveIMessageDmHistoryLimit(params: {
+  config: IMessageDmHistoryConfig;
+  sender?: string;
+  senderNormalized?: string;
+}): number {
+  const senderCandidates = [
+    normalizeOptionalString(params.senderNormalized),
+    normalizeOptionalString(params.sender),
+    params.sender ? normalizeIMessageHandle(params.sender) : undefined,
+  ].filter((candidate): candidate is string => Boolean(candidate));
+
+  for (const candidate of senderCandidates) {
+    const override = params.config.dms?.[candidate]?.historyLimit;
+    if (override !== undefined) {
+      return Math.max(0, override);
+    }
+  }
+
+  return Math.max(0, params.config.dmHistoryLimit ?? 0);
+}
+
+function historyRowSortValue(message: IMessagePayload): number {
+  if (typeof message.id === "number" && Number.isFinite(message.id)) {
+    return message.id;
+  }
+  const createdAtMs =
+    typeof message.created_at === "string" ? Date.parse(message.created_at) : Number.NaN;
+  return Number.isFinite(createdAtMs) ? createdAtMs : 0;
+}
+
+function isBeforeCurrentMessage(params: {
+  message: IMessagePayload;
+  currentMessage: IMessagePayload;
+}): boolean {
+  const { message, currentMessage } = params;
+  if (
+    typeof message.id === "number" &&
+    typeof currentMessage.id === "number" &&
+    Number.isFinite(message.id) &&
+    Number.isFinite(currentMessage.id)
+  ) {
+    return message.id < currentMessage.id;
+  }
+  const guid = normalizeOptionalString(message.guid);
+  const currentGuid = normalizeOptionalString(currentMessage.guid);
+  if (guid && currentGuid) {
+    return guid !== currentGuid;
+  }
+  return true;
+}
+
+function historyEntryFromMessage(message: IMessagePayload, fallbackSender: string) {
+  const body = normalizeOptionalString(message.text);
+  if (!body) {
+    return null;
+  }
+  const timestamp =
+    typeof message.created_at === "string" ? Date.parse(message.created_at) : Number.NaN;
+  return {
+    sender:
+      message.is_from_me === true
+        ? "Me"
+        : normalizeIMessageHandle(normalizeOptionalString(message.sender) ?? fallbackSender) ||
+          fallbackSender,
+    body,
+    ...(Number.isFinite(timestamp) ? { timestamp } : {}),
+  };
+}
+
+export async function resolveIMessageDmHistoryContext(params: {
+  client: IMessageRpcClient;
+  message: IMessagePayload;
+  senderNormalized: string;
+  limit: number;
+  envelopeOptions: ReturnType<typeof resolveEnvelopeFormatOptions>;
+  logVerbose?: (msg: string) => void;
+}): Promise<IMessageDmHistoryContext> {
+  const maxMessages = Math.max(0, Math.floor(params.limit));
+  const chatId =
+    typeof params.message.chat_id === "number" && Number.isFinite(params.message.chat_id)
+      ? params.message.chat_id
+      : undefined;
+  if (maxMessages <= 0 || chatId === undefined) {
+    return {};
+  }
+
+  let result: IMessageHistoryResult | undefined;
+  try {
+    result = await params.client.request<IMessageHistoryResult>(
+      "messages.history",
+      {
+        chat_id: chatId,
+        limit: maxMessages + 1,
+        attachments: false,
+      },
+      { timeoutMs: DM_HISTORY_RPC_TIMEOUT_MS },
+    );
+  } catch (err) {
+    params.logVerbose?.(`imessage: DM history fetch failed for chat_id=${chatId}: ${String(err)}`);
+    return {};
+  }
+
+  const rows = Array.isArray(result?.messages) ? result.messages : [];
+  const history = rows
+    .map((row) => parseIMessageNotification({ message: row }))
+    .filter((message): message is IMessagePayload => Boolean(message))
+    .filter((message) => message.is_group !== true)
+    .filter((message) => isBeforeCurrentMessage({ message, currentMessage: params.message }))
+    .toSorted((a, b) => historyRowSortValue(a) - historyRowSortValue(b))
+    .map((message) => historyEntryFromMessage(message, params.senderNormalized))
+    .filter((entry): entry is IMessageDmHistoryEntry => Boolean(entry))
+    .slice(-maxMessages);
+
+  if (history.length === 0) {
+    return {};
+  }
+
+  return {
+    inboundHistory: history,
+    body: history
+      .map((entry) =>
+        formatInboundEnvelope({
+          channel: "iMessage",
+          from: entry.sender,
+          timestamp: entry.timestamp,
+          body: entry.body,
+          chatType: "direct",
+          senderLabel: entry.sender,
+          envelope: params.envelopeOptions,
+        }),
+      )
+      .join("\n\n"),
+  };
+}
diff --git a/extensions/imessage/src/monitor/inbound-processing.test.ts b/extensions/imessage/src/monitor/inbound-processing.test.ts
index 46afe5cf407..0345286a447 100644
--- a/extensions/imessage/src/monitor/inbound-processing.test.ts
+++ b/extensions/imessage/src/monitor/inbound-processing.test.ts
@@ -794,6 +794,62 @@ describe("buildIMessageInboundContext", () => {
     expect(ctxPayload.MessageSid).toBe("1");
     expect(ctxPayload.MessageSidFull).toBe("p:0/GUID-current");
   });
+
+  it("prepends direct-message history when supplied", async () => {
+    const decision = await resolveIMessageInboundDecision({
+      cfg: {} as OpenClawConfig,
+      accountId: "default",
+      message: {
+        id: 12346,
+        guid: "p:0/GUID-current-history",
+        sender: "+15555550123",
+        text: "current",
+        is_from_me: false,
+        is_group: false,
+      },
+      opts: undefined,
+      messageText: "current",
+      bodyText: "current",
+      allowFrom: ["*"],
+      groupAllowFrom: [],
+      groupPolicy: "open",
+      dmPolicy: "open",
+      storeAllowFrom: [],
+      historyLimit: 0,
+      groupHistories: new Map(),
+      echoCache: undefined,
+      selfChatCache: undefined,
+      logVerbose: undefined,
+    });
+    expect(decision.kind).toBe("dispatch");
+    if (decision.kind !== "dispatch") {
+      return;
+    }
+
+    const { ctxPayload, inboundHistory } = buildIMessageInboundContext({
+      cfg: {} as OpenClawConfig,
+      decision,
+      message: {
+        id: 12346,
+        guid: "p:0/GUID-current-history",
+        sender: "+15555550123",
+        text: "current",
+        is_from_me: false,
+        is_group: false,
+      },
+      historyLimit: 0,
+      groupHistories: new Map(),
+      dmHistory: {
+        body: "[iMessage from +15555550123]\nprevious\n[/iMessage]",
+        inboundHistory: [{ sender: "+15555550123", body: "previous" }],
+      },
+    });
+
+    expect(ctxPayload.Body).toContain("previous");
+    expect(ctxPayload.Body).toContain("current");
+    expect(ctxPayload.InboundHistory).toEqual([{ sender: "+15555550123", body: "previous" }]);
+    expect(inboundHistory).toEqual([{ sender: "+15555550123", body: "previous" }]);
+  });
 });
 
 describe("resolveIMessageInboundDecision command auth", () => {
diff --git a/extensions/imessage/src/monitor/inbound-processing.ts b/extensions/imessage/src/monitor/inbound-processing.ts
index e8c6910ecc5..1dea9e5cc33 100644
--- a/extensions/imessage/src/monitor/inbound-processing.ts
+++ b/extensions/imessage/src/monitor/inbound-processing.ts
@@ -38,6 +38,7 @@ import {
   normalizeIMessageHandle,
   parseIMessageAllowTarget,
 } from "../targets.js";
+import type { IMessageDmHistoryContext } from "./dm-history.js";
 import {
   type IMessageReactionContext,
   resolveIMessageReactionContext,
@@ -808,6 +809,7 @@ export function buildIMessageInboundContext(params: {
   };
   historyLimit: number;
   groupHistories: Map<string, HistoryEntry[]>;
+  dmHistory?: IMessageDmHistoryContext;
 }): {
   ctxPayload: ReturnType<typeof finalizeInboundContext>;
   fromLabel: string;
@@ -867,6 +869,9 @@ export function buildIMessageInboundContext(params: {
   });
 
   let combinedBody = body;
+  if (!decision.isGroup && params.dmHistory?.body) {
+    combinedBody = `${params.dmHistory.body}\n\n${combinedBody}`;
+  }
   if (decision.isGroup && decision.historyKey) {
     const channelHistory = createChannelHistoryWindow({ historyMap: params.groupHistories });
     combinedBody = channelHistory.buildPendingContext({
@@ -888,12 +893,14 @@ export function buildIMessageInboundContext(params: {
 
   const imessageTo = (decision.isGroup ? chatTarget : undefined) || `imessage:${decision.sender}`;
   const inboundHistory =
-    decision.isGroup && decision.historyKey && params.historyLimit > 0
-      ? createChannelHistoryWindow({ historyMap: params.groupHistories }).buildInboundHistory({
-          historyKey: decision.historyKey,
-          limit: params.historyLimit,
-        })
-      : undefined;
+    !decision.isGroup && params.dmHistory?.inboundHistory
+      ? params.dmHistory.inboundHistory
+      : decision.isGroup && decision.historyKey && params.historyLimit > 0
+        ? createChannelHistoryWindow({ historyMap: params.groupHistories }).buildInboundHistory({
+            historyKey: decision.historyKey,
+            limit: params.historyLimit,
+          })
+        : undefined;
 
   const ctxPayload = finalizeInboundContext({
     Body: combinedBody,
diff --git a/extensions/imessage/src/monitor/monitor-provider.ts b/extensions/imessage/src/monitor/monitor-provider.ts
index 8780b2ffcfc..28f9af3429c 100644
--- a/extensions/imessage/src/monitor/monitor-provider.ts
+++ b/extensions/imessage/src/monitor/monitor-provider.ts
@@ -4,6 +4,7 @@ import { CHANNEL_APPROVAL_NATIVE_RUNTIME_CONTEXT_CAPABILITY } from "openclaw/plu
 import { logTypingFailure } from "openclaw/plugin-sdk/channel-feedback";
 import {
   createChannelInboundDebouncer,
+  resolveEnvelopeFormatOptions,
   shouldDebounceTextInbound,
 } from "openclaw/plugin-sdk/channel-inbound";
 import {
@@ -59,6 +60,7 @@ import { advanceIMessageCatchupCursor, resolveCatchupConfig } from "./catchup.js
 import { combineIMessagePayloads } from "./coalesce.js";
 import { repairIMessageConversationAnchor } from "./conversation-repair.js";
 import { createIMessageEchoCachingSend, deliverReplies } from "./deliver.js";
+import { resolveIMessageDmHistoryContext, resolveIMessageDmHistoryLimit } from "./dm-history.js";
 import { createSentMessageCache } from "./echo-cache.js";
 import {
   warnGroupAllowlistDropPerChatOnce,
@@ -631,6 +633,24 @@ export async function monitorIMessageProvider(opts: MonitorIMessageOpts = {}): P
       storePath,
       sessionKey: decision.route.sessionKey,
     });
+    const dmHistoryLimit = !decision.isGroup
+      ? resolveIMessageDmHistoryLimit({
+          config: imessageCfg,
+          sender: decision.sender,
+          senderNormalized: decision.senderNormalized,
+        })
+      : 0;
+    const dmHistory =
+      !decision.isGroup && dmHistoryLimit > 0 && !previousTimestamp
+        ? await resolveIMessageDmHistoryContext({
+            client: getActiveClient(),
+            message,
+            senderNormalized: decision.senderNormalized,
+            limit: dmHistoryLimit,
+            envelopeOptions: resolveEnvelopeFormatOptions(cfg),
+            logVerbose,
+          })
+        : undefined;
     const { ctxPayload, chatTarget } = buildIMessageInboundContext({
       cfg,
       decision,
@@ -639,6 +659,7 @@ export async function monitorIMessageProvider(opts: MonitorIMessageOpts = {}): P
       remoteHost,
       historyLimit,
       groupHistories,
+      dmHistory,
       media: {
         path: mediaPath,
         type: mediaType,