diff --git a/lib/repl.js b/lib/repl.js
index 88b0f5658489fc..b2b4574b70e85d 100644
--- a/lib/repl.js
+++ b/lib/repl.js
@@ -325,7 +325,7 @@ function REPLServer(prompt,
     let pwd;
     try {
       const { pathToFileURL } = require('url');
-      pwd = pathToFileURL(process.cwd()).href;
+      pwd = pathToFileURL(`${process.cwd()}/`).href;
     } catch {
     }
     while (true) {
diff --git a/test/parallel/test-repl-dynamic-import.js b/test/parallel/test-repl-dynamic-import.js
new file mode 100644
index 00000000000000..bd2cdc415d9a41
--- /dev/null
+++ b/test/parallel/test-repl-dynamic-import.js
@@ -0,0 +1,46 @@
+'use strict';
+
+// Flags: --experimental-modules
+
+const common = require('../common');
+const fixtures = require('../common/fixtures');
+const assert = require('assert');
+const net = require('net');
+
+if (!common.isMainThread)
+  common.skip('process.chdir is not available in Workers');
+
+process.chdir(fixtures.fixturesDir);
+const repl = require('repl');
+
+const server = net.createServer((conn) => {
+  repl.start('', conn).on('exit', () => {
+    conn.destroy();
+    server.close();
+  });
+});
+
+const host = common.localhostIPv4;
+const port = 0;
+const options = { host, port };
+
+let answer = '';
+let expectedDataEvents = 2;
+server.listen(options, function() {
+  options.port = this.address().port;
+  const conn = net.connect(options);
+  conn.setEncoding('utf8');
+  conn.on('data', (data) => {
+    answer += data;
+    if (--expectedDataEvents === 0) {
+      conn.write('.exit\n');
+    }
+  });
+  conn.write('import("./es-modules/message.mjs").then(console.log)\n');
+});
+
+process.on('exit', function() {
+  assert.strictEqual(/Cannot find module/.test(answer), false);
+  assert.strictEqual(/Error/.test(answer), false);
+  assert.strictEqual(/{ message: 'A message' }/.test(answer), true);
+});