diff --git a/lib/internal/modules/cjs/loader.js b/lib/internal/modules/cjs/loader.js
index 8cec27e6c4229b..a69978b8231c75 100644
--- a/lib/internal/modules/cjs/loader.js
+++ b/lib/internal/modules/cjs/loader.js
@@ -1091,14 +1091,20 @@ Module.prototype._compile = function(content, filename) {
     if (!resolvedArgv) {
       // We enter the repl if we're not given a filename argument.
       if (process.argv[1]) {
-        resolvedArgv = Module._resolveFilename(process.argv[1], null, false);
+        try {
+          resolvedArgv = Module._resolveFilename(process.argv[1], null, false);
+        } catch {
+          // We only expect this codepath to be reached in the case of a
+          // preloaded module (it will fail earlier with the main entry)
+          assert(Array.isArray(getOptionValue('--require')));
+        }
       } else {
         resolvedArgv = 'repl';
       }
     }
 
     // Set breakpoint on module start
-    if (!hasPausedEntry && filename === resolvedArgv) {
+    if (resolvedArgv && !hasPausedEntry && filename === resolvedArgv) {
       hasPausedEntry = true;
       inspectorWrapper = internalBinding('inspector').callAndPauseOnStart;
     }
diff --git a/test/fixtures/test-resolution-inspect-brk-main.ext b/test/fixtures/test-resolution-inspect-brk-main.ext
new file mode 100644
index 00000000000000..e69de29bb2d1d6
diff --git a/test/fixtures/test-resolution-inspect-brk-resolver.js b/test/fixtures/test-resolution-inspect-brk-resolver.js
new file mode 100644
index 00000000000000..fdfb5ca5b170c2
--- /dev/null
+++ b/test/fixtures/test-resolution-inspect-brk-resolver.js
@@ -0,0 +1,5 @@
+'use strict';
+// eslint-disable-next-line no-unused-vars
+const common = require('../common');
+
+require.extensions['.ext'] = require.extensions['.js'];
diff --git a/test/sequential/test-resolution-inspect-brk.js b/test/sequential/test-resolution-inspect-brk.js
new file mode 100644
index 00000000000000..2af32426c03f57
--- /dev/null
+++ b/test/sequential/test-resolution-inspect-brk.js
@@ -0,0 +1,29 @@
+'use strict';
+const common = require('../common');
+common.skipIfInspectorDisabled();
+
+// A test to ensure that preload modules are given a chance to execute before
+// resolving the main entry point with --inspect-brk active.
+
+const assert = require('assert');
+const cp = require('child_process');
+const path = require('path');
+
+function test(execArgv) {
+  const child = cp.spawn(process.execPath, execArgv);
+
+  child.stderr.once('data', common.mustCall(function() {
+    child.kill('SIGTERM');
+  }));
+
+  child.on('exit', common.mustCall(function(code, signal) {
+    assert.strictEqual(signal, 'SIGTERM');
+  }));
+}
+
+test([
+  '--require',
+  path.join(__dirname, '../fixtures/test-resolution-inspect-brk-resolver.js'),
+  '--inspect-brk',
+  '../fixtures/test-resolution-inspect-resolver-main.ext',
+]);