diff --git a/lib/internal/repl/utils.js b/lib/internal/repl/utils.js
index 84eddf6e86322d..e37d1841a8897b 100644
--- a/lib/internal/repl/utils.js
+++ b/lib/internal/repl/utils.js
@@ -299,7 +299,9 @@ function setupPreview(repl, contextSymbol, bufferSymbol, active) {
     // For similar reasons as `defaultEval`, wrap expressions starting with a
     // curly brace with parenthesis.
     if (StringPrototypeStartsWith(input, '{') &&
-        !StringPrototypeEndsWith(input, ';') && !wrapped) {
+        !StringPrototypeEndsWith(input, ';') &&
+        isValidSyntax(input) &&
+        !wrapped) {
       input = `(${input})`;
       wrapped = true;
     }
@@ -740,6 +742,27 @@ function setupReverseSearch(repl) {
   return { reverseSearch };
 }
 
+function isValidSyntax(input) {
+  const Parser = require('internal/deps/acorn/acorn/dist/acorn').Parser;
+  try {
+    Parser.parse(input, {
+      ecmaVersion: 'latest',
+      allowAwaitOutsideFunction: true,
+    });
+    return true;
+  } catch {
+    try {
+      Parser.parse(`_=${input}`, {
+        ecmaVersion: 'latest',
+        allowAwaitOutsideFunction: true,
+      });
+      return true;
+    } catch {
+      return false;
+    }
+  }
+}
+
 module.exports = {
   REPL_MODE_SLOPPY: Symbol('repl-sloppy'),
   REPL_MODE_STRICT,
@@ -747,4 +770,5 @@ module.exports = {
   kStandaloneREPL: Symbol('kStandaloneREPL'),
   setupPreview,
   setupReverseSearch,
+  isValidSyntax,
 };
diff --git a/lib/repl.js b/lib/repl.js
index 241e25f0f2095a..18d4bacfbe0d4e 100644
--- a/lib/repl.js
+++ b/lib/repl.js
@@ -163,6 +163,7 @@ const {
   kStandaloneREPL,
   setupPreview,
   setupReverseSearch,
+  isValidSyntax,
 } = require('internal/repl/utils');
 const {
   constants: {
@@ -420,7 +421,8 @@ function REPLServer(prompt,
     // an expression.  Note that if the above condition changes,
     // lib/internal/repl/utils.js needs to be changed to match.
     if (RegExpPrototypeExec(/^\s*{/, code) !== null &&
-        RegExpPrototypeExec(/;\s*$/, code) === null) {
+        RegExpPrototypeExec(/;\s*$/, code) === null &&
+        isValidSyntax(code)) {
       code = `(${StringPrototypeTrim(code)})\n`;
       wrappedCmd = true;
     }
@@ -1819,6 +1821,7 @@ module.exports = {
   REPL_MODE_SLOPPY,
   REPL_MODE_STRICT,
   Recoverable,
+  isValidSyntax,
 };
 
 ObjectDefineProperty(module.exports, 'builtinModules', {
diff --git a/test/parallel/test-repl-preview.js b/test/parallel/test-repl-preview.js
index 6eb2a169918a51..eb1724796d488e 100644
--- a/test/parallel/test-repl-preview.js
+++ b/test/parallel/test-repl-preview.js
@@ -157,6 +157,78 @@ async function tests(options) {
       '\x1B[90m1\x1B[39m\x1B[12G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
       '\x1B[33m1\x1B[39m',
     ]
+  }, {
+    input: 'aaaa',
+    noPreview: 'Uncaught ReferenceError: aaaa is not defined',
+    preview: [
+      'aaaa\r',
+      'Uncaught ReferenceError: aaaa is not defined',
+    ]
+  }, {
+    input: '/0',
+    noPreview: '/0',
+    preview: [
+      '/0\r',
+      '/0',
+      '^',
+      '',
+      'Uncaught SyntaxError: Invalid regular expression: missing /',
+    ]
+  }, {
+    input: '{})',
+    noPreview: '{})',
+    preview: [
+      '{})\r',
+      '{})',
+      '  ^',
+      '',
+      "Uncaught SyntaxError: Unexpected token ')'",
+    ],
+  }, {
+    input: "{ a: '{' }",
+    noPreview: "{ a: \x1B[32m'{'\x1B[39m }",
+    preview: [
+      "{ a: '{' }\r",
+      "{ a: \x1B[32m'{'\x1B[39m }",
+    ],
+  }, {
+    input: "{'{':0}",
+    noPreview: "{ \x1B[32m'{'\x1B[39m: \x1B[33m0\x1B[39m }",
+    preview: [
+      "{'{':0}",
+      "\x1B[90m{ '{': 0 }\x1B[39m\x1B[15G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r",
+      "{ \x1B[32m'{'\x1B[39m: \x1B[33m0\x1B[39m }",
+    ],
+  }, {
+    input: '{[Symbol.for("{")]: 0 }',
+    noPreview: '{ [\x1B[32mSymbol({)\x1B[39m]: \x1B[33m0\x1B[39m }',
+    preview: [
+      // eslint-disable-next-line max-len
+      '{[Sym\x1B[90mbol\x1B[39m\x1B[13G\x1B[0Kb\x1B[90mol\x1B[39m\x1B[14G\x1B[0Ko\x1B[90ml\x1B[39m\x1B[15G\x1B[0Kl.for("{")]: 0 }\r',
+      '{ [\x1B[32mSymbol({)\x1B[39m]: \x1B[33m0\x1B[39m }',
+    ],
+  }, {
+    input: '{},{}',
+    noPreview: '{}',
+    preview: [
+      '{},{}',
+      '\x1B[90m{}\x1B[39m\x1B[13G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
+      '{}',
+    ],
+  }, {
+    input: '{} //',
+    noPreview: 'repl > ',
+    preview: [
+      '{} //\r',
+    ],
+  }, {
+    input: '{throw 0}',
+    noPreview: 'Uncaught \x1B[33m0\x1B[39m',
+    preview: [
+      '{thr\x1B[90mow\x1B[39m\x1B[12G\x1B[0Ko\x1B[90mw\x1B[39m\x1B[13G\x1B[0Kw 0}',
+      '\x1B[90m0\x1B[39m\x1B[17G\x1B[1A\x1B[1B\x1B[2K\x1B[1A\r',
+      'Uncaught \x1B[33m0\x1B[39m',
+    ],
   }];
 
   const hasPreview = repl.terminal &&
@@ -177,8 +249,13 @@ async function tests(options) {
       assert.deepStrictEqual(lines, preview);
     } else {
       assert.ok(lines[0].includes(noPreview), lines.map(inspect));
-      if (preview.length !== 1 || preview[0] !== `${input}\r`)
-        assert.strictEqual(lines.length, 2);
+      if (preview.length !== 1 || preview[0] !== `${input}\r`) {
+        if (preview[preview.length - 1].includes('Uncaught SyntaxError')) {
+          assert.strictEqual(lines.length, 5);
+        } else {
+          assert.strictEqual(lines.length, 2);
+        }
+      }
     }
   }
 }
diff --git a/test/parallel/test-repl.js b/test/parallel/test-repl.js
index 4981816151f55b..02709b29adddc1 100644
--- a/test/parallel/test-repl.js
+++ b/test/parallel/test-repl.js
@@ -310,6 +310,19 @@ const errorTests = [
     expect: '[Function (anonymous)]'
   },
   // Multiline object
+  {
+    send: '{}),({}',
+    expect: '... ',
+  },
+  {
+    send: '}',
+    expect: [
+      '{}),({}',
+      kArrow,
+      '',
+      /^Uncaught SyntaxError: /,
+    ]
+  },
   {
     send: '{ a: ',
     expect: '... '