diff --git a/lib/repl.js b/lib/repl.js
index d598de3f51926f..6f8f9d42107a52 100644
--- a/lib/repl.js
+++ b/lib/repl.js
@@ -1225,8 +1225,6 @@ REPLServer.prototype.setPrompt = function setPrompt(prompt) {
 const importRE = /\bimport\s*\(\s*['"`](([\w@./:-]+\/)?(?:[\w@./:-]*))(?![^'"`])$/;
 const requireRE = /\brequire\s*\(\s*['"`](([\w@./:-]+\/)?(?:[\w@./:-]*))(?![^'"`])$/;
 const fsAutoCompleteRE = /fs(?:\.promises)?\.\s*[a-z][a-zA-Z]+\(\s*["'](.*)/;
-const simpleExpressionRE =
-    /(?:[\w$'"`[{(](?:(\w| |\t)*?['"`]|\$|['"`\]})])*\??(?:\.|])?)*?(?:[a-zA-Z_$])?(?:\w|\$)*\??\.?$/;
 const versionedFileNamesRe = /-\d+\.\d+/;
 
 function isIdentifier(str) {
@@ -1480,29 +1478,20 @@ function complete(line, callback) {
   } else if ((match = RegExpPrototypeExec(fsAutoCompleteRE, line)) !== null &&
              this.allowBlockingCompletions) {
     ({ 0: completionGroups, 1: completeOn } = completeFSFunctions(match));
-  // Handle variable member lookup.
-  // We support simple chained expressions like the following (no function
-  // calls, etc.). That is for simplicity and also because we *eval* that
-  // leading expression so for safety (see WARNING above) don't want to
-  // eval function calls.
-  //
-  //   foo.bar<|>     # completions for 'foo' with filter 'bar'
-  //   spam.eggs.<|>  # completions for 'spam.eggs' with filter ''
-  //   foo<|>         # all scope vars with filter 'foo'
-  //   foo.<|>        # completions for 'foo' with filter ''
   } else if (line.length === 0 ||
              RegExpPrototypeExec(/\w|\.|\$/, line[line.length - 1]) !== null) {
-    const { 0: match } = RegExpPrototypeExec(simpleExpressionRE, line) || [''];
-    if (line.length !== 0 && !match) {
+    const completeTarget = line.length === 0 ? line : findExpressionCompleteTarget(line);
+
+    if (line.length !== 0 && !completeTarget) {
       completionGroupsLoaded();
       return;
     }
     let expr = '';
-    completeOn = match;
+    completeOn = completeTarget;
     if (StringPrototypeEndsWith(line, '.')) {
-      expr = StringPrototypeSlice(match, 0, -1);
+      expr = StringPrototypeSlice(completeTarget, 0, -1);
     } else if (line.length !== 0) {
-      const bits = StringPrototypeSplit(match, '.');
+      const bits = StringPrototypeSplit(completeTarget, '.');
       filter = ArrayPrototypePop(bits);
       expr = ArrayPrototypeJoin(bits, '.');
     }
@@ -1531,7 +1520,7 @@ function complete(line, callback) {
     }
 
     return includesProxiesOrGetters(
-      StringPrototypeSplit(match, '.'),
+      StringPrototypeSplit(completeTarget, '.'),
       this.eval,
       this.context,
       (includes) => {
@@ -1642,6 +1631,100 @@ function complete(line, callback) {
   }
 }
 
+/**
+ * This function tries to extract a target for tab completion from code representing an expression.
+ *
+ * Such target is basically the last piece of the expression that can be evaluated for the potential
+ * tab completion.
+ *
+ * Some examples:
+ * - The complete target for `const a = obj.b` is `obj.b`
+ *   (because tab completion will evaluate and check the `obj.b` object)
+ * - The complete target for `tru` is `tru`
+ *   (since we'd ideally want to complete that to `true`)
+ * - The complete target for `{ a: tru` is `tru`
+ *   (like the last example, we'd ideally want that to complete to true)
+ * - There is no complete target for `{ a: true }`
+ *   (there is nothing to complete)
+ * @param {string} code the code representing the expression to analyze
+ * @returns {string|null} a substring of the code representing the complete target is there was one, `null` otherwise
+ */
+function findExpressionCompleteTarget(code) {
+  if (!code) {
+    return null;
+  }
+
+  if (code.at(-1) === '.') {
+    if (code.at(-2) === '?') {
+      // The code ends with the optional chaining operator (`?.`),
+      // such code can't generate a valid AST so we need to strip
+      // the suffix, run this function's logic and add back the
+      // optional chaining operator to the result if present
+      const result = findExpressionCompleteTarget(code.slice(0, -2));
+      return !result ? result : `${result}?.`;
+    }
+
+    // The code ends with a dot, such code can't generate a valid AST
+    // so we need to strip the suffix, run this function's logic and
+    // add back the dot to the result if present
+    const result = findExpressionCompleteTarget(code.slice(0, -1));
+    return !result ? result : `${result}.`;
+  }
+
+  let ast;
+  try {
+    ast = acornParse(code, { __proto__: null, sourceType: 'module', ecmaVersion: 'latest' });
+  } catch {
+    const keywords = code.split(' ');
+
+    if (keywords.length > 1) {
+      // Something went wrong with the parsing, however this can be due to incomplete code
+      // (that is for example missing a closing bracket, as for example `{ a: obj.te`), in
+      // this case we take the last code keyword and try again
+      // TODO(dario-piotrowicz): make this more robust, right now we only split by spaces
+      //                         but that's not always enough, for example it doesn't handle
+      //                         this code: `{ a: obj['hello world'].te`
+      return findExpressionCompleteTarget(keywords.at(-1));
+    }
+
+    // The ast parsing has legitimately failed so we return null
+    return null;
+  }
+
+  const lastBodyStatement = ast.body[ast.body.length - 1];
+
+  if (!lastBodyStatement) {
+    return null;
+  }
+
+  // If the last statement is a block we know there is not going to be a potential
+  // completion target (e.g. in `{ a: true }` there is no completion to be done)
+  if (lastBodyStatement.type === 'BlockStatement') {
+    return null;
+  }
+
+  // If the last statement is an expression and it has a right side, that's what we
+  // want to potentially complete on, so let's re-run the function's logic on that
+  if (lastBodyStatement.type === 'ExpressionStatement' && lastBodyStatement.expression.right) {
+    const exprRight = lastBodyStatement.expression.right;
+    const exprRightCode = code.slice(exprRight.start, exprRight.end);
+    return findExpressionCompleteTarget(exprRightCode);
+  }
+
+  // If the last statement is a variable declaration statement the last declaration is
+  // what we can potentially complete on, so let's re-run the function's logic on that
+  if (lastBodyStatement.type === 'VariableDeclaration') {
+    const lastDeclarationInit = lastBodyStatement.declarations.at(-1).init;
+    const lastDeclarationInitCode = code.slice(lastDeclarationInit.start, lastDeclarationInit.end);
+    return findExpressionCompleteTarget(lastDeclarationInitCode);
+  }
+
+  // If any of the above early returns haven't activated then it means that
+  // the potential complete target is the full code (e.g. the code represents
+  // a simple partial identifier, a member expression, etc...)
+  return code;
+}
+
 function includesProxiesOrGetters(exprSegments, evalFn, context, callback, currentExpr = '', idx = 0) {
   const currentSegment = exprSegments[idx];
   currentExpr += `${currentExpr.length === 0 ? '' : '.'}${currentSegment}`;
diff --git a/test/parallel/test-repl-tab-complete-computed-props.js b/test/parallel/test-repl-tab-complete-computed-props.js
index 753d01fdab017a..aee348b91223b2 100644
--- a/test/parallel/test-repl-tab-complete-computed-props.js
+++ b/test/parallel/test-repl-tab-complete-computed-props.js
@@ -109,6 +109,11 @@ describe('REPL tab object completion on computed properties', () => {
             [oneStr]: 1,
             ['Hello World']: 'hello world!',
           };
+
+          const lookupObj = {
+            stringLookup: helloWorldStr,
+            ['number lookup']: oneStr,
+          };
         `,
       ]);
     });
@@ -126,5 +131,29 @@ describe('REPL tab object completion on computed properties', () => {
       input: 'obj[helloWorldStr].tolocaleup',
       expectedCompletions: ['obj[helloWorldStr].toLocaleUpperCase'],
     }));
+
+    it('works with a simple inlined computed property', () => testCompletion(replServer, {
+      input: 'obj["Hello " + "World"].tolocaleup',
+      expectedCompletions: ['obj["Hello " + "World"].toLocaleUpperCase'],
+    }));
+
+    it('works with a ternary inlined computed property', () => testCompletion(replServer, {
+      input: 'obj[(1 + 2 > 5) ? oneStr : "Hello " + "World"].toLocaleUpperCase',
+      expectedCompletions: ['obj[(1 + 2 > 5) ? oneStr : "Hello " + "World"].toLocaleUpperCase'],
+    }));
+
+    it('works with an inlined computed property with a nested property lookup', () =>
+      testCompletion(replServer, {
+        input: 'obj[lookupObj.stringLookup].tolocaleupp',
+        expectedCompletions: ['obj[lookupObj.stringLookup].toLocaleUpperCase'],
+      })
+    );
+
+    it('works with an inlined computed property with a nested inlined computer property lookup', () =>
+      testCompletion(replServer, {
+        input: 'obj[lookupObj["number" + " lookup"]].toFi',
+        expectedCompletions: ['obj[lookupObj["number" + " lookup"]].toFixed'],
+      })
+    );
   });
 });