diff --git a/packages/babel-helper-member-expression-to-functions/src/index.js b/packages/babel-helper-member-expression-to-functions/src/index.js
index 1d8114a94d85..7724406d2b46 100644
--- a/packages/babel-helper-member-expression-to-functions/src/index.js
+++ b/packages/babel-helper-member-expression-to-functions/src/index.js
@@ -167,9 +167,8 @@ const handle = {
       const parentIsOptionalCall = parentPath.isOptionalCallExpression({
         callee: node,
       });
-      const isParenthesizedMemberCall =
-        parentPath.isCallExpression({ callee: node }) &&
-        node.extra?.parenthesized;
+      // if parentIsCall is true, it implies that node.extra.parenthesized is always true
+      const parentIsCall = parentPath.isCallExpression({ callee: node });
       startingOptional.replaceWith(toNonOptional(startingOptional, baseRef));
       if (parentIsOptionalCall) {
         if (parent.optional) {
@@ -177,7 +176,7 @@ const handle = {
         } else {
           parentPath.replaceWith(this.call(member, parent.arguments));
         }
-      } else if (isParenthesizedMemberCall) {
+      } else if (parentIsCall) {
         // `(a?.#b)()` to `(a == null ? void 0 : a.#b.bind(a))()`
         member.replaceWith(this.boundGet(member));
       } else {
diff --git a/packages/babel-plugin-proposal-class-properties/test/fixtures/private-loose/parenthesized-optional-member-call-with-transform/output.js b/packages/babel-plugin-proposal-class-properties/test/fixtures/private-loose/parenthesized-optional-member-call-with-transform/output.js
index b67e17103b8f..7b39559261e3 100644
--- a/packages/babel-plugin-proposal-class-properties/test/fixtures/private-loose/parenthesized-optional-member-call-with-transform/output.js
+++ b/packages/babel-plugin-proposal-class-properties/test/fixtures/private-loose/parenthesized-optional-member-call-with-transform/output.js
@@ -8,7 +8,7 @@ class Foo {
   }
 
   test() {
-    var _o$Foo$self$getSelf, _o$Foo$self$getSelf2, _fn$Foo$self$getSelf, _fn$Foo$self$getSelf2, _o$Foo, _o$Foo$self, _fn, _fn$Foo, _fn$Foo$self, _fn$Foo$self2;
+    var _o$Foo$self$getSelf, _o$Foo$self$getSelf2, _fn$Foo$self$getSelf, _fn$Foo$self$getSelf2, _o$Foo, _o$Foo$self, _fn, _fn$Foo, _fn$Foo$self;
 
     const o = {
       Foo: Foo
@@ -26,8 +26,8 @@ class Foo {
     (o === null || o === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(o.Foo, _m)[_m].bind(o.Foo))().toString();
     ((_o$Foo$self$getSelf = ((_o$Foo = o.Foo) == null ? void 0 : _o$Foo.self.getSelf.bind(_o$Foo.self))()) === null || _o$Foo$self$getSelf === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(_o$Foo$self$getSelf, _m)[_m].bind(_o$Foo$self$getSelf))();
     ((_o$Foo$self$getSelf2 = ((_o$Foo$self = o.Foo.self) == null ? void 0 : _o$Foo$self.getSelf.bind(_o$Foo$self))()) === null || _o$Foo$self$getSelf2 === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(_o$Foo$self$getSelf2, _m)[_m].bind(_o$Foo$self$getSelf2))();
-    ((_fn$Foo$self$getSelf = ((_fn = fn()) == null ? void 0 : (_fn$Foo = _fn.Foo) == null ? void 0 : _fn$Foo.self.getSelf.bind(_fn.Foo.self))()) === null || _fn$Foo$self$getSelf === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(_fn$Foo$self$getSelf, _m)[_m].bind(_fn$Foo$self$getSelf))();
-    ((_fn$Foo$self$getSelf2 = (fn == null ? void 0 : (_fn$Foo$self2 = _fn$Foo$self = fn().Foo.self) == null ? void 0 : _fn$Foo$self2.getSelf.bind(_fn$Foo$self))()) === null || _fn$Foo$self$getSelf2 === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(_fn$Foo$self$getSelf2, _m)[_m].bind(_fn$Foo$self$getSelf2))();
+    ((_fn$Foo$self$getSelf = ((_fn = fn()) == null ? void 0 : (_fn$Foo = _fn.Foo) == null ? void 0 : _fn$Foo.self.getSelf.bind(_fn$Foo.self))()) === null || _fn$Foo$self$getSelf === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(_fn$Foo$self$getSelf, _m)[_m].bind(_fn$Foo$self$getSelf))();
+    ((_fn$Foo$self$getSelf2 = (fn == null ? void 0 : (_fn$Foo$self = fn().Foo.self) == null ? void 0 : _fn$Foo$self.getSelf.bind(_fn$Foo$self))()) === null || _fn$Foo$self$getSelf2 === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(_fn$Foo$self$getSelf2, _m)[_m].bind(_fn$Foo$self$getSelf2))();
   }
 
 }
diff --git a/packages/babel-plugin-proposal-class-properties/test/fixtures/private/parenthesized-optional-member-call-with-transform/output.js b/packages/babel-plugin-proposal-class-properties/test/fixtures/private/parenthesized-optional-member-call-with-transform/output.js
index 7f51bfebb3cb..962b865ed654 100644
--- a/packages/babel-plugin-proposal-class-properties/test/fixtures/private/parenthesized-optional-member-call-with-transform/output.js
+++ b/packages/babel-plugin-proposal-class-properties/test/fixtures/private/parenthesized-optional-member-call-with-transform/output.js
@@ -4,7 +4,7 @@ class Foo {
   }
 
   test() {
-    var _o$Foo, _o$Foo2, _o$Foo3, _o$Foo$self$getSelf, _o$Foo$self$getSelf2, _fn$Foo$self$getSelf, _fn$Foo$self$getSelf2, _o$Foo4, _o$Foo4$self, _o$Foo$self, _fn, _fn$Foo$self, _fn$Foo, _fn$Foo$self2, _fn$Foo$self3;
+    var _o$Foo, _o$Foo2, _o$Foo3, _o$Foo$self$getSelf, _o$Foo$self$getSelf2, _fn$Foo$self$getSelf, _fn$Foo$self$getSelf2, _o$Foo4, _o$Foo4$self, _o$Foo$self, _fn, _fn$Foo, _fn$Foo$self, _fn$Foo$self2;
 
     const o = {
       Foo: Foo
@@ -23,7 +23,7 @@ class Foo {
     ((_o$Foo$self$getSelf = ((_o$Foo4 = o.Foo) === null || _o$Foo4 === void 0 ? void 0 : (_o$Foo4$self = _o$Foo4.self).getSelf.bind(_o$Foo4$self))()) === null || _o$Foo$self$getSelf === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(_o$Foo$self$getSelf, Foo, _m).bind(_o$Foo$self$getSelf))();
     ((_o$Foo$self$getSelf2 = ((_o$Foo$self = o.Foo.self) === null || _o$Foo$self === void 0 ? void 0 : _o$Foo$self.getSelf.bind(_o$Foo$self))()) === null || _o$Foo$self$getSelf2 === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(_o$Foo$self$getSelf2, Foo, _m).bind(_o$Foo$self$getSelf2))();
     ((_fn$Foo$self$getSelf = ((_fn = fn()) === null || _fn === void 0 ? void 0 : (_fn$Foo = _fn.Foo) === null || _fn$Foo === void 0 ? void 0 : (_fn$Foo$self = _fn$Foo.self).getSelf.bind(_fn$Foo$self))()) === null || _fn$Foo$self$getSelf === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(_fn$Foo$self$getSelf, Foo, _m).bind(_fn$Foo$self$getSelf))();
-    ((_fn$Foo$self$getSelf2 = (fn === null || fn === void 0 ? void 0 : (_fn$Foo$self3 = _fn$Foo$self2 = fn().Foo.self) === null || _fn$Foo$self3 === void 0 ? void 0 : _fn$Foo$self3.getSelf.bind(_fn$Foo$self2))()) === null || _fn$Foo$self$getSelf2 === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(_fn$Foo$self$getSelf2, Foo, _m).bind(_fn$Foo$self$getSelf2))();
+    ((_fn$Foo$self$getSelf2 = (fn === null || fn === void 0 ? void 0 : (_fn$Foo$self2 = fn().Foo.self) === null || _fn$Foo$self2 === void 0 ? void 0 : _fn$Foo$self2.getSelf.bind(_fn$Foo$self2))()) === null || _fn$Foo$self$getSelf2 === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(_fn$Foo$self$getSelf2, Foo, _m).bind(_fn$Foo$self$getSelf2))();
   }
 
 }
diff --git a/packages/babel-plugin-proposal-optional-chaining/src/index.js b/packages/babel-plugin-proposal-optional-chaining/src/index.js
index c7346891244a..a1f03bf94c95 100644
--- a/packages/babel-plugin-proposal-optional-chaining/src/index.js
+++ b/packages/babel-plugin-proposal-optional-chaining/src/index.js
@@ -24,8 +24,20 @@ export default declare((api, options) => {
     visitor: {
       "OptionalCallExpression|OptionalMemberExpression"(path) {
         const { scope } = path;
-        const parentPath = path.findParent(p => !p.isParenthesizedExpression());
+        // maybeParenthesized points to the outermost parenthesizedExpression
+        // or the path itself
+        let maybeParenthesized = path;
+        const parentPath = path.findParent(p => {
+          if (!p.isParenthesizedExpression()) return true;
+          maybeParenthesized = p;
+        });
         let isDeleteOperation = false;
+        const parentIsCall =
+          parentPath.isCallExpression({ callee: maybeParenthesized.node }) &&
+          // note that the first condition must implies that `path.optional` is `true`,
+          // otherwise the parentPath should be an OptionalCallExpressioin
+          path.isOptionalMemberExpression();
+
         const optionals = [];
 
         let optionalPath = path;
@@ -116,14 +128,10 @@ export default declare((api, options) => {
           }
           let replacement = replacementPath.node;
           // Ensure (a?.b)() has proper `this`
-          if (
-            t.isMemberExpression(replacement) &&
-            (replacement.extra?.parenthesized ||
-              // if replacementPath.parentPath does not equal parentPath,
-              // it must be unwrapped from parenthesized expression.
-              replacementPath.parentPath !== parentPath) &&
-            parentPath.isCallExpression()
-          ) {
+          // The `parentIsCall` is constant within loop, we should check i === 0
+          // to ensure that it is only applied to the first optional chain element
+          // i.e. `?.b` in `(a?.b.c)()`
+          if (i === 0 && parentIsCall) {
             // `(a?.b)()` to `(a == null ? undefined : a.b.bind(a))()`
             const { object } = replacement;
             let baseRef;
diff --git a/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/containers/input.js b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/containers/input.js
index d699b16fa16f..bd8e7b16d459 100644
--- a/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/containers/input.js
+++ b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/containers/input.js
@@ -2,5 +2,6 @@ var street = user.address?.street
 street = user.address?.street
 
 test(a?.b,  1);
+test((a?.b), 1);
 
 (1, a?.b, 2);
diff --git a/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/containers/output.js b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/containers/output.js
index d2a39179ca94..7d4419088c62 100644
--- a/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/containers/output.js
+++ b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/containers/output.js
@@ -1,6 +1,7 @@
-var _user$address, _user$address2, _a, _a2;
+var _user$address, _user$address2, _a, _a2, _a3;
 
 var street = (_user$address = user.address) === null || _user$address === void 0 ? void 0 : _user$address.street;
 street = (_user$address2 = user.address) === null || _user$address2 === void 0 ? void 0 : _user$address2.street;
 test((_a = a) === null || _a === void 0 ? void 0 : _a.b, 1);
-1, (_a2 = a) === null || _a2 === void 0 ? void 0 : _a2.b, 2;
+test((_a2 = a) === null || _a2 === void 0 ? void 0 : _a2.b, 1);
+1, (_a3 = a) === null || _a3 === void 0 ? void 0 : _a3.b, 2;
diff --git a/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-expression-containers/input.js b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-expression-containers/input.js
new file mode 100644
index 000000000000..bd8e7b16d459
--- /dev/null
+++ b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-expression-containers/input.js
@@ -0,0 +1,7 @@
+var street = user.address?.street
+street = user.address?.street
+
+test(a?.b,  1);
+test((a?.b), 1);
+
+(1, a?.b, 2);
diff --git a/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-expression-containers/options.json b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-expression-containers/options.json
new file mode 100644
index 000000000000..eae39736acf4
--- /dev/null
+++ b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-expression-containers/options.json
@@ -0,0 +1,6 @@
+{
+  "plugins": ["proposal-optional-chaining"],
+  "parserOpts": {
+    "createParenthesizedExpressions": true
+  }
+}
diff --git a/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-expression-containers/output.js b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-expression-containers/output.js
new file mode 100644
index 000000000000..72b42c86c35f
--- /dev/null
+++ b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-expression-containers/output.js
@@ -0,0 +1,7 @@
+var _user$address, _user$address2, _a, _a2, _a3;
+
+var street = (_user$address = user.address) === null || _user$address === void 0 ? void 0 : _user$address.street;
+street = (_user$address2 = user.address) === null || _user$address2 === void 0 ? void 0 : _user$address2.street;
+test((_a = a) === null || _a === void 0 ? void 0 : _a.b, 1);
+test(((_a2 = a) === null || _a2 === void 0 ? void 0 : _a2.b), 1);
+((1, (_a3 = a) === null || _a3 === void 0 ? void 0 : _a3.b, 2));
diff --git a/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-member-call-loose/output.js b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-member-call-loose/output.js
index 80c198711db7..20db389f8f92 100644
--- a/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-member-call-loose/output.js
+++ b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-member-call-loose/output.js
@@ -13,7 +13,7 @@ class Foo {
   }
 
   test() {
-    var _o$Foo$self$getSelf, _o$Foo, _o$Foo$self$getSelf2, _o$Foo$self, _fn$Foo$self$getSelf, _fn, _fn$Foo, _fn$Foo$self$getSelf2, _fn$Foo$self, _fn$Foo$self2;
+    var _o$Foo$self$getSelf, _o$Foo, _o$Foo$self$getSelf2, _o$Foo$self, _fn$Foo$self$getSelf, _fn, _fn$Foo, _fn$Foo$self$getSelf2, _fn$Foo$self;
 
     const Foo = this;
     const o = {
@@ -32,8 +32,8 @@ class Foo {
     (o == null ? void 0 : o.Foo.m.bind(o.Foo))().toString();
     ((_o$Foo$self$getSelf = ((_o$Foo = o.Foo) == null ? void 0 : _o$Foo.self.getSelf.bind(_o$Foo.self))()) == null ? void 0 : _o$Foo$self$getSelf.m.bind(_o$Foo$self$getSelf))();
     ((_o$Foo$self$getSelf2 = ((_o$Foo$self = o.Foo.self) == null ? void 0 : _o$Foo$self.getSelf.bind(_o$Foo$self))()) == null ? void 0 : _o$Foo$self$getSelf2.m.bind(_o$Foo$self$getSelf2))();
-    ((_fn$Foo$self$getSelf = ((_fn = fn()) == null ? void 0 : (_fn$Foo = _fn.Foo) == null ? void 0 : _fn$Foo.self.getSelf.bind(_fn.Foo.self))()) == null ? void 0 : _fn$Foo$self$getSelf.m.bind(_fn$Foo$self$getSelf))();
-    ((_fn$Foo$self$getSelf2 = (fn == null ? void 0 : (_fn$Foo$self2 = _fn$Foo$self = fn().Foo.self) == null ? void 0 : _fn$Foo$self2.getSelf.bind(_fn$Foo$self))()) == null ? void 0 : _fn$Foo$self$getSelf2.m.bind(_fn$Foo$self$getSelf2))();
+    ((_fn$Foo$self$getSelf = ((_fn = fn()) == null ? void 0 : (_fn$Foo = _fn.Foo) == null ? void 0 : _fn$Foo.self.getSelf.bind(_fn$Foo.self))()) == null ? void 0 : _fn$Foo$self$getSelf.m.bind(_fn$Foo$self$getSelf))();
+    ((_fn$Foo$self$getSelf2 = (fn == null ? void 0 : (_fn$Foo$self = fn().Foo.self) == null ? void 0 : _fn$Foo$self.getSelf.bind(_fn$Foo$self))()) == null ? void 0 : _fn$Foo$self$getSelf2.m.bind(_fn$Foo$self$getSelf2))();
   }
 
 }
diff --git a/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-member-call/output.js b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-member-call/output.js
index a41ae311d626..fb1fc9fbbbb4 100644
--- a/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-member-call/output.js
+++ b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/parenthesized-member-call/output.js
@@ -13,7 +13,7 @@ class Foo {
   }
 
   test() {
-    var _o$Foo, _o$Foo2, _o$Foo3, _o$Foo$self$getSelf, _o$Foo4, _o$Foo4$self, _o$Foo$self$getSelf2, _o$Foo$self, _fn$Foo$self$getSelf, _fn, _fn$Foo$self, _fn$Foo, _fn$Foo$self$getSelf2, _fn$Foo$self2, _fn$Foo$self3;
+    var _o$Foo, _o$Foo2, _o$Foo3, _o$Foo$self$getSelf, _o$Foo4, _o$Foo4$self, _o$Foo$self$getSelf2, _o$Foo$self, _fn$Foo$self$getSelf, _fn, _fn$Foo, _fn$Foo$self, _fn$Foo$self$getSelf2, _fn$Foo$self2;
 
     const Foo = this;
     const o = {
@@ -33,7 +33,7 @@ class Foo {
     ((_o$Foo$self$getSelf = ((_o$Foo4 = o.Foo) === null || _o$Foo4 === void 0 ? void 0 : (_o$Foo4$self = _o$Foo4.self).getSelf.bind(_o$Foo4$self))()) === null || _o$Foo$self$getSelf === void 0 ? void 0 : _o$Foo$self$getSelf.m.bind(_o$Foo$self$getSelf))();
     ((_o$Foo$self$getSelf2 = ((_o$Foo$self = o.Foo.self) === null || _o$Foo$self === void 0 ? void 0 : _o$Foo$self.getSelf.bind(_o$Foo$self))()) === null || _o$Foo$self$getSelf2 === void 0 ? void 0 : _o$Foo$self$getSelf2.m.bind(_o$Foo$self$getSelf2))();
     ((_fn$Foo$self$getSelf = ((_fn = fn()) === null || _fn === void 0 ? void 0 : (_fn$Foo = _fn.Foo) === null || _fn$Foo === void 0 ? void 0 : (_fn$Foo$self = _fn$Foo.self).getSelf.bind(_fn$Foo$self))()) === null || _fn$Foo$self$getSelf === void 0 ? void 0 : _fn$Foo$self$getSelf.m.bind(_fn$Foo$self$getSelf))();
-    ((_fn$Foo$self$getSelf2 = (fn === null || fn === void 0 ? void 0 : (_fn$Foo$self3 = _fn$Foo$self2 = fn().Foo.self) === null || _fn$Foo$self3 === void 0 ? void 0 : _fn$Foo$self3.getSelf.bind(_fn$Foo$self2))()) === null || _fn$Foo$self$getSelf2 === void 0 ? void 0 : _fn$Foo$self$getSelf2.m.bind(_fn$Foo$self$getSelf2))();
+    ((_fn$Foo$self$getSelf2 = (fn === null || fn === void 0 ? void 0 : (_fn$Foo$self2 = fn().Foo.self) === null || _fn$Foo$self2 === void 0 ? void 0 : _fn$Foo$self2.getSelf.bind(_fn$Foo$self2))()) === null || _fn$Foo$self$getSelf2 === void 0 ? void 0 : _fn$Foo$self$getSelf2.m.bind(_fn$Foo$self$getSelf2))();
   }
 
 }