diff --git a/src/auto-reply/reply/get-reply-run.ts b/src/auto-reply/reply/get-reply-run.ts
index c8451fd88f6..defebe86799 100644
--- a/src/auto-reply/reply/get-reply-run.ts
+++ b/src/auto-reply/reply/get-reply-run.ts
@@ -307,7 +307,9 @@ export async function runPreparedReply(
   );
   const baseBodyForPrompt = isBareSessionReset
     ? baseBodyFinal
-    : [inboundUserContext, baseBodyFinal].filter(Boolean).join("\n\n");
+    : inboundUserContext
+      ? `${inboundUserContext}\n\n---\n**User Message:**\n${baseBodyFinal}`
+      : baseBodyFinal;
   const baseBodyTrimmed = baseBodyForPrompt.trim();
   const hasMediaAttachment = Boolean(
     sessionCtx.MediaPath || (sessionCtx.MediaPaths && sessionCtx.MediaPaths.length > 0),
diff --git a/src/auto-reply/reply/strip-inbound-meta.test.ts b/src/auto-reply/reply/strip-inbound-meta.test.ts
index 9bdb20edcee..62b3c8e029c 100644
--- a/src/auto-reply/reply/strip-inbound-meta.test.ts
+++ b/src/auto-reply/reply/strip-inbound-meta.test.ts
@@ -146,6 +146,28 @@ Hello`;
   });
 });
 
+describe("user-message separator stripping", () => {
+  it("strips separator after metadata removal", () => {
+    const input = `${CONV_BLOCK}\n\n---\n**User Message:**\nHello world`;
+    expect(stripInboundMetadata(input)).toBe("Hello world");
+  });
+
+  it("strips separator with multiple metadata blocks", () => {
+    const input = `${CONV_BLOCK}\n\n${SENDER_BLOCK}\n\n---\n**User Message:**\nHello world`;
+    expect(stripInboundMetadata(input)).toBe("Hello world");
+  });
+
+  it("preserves separator when no metadata blocks are present", () => {
+    const input = `---\n**User Message:**\nHello world`;
+    expect(stripInboundMetadata(input)).toBe(input);
+  });
+
+  it("preserves user content starting with --- when it is not the separator", () => {
+    const input = `${CONV_BLOCK}\n\n---\nSome regular content`;
+    expect(stripInboundMetadata(input)).toBe("---\nSome regular content");
+  });
+});
+
 describe("extractInboundSenderLabel", () => {
   it("returns the sender label block when present", () => {
     const input = `${CONV_BLOCK}\n\n${SENDER_BLOCK}\n\nHello from user`;
diff --git a/src/auto-reply/reply/strip-inbound-meta.ts b/src/auto-reply/reply/strip-inbound-meta.ts
index 80e12a3fc20..089955bf47d 100644
--- a/src/auto-reply/reply/strip-inbound-meta.ts
+++ b/src/auto-reply/reply/strip-inbound-meta.ts
@@ -184,7 +184,16 @@ export function stripInboundMetadata(text: string): string {
     result.push(line);
   }
 
-  return result.join("\n").replace(/^\n+/, "").replace(/\n+$/, "");
+  return stripUserMessageSeparator(result.join("\n").replace(/^\n+/, "").replace(/\n+$/, ""));
+}
+
+/**
+ * Removes the `---\n**User Message:**` separator injected between metadata and
+ * user content.  Called after metadata blocks have already been stripped so the
+ * separator (if any) is now a leading artefact in the remaining text.
+ */
+function stripUserMessageSeparator(text: string): string {
+  return text.replace(/^[\t ]*---[\t ]*\n[\t ]*\*\*User Message:\*\*[\t ]*\n?/, "");
 }
 
 export function stripLeadingInboundMetadata(text: string): string {
@@ -232,7 +241,7 @@ export function stripLeadingInboundMetadata(text: string): string {
   }
 
   const strippedRemainder = stripTrailingUntrustedContextSuffix(lines.slice(index));
-  return strippedRemainder.join("\n");
+  return stripUserMessageSeparator(strippedRemainder.join("\n"));
 }
 
 export function extractInboundSenderLabel(text: string): string | null {