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 0e5ef5ecb8e1..e14c0abe50ba 100644
--- a/packages/babel-helper-member-expression-to-functions/src/index.js
+++ b/packages/babel-helper-member-expression-to-functions/src/index.js
@@ -29,6 +29,38 @@ class AssignmentMemoiser {
   }
 }
 
+/**
+ * Test if a NodePath will be cast to boolean when evaluated.
+ *
+ * @example
+ * // returns true
+ * const nodePathAQDotB = NodePath("if (a?.#b) {}").get("test"); // a?.#b
+ * willPathCastToBoolean(nodePathAQDotB)
+ * @example
+ * // returns false
+ * willPathCastToBoolean(NodePath("a?.#b"))
+ * @todo Respect transparent expression wrappers
+ * @see {@link packages/babel-plugin-proposal-optional-chaining/src/index.js}
+ * @param {NodePath} path
+ * @returns {boolean}
+ */
+
+function willPathCastToBoolean(path: NodePath): boolean {
+  const maybeWrapped = path;
+  const { node, parentPath } = maybeWrapped;
+  if (parentPath.isLogicalExpression()) {
+    const { operator } = parentPath.node;
+    if (operator === "&&" || operator === "||") {
+      return willPathCastToBoolean(parentPath);
+    }
+  }
+  return (
+    parentPath.isConditional({ test: node }) ||
+    parentPath.isUnaryExpression({ operator: "!" }) ||
+    parentPath.isLoop({ test: node })
+  );
+}
+
 function toNonOptional(path, base) {
   const { node } = path;
   if (path.isOptionalMemberExpression()) {
@@ -129,6 +161,8 @@ const handle = {
         return;
       }
 
+      const willEndPathCastToBoolean = willPathCastToBoolean(endPath);
+
       const rootParentPath = endPath.parentPath;
       if (
         rootParentPath.isUpdateExpression({ argument: node }) ||
@@ -238,33 +272,60 @@ const handle = {
         regular = endParentPath.node;
       }
 
-      replacementPath.replaceWith(
-        t.conditionalExpression(
-          t.logicalExpression(
-            "||",
-            t.binaryExpression(
-              "===",
-              baseNeedsMemoised
-                ? t.assignmentExpression(
-                    "=",
-                    t.cloneNode(baseRef),
-                    t.cloneNode(startingNode),
-                  )
-                : t.cloneNode(baseRef),
-              t.nullLiteral(),
-            ),
-            t.binaryExpression(
-              "===",
-              t.cloneNode(baseRef),
-              scope.buildUndefinedNode(),
-            ),
+      if (willEndPathCastToBoolean) {
+        const nonNullishCheck = t.logicalExpression(
+          "&&",
+          t.binaryExpression(
+            "!==",
+            baseNeedsMemoised
+              ? t.assignmentExpression(
+                  "=",
+                  t.cloneNode(baseRef),
+                  t.cloneNode(startingNode),
+                )
+              : t.cloneNode(baseRef),
+            t.nullLiteral(),
           ),
-          isDeleteOperation
-            ? t.booleanLiteral(true)
-            : scope.buildUndefinedNode(),
-          regular,
-        ),
-      );
+          t.binaryExpression(
+            "!==",
+            t.cloneNode(baseRef),
+            scope.buildUndefinedNode(),
+          ),
+        );
+        replacementPath.replaceWith(
+          t.logicalExpression("&&", nonNullishCheck, regular),
+        );
+      } else {
+        // todo: respect assumptions.noDocumentAll when assumptions are implemented
+        const nullishCheck = t.logicalExpression(
+          "||",
+          t.binaryExpression(
+            "===",
+            baseNeedsMemoised
+              ? t.assignmentExpression(
+                  "=",
+                  t.cloneNode(baseRef),
+                  t.cloneNode(startingNode),
+                )
+              : t.cloneNode(baseRef),
+            t.nullLiteral(),
+          ),
+          t.binaryExpression(
+            "===",
+            t.cloneNode(baseRef),
+            scope.buildUndefinedNode(),
+          ),
+        );
+        replacementPath.replaceWith(
+          t.conditionalExpression(
+            nullishCheck,
+            isDeleteOperation
+              ? t.booleanLiteral(true)
+              : scope.buildUndefinedNode(),
+            regular,
+          ),
+        );
+      }
 
       // context and isDeleteOperation can not be both truthy
       if (context) {
diff --git a/packages/babel-plugin-proposal-class-properties/test/fixtures/private-loose/optional-chain-cast-to-boolean/exec.js b/packages/babel-plugin-proposal-class-properties/test/fixtures/private-loose/optional-chain-cast-to-boolean/exec.js
new file mode 100644
index 000000000000..1c53f4066b61
--- /dev/null
+++ b/packages/babel-plugin-proposal-class-properties/test/fixtures/private-loose/optional-chain-cast-to-boolean/exec.js
@@ -0,0 +1,108 @@
+class C {
+  static #a = {
+    b: {
+      c: {
+        d: 2,
+      },
+    },
+  };
+  static testIf(o) {
+    if (o?.#a.b.c.d) {
+      return true;
+    }
+    return false;
+  }
+  static testConditional(o) {
+    return o?.#a.b?.c.d ? true : false;
+  }
+  static testLoop(o) {
+    while (o?.#a.b.c.d) {
+      for (; o?.#a.b.c?.d; ) {
+        let i = 0;
+        do {
+          i++;
+          if (i === 2) {
+            return true;
+          }
+        } while (o?.#a.b?.c.d);
+      }
+    }
+    return false;
+  }
+  static testNegate(o) {
+    return !!o?.#a.b?.c.d;
+  }
+  static testIfDeep(o) {
+    if (o.obj?.#a.b?.c.d) {
+      return true;
+    }
+    return false;
+  }
+  static testConditionalDeep(o) {
+    return o.obj?.#a.b?.c.d ? true : false;
+  }
+  static testLoopDeep(o) {
+    while (o.obj?.#a.b.c.d) {
+      for (; o.obj?.#a.b.c?.d; ) {
+        let i = 0;
+        do {
+          i++;
+          if (i === 2) {
+            return true;
+          }
+        } while (o.obj?.#a.b?.c.d);
+      }
+    }
+    return false;
+  }
+  static testNegateDeep(o) {
+    return !!o.obj?.#a.b?.c.d;
+  }
+
+  static testLogicalInIf(o) {
+    if (o?.#a.b?.c.d && o?.#a?.b.c.d) {
+      return true;
+    }
+    return false;
+  }
+
+  static testLogicalInReturn(o) {
+    return o?.#a.b?.c.d && o?.#a?.b.c.d;
+  }
+
+  static test() {
+    const c = C;
+    expect(C.testIf(c)).toBe(true);
+    expect(C.testConditional(c)).toBe(true);
+    expect(C.testLoop(c)).toBe(true);
+    expect(C.testNegate(c)).toBe(true);
+
+    expect(C.testIfDeep({ obj: c })).toBe(true);
+    expect(C.testConditionalDeep({ obj: c })).toBe(true);
+    expect(C.testLoopDeep({ obj: c })).toBe(true);
+    expect(C.testNegateDeep({ obj: c })).toBe(true);
+
+    expect(C.testLogicalInIf(c)).toBe(true);
+    expect(C.testLogicalInReturn(c)).toBe(2);
+  }
+
+  static testNullish() {
+    for (const n of [null, undefined]) {
+      expect(C.testIf(n)).toBe(false);
+      expect(C.testConditional(n)).toBe(false);
+      expect(C.testLoop(n)).toBe(false);
+      expect(C.testNegate(n)).toBe(false);
+
+      expect(C.testIfDeep({ obj: n })).toBe(false);
+      expect(C.testConditionalDeep({ obj: n })).toBe(false);
+      expect(C.testLoopDeep({ obj: n })).toBe(false);
+      expect(C.testNegateDeep({ obj: n })).toBe(false);
+
+      expect(C.testLogicalInIf(n)).toBe(false);
+      expect(C.testLogicalInReturn(n)).toBe(undefined);
+    }
+  }
+}
+
+C.test();
+C.testNullish();
diff --git a/packages/babel-plugin-proposal-class-properties/test/fixtures/private-loose/optional-chain-cast-to-boolean/input.js b/packages/babel-plugin-proposal-class-properties/test/fixtures/private-loose/optional-chain-cast-to-boolean/input.js
new file mode 100644
index 000000000000..b58d13bee0ac
--- /dev/null
+++ b/packages/babel-plugin-proposal-class-properties/test/fixtures/private-loose/optional-chain-cast-to-boolean/input.js
@@ -0,0 +1,75 @@
+class C {
+  static #a = {
+    b: {
+      c: {
+        d: 2,
+      },
+    },
+  };
+  static testIf(o) {
+    if (o?.#a.b.c.d) {
+      return true;
+    }
+    return false;
+  }
+  static testConditional(o) {
+    return o?.#a.b?.c.d ? true : false;
+  }
+  static testLoop(o) {
+    while (o?.#a.b.c.d) {
+      for (; o?.#a.b.c?.d; ) {
+        let i = 0;
+        do {
+          i++;
+          if (i === 2) {
+            return true;
+          }
+        } while (o?.#a.b?.c.d);
+      }
+    }
+    return false;
+  }
+  static testNegate(o) {
+    return !!o?.#a.b?.c.d;
+  }
+  static testIfDeep(o) {
+    if (o.obj?.#a.b?.c.d) {
+      return true;
+    }
+    return false;
+  }
+  static testConditionalDeep(o) {
+    return o.obj?.#a.b?.c.d ? true : false;
+  }
+  static testLoopDeep(o) {
+    while (o.obj?.#a.b.c.d) {
+      for (; o.obj?.#a.b.c?.d; ) {
+        let i = 0;
+        do {
+          i++;
+          if (i === 2) {
+            return true;
+          }
+        } while (o.obj?.#a.b?.c.d);
+      }
+    }
+    return false;
+  }
+  static testNegateDeep(o) {
+    return !!o.obj?.#a.b?.c.d;
+  }
+
+  static testLogicalInIf(o) {
+    if (o?.#a.b?.c.d && o?.#a?.b.c.d) {
+      return true;
+    }
+    return false;
+  }
+
+  static testLogicalInReturn(o) {
+    return o?.#a.b?.c.d && o?.#a?.b.c.d;
+  }
+}
+
+C.test();
+C.testNullish();
diff --git a/packages/babel-plugin-proposal-class-properties/test/fixtures/private-loose/optional-chain-cast-to-boolean/output.js b/packages/babel-plugin-proposal-class-properties/test/fixtures/private-loose/optional-chain-cast-to-boolean/output.js
new file mode 100644
index 000000000000..95ef49e9d891
--- /dev/null
+++ b/packages/babel-plugin-proposal-class-properties/test/fixtures/private-loose/optional-chain-cast-to-boolean/output.js
@@ -0,0 +1,127 @@
+var _a = babelHelpers.classPrivateFieldLooseKey("a");
+
+var C = /*#__PURE__*/function () {
+  "use strict";
+
+  function C() {
+    babelHelpers.classCallCheck(this, C);
+  }
+
+  babelHelpers.createClass(C, null, [{
+    key: "testIf",
+    value: function testIf(o) {
+      if (o !== null && o !== void 0 && babelHelpers.classPrivateFieldLooseBase(o, _a)[_a].b.c.d) {
+        return true;
+      }
+
+      return false;
+    }
+  }, {
+    key: "testConditional",
+    value: function testConditional(o) {
+      return (o === null || o === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(o, _a)[_a].b)?.c.d ? true : false;
+    }
+  }, {
+    key: "testLoop",
+    value: function testLoop(o) {
+      while (o !== null && o !== void 0 && babelHelpers.classPrivateFieldLooseBase(o, _a)[_a].b.c.d) {
+        for (; (o === null || o === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(o, _a)[_a].b.c)?.d;) {
+          var i = 0;
+
+          do {
+            i++;
+
+            if (i === 2) {
+              return true;
+            }
+          } while ((o === null || o === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(o, _a)[_a].b)?.c.d);
+        }
+      }
+
+      return false;
+    }
+  }, {
+    key: "testNegate",
+    value: function testNegate(o) {
+      return !!(o === null || o === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(o, _a)[_a].b)?.c.d;
+    }
+  }, {
+    key: "testIfDeep",
+    value: function testIfDeep(o) {
+      var _o$obj;
+
+      if (((_o$obj = o.obj) === null || _o$obj === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(_o$obj, _a)[_a].b)?.c.d) {
+        return true;
+      }
+
+      return false;
+    }
+  }, {
+    key: "testConditionalDeep",
+    value: function testConditionalDeep(o) {
+      var _o$obj2;
+
+      return ((_o$obj2 = o.obj) === null || _o$obj2 === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(_o$obj2, _a)[_a].b)?.c.d ? true : false;
+    }
+  }, {
+    key: "testLoopDeep",
+    value: function testLoopDeep(o) {
+      while ((_o$obj3 = o.obj) !== null && _o$obj3 !== void 0 && babelHelpers.classPrivateFieldLooseBase(_o$obj3, _a)[_a].b.c.d) {
+        var _o$obj3;
+
+        for (; ((_o$obj4 = o.obj) === null || _o$obj4 === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(_o$obj4, _a)[_a].b.c)?.d;) {
+          var _o$obj4;
+
+          var i = 0;
+
+          do {
+            var _o$obj5;
+
+            i++;
+
+            if (i === 2) {
+              return true;
+            }
+          } while (((_o$obj5 = o.obj) === null || _o$obj5 === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(_o$obj5, _a)[_a].b)?.c.d);
+        }
+      }
+
+      return false;
+    }
+  }, {
+    key: "testNegateDeep",
+    value: function testNegateDeep(o) {
+      var _o$obj6;
+
+      return !!((_o$obj6 = o.obj) === null || _o$obj6 === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(_o$obj6, _a)[_a].b)?.c.d;
+    }
+  }, {
+    key: "testLogicalInIf",
+    value: function testLogicalInIf(o) {
+      if ((o === null || o === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(o, _a)[_a].b)?.c.d && (o === null || o === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(o, _a)[_a])?.b.c.d) {
+        return true;
+      }
+
+      return false;
+    }
+  }, {
+    key: "testLogicalInReturn",
+    value: function testLogicalInReturn(o) {
+      return (o === null || o === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(o, _a)[_a].b)?.c.d && (o === null || o === void 0 ? void 0 : babelHelpers.classPrivateFieldLooseBase(o, _a)[_a])?.b.c.d;
+    }
+  }]);
+  return C;
+}();
+
+Object.defineProperty(C, _a, {
+  writable: true,
+  value: {
+    b: {
+      c: {
+        d: 2
+      }
+    }
+  }
+});
+C.test();
+C.testNullish();
diff --git a/packages/babel-plugin-proposal-class-properties/test/fixtures/private/optional-chain-cast-to-boolean/exec.js b/packages/babel-plugin-proposal-class-properties/test/fixtures/private/optional-chain-cast-to-boolean/exec.js
new file mode 100644
index 000000000000..1c53f4066b61
--- /dev/null
+++ b/packages/babel-plugin-proposal-class-properties/test/fixtures/private/optional-chain-cast-to-boolean/exec.js
@@ -0,0 +1,108 @@
+class C {
+  static #a = {
+    b: {
+      c: {
+        d: 2,
+      },
+    },
+  };
+  static testIf(o) {
+    if (o?.#a.b.c.d) {
+      return true;
+    }
+    return false;
+  }
+  static testConditional(o) {
+    return o?.#a.b?.c.d ? true : false;
+  }
+  static testLoop(o) {
+    while (o?.#a.b.c.d) {
+      for (; o?.#a.b.c?.d; ) {
+        let i = 0;
+        do {
+          i++;
+          if (i === 2) {
+            return true;
+          }
+        } while (o?.#a.b?.c.d);
+      }
+    }
+    return false;
+  }
+  static testNegate(o) {
+    return !!o?.#a.b?.c.d;
+  }
+  static testIfDeep(o) {
+    if (o.obj?.#a.b?.c.d) {
+      return true;
+    }
+    return false;
+  }
+  static testConditionalDeep(o) {
+    return o.obj?.#a.b?.c.d ? true : false;
+  }
+  static testLoopDeep(o) {
+    while (o.obj?.#a.b.c.d) {
+      for (; o.obj?.#a.b.c?.d; ) {
+        let i = 0;
+        do {
+          i++;
+          if (i === 2) {
+            return true;
+          }
+        } while (o.obj?.#a.b?.c.d);
+      }
+    }
+    return false;
+  }
+  static testNegateDeep(o) {
+    return !!o.obj?.#a.b?.c.d;
+  }
+
+  static testLogicalInIf(o) {
+    if (o?.#a.b?.c.d && o?.#a?.b.c.d) {
+      return true;
+    }
+    return false;
+  }
+
+  static testLogicalInReturn(o) {
+    return o?.#a.b?.c.d && o?.#a?.b.c.d;
+  }
+
+  static test() {
+    const c = C;
+    expect(C.testIf(c)).toBe(true);
+    expect(C.testConditional(c)).toBe(true);
+    expect(C.testLoop(c)).toBe(true);
+    expect(C.testNegate(c)).toBe(true);
+
+    expect(C.testIfDeep({ obj: c })).toBe(true);
+    expect(C.testConditionalDeep({ obj: c })).toBe(true);
+    expect(C.testLoopDeep({ obj: c })).toBe(true);
+    expect(C.testNegateDeep({ obj: c })).toBe(true);
+
+    expect(C.testLogicalInIf(c)).toBe(true);
+    expect(C.testLogicalInReturn(c)).toBe(2);
+  }
+
+  static testNullish() {
+    for (const n of [null, undefined]) {
+      expect(C.testIf(n)).toBe(false);
+      expect(C.testConditional(n)).toBe(false);
+      expect(C.testLoop(n)).toBe(false);
+      expect(C.testNegate(n)).toBe(false);
+
+      expect(C.testIfDeep({ obj: n })).toBe(false);
+      expect(C.testConditionalDeep({ obj: n })).toBe(false);
+      expect(C.testLoopDeep({ obj: n })).toBe(false);
+      expect(C.testNegateDeep({ obj: n })).toBe(false);
+
+      expect(C.testLogicalInIf(n)).toBe(false);
+      expect(C.testLogicalInReturn(n)).toBe(undefined);
+    }
+  }
+}
+
+C.test();
+C.testNullish();
diff --git a/packages/babel-plugin-proposal-class-properties/test/fixtures/private/optional-chain-cast-to-boolean/input.js b/packages/babel-plugin-proposal-class-properties/test/fixtures/private/optional-chain-cast-to-boolean/input.js
new file mode 100644
index 000000000000..b58d13bee0ac
--- /dev/null
+++ b/packages/babel-plugin-proposal-class-properties/test/fixtures/private/optional-chain-cast-to-boolean/input.js
@@ -0,0 +1,75 @@
+class C {
+  static #a = {
+    b: {
+      c: {
+        d: 2,
+      },
+    },
+  };
+  static testIf(o) {
+    if (o?.#a.b.c.d) {
+      return true;
+    }
+    return false;
+  }
+  static testConditional(o) {
+    return o?.#a.b?.c.d ? true : false;
+  }
+  static testLoop(o) {
+    while (o?.#a.b.c.d) {
+      for (; o?.#a.b.c?.d; ) {
+        let i = 0;
+        do {
+          i++;
+          if (i === 2) {
+            return true;
+          }
+        } while (o?.#a.b?.c.d);
+      }
+    }
+    return false;
+  }
+  static testNegate(o) {
+    return !!o?.#a.b?.c.d;
+  }
+  static testIfDeep(o) {
+    if (o.obj?.#a.b?.c.d) {
+      return true;
+    }
+    return false;
+  }
+  static testConditionalDeep(o) {
+    return o.obj?.#a.b?.c.d ? true : false;
+  }
+  static testLoopDeep(o) {
+    while (o.obj?.#a.b.c.d) {
+      for (; o.obj?.#a.b.c?.d; ) {
+        let i = 0;
+        do {
+          i++;
+          if (i === 2) {
+            return true;
+          }
+        } while (o.obj?.#a.b?.c.d);
+      }
+    }
+    return false;
+  }
+  static testNegateDeep(o) {
+    return !!o.obj?.#a.b?.c.d;
+  }
+
+  static testLogicalInIf(o) {
+    if (o?.#a.b?.c.d && o?.#a?.b.c.d) {
+      return true;
+    }
+    return false;
+  }
+
+  static testLogicalInReturn(o) {
+    return o?.#a.b?.c.d && o?.#a?.b.c.d;
+  }
+}
+
+C.test();
+C.testNullish();
diff --git a/packages/babel-plugin-proposal-class-properties/test/fixtures/private/optional-chain-cast-to-boolean/output.js b/packages/babel-plugin-proposal-class-properties/test/fixtures/private/optional-chain-cast-to-boolean/output.js
new file mode 100644
index 000000000000..c2204496280b
--- /dev/null
+++ b/packages/babel-plugin-proposal-class-properties/test/fixtures/private/optional-chain-cast-to-boolean/output.js
@@ -0,0 +1,125 @@
+var C = /*#__PURE__*/function () {
+  "use strict";
+
+  function C() {
+    babelHelpers.classCallCheck(this, C);
+  }
+
+  babelHelpers.createClass(C, null, [{
+    key: "testIf",
+    value: function testIf(o) {
+      if (o !== null && o !== void 0 && babelHelpers.classStaticPrivateFieldSpecGet(o, C, _a).b.c.d) {
+        return true;
+      }
+
+      return false;
+    }
+  }, {
+    key: "testConditional",
+    value: function testConditional(o) {
+      return (o === null || o === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(o, C, _a).b)?.c.d ? true : false;
+    }
+  }, {
+    key: "testLoop",
+    value: function testLoop(o) {
+      while (o !== null && o !== void 0 && babelHelpers.classStaticPrivateFieldSpecGet(o, C, _a).b.c.d) {
+        for (; (o === null || o === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(o, C, _a).b.c)?.d;) {
+          var i = 0;
+
+          do {
+            i++;
+
+            if (i === 2) {
+              return true;
+            }
+          } while ((o === null || o === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(o, C, _a).b)?.c.d);
+        }
+      }
+
+      return false;
+    }
+  }, {
+    key: "testNegate",
+    value: function testNegate(o) {
+      return !!(o === null || o === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(o, C, _a).b)?.c.d;
+    }
+  }, {
+    key: "testIfDeep",
+    value: function testIfDeep(o) {
+      var _o$obj;
+
+      if (((_o$obj = o.obj) === null || _o$obj === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(_o$obj, C, _a).b)?.c.d) {
+        return true;
+      }
+
+      return false;
+    }
+  }, {
+    key: "testConditionalDeep",
+    value: function testConditionalDeep(o) {
+      var _o$obj2;
+
+      return ((_o$obj2 = o.obj) === null || _o$obj2 === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(_o$obj2, C, _a).b)?.c.d ? true : false;
+    }
+  }, {
+    key: "testLoopDeep",
+    value: function testLoopDeep(o) {
+      while ((_o$obj3 = o.obj) !== null && _o$obj3 !== void 0 && babelHelpers.classStaticPrivateFieldSpecGet(_o$obj3, C, _a).b.c.d) {
+        var _o$obj3;
+
+        for (; ((_o$obj4 = o.obj) === null || _o$obj4 === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(_o$obj4, C, _a).b.c)?.d;) {
+          var _o$obj4;
+
+          var i = 0;
+
+          do {
+            var _o$obj5;
+
+            i++;
+
+            if (i === 2) {
+              return true;
+            }
+          } while (((_o$obj5 = o.obj) === null || _o$obj5 === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(_o$obj5, C, _a).b)?.c.d);
+        }
+      }
+
+      return false;
+    }
+  }, {
+    key: "testNegateDeep",
+    value: function testNegateDeep(o) {
+      var _o$obj6;
+
+      return !!((_o$obj6 = o.obj) === null || _o$obj6 === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(_o$obj6, C, _a).b)?.c.d;
+    }
+  }, {
+    key: "testLogicalInIf",
+    value: function testLogicalInIf(o) {
+      if ((o === null || o === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(o, C, _a).b)?.c.d && (o === null || o === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(o, C, _a))?.b.c.d) {
+        return true;
+      }
+
+      return false;
+    }
+  }, {
+    key: "testLogicalInReturn",
+    value: function testLogicalInReturn(o) {
+      return (o === null || o === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(o, C, _a).b)?.c.d && (o === null || o === void 0 ? void 0 : babelHelpers.classStaticPrivateFieldSpecGet(o, C, _a))?.b.c.d;
+    }
+  }]);
+  return C;
+}();
+
+var _a = {
+  writable: true,
+  value: {
+    b: {
+      c: {
+        d: 2
+      }
+    }
+  }
+};
+C.test();
+C.testNullish();
diff --git a/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/cast-to-boolean/exec.js b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/cast-to-boolean/exec.js
new file mode 100644
index 000000000000..c7e855e79489
--- /dev/null
+++ b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/cast-to-boolean/exec.js
@@ -0,0 +1,109 @@
+class C {
+  static testIf(o) {
+    if (o?.a.b.c.d) {
+      return true;
+    }
+    return false;
+  }
+  static testConditional(o) {
+    return o?.a.b?.c.d ? true : false;
+  }
+  static testLoop(o) {
+    while (o?.a.b.c.d) {
+      for (; o?.a.b.c?.d; ) {
+        let i = 0;
+        do {
+          i++;
+          if (i === 2) {
+            return true;
+          }
+        } while (o?.a.b?.c.d);
+      }
+    }
+    return false;
+  }
+  static testNegate(o) {
+    return !!o?.a.b?.c.d;
+  }
+  static testIfDeep(o) {
+    if (o.obj?.a.b?.c.d) {
+      return true;
+    }
+    return false;
+  }
+  static testConditionalDeep(o) {
+    return o.obj?.a.b?.c.d ? true : false;
+  }
+  static testLoopDeep(o) {
+    while (o.obj?.a.b.c.d) {
+      for (; o.obj?.a.b.c?.d; ) {
+        let i = 0;
+        do {
+          i++;
+          if (i === 2) {
+            return true;
+          }
+        } while (o.obj?.a.b?.c.d);
+      }
+    }
+    return false;
+  }
+  static testNegateDeep(o) {
+    return !!o.obj?.a.b?.c.d;
+  }
+
+  static testLogicalInIf(o) {
+    if (o?.a.b?.c.d && o?.a?.b.c.d) {
+      return true;
+    }
+    return false;
+  }
+
+  static testLogicalInReturn(o) {
+    return o?.a.b?.c.d && o?.a?.b.c.d;
+  }
+
+  static test() {
+    const c = {
+      a: {
+        b: {
+          c: {
+            d: 2,
+          },
+        },
+      },
+    };
+    expect(C.testIf(c)).toBe(true);
+    expect(C.testConditional(c)).toBe(true);
+    expect(C.testLoop(c)).toBe(true);
+    expect(C.testNegate(c)).toBe(true);
+
+    expect(C.testIfDeep({ obj: c })).toBe(true);
+    expect(C.testConditionalDeep({ obj: c })).toBe(true);
+    expect(C.testLoopDeep({ obj: c })).toBe(true);
+    expect(C.testNegateDeep({ obj: c })).toBe(true);
+
+    expect(C.testLogicalInIf(c)).toBe(true);
+    expect(C.testLogicalInReturn(c)).toBe(2);
+  }
+
+  static testNullish() {
+    for (const n of [null, undefined]) {
+      expect(C.testIf(n)).toBe(false);
+      expect(C.testConditional(n)).toBe(false);
+      expect(C.testLoop(n)).toBe(false);
+      expect(C.testNegate(n)).toBe(false);
+
+      expect(C.testIfDeep({ obj: n })).toBe(false);
+      expect(C.testConditionalDeep({ obj: n })).toBe(false);
+      expect(C.testLoopDeep({ obj: n })).toBe(false);
+      expect(C.testNegateDeep({ obj: n })).toBe(false);
+
+      expect(C.testLogicalInIf(n)).toBe(false);
+      expect(C.testLogicalInReturn(n)).toBe(undefined);
+    }
+  }
+}
+
+C.test();
+C.testNullish();
diff --git a/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/cast-to-boolean/input.js b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/cast-to-boolean/input.js
new file mode 100644
index 000000000000..aa3b561b3c55
--- /dev/null
+++ b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/cast-to-boolean/input.js
@@ -0,0 +1,68 @@
+class C {
+  static testIf(o) {
+    if (o?.a.b.c.d) {
+      return true;
+    }
+    return false;
+  }
+  static testConditional(o) {
+    return o?.a.b?.c.d ? true : false;
+  }
+  static testLoop(o) {
+    while (o?.a.b.c.d) {
+      for (; o?.a.b.c?.d; ) {
+        let i = 0;
+        do {
+          i++;
+          if (i === 2) {
+            return true;
+          }
+        } while (o?.a.b?.c.d);
+      }
+    }
+    return false;
+  }
+  static testNegate(o) {
+    return !!o?.a.b?.c.d;
+  }
+  static testIfDeep(o) {
+    if (o.obj?.a.b?.c.d) {
+      return true;
+    }
+    return false;
+  }
+  static testConditionalDeep(o) {
+    return o.obj?.a.b?.c.d ? true : false;
+  }
+  static testLoopDeep(o) {
+    while (o.obj?.a.b.c.d) {
+      for (; o.obj?.a.b.c?.d; ) {
+        let i = 0;
+        do {
+          i++;
+          if (i === 2) {
+            return true;
+          }
+        } while (o.obj?.a.b?.c.d);
+      }
+    }
+    return false;
+  }
+  static testNegateDeep(o) {
+    return !!o.obj?.a.b?.c.d;
+  }
+
+  static testLogicalInIf(o) {
+    if (o?.a.b?.c.d && o?.a?.b.c.d) {
+      return true;
+    }
+    return false;
+  }
+
+  static testLogicalInReturn(o) {
+    return o?.a.b?.c.d && o?.a?.b.c.d;
+  }
+}
+
+C.test();
+C.testNullish();
diff --git a/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/cast-to-boolean/output.js b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/cast-to-boolean/output.js
new file mode 100644
index 000000000000..75c7c73fd950
--- /dev/null
+++ b/packages/babel-plugin-proposal-optional-chaining/test/fixtures/general/cast-to-boolean/output.js
@@ -0,0 +1,109 @@
+class C {
+  static testIf(o) {
+    if (o !== null && o !== void 0 && o.a.b.c.d) {
+      return true;
+    }
+
+    return false;
+  }
+
+  static testConditional(o) {
+    var _o$a$b;
+
+    return o !== null && o !== void 0 && (_o$a$b = o.a.b) !== null && _o$a$b !== void 0 && _o$a$b.c.d ? true : false;
+  }
+
+  static testLoop(o) {
+    while (o !== null && o !== void 0 && o.a.b.c.d) {
+      for (; o !== null && o !== void 0 && (_o$a$b$c = o.a.b.c) !== null && _o$a$b$c !== void 0 && _o$a$b$c.d;) {
+        var _o$a$b$c;
+
+        let i = 0;
+
+        do {
+          var _o$a$b2;
+
+          i++;
+
+          if (i === 2) {
+            return true;
+          }
+        } while (o !== null && o !== void 0 && (_o$a$b2 = o.a.b) !== null && _o$a$b2 !== void 0 && _o$a$b2.c.d);
+      }
+    }
+
+    return false;
+  }
+
+  static testNegate(o) {
+    var _o$a$b3;
+
+    return !!(o !== null && o !== void 0 && (_o$a$b3 = o.a.b) !== null && _o$a$b3 !== void 0 && _o$a$b3.c.d);
+  }
+
+  static testIfDeep(o) {
+    var _o$obj, _o$obj$a$b;
+
+    if ((_o$obj = o.obj) !== null && _o$obj !== void 0 && (_o$obj$a$b = _o$obj.a.b) !== null && _o$obj$a$b !== void 0 && _o$obj$a$b.c.d) {
+      return true;
+    }
+
+    return false;
+  }
+
+  static testConditionalDeep(o) {
+    var _o$obj2, _o$obj2$a$b;
+
+    return (_o$obj2 = o.obj) !== null && _o$obj2 !== void 0 && (_o$obj2$a$b = _o$obj2.a.b) !== null && _o$obj2$a$b !== void 0 && _o$obj2$a$b.c.d ? true : false;
+  }
+
+  static testLoopDeep(o) {
+    while ((_o$obj3 = o.obj) !== null && _o$obj3 !== void 0 && _o$obj3.a.b.c.d) {
+      var _o$obj3;
+
+      for (; (_o$obj4 = o.obj) !== null && _o$obj4 !== void 0 && (_o$obj4$a$b$c = _o$obj4.a.b.c) !== null && _o$obj4$a$b$c !== void 0 && _o$obj4$a$b$c.d;) {
+        var _o$obj4, _o$obj4$a$b$c;
+
+        let i = 0;
+
+        do {
+          var _o$obj5, _o$obj5$a$b;
+
+          i++;
+
+          if (i === 2) {
+            return true;
+          }
+        } while ((_o$obj5 = o.obj) !== null && _o$obj5 !== void 0 && (_o$obj5$a$b = _o$obj5.a.b) !== null && _o$obj5$a$b !== void 0 && _o$obj5$a$b.c.d);
+      }
+    }
+
+    return false;
+  }
+
+  static testNegateDeep(o) {
+    var _o$obj6, _o$obj6$a$b;
+
+    return !!((_o$obj6 = o.obj) !== null && _o$obj6 !== void 0 && (_o$obj6$a$b = _o$obj6.a.b) !== null && _o$obj6$a$b !== void 0 && _o$obj6$a$b.c.d);
+  }
+
+  static testLogicalInIf(o) {
+    var _o$a$b4, _o$a;
+
+    if (o !== null && o !== void 0 && (_o$a$b4 = o.a.b) !== null && _o$a$b4 !== void 0 && _o$a$b4.c.d && o !== null && o !== void 0 && (_o$a = o.a) !== null && _o$a !== void 0 && _o$a.b.c.d) {
+      return true;
+    }
+
+    return false;
+  }
+
+  static testLogicalInReturn(o) {
+    var _o$a$b5, _o$a2;
+
+    return (o === null || o === void 0 ? void 0 : (_o$a$b5 = o.a.b) === null || _o$a$b5 === void 0 ? void 0 : _o$a$b5.c.d) && (o === null || o === void 0 ? void 0 : (_o$a2 = o.a) === null || _o$a2 === void 0 ? void 0 : _o$a2.b.c.d);
+  }
+
+}
+
+C.test();
+C.testNullish();