diff --git a/lib/internal/main/watch_mode.js b/lib/internal/main/watch_mode.js
index 06c2c8602da444..5f9608dcb14971 100644
--- a/lib/internal/main/watch_mode.js
+++ b/lib/internal/main/watch_mode.js
@@ -34,10 +34,8 @@ markBootstrapComplete();
 
 const kKillSignal = convertToValidSignal(getOptionValue('--watch-kill-signal'));
 const kShouldFilterModules = getOptionValue('--watch-path').length === 0;
-const kEnvFiles = [
-  ...getOptionValue('--env-file'),
-  ...getOptionValue('--env-file-if-exists'),
-];
+const kEnvFiles = getOptionValue('--env-file');
+const kOptionalEnvFiles = getOptionValue('--env-file-if-exists');
 const kWatchedPaths = ArrayPrototypeMap(getOptionValue('--watch-path'), (path) => resolve(path));
 const kPreserveOutput = getOptionValue('--watch-preserve-output');
 const kCommand = ArrayPrototypeSlice(process.argv, 1);
@@ -105,6 +103,18 @@ function start() {
   if (kEnvFiles.length > 0) {
     ArrayPrototypeForEach(kEnvFiles, (file) => watcher.filterFile(resolve(file)));
   }
+  if (kOptionalEnvFiles.length > 0) {
+    ArrayPrototypeForEach(kOptionalEnvFiles, (file) => {
+      try {
+        watcher.filterFile(resolve(file));
+      } catch (error) {
+        if (error?.code !== 'ENOENT' && error?.code !== 'ENOTDIR') {
+          throw error;
+        }
+        // Failed watching the file, ignore
+      }
+    });
+  }
   child.once('exit', (code) => {
     exited = true;
     const waitingForChanges = 'Waiting for file changes before restarting...';
@@ -160,6 +170,7 @@ async function stop(child) {
 }
 
 let restarting = false;
+
 async function restart(child) {
   if (restarting) return;
   restarting = true;
@@ -198,5 +209,6 @@ function signalHandler(signal) {
     process.exit(exitCode ?? kNoFailure);
   };
 }
+
 process.on('SIGTERM', signalHandler('SIGTERM'));
 process.on('SIGINT', signalHandler('SIGINT'));
diff --git a/test/sequential/test-watch-mode.mjs b/test/sequential/test-watch-mode.mjs
index a5cac129ad1c21..39ad7ef72ada00 100644
--- a/test/sequential/test-watch-mode.mjs
+++ b/test/sequential/test-watch-mode.mjs
@@ -277,6 +277,27 @@ describe('watch mode', { concurrency: !process.env.TEST_PARALLEL, timeout: 60_00
     }
   });
 
+  it('should not crash when --env-file-if-exists points to a missing file', async () => {
+    const envKey = `TEST_ENV_${Date.now()}`;
+    const jsFile = createTmpFile(`console.log('ENV: ' + process.env.${envKey});`);
+    const missingEnvFile = path.join(tmpdir.path, `missing-${Date.now()}.env`);
+    const { done, restart } = runInBackground({
+      args: ['--watch-path', tmpdir.path, `--env-file-if-exists=${missingEnvFile}`, jsFile],
+    });
+
+    try {
+      const { stderr, stdout } = await restart();
+
+      assert.doesNotMatch(stderr, /ENOENT: no such file or directory, watch/);
+      assert.deepStrictEqual(stdout, [
+        'ENV: undefined',
+        `Completed running ${inspect(jsFile)}. Waiting for file changes before restarting...`,
+      ]);
+    } finally {
+      await done();
+    }
+  });
+
   it('should watch changes to a failing file', async () => {
     const file = createTmpFile('throw new Error("fails");');
     const { stderr, stdout } = await runWriteSucceed({