diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 438e46eca11b6..f5965b1699758 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -33868,7 +33868,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             // get the original type -- represented as the type constraint of the 'this' type
             containingType = (containingType as TypeParameter).isThisType ? getConstraintOfTypeParameter(containingType as TypeParameter)! : getBaseConstraintOfType(containingType as TypeParameter)!; // TODO: GH#18217 Use a different variable that's allowed to be undefined
         }
-        if (!containingType || !hasBaseType(containingType, enclosingClass)) {
+        if (!containingType || !hasBaseType(containingType, enclosingClass) && !isNodeWithinClass(location, getClassLikeDeclarationOfSymbol(getParentOfSymbol(prop)!)!)) {
             if (errorNode) {
                 error(errorNode, Diagnostics.Property_0_is_protected_and_only_accessible_through_an_instance_of_class_1_This_is_an_instance_of_class_2, symbolToString(prop), typeToString(enclosingClass), typeToString(containingType));
             }
diff --git a/tests/baselines/reference/protectedClassPropertyAccessibleWithinNestedSubclass2.symbols b/tests/baselines/reference/protectedClassPropertyAccessibleWithinNestedSubclass2.symbols
new file mode 100644
index 0000000000000..5b50d1b6ec317
--- /dev/null
+++ b/tests/baselines/reference/protectedClassPropertyAccessibleWithinNestedSubclass2.symbols
@@ -0,0 +1,72 @@
+//// [tests/cases/conformance/classes/members/accessibility/protectedClassPropertyAccessibleWithinNestedSubclass2.ts] ////
+
+=== protectedClassPropertyAccessibleWithinNestedSubclass2.ts ===
+// https://github.com/microsoft/TypeScript/issues/59989
+
+export class Foo {
+>Foo : Symbol(Foo, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 0, 0))
+
+  protected thisIsProtected = 1;
+>thisIsProtected : Symbol(Foo.thisIsProtected, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 2, 18))
+
+  private thisIsPrivate = 1;
+>thisIsPrivate : Symbol(Foo.thisIsPrivate, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 3, 32))
+
+  bar(): Foo {
+>bar : Symbol(Foo.bar, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 4, 28))
+>Foo : Symbol(Foo, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 0, 0))
+
+    const that = this;
+>that : Symbol(that, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 7, 9))
+>this : Symbol(Foo, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 0, 0))
+
+    return new (class extends Foo {
+>Foo : Symbol(Foo, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 0, 0))
+
+      something() {
+>something : Symbol((Anonymous class).something, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 9, 35))
+
+        return that.thisIsPrivate + that.thisIsProtected; // ok
+>that.thisIsPrivate : Symbol(Foo.thisIsPrivate, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 3, 32))
+>that : Symbol(that, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 7, 9))
+>thisIsPrivate : Symbol(Foo.thisIsPrivate, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 3, 32))
+>that.thisIsProtected : Symbol(Foo.thisIsProtected, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 2, 18))
+>that : Symbol(that, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 7, 9))
+>thisIsProtected : Symbol(Foo.thisIsProtected, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 2, 18))
+      }
+    })();
+  }
+}
+
+export class Foo2 {
+>Foo2 : Symbol(Foo2, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 15, 1))
+
+  protected thisIsProtected = 1;
+>thisIsProtected : Symbol(Foo2.thisIsProtected, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 17, 19))
+
+  private thisIsPrivate = 1;
+>thisIsPrivate : Symbol(Foo2.thisIsPrivate, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 18, 32))
+
+  bar() {
+>bar : Symbol(Foo2.bar, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 19, 28))
+
+    const that = this;
+>that : Symbol(that, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 22, 9))
+>this : Symbol(Foo2, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 15, 1))
+
+    return new (class {
+      something() {
+>something : Symbol((Anonymous class).something, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 24, 23))
+
+        return that.thisIsPrivate + that.thisIsProtected; // ok
+>that.thisIsPrivate : Symbol(Foo2.thisIsPrivate, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 18, 32))
+>that : Symbol(that, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 22, 9))
+>thisIsPrivate : Symbol(Foo2.thisIsPrivate, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 18, 32))
+>that.thisIsProtected : Symbol(Foo2.thisIsProtected, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 17, 19))
+>that : Symbol(that, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 22, 9))
+>thisIsProtected : Symbol(Foo2.thisIsProtected, Decl(protectedClassPropertyAccessibleWithinNestedSubclass2.ts, 17, 19))
+      }
+    })();
+  }
+}
+
diff --git a/tests/baselines/reference/protectedClassPropertyAccessibleWithinNestedSubclass2.types b/tests/baselines/reference/protectedClassPropertyAccessibleWithinNestedSubclass2.types
new file mode 100644
index 0000000000000..7e616bdaeaf0d
--- /dev/null
+++ b/tests/baselines/reference/protectedClassPropertyAccessibleWithinNestedSubclass2.types
@@ -0,0 +1,123 @@
+//// [tests/cases/conformance/classes/members/accessibility/protectedClassPropertyAccessibleWithinNestedSubclass2.ts] ////
+
+=== protectedClassPropertyAccessibleWithinNestedSubclass2.ts ===
+// https://github.com/microsoft/TypeScript/issues/59989
+
+export class Foo {
+>Foo : Foo
+>    : ^^^
+
+  protected thisIsProtected = 1;
+>thisIsProtected : number
+>                : ^^^^^^
+>1 : 1
+>  : ^
+
+  private thisIsPrivate = 1;
+>thisIsPrivate : number
+>              : ^^^^^^
+>1 : 1
+>  : ^
+
+  bar(): Foo {
+>bar : () => Foo
+>    : ^^^^^^   
+
+    const that = this;
+>that : this
+>     : ^^^^
+>this : this
+>     : ^^^^
+
+    return new (class extends Foo {
+>new (class extends Foo {      something() {        return that.thisIsPrivate + that.thisIsProtected; // ok      }    })() : (Anonymous class)
+>                                                                                                                          : ^^^^^^^^^^^^^^^^^
+>(class extends Foo {      something() {        return that.thisIsPrivate + that.thisIsProtected; // ok      }    }) : typeof (Anonymous class)
+>                                                                                                                    : ^^^^^^^^^^^^^^^^^^^^^^^^
+>class extends Foo {      something() {        return that.thisIsPrivate + that.thisIsProtected; // ok      }    } : typeof (Anonymous class)
+>                                                                                                                  : ^^^^^^^^^^^^^^^^^^^^^^^^
+>Foo : Foo
+>    : ^^^
+
+      something() {
+>something : () => number
+>          : ^^^^^^^^^^^^
+
+        return that.thisIsPrivate + that.thisIsProtected; // ok
+>that.thisIsPrivate + that.thisIsProtected : number
+>                                          : ^^^^^^
+>that.thisIsPrivate : number
+>                   : ^^^^^^
+>that : this
+>     : ^^^^
+>thisIsPrivate : number
+>              : ^^^^^^
+>that.thisIsProtected : number
+>                     : ^^^^^^
+>that : this
+>     : ^^^^
+>thisIsProtected : number
+>                : ^^^^^^
+      }
+    })();
+  }
+}
+
+export class Foo2 {
+>Foo2 : Foo2
+>     : ^^^^
+
+  protected thisIsProtected = 1;
+>thisIsProtected : number
+>                : ^^^^^^
+>1 : 1
+>  : ^
+
+  private thisIsPrivate = 1;
+>thisIsPrivate : number
+>              : ^^^^^^
+>1 : 1
+>  : ^
+
+  bar() {
+>bar : () => (Anonymous class)
+>    : ^^^^^^^^^^^^^^^^^^^^^^^
+
+    const that = this;
+>that : this
+>     : ^^^^
+>this : this
+>     : ^^^^
+
+    return new (class {
+>new (class {      something() {        return that.thisIsPrivate + that.thisIsProtected; // ok      }    })() : (Anonymous class)
+>                                                                                                              : ^^^^^^^^^^^^^^^^^
+>(class {      something() {        return that.thisIsPrivate + that.thisIsProtected; // ok      }    }) : typeof (Anonymous class)
+>                                                                                                        : ^^^^^^^^^^^^^^^^^^^^^^^^
+>class {      something() {        return that.thisIsPrivate + that.thisIsProtected; // ok      }    } : typeof (Anonymous class)
+>                                                                                                      : ^^^^^^^^^^^^^^^^^^^^^^^^
+
+      something() {
+>something : () => number
+>          : ^^^^^^^^^^^^
+
+        return that.thisIsPrivate + that.thisIsProtected; // ok
+>that.thisIsPrivate + that.thisIsProtected : number
+>                                          : ^^^^^^
+>that.thisIsPrivate : number
+>                   : ^^^^^^
+>that : this
+>     : ^^^^
+>thisIsPrivate : number
+>              : ^^^^^^
+>that.thisIsProtected : number
+>                     : ^^^^^^
+>that : this
+>     : ^^^^
+>thisIsProtected : number
+>                : ^^^^^^
+      }
+    })();
+  }
+}
+
diff --git a/tests/cases/conformance/classes/members/accessibility/protectedClassPropertyAccessibleWithinNestedSubclass2.ts b/tests/cases/conformance/classes/members/accessibility/protectedClassPropertyAccessibleWithinNestedSubclass2.ts
new file mode 100644
index 0000000000000..cc3eb8798b563
--- /dev/null
+++ b/tests/cases/conformance/classes/members/accessibility/protectedClassPropertyAccessibleWithinNestedSubclass2.ts
@@ -0,0 +1,34 @@
+// @strict: true
+// @noEmit: true
+
+// https://github.com/microsoft/TypeScript/issues/59989
+
+export class Foo {
+  protected thisIsProtected = 1;
+  private thisIsPrivate = 1;
+
+  bar(): Foo {
+    const that = this;
+
+    return new (class extends Foo {
+      something() {
+        return that.thisIsPrivate + that.thisIsProtected; // ok
+      }
+    })();
+  }
+}
+
+export class Foo2 {
+  protected thisIsProtected = 1;
+  private thisIsPrivate = 1;
+
+  bar() {
+    const that = this;
+
+    return new (class {
+      something() {
+        return that.thisIsPrivate + that.thisIsProtected; // ok
+      }
+    })();
+  }
+}