diff --git a/hindsight-integrations/openclaw/src/index.test.ts b/hindsight-integrations/openclaw/src/index.test.ts
index 96d31bca1..399ed2199 100644
--- a/hindsight-integrations/openclaw/src/index.test.ts
+++ b/hindsight-integrations/openclaw/src/index.test.ts
@@ -1041,6 +1041,45 @@ describe("sliceLastTurnsByUserBoundary", () => {
     const messages = [{ role: "user", content: "Hello" }];
     expect(sliceLastTurnsByUserBoundary(messages, 0)).toEqual([]);
   });
+
+  it("skips synthetic user messages that contain only tool_result blocks", () => {
+    const messages = [
+      { role: "user", content: [{ type: "text", text: "Real user input 1" }] },
+      { role: "assistant", content: [{ type: "text", text: "Assistant reply 1" }] },
+      {
+        role: "user",
+        content: [{ type: "tool_result", content: "Tool output for call 1" }],
+      },
+      {
+        role: "user",
+        content: [{ type: "tool_result", content: "Tool output for call 2" }],
+      },
+      { role: "assistant", content: [{ type: "text", text: "Assistant after tools" }] },
+      { role: "user", content: [{ type: "text", text: "Real user input 2" }] },
+      { role: "assistant", content: [{ type: "text", text: "Assistant reply 2" }] },
+    ];
+    // 3 user turns requested, but only 2 have real text content.
+    // Should fall back to returning all messages.
+    const result = sliceLastTurnsByUserBoundary(messages, 3);
+    expect(result).toEqual(messages);
+  });
+
+  it("uses real user turns when tool_result synthetic messages are present", () => {
+    const messages = [
+      { role: "user", content: [{ type: "text", text: "Real user input 1" }] },
+      { role: "assistant", content: [{ type: "text", text: "Assistant reply 1" }] },
+      {
+        role: "user",
+        content: [{ type: "tool_result", content: "Tool output 1" }],
+      },
+      { role: "assistant", content: [{ type: "text", text: "Assistant after tool 1" }] },
+      { role: "user", content: [{ type: "text", text: "Real user input 2" }] },
+      { role: "assistant", content: [{ type: "text", text: "Assistant reply 2" }] },
+    ];
+    // 2 real user turns. Should start at message 0 (first real user).
+    const result = sliceLastTurnsByUserBoundary(messages, 2);
+    expect(result).toEqual(messages);
+  });
 });
 
 // ---------------------------------------------------------------------------
diff --git a/hindsight-integrations/openclaw/src/index.ts b/hindsight-integrations/openclaw/src/index.ts
index db25123d7..054c7e11c 100644
--- a/hindsight-integrations/openclaw/src/index.ts
+++ b/hindsight-integrations/openclaw/src/index.ts
@@ -3032,11 +3032,31 @@ export function sliceLastTurnsByUserBoundary(messages: any[], turns: number): an
     return [];
   }
 
+  // Count only user messages that contain actual text content.
+  // OpenClaw normalizes tool_result blocks into role:"user" messages with a
+  // tool_result content block. Without this filter those synthetic messages
+  // would be counted as real user turns, causing the window to exclude actual
+  // user input from the retained transcript.
+  function hasRealTextContent(msg: any): boolean {
+    if (msg?.role !== "user") return false;
+    const content = msg.content;
+    if (typeof content === "string") return content.trim().length > 0;
+    if (Array.isArray(content)) {
+      return content.some(
+        (b: any) =>
+          b?.type === "text" &&
+          typeof b?.text === "string" &&
+          b.text.trim().length > 0,
+      );
+    }
+    return false;
+  }
+
   let userTurnsSeen = 0;
   let startIndex = -1;
 
   for (let i = messages.length - 1; i >= 0; i--) {
-    if (messages[i]?.role === "user") {
+    if (messages[i]?.role === "user" && hasRealTextContent(messages[i])) {
       userTurnsSeen += 1;
       if (userTurnsSeen >= turns) {
         startIndex = i;