diff --git a/lib/internal/loader/Loader.js b/lib/internal/loader/Loader.js
index 57c70188d66..b1b99814f4f 100644
--- a/lib/internal/loader/Loader.js
+++ b/lib/internal/loader/Loader.js
@@ -47,6 +47,7 @@ class Loader {
       throw new errors.TypeError('ERR_INVALID_ARG_TYPE',
                                  'parentURL', 'string');
     }
+
     const { url, format } = await this.resolver(specifier, parentURL,
                                                 ModuleRequest.resolve);
 
diff --git a/lib/internal/loader/ModuleRequest.js b/lib/internal/loader/ModuleRequest.js
index 88e48ae9d3e..72f3dd3ee57 100644
--- a/lib/internal/loader/ModuleRequest.js
+++ b/lib/internal/loader/ModuleRequest.js
@@ -88,7 +88,14 @@ exports.resolve = (specifier, parentURL) => {
     };
   }
 
-  let url = search(specifier, parentURL);
+  let url;
+  try {
+    url = search(specifier, parentURL);
+  } catch (e) {
+    if (e.message && e.message.startsWith('Cannot find module'))
+      e.code = 'MODULE_NOT_FOUND';
+    throw e;
+  }
 
   if (url.protocol !== 'file:') {
     throw new errors.Error('ERR_INVALID_PROTOCOL',
diff --git a/lib/module.js b/lib/module.js
index 92b8fbbc392..d210c916252 100644
--- a/lib/module.js
+++ b/lib/module.js
@@ -424,39 +424,28 @@ Module._load = function(request, parent, isMain) {
     debug('Module._load REQUEST %s parent: %s', request, parent.id);
   }
 
-  var filename = null;
-
-  if (isMain) {
-    try {
-      filename = Module._resolveFilename(request, parent, isMain);
-    } catch (e) {
-      // try to keep stack
-      e.stack;
-      throw e;
-    }
-    if (experimentalModules) {
-      (async () => {
-        // loader setup
-        if (!ESMLoader) {
-          ESMLoader = new Loader();
-          const userLoader = process.binding('config').userLoader;
-          if (userLoader) {
-            const hooks = await new Loader().import(userLoader);
-            ESMLoader.hook(hooks);
-          }
+  if (isMain && experimentalModules) {
+    (async () => {
+      // loader setup
+      if (!ESMLoader) {
+        ESMLoader = new Loader();
+        const userLoader = process.binding('config').userLoader;
+        if (userLoader) {
+          const hooks = await new Loader().import(userLoader);
+          ESMLoader.hook(hooks);
         }
-        await ESMLoader.import(getURLFromFilePath(filename).href);
-      })()
-      .catch((e) => {
-        console.error(e);
-        process.exit(1);
-      });
-      return;
-    }
-  } else {
-    filename = Module._resolveFilename(request, parent, isMain);
+      }
+      await ESMLoader.import(getURLFromFilePath(request).href);
+    })()
+    .catch((e) => {
+      console.error(e);
+      process.exit(1);
+    });
+    return;
   }
 
+  var filename = Module._resolveFilename(request, parent, isMain);
+
   var cachedModule = Module._cache[filename];
   if (cachedModule) {
     updateChildren(parent, cachedModule, true);
diff --git a/src/module_wrap.cc b/src/module_wrap.cc
index 829248b681c..bda760369e9 100644
--- a/src/module_wrap.cc
+++ b/src/module_wrap.cc
@@ -442,6 +442,11 @@ URL resolve_directory(const URL& search, bool read_pkg_json) {
 URL Resolve(std::string specifier, const URL* base, bool read_pkg_json) {
   URL pure_url(specifier);
   if (!(pure_url.flags() & URL_FLAGS_FAILED)) {
+    // just check existence, without altering
+    auto check = check_file(pure_url, true);
+    if (check.failed) {
+      return URL("");
+    }
     return pure_url;
   }
   if (specifier.length() == 0) {
@@ -493,9 +498,8 @@ void ModuleWrap::Resolve(const FunctionCallbackInfo<Value>& args) {
 
   URL result = node::loader::Resolve(*specifier_utf, &url, true);
   if (result.flags() & URL_FLAGS_FAILED) {
-    std::string msg = "module ";
+    std::string msg = "Cannot find module ";
     msg += *specifier_utf;
-    msg += " not found";
     env->ThrowError(msg.c_str());
     return;
   }
diff --git a/test/es-module/test-esm-preserve-symlinks-not-found-plain.mjs b/test/es-module/test-esm-preserve-symlinks-not-found-plain.mjs
new file mode 100644
index 00000000000..bfeb71ef3a6
--- /dev/null
+++ b/test/es-module/test-esm-preserve-symlinks-not-found-plain.mjs
@@ -0,0 +1,3 @@
+// Flags: --experimental-modules --loader ./test/fixtures/es-module-loaders/not-found-assert-loader.mjs
+/* eslint-disable required-modules */
+import './not-found.js';
diff --git a/test/es-module/test-esm-preserve-symlinks-not-found.mjs b/test/es-module/test-esm-preserve-symlinks-not-found.mjs
new file mode 100644
index 00000000000..22c888028e7
--- /dev/null
+++ b/test/es-module/test-esm-preserve-symlinks-not-found.mjs
@@ -0,0 +1,3 @@
+// Flags: --experimental-modules --loader ./test/fixtures/es-module-loaders/not-found-assert-loader.mjs
+/* eslint-disable required-modules */
+import './not-found';
diff --git a/test/fixtures/es-module-loaders/not-found-assert-loader.mjs b/test/fixtures/es-module-loaders/not-found-assert-loader.mjs
new file mode 100644
index 00000000000..7718cc7c4ba
--- /dev/null
+++ b/test/fixtures/es-module-loaders/not-found-assert-loader.mjs
@@ -0,0 +1,22 @@
+import assert from 'assert';
+
+// a loader that asserts that the defaultResolve will throw "not found"
+// (skipping the top-level main of course)
+let mainLoad = true;
+export async function resolve (specifier, base, defaultResolve) {
+  if (mainLoad) {
+    mainLoad = false;
+    return defaultResolve(specifier, base);
+  }
+  try {
+    await defaultResolve(specifier, base);
+  }
+  catch (e) {
+    assert.equal(e.code, 'MODULE_NOT_FOUND');
+    return {
+      format: 'builtin',
+      url: 'fs'
+    };
+  }
+  assert.fail(`Module resolution for ${specifier} should be throw MODULE_NOT_FOUND`);
+}
diff --git a/test/parallel/test-module-main-fail.js b/test/parallel/test-module-main-fail.js
new file mode 100644
index 00000000000..a6457f33b65
--- /dev/null
+++ b/test/parallel/test-module-main-fail.js
@@ -0,0 +1,21 @@
+'use strict';
+require('../common');
+const assert = require('assert');
+const { execFileSync } = require('child_process');
+
+const entryPoints = ['iDoNotExist', 'iDoNotExist.js', 'iDoNotExist.mjs'];
+const flags = [[], ['--experimental-modules']];
+const node = process.argv[0];
+
+for (const args of flags) {
+  for (const entryPoint of entryPoints) {
+    try {
+      execFileSync(node, args.concat(entryPoint), { stdio: 'pipe' });
+    } catch (e) {
+      assert(e.toString().match(/Error: Cannot find module/));
+      continue;
+    }
+    assert.fail('Executing node with inexistent entry point should ' +
+                `fail. Entry point: ${entryPoint}, Flags: [${args}]`);
+  }
+}
diff --git a/test/parallel/test-module-main-preserve-symlinks-fail.js b/test/parallel/test-module-main-preserve-symlinks-fail.js
new file mode 100644
index 00000000000..b46497b6252
--- /dev/null
+++ b/test/parallel/test-module-main-preserve-symlinks-fail.js
@@ -0,0 +1,21 @@
+'use strict';
+require('../common');
+const assert = require('assert');
+const { execFileSync } = require('child_process');
+
+const entryPoints = ['iDoNotExist', 'iDoNotExist.js', 'iDoNotExist.mjs'];
+const flags = [[], ['--experimental-modules', '--preserve-symlinks']];
+const node = process.argv[0];
+
+for (const args of flags) {
+  for (const entryPoint of entryPoints) {
+    try {
+      execFileSync(node, args.concat(entryPoint));
+    } catch (e) {
+      assert(e.toString().match(/Error: Cannot find module/));
+      continue;
+    }
+    assert.fail('Executing node with inexistent entry point should ' +
+                `fail. Entry point: ${entryPoint}, Flags: [${args}]`);
+  }
+}