diff --git a/src/agents/clawdbot-tools.ts b/src/agents/clawdbot-tools.ts
index 4ff11a9d1..28e71bf19 100644
--- a/src/agents/clawdbot-tools.ts
+++ b/src/agents/clawdbot-tools.ts
@@ -75,7 +75,9 @@ export function createClawdbotTools(options?: {
     }),
     createCanvasTool(),
     createNodesTool(),
-    createCronTool(),
+    createCronTool({
+      agentSessionKey: options?.agentSessionKey,
+    }),
     createMessageTool({
       agentAccountId: options?.agentAccountId,
       config: options?.config,
diff --git a/src/agents/system-prompt.ts b/src/agents/system-prompt.ts
index 03c636b96..7c53e501d 100644
--- a/src/agents/system-prompt.ts
+++ b/src/agents/system-prompt.ts
@@ -173,7 +173,7 @@ export function buildAgentSystemPrompt(params: {
     browser: "Control web browser",
     canvas: "Present/eval/snapshot the Canvas",
     nodes: "List/describe/notify/camera/screen on paired nodes",
-    cron: "Manage cron jobs and wake events (use for reminders)",
+    cron: "Manage cron jobs and wake events (use for reminders; include recent context in reminder text if appropriate)",
     message: "Send messages and channel actions",
     gateway: "Restart, apply config, or run updates on the running Clawdbot process",
     agents_list: "List agent ids allowed for sessions_spawn",
@@ -319,7 +319,7 @@ export function buildAgentSystemPrompt(params: {
           "- browser: control clawd's dedicated browser",
           "- canvas: present/eval/snapshot the Canvas",
           "- nodes: list/describe/notify/camera/screen on paired nodes",
-          "- cron: manage cron jobs and wake events (use for reminders)",
+          "- cron: manage cron jobs and wake events (use for reminders; include recent context in reminder text if appropriate)",
           "- sessions_list: list sessions",
           "- sessions_history: fetch session history",
           "- sessions_send: send to another session",
diff --git a/src/agents/tools/cron-tool.test.ts b/src/agents/tools/cron-tool.test.ts
index 6e65acb83..b162ce41a 100644
--- a/src/agents/tools/cron-tool.test.ts
+++ b/src/agents/tools/cron-tool.test.ts
@@ -84,4 +84,47 @@ describe("cron tool", () => {
       payload: { kind: "systemEvent", text: "hello" },
     });
   });
+
+  it("adds recent context for systemEvent reminders when session key is available", async () => {
+    callGatewayMock
+      .mockResolvedValueOnce({
+        messages: [
+          { role: "user", content: [{ type: "text", text: "Discussed Q2 budget" }] },
+          {
+            role: "assistant",
+            content: [{ type: "text", text: "We agreed to review on Tuesday." }],
+          },
+          { role: "user", content: [{ type: "text", text: "Remind me about the thing at 2pm" }] },
+        ],
+      })
+      .mockResolvedValueOnce({ ok: true });
+
+    const tool = createCronTool({ agentSessionKey: "main" });
+    await tool.execute("call3", {
+      action: "add",
+      job: {
+        name: "reminder",
+        schedule: { atMs: 123 },
+        payload: { text: "Reminder: the thing." },
+      },
+    });
+
+    expect(callGatewayMock).toHaveBeenCalledTimes(2);
+    const historyCall = callGatewayMock.mock.calls[0]?.[0] as {
+      method?: string;
+      params?: unknown;
+    };
+    expect(historyCall.method).toBe("chat.history");
+
+    const cronCall = callGatewayMock.mock.calls[1]?.[0] as {
+      method?: string;
+      params?: { payload?: { text?: string } };
+    };
+    expect(cronCall.method).toBe("cron.add");
+    const text = cronCall.params?.payload?.text ?? "";
+    expect(text).toContain("Recent context:");
+    expect(text).toContain("User: Discussed Q2 budget");
+    expect(text).toContain("Assistant: We agreed to review on Tuesday.");
+    expect(text).toContain("User: Remind me about the thing at 2pm");
+  });
 });
diff --git a/src/agents/tools/cron-tool.ts b/src/agents/tools/cron-tool.ts
index cee9aed27..75af0becd 100644
--- a/src/agents/tools/cron-tool.ts
+++ b/src/agents/tools/cron-tool.ts
@@ -1,8 +1,11 @@
 import { Type } from "@sinclair/typebox";
 import { normalizeCronJobCreate, normalizeCronJobPatch } from "../../cron/normalize.js";
+import { loadConfig } from "../../config/config.js";
+import { truncateUtf16Safe } from "../../utils.js";
 import { optionalStringEnum, stringEnum } from "../schema/typebox.js";
 import { type AnyAgentTool, jsonResult, readStringParam } from "./common.js";
 import { callGatewayTool, type GatewayCallOptions } from "./gateway.js";
+import { resolveInternalSessionKey, resolveMainSessionAlias } from "./sessions-helpers.js";
 
 // NOTE: We use Type.Object({}, { additionalProperties: true }) for job/patch
 // instead of CronAddParamsSchema/CronJobPatchSchema because the gateway schemas
@@ -13,6 +16,11 @@ const CRON_ACTIONS = ["status", "list", "add", "update", "remove", "run", "runs"
 
 const CRON_WAKE_MODES = ["now", "next-heartbeat"] as const;
 
+const REMINDER_CONTEXT_MESSAGES = 3;
+const REMINDER_CONTEXT_PER_MESSAGE_MAX = 220;
+const REMINDER_CONTEXT_TOTAL_MAX = 700;
+const REMINDER_CONTEXT_MARKER = "\n\nRecent context:\n";
+
 // Flattened schema: runtime validates per-action requirements.
 const CronToolSchema = Type.Object({
   action: stringEnum(CRON_ACTIONS),
@@ -28,7 +36,90 @@ const CronToolSchema = Type.Object({
   mode: optionalStringEnum(CRON_WAKE_MODES),
 });
 
-export function createCronTool(): AnyAgentTool {
+type CronToolOptions = {
+  agentSessionKey?: string;
+};
+
+type ChatMessage = {
+  role?: unknown;
+  content?: unknown;
+};
+
+function stripExistingContext(text: string) {
+  const index = text.indexOf(REMINDER_CONTEXT_MARKER);
+  if (index === -1) return text;
+  return text.slice(0, index).trim();
+}
+
+function truncateText(input: string, maxLen: number) {
+  if (input.length <= maxLen) return input;
+  const truncated = truncateUtf16Safe(input, Math.max(0, maxLen - 3)).trimEnd();
+  return `${truncated}...`;
+}
+
+function normalizeContextText(raw: string) {
+  return raw.replace(/\s+/g, " ").trim();
+}
+
+function extractMessageText(message: ChatMessage): { role: string; text: string } | null {
+  const role = typeof message.role === "string" ? message.role : "";
+  if (role !== "user" && role !== "assistant") return null;
+  const content = message.content;
+  if (typeof content === "string") {
+    const normalized = normalizeContextText(content);
+    return normalized ? { role, text: normalized } : null;
+  }
+  if (!Array.isArray(content)) return null;
+  const chunks: string[] = [];
+  for (const block of content) {
+    if (!block || typeof block !== "object") continue;
+    if ((block as { type?: unknown }).type !== "text") continue;
+    const text = (block as { text?: unknown }).text;
+    if (typeof text === "string" && text.trim()) {
+      chunks.push(text);
+    }
+  }
+  const joined = normalizeContextText(chunks.join(" "));
+  return joined ? { role, text: joined } : null;
+}
+
+async function buildReminderContextLines(params: {
+  agentSessionKey?: string;
+  gatewayOpts: GatewayCallOptions;
+}) {
+  const sessionKey = params.agentSessionKey?.trim();
+  if (!sessionKey) return [];
+  const cfg = loadConfig();
+  const { mainKey, alias } = resolveMainSessionAlias(cfg);
+  const resolvedKey = resolveInternalSessionKey({ key: sessionKey, alias, mainKey });
+  try {
+    const res = (await callGatewayTool("chat.history", params.gatewayOpts, {
+      sessionKey: resolvedKey,
+      limit: 12,
+    })) as { messages?: unknown[] };
+    const messages = Array.isArray(res?.messages) ? res.messages : [];
+    const parsed = messages
+      .map((msg) => extractMessageText(msg as ChatMessage))
+      .filter((msg): msg is { role: string; text: string } => Boolean(msg));
+    const recent = parsed.slice(-REMINDER_CONTEXT_MESSAGES);
+    if (recent.length === 0) return [];
+    const lines: string[] = [];
+    let total = 0;
+    for (const entry of recent) {
+      const label = entry.role === "user" ? "User" : "Assistant";
+      const text = truncateText(entry.text, REMINDER_CONTEXT_PER_MESSAGE_MAX);
+      const line = `- ${label}: ${text}`;
+      total += line.length;
+      if (total > REMINDER_CONTEXT_TOTAL_MAX) break;
+      lines.push(line);
+    }
+    return lines;
+  } catch {
+    return [];
+  }
+}
+
+export function createCronTool(opts?: CronToolOptions): AnyAgentTool {
   return {
     label: "Cron",
     name: "cron",
@@ -58,6 +149,24 @@ export function createCronTool(): AnyAgentTool {
             throw new Error("job required");
           }
           const job = normalizeCronJobCreate(params.job) ?? params.job;
+          if (
+            job &&
+            typeof job === "object" &&
+            "payload" in job &&
+            (job as { payload?: { kind?: string; text?: string } }).payload?.kind === "systemEvent"
+          ) {
+            const payload = (job as { payload: { kind: string; text: string } }).payload;
+            if (typeof payload.text === "string" && payload.text.trim()) {
+              const contextLines = await buildReminderContextLines({
+                agentSessionKey: opts?.agentSessionKey,
+                gatewayOpts,
+              });
+              if (contextLines.length > 0) {
+                const baseText = stripExistingContext(payload.text);
+                payload.text = `${baseText}${REMINDER_CONTEXT_MARKER}${contextLines.join("\n")}`;
+              }
+            }
+          }
           return jsonResult(await callGatewayTool("cron.add", gatewayOpts, job));
         }
         case "update": {