diff --git a/src/resources/extensions/gsd/session-forensics.ts b/src/resources/extensions/gsd/session-forensics.ts
index 04894fe1f..e5dbe78e0 100644
--- a/src/resources/extensions/gsd/session-forensics.ts
+++ b/src/resources/extensions/gsd/session-forensics.ts
@@ -172,7 +172,17 @@ export function extractTrace(entries: unknown[]): ExecutionTrace {
       }
 
       if (isError && resultText) {
-        errors.push(resultText.slice(0, 300));
+        // Filter out benign "errors" that are normal during code exploration:
+        // - grep/rg/find returning exit code 1 (no matches) is expected POSIX behavior
+        // - User interrupts (Escape/skip) are intentional, not failures
+        const trimmed = resultText.trim();
+        const isBenignNoMatch = pending?.name === "bash" &&
+          /^\(no output\)\s*\n\s*Command exited with code 1$/m.test(trimmed);
+        const isUserSkip = /^Skipped due to queued user message/i.test(trimmed);
+
+        if (!isBenignNoMatch && !isUserSkip) {
+          errors.push(resultText.slice(0, 300));
+        }
       }
     }
   }
diff --git a/src/resources/extensions/gsd/tests/forensics-error-filter.test.ts b/src/resources/extensions/gsd/tests/forensics-error-filter.test.ts
new file mode 100644
index 000000000..9575e729f
--- /dev/null
+++ b/src/resources/extensions/gsd/tests/forensics-error-filter.test.ts
@@ -0,0 +1,121 @@
+/**
+ * Regression test for #2539: extractTrace should not count benign bash
+ * exit-code-1 (grep no-match) or user skips as errors.
+ */
+import { describe, test } from "node:test";
+import assert from "node:assert/strict";
+
+import { extractTrace } from "../session-forensics.ts";
+
+/**
+ * Build a minimal JSONL entry pair: assistant tool_use → toolResult.
+ * This is the shape extractTrace() expects from session activity files.
+ */
+function makeToolPair(
+  toolName: string,
+  input: Record<string, unknown>,
+  resultText: string,
+  isError: boolean,
+): unknown[] {
+  const toolCallId = `toolu_${Math.random().toString(36).slice(2, 10)}`;
+  return [
+    {
+      type: "message",
+      message: {
+        role: "assistant",
+        content: [
+          {
+            type: "toolCall",
+            id: toolCallId,
+            name: toolName,
+            arguments: input,
+          },
+        ],
+      },
+    },
+    {
+      type: "message",
+      message: {
+        role: "toolResult",
+        toolCallId,
+        toolName,
+        isError,
+        content: [{ type: "text", text: resultText }],
+      },
+    },
+  ];
+}
+
+describe("extractTrace error filtering (#2539)", () => {
+  test("grep exit-code-1 (no matches) is not counted as an error", () => {
+    const entries = makeToolPair(
+      "bash",
+      { command: "grep -rn 'nonexistent' src/" },
+      "(no output)\nCommand exited with code 1",
+      true,
+    );
+    const trace = extractTrace(entries);
+    assert.equal(trace.errors.length, 0, "grep no-match should not be an error");
+  });
+
+  test("user skip is not counted as an error", () => {
+    const entries = makeToolPair(
+      "bash",
+      { command: "npm run test" },
+      "Skipped due to queued user message",
+      true,
+    );
+    const trace = extractTrace(entries);
+    assert.equal(trace.errors.length, 0, "user skip should not be an error");
+  });
+
+  test("real bash error is still counted", () => {
+    const entries = makeToolPair(
+      "bash",
+      { command: "cat /nonexistent" },
+      "cat: /nonexistent: No such file or directory\nCommand exited with code 1",
+      true,
+    );
+    const trace = extractTrace(entries);
+    assert.equal(trace.errors.length, 1, "real error should still be counted");
+    assert.match(trace.errors[0], /No such file or directory/);
+  });
+
+  test("non-bash tool error is still counted", () => {
+    const entries = makeToolPair(
+      "edit",
+      { path: "foo.ts", oldText: "x", newText: "y" },
+      "oldText not found in file",
+      true,
+    );
+    const trace = extractTrace(entries);
+    assert.equal(trace.errors.length, 1, "non-bash tool errors should still be counted");
+  });
+
+  test("mixed entries: only real errors are counted", () => {
+    const entries = [
+      // benign grep no-match
+      ...makeToolPair("bash", { command: "grep -rn 'pattern' src/" }, "(no output)\nCommand exited with code 1", true),
+      // user skip
+      ...makeToolPair("bash", { command: "npm test" }, "Skipped due to queued user message", true),
+      // real error
+      ...makeToolPair("bash", { command: "node broken.js" }, "SyntaxError: Unexpected token\nCommand exited with code 1", true),
+      // successful command (not an error)
+      ...makeToolPair("bash", { command: "echo hello" }, "hello", false),
+    ];
+    const trace = extractTrace(entries);
+    assert.equal(trace.errors.length, 1, "only the real error should be counted");
+    assert.match(trace.errors[0], /SyntaxError/);
+  });
+
+  test("exit code 1 with actual output is still an error", () => {
+    const entries = makeToolPair(
+      "bash",
+      { command: "npm run lint" },
+      "src/foo.ts:10:5 - error TS2304: Cannot find name 'x'\nCommand exited with code 1",
+      true,
+    );
+    const trace = extractTrace(entries);
+    assert.equal(trace.errors.length, 1, "lint error with output should be counted");
+  });
+});