diff --git a/src/Agent.php b/src/Agent.php
index b429c81e..3e276a33 100644
--- a/src/Agent.php
+++ b/src/Agent.php
@@ -280,6 +280,8 @@ public function send() : bool
                 return false;
             }
 
+            $this->request->stopIfRunning();
+
             return $this->connector->sendCommand($this->request);
         } catch (NotConnected $notConnected) {
             $this->logger->error($notConnected->getMessage());
diff --git a/src/Events/Request/Request.php b/src/Events/Request/Request.php
index b047156d..15d9d195 100644
--- a/src/Events/Request/Request.php
+++ b/src/Events/Request/Request.php
@@ -39,6 +39,15 @@ public function __construct()
         $this->currentCommand = $this;
     }
 
+    public function stopIfRunning() : void
+    {
+        if ($this->timer->getStop() !== null) {
+            return;
+        }
+
+        $this->stop();
+    }
+
     public function stop(?float $overrideTimestamp = null) : void
     {
         $this->timer->stop($overrideTimestamp);
diff --git a/tests/Unit/Events/Request/RequestTest.php b/tests/Unit/Events/Request/RequestTest.php
index 897c9938..3626f4dc 100644
--- a/tests/Unit/Events/Request/RequestTest.php
+++ b/tests/Unit/Events/Request/RequestTest.php
@@ -6,8 +6,11 @@
 
 use PHPUnit\Framework\TestCase;
 use Scoutapm\Events\Request\Request;
+use function json_decode;
+use function json_encode;
 use function next;
 use function reset;
+use function time;
 
 /** @covers \Scoutapm\Events\Request\Request */
 final class RequestTest extends TestCase
@@ -21,8 +24,34 @@ public function testCanBeInitialized() : void
     public function testCanBeStopped() : void
     {
         $request = new Request();
+
+        self::assertNull(json_decode(json_encode($request), true)['BatchCommand']['commands'][1]['FinishRequest']['timestamp']);
+
         $request->stop();
-        self::assertNotNull($request);
+
+        self::assertIsString(json_decode(json_encode($request), true)['BatchCommand']['commands'][1]['FinishRequest']['timestamp']);
+    }
+
+    public function testRequestIsStoppedIfRunning() : void
+    {
+        $request = new Request();
+
+        self::assertNull(json_decode(json_encode($request), true)['BatchCommand']['commands'][1]['FinishRequest']['timestamp']);
+
+        $request->stopIfRunning();
+
+        self::assertIsString(json_decode(json_encode($request), true)['BatchCommand']['commands'][1]['FinishRequest']['timestamp']);
+    }
+
+    public function testRequestFinishTimestampIsNotChangedWhenStopIfRunningIsCalledOnAStoppedRequest() : void
+    {
+        $request = new Request();
+        $request->stop(time() - 100.0);
+        $originalStopTime = json_decode(json_encode($request), true)['BatchCommand']['commands'][1]['FinishRequest']['timestamp'];
+
+        $request->stopIfRunning();
+
+        self::assertSame($originalStopTime, json_decode(json_encode($request), true)['BatchCommand']['commands'][1]['FinishRequest']['timestamp']);
     }
 
     public function testJsonSerializes() : void