diff --git a/lib/internal/repl/utils.js b/lib/internal/repl/utils.js
index 49a40e3030a3e2..476760a08d5934 100644
--- a/lib/internal/repl/utils.js
+++ b/lib/internal/repl/utils.js
@@ -136,6 +136,8 @@ function setupPreview(repl, contextSymbol, bufferSymbol, active) {
   let previewCompletionCounter = 0;
   let completionPreview = null;
 
+  let wrapped = false;
+
   function getPreviewPos() {
     const displayPos = repl._getDisplayPos(`${repl._prompt}${repl.line}`);
     const cursorPos = repl.line.length !== repl.cursor ?
@@ -244,8 +246,9 @@ function setupPreview(repl, contextSymbol, bufferSymbol, active) {
   function getInputPreview(input, callback) {
     // For similar reasons as `defaultEval`, wrap expressions starting with a
     // curly brace with parenthesis.
-    if (input.startsWith('{') && !input.endsWith(';')) {
+    if (input.startsWith('{') && !input.endsWith(';') && !wrapped) {
       input = `(${input})`;
+      wrapped = true;
     }
     sendInspectorCommand((session) => {
       session.post('Runtime.evaluate', {
@@ -329,13 +332,19 @@ function setupPreview(repl, contextSymbol, bufferSymbol, active) {
       return;
     }
 
-    getInputPreview(line, (error, inspected) => {
+    const inputPreviewCallback = (error, inspected) => {
+      if (inspected === null) {
+        return;
+      }
+
+      wrapped = false;
+
       // Ignore the output if the value is identical to the current line and the
       // former preview is not identical to this preview.
-      if ((line === inspected && lastInputPreview !== inspected) ||
-          inspected === null) {
+      if (line === inspected && lastInputPreview !== inspected) {
         return;
       }
+
       if (error) {
         debug('Error while generating preview', error);
         return;
@@ -386,7 +395,13 @@ function setupPreview(repl, contextSymbol, bufferSymbol, active) {
       repl.output.write(`\n${result}`);
       cursorTo(repl.output, cursorPos.cols);
       moveCursor(repl.output, 0, -rows - 1);
-    });
+    };
+
+    getInputPreview(line, inputPreviewCallback);
+    if (wrapped) {
+      getInputPreview(line, inputPreviewCallback);
+    }
+    wrapped = false;
   };
 
   // -------------------------------------------------------------------------//
diff --git a/test/parallel/test-repl-preview.js b/test/parallel/test-repl-preview.js
index b36b99cca7c40e..b8dbbf3f9a993d 100644
--- a/test/parallel/test-repl-preview.js
+++ b/test/parallel/test-repl-preview.js
@@ -4,6 +4,7 @@ const common = require('../common');
 const assert = require('assert');
 const { REPLServer } = require('repl');
 const { Stream } = require('stream');
+const { inspect } = require('util');
 
 common.skipIfInspectorDisabled();
 
@@ -76,78 +77,111 @@ async function tests(options) {
     'function koo() { console.log("abc"); }',
     'a = undefined;'
   ]);
-  const testCases = [
-    ['foo', [2, 4], '[Function: foo]',
-     'foo',
-     '\x1B[90m[Function: foo]\x1B[39m\x1B[11G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
-     '\x1B[36m[Function: foo]\x1B[39m',
-     '\x1B[1G\x1B[0Jrepl > \x1B[8G'],
-    ['koo', [2, 4], '[Function: koo]',
-     'k\x1B[90moo\x1B[39m\x1B[9G\x1B[0Ko\x1B[90mo\x1B[39m\x1B[10G\x1B[0Ko',
-     '\x1B[90m[Function: koo]\x1B[39m\x1B[11G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
-     '\x1B[36m[Function: koo]\x1B[39m',
-     '\x1B[1G\x1B[0Jrepl > \x1B[8G'],
-    ['a', [1, 2], undefined],
-    [" { b: 1 }['b'] === 1", [2, 6], '\x1B[33mtrue\x1B[39m',
-     " { b: 1 }['b']",
-     '\x1B[90m1\x1B[39m\x1B[22G\x1B[1A\x1B[1B\x1B[2K\x1B[1A ',
-     '\x1B[90m1\x1B[39m\x1B[23G\x1B[1A\x1B[1B\x1B[2K\x1B[1A=== 1',
-     '\x1B[90mtrue\x1B[39m\x1B[28G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
-     '\x1B[33mtrue\x1B[39m',
-     '\x1B[1G\x1B[0Jrepl > \x1B[8G'
-    ],
-    ["{ b: 1 }['b'] === 1;", [2, 7], '\x1B[33mfalse\x1B[39m',
-     "{ b: 1 }['b']",
-     '\x1B[90m1\x1B[39m\x1B[21G\x1B[1A\x1B[1B\x1B[2K\x1B[1A ',
-     '\x1B[90m1\x1B[39m\x1B[22G\x1B[1A\x1B[1B\x1B[2K\x1B[1A=== 1',
-     '\x1B[90mtrue\x1B[39m\x1B[27G\x1B[1A\x1B[1B\x1B[2K\x1B[1A;',
-     '\x1B[90mfalse\x1B[39m\x1B[28G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
-     '\x1B[33mfalse\x1B[39m',
-     '\x1B[1G\x1B[0Jrepl > \x1B[8G'
-    ],
-    ['{ a: true }', [2, 3], '{ a: \x1B[33mtrue\x1B[39m }',
-     '{ a: tru\x1B[90me\x1B[39m\x1B[16G\x1B[0Ke }\r',
-     '{ a: \x1B[33mtrue\x1B[39m }',
-     '\x1B[1G\x1B[0Jrepl > \x1B[8G'],
-    ['1n + 2n', [2, 5], '\x1B[33m3n\x1B[39m',
-     '1n + 2',
-     '\x1B[90mType[39m\x1B[14G\x1B[1A\x1B[1B\x1B[2K\x1B[1An',
-     '\x1B[90m3n\x1B[39m\x1B[15G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
-     '\x1B[33m3n\x1B[39m',
-     '\x1B[1G\x1B[0Jrepl > \x1B[8G'],
-    ['{ a: true };', [2, 4], '\x1B[33mtrue\x1B[39m',
-     '{ a: tru\x1B[90me\x1B[39m\x1B[16G\x1B[0Ke };',
-     '\x1B[90mtrue\x1B[39m\x1B[20G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
-     '\x1B[33mtrue\x1B[39m',
-     '\x1B[1G\x1B[0Jrepl > \x1B[8G'],
-    [' \t { a: true};', [2, 5], '\x1B[33mtrue\x1B[39m',
-     '  { a: tru\x1B[90me\x1B[39m\x1B[18G\x1B[0Ke}',
-     '\x1B[90m{ a: true }\x1B[39m\x1B[20G\x1B[1A\x1B[1B\x1B[2K\x1B[1A;',
-     '\x1B[90mtrue\x1B[39m\x1B[21G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
-     '\x1B[33mtrue\x1B[39m',
-     '\x1B[1G\x1B[0Jrepl > \x1B[8G']
-  ];
+
+  const testCases = [{
+    input: 'foo',
+    noPreview: '[Function: foo]',
+    preview: [
+      'foo',
+      '\x1B[90m[Function: foo]\x1B[39m\x1B[11G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
+      '\x1B[36m[Function: foo]\x1B[39m'
+    ]
+  }, {
+    input: 'koo',
+    noPreview: '[Function: koo]',
+    preview: [
+      'k\x1B[90moo\x1B[39m\x1B[9G\x1B[0Ko\x1B[90mo\x1B[39m\x1B[10G\x1B[0Ko',
+      '\x1B[90m[Function: koo]\x1B[39m\x1B[11G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
+      '\x1B[36m[Function: koo]\x1B[39m'
+    ]
+  }, {
+    input: 'a',
+    noPreview: 'repl > ', // No "undefined" output.
+    preview: ['a\r'] // No "undefined" preview.
+  }, {
+    input: " { b: 1 }['b'] === 1",
+    noPreview: '\x1B[33mtrue\x1B[39m',
+    preview: [
+      " { b: 1 }['b']",
+      '\x1B[90m1\x1B[39m\x1B[22G\x1B[1A\x1B[1B\x1B[2K\x1B[1A ',
+      '\x1B[90m1\x1B[39m\x1B[23G\x1B[1A\x1B[1B\x1B[2K\x1B[1A=== 1',
+      '\x1B[90mtrue\x1B[39m\x1B[28G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
+      '\x1B[33mtrue\x1B[39m'
+    ]
+  }, {
+    input: "{ b: 1 }['b'] === 1;",
+    noPreview: '\x1B[33mfalse\x1B[39m',
+    preview: [
+      "{ b: 1 }['b']",
+      '\x1B[90m1\x1B[39m\x1B[21G\x1B[1A\x1B[1B\x1B[2K\x1B[1A ',
+      '\x1B[90m1\x1B[39m\x1B[22G\x1B[1A\x1B[1B\x1B[2K\x1B[1A=== 1',
+      '\x1B[90mtrue\x1B[39m\x1B[27G\x1B[1A\x1B[1B\x1B[2K\x1B[1A;',
+      '\x1B[90mfalse\x1B[39m\x1B[28G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
+      '\x1B[33mfalse\x1B[39m'
+    ]
+  }, {
+    input: '{ a: true }',
+    noPreview: '{ a: \x1B[33mtrue\x1B[39m }',
+    preview: [
+      '{ a: tru\x1B[90me\x1B[39m\x1B[16G\x1B[0Ke }\r',
+      '{ a: \x1B[33mtrue\x1B[39m }'
+    ]
+  }, {
+    input: '{ a: true };',
+    noPreview: '\x1B[33mtrue\x1B[39m',
+    preview: [
+      '{ a: tru\x1B[90me\x1B[39m\x1B[16G\x1B[0Ke };',
+      '\x1B[90mtrue\x1B[39m\x1B[20G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
+      '\x1B[33mtrue\x1B[39m'
+    ]
+  }, {
+    input: ' \t { a: true};',
+    noPreview: '\x1B[33mtrue\x1B[39m',
+    preview: [
+      '  { a: tru\x1B[90me\x1B[39m\x1B[18G\x1B[0Ke}',
+      '\x1B[90m{ a: true }\x1B[39m\x1B[20G\x1B[1A\x1B[1B\x1B[2K\x1B[1A;',
+      '\x1B[90mtrue\x1B[39m\x1B[21G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
+      '\x1B[33mtrue\x1B[39m'
+    ]
+  }, {
+    input: '1n + 2n',
+    noPreview: '\x1B[33m3n\x1B[39m',
+    preview: [
+      '1n + 2',
+      '\x1B[90mType[39m\x1B[14G\x1B[1A\x1B[1B\x1B[2K\x1B[1An',
+      '\x1B[90m3n\x1B[39m\x1B[15G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
+      '\x1B[33m3n\x1B[39m'
+    ]
+  }, {
+    input: '{};1',
+    noPreview: '\x1B[33m1\x1B[39m',
+    preview: [
+      '{};1',
+      '\x1B[90m1\x1B[39m\x1B[12G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
+      '\x1B[33m1\x1B[39m'
+    ]
+  }];
 
   const hasPreview = repl.terminal &&
     (options.preview !== undefined ? !!options.preview : true);
 
-  for (const [input, length, expected, ...preview] of testCases) {
+  for (const { input, noPreview, preview } of testCases) {
     console.log(`Testing ${input}`);
 
     const toBeRun = input.split('\n');
     let lines = await runAndWait(toBeRun, repl);
 
-    assert.strictEqual(lines.length, length[+hasPreview]);
-    if (expected === undefined) {
-      assert(!lines.some((e) => e.includes('undefined')));
-    } else if (hasPreview) {
+    if (hasPreview) {
       // Remove error messages. That allows the code to run in different
       // engines.
       // eslint-disable-next-line no-control-regex
       lines = lines.map((line) => line.replace(/Error: .+?\x1B/, ''));
+      assert.strictEqual(lines.pop(), '\x1B[1G\x1B[0Jrepl > \x1B[8G');
       assert.deepStrictEqual(lines, preview);
     } else {
-      assert.ok(lines[0].includes(expected), lines);
+      assert.ok(lines[0].includes(noPreview), lines.map(inspect));
+      if (preview.length !== 1 || preview[0] !== `${input}\r`)
+        assert.strictEqual(lines.length, 2);
     }
   }
 }
diff --git a/test/parallel/test-repl.js b/test/parallel/test-repl.js
index b0dad397ccc06b..dcb3fa40630423 100644
--- a/test/parallel/test-repl.js
+++ b/test/parallel/test-repl.js
@@ -457,6 +457,28 @@ const errorTests = [
       /'thefourtheye'/
     ]
   },
+  // Check for wrapped objects.
+  {
+    send: '{ a: 1 }.a', // ({ a: 1 }.a);
+    expect: '1'
+  },
+  {
+    send: '{ a: 1 }.a;', // { a: 1 }.a;
+    expect: [
+      kSource,
+      kArrow,
+      '',
+      /^Uncaught SyntaxError: /
+    ]
+  },
+  {
+    send: '{ a: 1 }["a"] === 1', // ({ a: 1 }['a'] === 1);
+    expect: 'true'
+  },
+  {
+    send: '{ a: 1 }["a"] === 1;', // { a: 1 }; ['a'] === 1;
+    expect: 'false'
+  },
   // Empty lines in the REPL should be allowed
   {
     send: '\n\r\n\r\n',