diff --git a/cli/tests/integration/inspector_tests.rs b/cli/tests/integration/inspector_tests.rs
index 520a5b4f78..e901e26331 100644
--- a/cli/tests/integration/inspector_tests.rs
+++ b/cli/tests/integration/inspector_tests.rs
@@ -519,3 +519,76 @@ async fn inspector_connect_non_ws() {
   child.kill().unwrap();
   child.wait().unwrap();
 }
+
+#[tokio::test]
+async fn inspector_break_on_first_line_in_test() {
+  let script = util::testdata_path().join("inspector_test.js");
+  let mut child = util::deno_cmd()
+    .arg("test")
+    .arg(inspect_flag_with_unique_port("--inspect-brk"))
+    .arg(script)
+    .stdout(std::process::Stdio::piped())
+    .stderr(std::process::Stdio::piped())
+    .spawn()
+    .unwrap();
+
+  let stderr = child.stderr.as_mut().unwrap();
+  let mut stderr_lines =
+    std::io::BufReader::new(stderr).lines().map(|r| r.unwrap());
+  let ws_url = extract_ws_url_from_stderr(&mut stderr_lines);
+
+  let (socket, response) = tokio_tungstenite::connect_async(ws_url)
+    .await
+    .expect("Can't connect");
+  assert_eq!(response.status(), 101); // Switching protocols.
+
+  let (mut socket_tx, socket_rx) = socket.split();
+  let mut socket_rx =
+    socket_rx.map(|msg| msg.unwrap().to_string()).filter(|msg| {
+      let pass = !msg.starts_with(r#"{"method":"Debugger.scriptParsed","#);
+      futures::future::ready(pass)
+    });
+
+  let stdout = child.stdout.as_mut().unwrap();
+  let mut stdout_lines =
+    std::io::BufReader::new(stdout).lines().map(|r| r.unwrap());
+
+  use TestStep::*;
+  let test_steps = vec![
+    WsSend(r#"{"id":1,"method":"Runtime.enable"}"#),
+    WsSend(r#"{"id":2,"method":"Debugger.enable"}"#),
+    WsRecv(
+      r#"{"method":"Runtime.executionContextCreated","params":{"context":{"id":1,"#,
+    ),
+    WsRecv(r#"{"id":1,"result":{}}"#),
+    WsRecv(r#"{"id":2,"result":{"debuggerId":"#),
+    WsSend(r#"{"id":3,"method":"Runtime.runIfWaitingForDebugger"}"#),
+    WsRecv(r#"{"id":3,"result":{}}"#),
+    WsRecv(r#"{"method":"Debugger.paused","#),
+    WsSend(
+      r#"{"id":4,"method":"Runtime.evaluate","params":{"expression":"Deno.core.print(\"hello from the inspector\\n\")","contextId":1,"includeCommandLineAPI":true,"silent":false,"returnByValue":true}}"#,
+    ),
+    WsRecv(r#"{"id":4,"result":{"result":{"type":"undefined"}}}"#),
+    StdOut("hello from the inspector"),
+    WsSend(r#"{"id":5,"method":"Debugger.resume"}"#),
+    WsRecv(r#"{"id":5,"result":{}}"#),
+    StdOut("running 1 test from"),
+    StdOut("test has finished running"),
+  ];
+
+  for step in test_steps {
+    match step {
+      StdOut(s) => assert!(
+        &stdout_lines.next().unwrap().contains(s),
+        "Doesn't contain {}",
+        s
+      ),
+      WsRecv(s) => assert!(socket_rx.next().await.unwrap().starts_with(s)),
+      WsSend(s) => socket_tx.send(s.into()).await.unwrap(),
+      _ => unreachable!(),
+    }
+  }
+
+  child.kill().unwrap();
+  child.wait().unwrap();
+}
diff --git a/cli/tests/testdata/inspector_test.js b/cli/tests/testdata/inspector_test.js
new file mode 100644
index 0000000000..86cd48854c
--- /dev/null
+++ b/cli/tests/testdata/inspector_test.js
@@ -0,0 +1,3 @@
+Deno.test("basic test", () => {
+  console.log("test has finished running");
+});
diff --git a/runtime/worker.rs b/runtime/worker.rs
index 545128dffb..087185729f 100644
--- a/runtime/worker.rs
+++ b/runtime/worker.rs
@@ -229,6 +229,7 @@ impl MainWorker {
     module_specifier: &ModuleSpecifier,
   ) -> Result<(), AnyError> {
     let id = self.preload_module(module_specifier, false).await?;
+    self.wait_for_inspector_session();
     self.evaluate_module(id).await
   }