diff --git a/cli/tests/integration/inspector_tests.rs b/cli/tests/integration/inspector_tests.rs
index e901e26331..f5365ac994 100644
--- a/cli/tests/integration/inspector_tests.rs
+++ b/cli/tests/integration/inspector_tests.rs
@@ -97,6 +97,8 @@ async fn inspector_break_on_first_line() {
 
   use TestStep::*;
   let test_steps = vec![
+    StdErr("Visit chrome://inspect to connect to the debugger."),
+    StdErr("Deno is waiting for debugger to connect."),
     WsSend(r#"{"id":1,"method":"Runtime.enable"}"#),
     WsSend(r#"{"id":2,"method":"Debugger.enable"}"#),
     WsRecv(
@@ -119,10 +121,10 @@ async fn inspector_break_on_first_line() {
 
   for step in test_steps {
     match step {
+      StdErr(s) => assert_eq!(&stderr_lines.next().unwrap(), s),
       StdOut(s) => assert_eq!(&stdout_lines.next().unwrap(), s),
       WsRecv(s) => assert!(socket_rx.next().await.unwrap().starts_with(s)),
       WsSend(s) => socket_tx.send(s.into()).await.unwrap(),
-      _ => unreachable!(),
     }
   }
 
@@ -276,6 +278,8 @@ async fn inspector_does_not_hang() {
 
   use TestStep::*;
   let test_steps = vec![
+    StdErr("Visit chrome://inspect to connect to the debugger."),
+    StdErr("Deno is waiting for debugger to connect."),
     WsSend(r#"{"id":1,"method":"Runtime.enable"}"#),
     WsSend(r#"{"id":2,"method":"Debugger.enable"}"#),
     WsRecv(
@@ -293,6 +297,7 @@ async fn inspector_does_not_hang() {
 
   for step in test_steps {
     match step {
+      StdErr(s) => assert_eq!(&stderr_lines.next().unwrap(), s),
       WsRecv(s) => assert!(socket_rx.next().await.unwrap().starts_with(s)),
       WsSend(s) => socket_tx.send(s.into()).await.unwrap(),
       _ => unreachable!(),
@@ -397,6 +402,7 @@ async fn inspector_runtime_evaluate_does_not_crash() {
 
   use TestStep::*;
   let test_steps = vec![
+    StdErr("Visit chrome://inspect to connect to the debugger."),
     WsSend(r#"{"id":1,"method":"Runtime.enable"}"#),
     WsSend(r#"{"id":2,"method":"Debugger.enable"}"#),
     WsRecv(
@@ -555,6 +561,8 @@ async fn inspector_break_on_first_line_in_test() {
 
   use TestStep::*;
   let test_steps = vec![
+    StdErr("Visit chrome://inspect to connect to the debugger."),
+    StdErr("Deno is waiting for debugger to connect."),
     WsSend(r#"{"id":1,"method":"Runtime.enable"}"#),
     WsSend(r#"{"id":2,"method":"Debugger.enable"}"#),
     WsRecv(
@@ -583,9 +591,9 @@ async fn inspector_break_on_first_line_in_test() {
         "Doesn't contain {}",
         s
       ),
+      StdErr(s) => assert_eq!(&stderr_lines.next().unwrap(), s),
       WsRecv(s) => assert!(socket_rx.next().await.unwrap().starts_with(s)),
       WsSend(s) => socket_tx.send(s.into()).await.unwrap(),
-      _ => unreachable!(),
     }
   }
 
diff --git a/runtime/inspector_server.rs b/runtime/inspector_server.rs
index 6ba4d088de..99aff06446 100644
--- a/runtime/inspector_server.rs
+++ b/runtime/inspector_server.rs
@@ -65,13 +65,18 @@ impl InspectorServer {
     &self,
     module_url: String,
     js_runtime: &mut JsRuntime,
+    should_break_on_first_statement: bool,
   ) {
     let inspector = js_runtime.inspector();
     let session_sender = inspector.get_session_sender();
     let deregister_rx = inspector.add_deregister_handler();
-    // TODO(bartlomieju): simplify
-    let info =
-      InspectorInfo::new(self.host, session_sender, deregister_rx, module_url);
+    let info = InspectorInfo::new(
+      self.host,
+      session_sender,
+      deregister_rx,
+      module_url,
+      should_break_on_first_statement,
+    );
     self.register_inspector_tx.unbounded_send(info).unwrap();
   }
 }
@@ -229,6 +234,10 @@ async fn server(
         "Debugger listening on {}",
         info.get_websocket_debugger_url()
       );
+      eprintln!("Visit chrome://inspect to connect to the debugger.");
+      if info.should_break_on_first_statement {
+        eprintln!("Deno is waiting for debugger to connect.");
+      }
       if inspector_map.borrow_mut().insert(info.uuid, info).is_some() {
         panic!("Inspector UUID already in map");
       }
@@ -336,7 +345,7 @@ async fn pump_websocket_messages(
     .map_err(|_| ());
 
   let inbound_pump = async move {
-    let result = websocket_rx
+    let _result = websocket_rx
       .map_ok(|msg| msg.into_data())
       .map_err(AnyError::from)
       .map_ok(|msg| {
@@ -345,10 +354,9 @@ async fn pump_websocket_messages(
       .try_collect::<()>()
       .await;
 
-    match result {
-      Ok(_) => eprintln!("Debugger session ended"),
-      Err(err) => eprintln!("Debugger session ended: {}.", err),
-    };
+    // Users don't care if there was an error coming from debugger,
+    // just about the fact that debugger did disconnect.
+    eprintln!("Debugger session ended");
 
     Ok(())
   };
@@ -364,6 +372,7 @@ pub struct InspectorInfo {
   pub new_session_tx: UnboundedSender<InspectorSessionProxy>,
   pub deregister_rx: oneshot::Receiver<()>,
   pub url: String,
+  pub should_break_on_first_statement: bool,
 }
 
 impl InspectorInfo {
@@ -372,6 +381,7 @@ impl InspectorInfo {
     new_session_tx: mpsc::UnboundedSender<InspectorSessionProxy>,
     deregister_rx: oneshot::Receiver<()>,
     url: String,
+    should_break_on_first_statement: bool,
   ) -> Self {
     Self {
       host,
@@ -380,6 +390,7 @@ impl InspectorInfo {
       new_session_tx,
       deregister_rx,
       url,
+      should_break_on_first_statement,
     }
   }
 
diff --git a/runtime/web_worker.rs b/runtime/web_worker.rs
index 24306fab59..e4c727977d 100644
--- a/runtime/web_worker.rs
+++ b/runtime/web_worker.rs
@@ -442,7 +442,11 @@ impl WebWorker {
     });
 
     if let Some(server) = options.maybe_inspector_server.clone() {
-      server.register_inspector(main_module.to_string(), &mut js_runtime);
+      server.register_inspector(
+        main_module.to_string(),
+        &mut js_runtime,
+        false,
+      );
     }
 
     let (internal_handle, external_handle) = {
diff --git a/runtime/worker.rs b/runtime/worker.rs
index 087185729f..3e245d331a 100644
--- a/runtime/worker.rs
+++ b/runtime/worker.rs
@@ -161,7 +161,11 @@ impl MainWorker {
     });
 
     if let Some(server) = options.maybe_inspector_server.clone() {
-      server.register_inspector(main_module.to_string(), &mut js_runtime);
+      server.register_inspector(
+        main_module.to_string(),
+        &mut js_runtime,
+        options.should_break_on_first_statement,
+      );
     }
 
     Self {