diff --git a/src/memory-host-sdk/host/session-files.test.ts b/src/memory-host-sdk/host/session-files.test.ts
index 1e506067997..20fd3790a20 100644
--- a/src/memory-host-sdk/host/session-files.test.ts
+++ b/src/memory-host-sdk/host/session-files.test.ts
@@ -32,6 +32,21 @@ afterEach(() => {
   }
 });
 
+function expectNoUnpairedSurrogates(value: string): void {
+  for (let index = 0; index < value.length; index += 1) {
+    const code = value.charCodeAt(index);
+    if (code >= 0xd800 && code <= 0xdbff) {
+      expect(index + 1).toBeLessThan(value.length);
+      const next = value.charCodeAt(index + 1);
+      expect(next).toBeGreaterThanOrEqual(0xdc00);
+      expect(next).toBeLessThanOrEqual(0xdfff);
+      index += 1;
+      continue;
+    }
+    expect(code < 0xdc00 || code > 0xdfff).toBe(true);
+  }
+}
+
 describe("listSessionFilesForAgent", () => {
   it("includes reset and deleted transcripts in session file listing", async () => {
     const sessionsDir = path.join(tmpDir, "agents", "main", "sessions");
@@ -237,6 +252,78 @@ describe("buildSessionEntry", () => {
     expect(entry!.content).toBe("User: Actual user text");
   });
 
+  it("wraps pathological long messages into multiple exported lines and repeats mappings", async () => {
+    const longWordyLine = Array.from({ length: 260 }, (_, idx) => `segment-${idx}`).join(" ");
+    const timestamp = Date.parse("2026-04-05T10:00:00.000Z");
+    const jsonlLines = [
+      JSON.stringify({
+        type: "message",
+        timestamp: "2026-04-05T10:00:00.000Z",
+        message: { role: "user", content: longWordyLine },
+      }),
+    ];
+    const filePath = path.join(tmpDir, "wrapped-session.jsonl");
+    await fs.writeFile(filePath, jsonlLines.join("\n"));
+
+    const entry = await buildSessionEntry(filePath);
+    expect(entry).not.toBeNull();
+
+    const contentLines = entry!.content.split("\n");
+    expect(contentLines.length).toBeGreaterThan(1);
+    expect(contentLines.every((line) => line.startsWith("User: "))).toBe(true);
+    expect(contentLines.every((line) => line.length <= 810)).toBe(true);
+    expect(entry!.lineMap).toEqual(contentLines.map(() => 1));
+    expect(entry!.messageTimestampsMs).toEqual(contentLines.map(() => timestamp));
+  });
+
+  it("hard-wraps pathological long tokens without spaces", async () => {
+    const giantToken = "x".repeat(1800);
+    const jsonlLines = [
+      JSON.stringify({
+        type: "message",
+        message: { role: "assistant", content: giantToken },
+      }),
+    ];
+    const filePath = path.join(tmpDir, "hard-wrapped-session.jsonl");
+    await fs.writeFile(filePath, jsonlLines.join("\n"));
+
+    const entry = await buildSessionEntry(filePath);
+    expect(entry).not.toBeNull();
+
+    const contentLines = entry!.content.split("\n");
+    expect(contentLines.length).toBe(3);
+    expect(contentLines.every((line) => line.startsWith("Assistant: "))).toBe(true);
+    expect(contentLines[0].length).toBeLessThanOrEqual(811);
+    expect(contentLines[1].length).toBeLessThanOrEqual(811);
+    expect(entry!.lineMap).toEqual([1, 1, 1]);
+    expect(entry!.messageTimestampsMs).toEqual([0, 0, 0]);
+  });
+
+  it("does not split surrogate pairs when hard-wrapping astral unicode without spaces", async () => {
+    const astralChar = "\u{20000}";
+    const giantToken = astralChar.repeat(1200);
+    const jsonlLines = [
+      JSON.stringify({
+        type: "message",
+        message: { role: "assistant", content: giantToken },
+      }),
+    ];
+    const filePath = path.join(tmpDir, "surrogate-safe-session.jsonl");
+    await fs.writeFile(filePath, jsonlLines.join("\n"));
+
+    const entry = await buildSessionEntry(filePath);
+    expect(entry).not.toBeNull();
+
+    const contentLines = entry!.content.split("\n");
+    expect(contentLines.length).toBeGreaterThan(1);
+    expect(entry!.lineMap).toEqual(contentLines.map(() => 1));
+    expect(entry!.messageTimestampsMs).toEqual(contentLines.map(() => 0));
+    for (const line of contentLines) {
+      expect(line.startsWith("Assistant: ")).toBe(true);
+      expectNoUnpairedSurrogates(line);
+    }
+  });
+
   it("preserves assistant messages that happen to contain sentinel-like text", async () => {
     // Assistant role must NOT be stripped — only user messages carry inbound
     // envelopes, and assistants may legitimately discuss metadata formats.
diff --git a/src/memory-host-sdk/host/session-files.ts b/src/memory-host-sdk/host/session-files.ts
index bc30386061b..b24e08fb33f 100644
--- a/src/memory-host-sdk/host/session-files.ts
+++ b/src/memory-host-sdk/host/session-files.ts
@@ -10,6 +10,11 @@ import { hashText } from "./internal.js";
 
 const log = createSubsystemLogger("memory");
 const DREAMING_NARRATIVE_RUN_PREFIX = "dreaming-narrative-";
+// Keep the historical one-line-per-message export shape for normal turns, but
+// wrap pathological long messages so downstream indexers never ingest a single
+// toxic line. Wrapped continuation lines still map back to the same JSONL line.
+// This limit applies to content only; the role label adds up to 11 chars.
+const SESSION_EXPORT_CONTENT_WRAP_CHARS = 800;
 
 export type SessionFileEntry = {
   path: string;
@@ -203,6 +208,65 @@ function collectRawSessionText(content: unknown): string | null {
   return parts.length > 0 ? parts.join("\n") : null;
 }
 
+function isHighSurrogate(code: number): boolean {
+  return code >= 0xd800 && code <= 0xdbff;
+}
+
+function isLowSurrogate(code: number): boolean {
+  return code >= 0xdc00 && code <= 0xdfff;
+}
+
+function splitLongSessionLine(
+  text: string,
+  maxChars: number = SESSION_EXPORT_CONTENT_WRAP_CHARS,
+): string[] {
+  const normalized = text.trim();
+  if (!normalized) {
+    return [];
+  }
+  if (normalized.length <= maxChars) {
+    return [normalized];
+  }
+
+  const segments: string[] = [];
+  let cursor = 0;
+  while (cursor < normalized.length) {
+    const remaining = normalized.length - cursor;
+    if (remaining <= maxChars) {
+      segments.push(normalized.slice(cursor).trim());
+      break;
+    }
+
+    const limit = cursor + maxChars;
+    let splitAt = limit;
+    for (let index = limit; index > cursor; index -= 1) {
+      if (normalized[index] === " ") {
+        splitAt = index;
+        break;
+      }
+    }
+    if (
+      splitAt < normalized.length &&
+      splitAt > cursor &&
+      isHighSurrogate(normalized.charCodeAt(splitAt - 1)) &&
+      isLowSurrogate(normalized.charCodeAt(splitAt))
+    ) {
+      splitAt -= 1;
+    }
+    segments.push(normalized.slice(cursor, splitAt).trim());
+    cursor = splitAt;
+    while (cursor < normalized.length && normalized[cursor] === " ") {
+      cursor += 1;
+    }
+  }
+
+  return segments.filter(Boolean);
+}
+
+function renderSessionExportLines(label: string, text: string): string[] {
+  return splitLongSessionLine(text).map((segment) => `${label}: ${segment}`);
+}
+
 /**
  * Strip OpenClaw-injected inbound metadata envelopes from a raw text block.
  *
@@ -310,14 +374,14 @@ export async function buildSessionEntry(
       }
       const safe = redactSensitiveText(text, { mode: "tools" });
       const label = message.role === "user" ? "User" : "Assistant";
-      collected.push(`${label}: ${safe}`);
-      lineMap.push(jsonlIdx + 1);
-      messageTimestampsMs.push(
-        parseSessionTimestampMs(
-          record as { timestamp?: unknown },
-          message as { timestamp?: unknown },
-        ),
+      const renderedLines = renderSessionExportLines(label, safe);
+      const timestampMs = parseSessionTimestampMs(
+        record as { timestamp?: unknown },
+        message as { timestamp?: unknown },
       );
+      collected.push(...renderedLines);
+      lineMap.push(...renderedLines.map(() => jsonlIdx + 1));
+      messageTimestampsMs.push(...renderedLines.map(() => timestampMs));
     }
     const content = collected.join("\n");
     return {