diff --git a/src/inspector_socket_server.cc b/src/inspector_socket_server.cc
index 29e0c128026ed0..299664da9a1693 100644
--- a/src/inspector_socket_server.cc
+++ b/src/inspector_socket_server.cc
@@ -234,6 +234,7 @@ void PrintDebuggerReadyMessage(
     const std::string& host,
     const std::vector<InspectorSocketServer::ServerSocketPtr>& server_sockets,
     const std::vector<std::string>& ids,
+    const char* verb,
     bool publish_uid_stderr,
     FILE* out) {
   if (!publish_uid_stderr || out == nullptr) {
@@ -241,7 +242,8 @@ void PrintDebuggerReadyMessage(
   }
   for (const auto& server_socket : server_sockets) {
     for (const std::string& id : ids) {
-      fprintf(out, "Debugger listening on %s\n",
+      fprintf(out, "Debugger %s on %s\n",
+              verb,
               FormatWsAddress(host, server_socket->port(), id, true).c_str());
     }
   }
@@ -300,6 +302,7 @@ void InspectorSocketServer::SessionTerminated(int session_id) {
       PrintDebuggerReadyMessage(host_,
                                 server_sockets_,
                                 delegate_->GetTargetIds(),
+                                "ending",
                                 inspect_publish_uid_.console,
                                 out_);
     }
@@ -425,6 +428,7 @@ bool InspectorSocketServer::Start() {
   PrintDebuggerReadyMessage(host_,
                             server_sockets_,
                             delegate_->GetTargetIds(),
+                            "listening",
                             inspect_publish_uid_.console,
                             out_);
   return true;
diff --git a/test/known_issues/test-debugger-restart-message.js b/test/sequential/test-debugger-restart-message.js
similarity index 50%
rename from test/known_issues/test-debugger-restart-message.js
rename to test/sequential/test-debugger-restart-message.js
index 478806effbb39c..bcd06b4e230131 100644
--- a/test/known_issues/test-debugger-restart-message.js
+++ b/test/sequential/test-debugger-restart-message.js
@@ -1,30 +1,12 @@
 'use strict';
 
-// Refs: https://github.com/nodejs/node/issues/39272
-
 const common = require('../common');
 
-const assert = require('assert');
-
-// When this is moved out of known_issues, this skip can be removed.
-if (common.isOSX) {
-  assert.fail('does not fail reliably on macOS in CI');
-}
+common.skipIfInspectorDisabled();
 
-// When this is moved out of known_issues, this can be removed and replaced with
-// the commented-out use of common.skipIfInspectorDisabled() below.
-if (!process.features.inspector) {
-  assert.fail('Known issues test should fail, so if the inspector is disabled');
-}
-
-// Will need to uncomment this when moved out of known_issues.
-// common.skipIfInspectorDisabled();
+const assert = require('assert');
 
-// This can be reduced to 2 or even 1 (and the loop removed) once the debugger
-// is fixed. It's set higher to make sure that the error is tripped reliably
-// in CI. On most systems, the error will be tripped on the first test, but
-// on a few platforms in CI, it needs to be many times.
-const RESTARTS = 16;
+const RESTARTS = 10;
 
 const fixtures = require('../common/fixtures');
 const startCLI = require('../common/debugger');