diff --git a/tests/baselines/reference/typeVariableTypeGuards.js b/tests/baselines/reference/typeVariableTypeGuards.js
new file mode 100644
index 00000000000..c1337561b32
--- /dev/null
+++ b/tests/baselines/reference/typeVariableTypeGuards.js
@@ -0,0 +1,147 @@
+//// [typeVariableTypeGuards.ts]
+// Repro from #14091
+
+interface Foo {
+    foo(): void
+}
+
+class A<P extends Partial<Foo>> {
+    props: Readonly<P>
+    doSomething() {
+        this.props.foo && this.props.foo()
+    }
+}
+
+// Repro from #14415
+
+interface Banana {
+    color: 'yellow';
+}
+
+class Monkey<T extends Banana | undefined> {
+    a: T;
+    render() {
+        if (this.a) {
+            this.a.color;
+        }
+    }
+}
+
+interface BigBanana extends Banana {
+}
+
+class BigMonkey extends Monkey<BigBanana> {
+    render() {
+        if (this.a) {
+            this.a.color;
+        }
+    }
+}
+
+// Another repro
+
+type Item = {
+    (): string;
+    x: string;
+}
+
+function f1<T extends Item | undefined>(obj: T) {
+    if (obj) {
+        obj.x;
+        obj["x"];
+        obj();
+    }
+}
+
+function f2<T extends Item | undefined>(obj: T | undefined) {
+    if (obj) {
+        obj.x;
+        obj["x"];
+        obj();
+    }
+}
+
+function f3<T extends Item | undefined>(obj: T | null) {
+    if (obj) {
+        obj.x;
+        obj["x"];
+        obj();
+    }
+}
+
+function f4<T extends string[] | undefined>(obj: T | undefined, x: number) {
+    if (obj) {
+        obj[x].length;
+    }
+}
+
+
+//// [typeVariableTypeGuards.js]
+"use strict";
+// Repro from #14091
+var __extends = (this && this.__extends) || (function () {
+    var extendStatics = Object.setPrototypeOf ||
+        ({ __proto__: [] } instanceof Array && function (d, b) { d.__proto__ = b; }) ||
+        function (d, b) { for (var p in b) if (b.hasOwnProperty(p)) d[p] = b[p]; };
+    return function (d, b) {
+        extendStatics(d, b);
+        function __() { this.constructor = d; }
+        d.prototype = b === null ? Object.create(b) : (__.prototype = b.prototype, new __());
+    };
+})();
+var A = (function () {
+    function A() {
+    }
+    A.prototype.doSomething = function () {
+        this.props.foo && this.props.foo();
+    };
+    return A;
+}());
+var Monkey = (function () {
+    function Monkey() {
+    }
+    Monkey.prototype.render = function () {
+        if (this.a) {
+            this.a.color;
+        }
+    };
+    return Monkey;
+}());
+var BigMonkey = (function (_super) {
+    __extends(BigMonkey, _super);
+    function BigMonkey() {
+        return _super !== null && _super.apply(this, arguments) || this;
+    }
+    BigMonkey.prototype.render = function () {
+        if (this.a) {
+            this.a.color;
+        }
+    };
+    return BigMonkey;
+}(Monkey));
+function f1(obj) {
+    if (obj) {
+        obj.x;
+        obj["x"];
+        obj();
+    }
+}
+function f2(obj) {
+    if (obj) {
+        obj.x;
+        obj["x"];
+        obj();
+    }
+}
+function f3(obj) {
+    if (obj) {
+        obj.x;
+        obj["x"];
+        obj();
+    }
+}
+function f4(obj, x) {
+    if (obj) {
+        obj[x].length;
+    }
+}
diff --git a/tests/baselines/reference/typeVariableTypeGuards.symbols b/tests/baselines/reference/typeVariableTypeGuards.symbols
new file mode 100644
index 00000000000..e0c21e12adb
--- /dev/null
+++ b/tests/baselines/reference/typeVariableTypeGuards.symbols
@@ -0,0 +1,202 @@
+=== tests/cases/compiler/typeVariableTypeGuards.ts ===
+// Repro from #14091
+
+interface Foo {
+>Foo : Symbol(Foo, Decl(typeVariableTypeGuards.ts, 0, 0))
+
+    foo(): void
+>foo : Symbol(Foo.foo, Decl(typeVariableTypeGuards.ts, 2, 15))
+}
+
+class A<P extends Partial<Foo>> {
+>A : Symbol(A, Decl(typeVariableTypeGuards.ts, 4, 1))
+>P : Symbol(P, Decl(typeVariableTypeGuards.ts, 6, 8))
+>Partial : Symbol(Partial, Decl(lib.d.ts, --, --))
+>Foo : Symbol(Foo, Decl(typeVariableTypeGuards.ts, 0, 0))
+
+    props: Readonly<P>
+>props : Symbol(A.props, Decl(typeVariableTypeGuards.ts, 6, 33))
+>Readonly : Symbol(Readonly, Decl(lib.d.ts, --, --))
+>P : Symbol(P, Decl(typeVariableTypeGuards.ts, 6, 8))
+
+    doSomething() {
+>doSomething : Symbol(A.doSomething, Decl(typeVariableTypeGuards.ts, 7, 22))
+
+        this.props.foo && this.props.foo()
+>this.props.foo : Symbol(foo)
+>this.props : Symbol(A.props, Decl(typeVariableTypeGuards.ts, 6, 33))
+>this : Symbol(A, Decl(typeVariableTypeGuards.ts, 4, 1))
+>props : Symbol(A.props, Decl(typeVariableTypeGuards.ts, 6, 33))
+>foo : Symbol(foo)
+>this.props.foo : Symbol(foo)
+>this.props : Symbol(A.props, Decl(typeVariableTypeGuards.ts, 6, 33))
+>this : Symbol(A, Decl(typeVariableTypeGuards.ts, 4, 1))
+>props : Symbol(A.props, Decl(typeVariableTypeGuards.ts, 6, 33))
+>foo : Symbol(foo)
+    }
+}
+
+// Repro from #14415
+
+interface Banana {
+>Banana : Symbol(Banana, Decl(typeVariableTypeGuards.ts, 11, 1))
+
+    color: 'yellow';
+>color : Symbol(Banana.color, Decl(typeVariableTypeGuards.ts, 15, 18))
+}
+
+class Monkey<T extends Banana | undefined> {
+>Monkey : Symbol(Monkey, Decl(typeVariableTypeGuards.ts, 17, 1))
+>T : Symbol(T, Decl(typeVariableTypeGuards.ts, 19, 13))
+>Banana : Symbol(Banana, Decl(typeVariableTypeGuards.ts, 11, 1))
+
+    a: T;
+>a : Symbol(Monkey.a, Decl(typeVariableTypeGuards.ts, 19, 44))
+>T : Symbol(T, Decl(typeVariableTypeGuards.ts, 19, 13))
+
+    render() {
+>render : Symbol(Monkey.render, Decl(typeVariableTypeGuards.ts, 20, 9))
+
+        if (this.a) {
+>this.a : Symbol(Monkey.a, Decl(typeVariableTypeGuards.ts, 19, 44))
+>this : Symbol(Monkey, Decl(typeVariableTypeGuards.ts, 17, 1))
+>a : Symbol(Monkey.a, Decl(typeVariableTypeGuards.ts, 19, 44))
+
+            this.a.color;
+>this.a.color : Symbol(Banana.color, Decl(typeVariableTypeGuards.ts, 15, 18))
+>this.a : Symbol(Monkey.a, Decl(typeVariableTypeGuards.ts, 19, 44))
+>this : Symbol(Monkey, Decl(typeVariableTypeGuards.ts, 17, 1))
+>a : Symbol(Monkey.a, Decl(typeVariableTypeGuards.ts, 19, 44))
+>color : Symbol(Banana.color, Decl(typeVariableTypeGuards.ts, 15, 18))
+        }
+    }
+}
+
+interface BigBanana extends Banana {
+>BigBanana : Symbol(BigBanana, Decl(typeVariableTypeGuards.ts, 26, 1))
+>Banana : Symbol(Banana, Decl(typeVariableTypeGuards.ts, 11, 1))
+}
+
+class BigMonkey extends Monkey<BigBanana> {
+>BigMonkey : Symbol(BigMonkey, Decl(typeVariableTypeGuards.ts, 29, 1))
+>Monkey : Symbol(Monkey, Decl(typeVariableTypeGuards.ts, 17, 1))
+>BigBanana : Symbol(BigBanana, Decl(typeVariableTypeGuards.ts, 26, 1))
+
+    render() {
+>render : Symbol(BigMonkey.render, Decl(typeVariableTypeGuards.ts, 31, 43))
+
+        if (this.a) {
+>this.a : Symbol(Monkey.a, Decl(typeVariableTypeGuards.ts, 19, 44))
+>this : Symbol(BigMonkey, Decl(typeVariableTypeGuards.ts, 29, 1))
+>a : Symbol(Monkey.a, Decl(typeVariableTypeGuards.ts, 19, 44))
+
+            this.a.color;
+>this.a.color : Symbol(Banana.color, Decl(typeVariableTypeGuards.ts, 15, 18))
+>this.a : Symbol(Monkey.a, Decl(typeVariableTypeGuards.ts, 19, 44))
+>this : Symbol(BigMonkey, Decl(typeVariableTypeGuards.ts, 29, 1))
+>a : Symbol(Monkey.a, Decl(typeVariableTypeGuards.ts, 19, 44))
+>color : Symbol(Banana.color, Decl(typeVariableTypeGuards.ts, 15, 18))
+        }
+    }
+}
+
+// Another repro
+
+type Item = {
+>Item : Symbol(Item, Decl(typeVariableTypeGuards.ts, 37, 1))
+
+    (): string;
+    x: string;
+>x : Symbol(x, Decl(typeVariableTypeGuards.ts, 42, 15))
+}
+
+function f1<T extends Item | undefined>(obj: T) {
+>f1 : Symbol(f1, Decl(typeVariableTypeGuards.ts, 44, 1))
+>T : Symbol(T, Decl(typeVariableTypeGuards.ts, 46, 12))
+>Item : Symbol(Item, Decl(typeVariableTypeGuards.ts, 37, 1))
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 46, 40))
+>T : Symbol(T, Decl(typeVariableTypeGuards.ts, 46, 12))
+
+    if (obj) {
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 46, 40))
+
+        obj.x;
+>obj.x : Symbol(x, Decl(typeVariableTypeGuards.ts, 42, 15))
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 46, 40))
+>x : Symbol(x, Decl(typeVariableTypeGuards.ts, 42, 15))
+
+        obj["x"];
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 46, 40))
+>"x" : Symbol(x, Decl(typeVariableTypeGuards.ts, 42, 15))
+
+        obj();
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 46, 40))
+    }
+}
+
+function f2<T extends Item | undefined>(obj: T | undefined) {
+>f2 : Symbol(f2, Decl(typeVariableTypeGuards.ts, 52, 1))
+>T : Symbol(T, Decl(typeVariableTypeGuards.ts, 54, 12))
+>Item : Symbol(Item, Decl(typeVariableTypeGuards.ts, 37, 1))
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 54, 40))
+>T : Symbol(T, Decl(typeVariableTypeGuards.ts, 54, 12))
+
+    if (obj) {
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 54, 40))
+
+        obj.x;
+>obj.x : Symbol(x, Decl(typeVariableTypeGuards.ts, 42, 15))
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 54, 40))
+>x : Symbol(x, Decl(typeVariableTypeGuards.ts, 42, 15))
+
+        obj["x"];
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 54, 40))
+>"x" : Symbol(x, Decl(typeVariableTypeGuards.ts, 42, 15))
+
+        obj();
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 54, 40))
+    }
+}
+
+function f3<T extends Item | undefined>(obj: T | null) {
+>f3 : Symbol(f3, Decl(typeVariableTypeGuards.ts, 60, 1))
+>T : Symbol(T, Decl(typeVariableTypeGuards.ts, 62, 12))
+>Item : Symbol(Item, Decl(typeVariableTypeGuards.ts, 37, 1))
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 62, 40))
+>T : Symbol(T, Decl(typeVariableTypeGuards.ts, 62, 12))
+
+    if (obj) {
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 62, 40))
+
+        obj.x;
+>obj.x : Symbol(x, Decl(typeVariableTypeGuards.ts, 42, 15))
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 62, 40))
+>x : Symbol(x, Decl(typeVariableTypeGuards.ts, 42, 15))
+
+        obj["x"];
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 62, 40))
+>"x" : Symbol(x, Decl(typeVariableTypeGuards.ts, 42, 15))
+
+        obj();
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 62, 40))
+    }
+}
+
+function f4<T extends string[] | undefined>(obj: T | undefined, x: number) {
+>f4 : Symbol(f4, Decl(typeVariableTypeGuards.ts, 68, 1))
+>T : Symbol(T, Decl(typeVariableTypeGuards.ts, 70, 12))
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 70, 44))
+>T : Symbol(T, Decl(typeVariableTypeGuards.ts, 70, 12))
+>x : Symbol(x, Decl(typeVariableTypeGuards.ts, 70, 63))
+
+    if (obj) {
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 70, 44))
+
+        obj[x].length;
+>obj[x].length : Symbol(String.length, Decl(lib.d.ts, --, --))
+>obj : Symbol(obj, Decl(typeVariableTypeGuards.ts, 70, 44))
+>x : Symbol(x, Decl(typeVariableTypeGuards.ts, 70, 63))
+>length : Symbol(String.length, Decl(lib.d.ts, --, --))
+    }
+}
+
diff --git a/tests/baselines/reference/typeVariableTypeGuards.types b/tests/baselines/reference/typeVariableTypeGuards.types
new file mode 100644
index 00000000000..a20129440a0
--- /dev/null
+++ b/tests/baselines/reference/typeVariableTypeGuards.types
@@ -0,0 +1,212 @@
+=== tests/cases/compiler/typeVariableTypeGuards.ts ===
+// Repro from #14091
+
+interface Foo {
+>Foo : Foo
+
+    foo(): void
+>foo : () => void
+}
+
+class A<P extends Partial<Foo>> {
+>A : A<P>
+>P : P
+>Partial : Partial<T>
+>Foo : Foo
+
+    props: Readonly<P>
+>props : Readonly<P>
+>Readonly : Readonly<T>
+>P : P
+
+    doSomething() {
+>doSomething : () => void
+
+        this.props.foo && this.props.foo()
+>this.props.foo && this.props.foo() : void
+>this.props.foo : P["foo"]
+>this.props : Readonly<P>
+>this : this
+>props : Readonly<P>
+>foo : P["foo"]
+>this.props.foo() : void
+>this.props.foo : () => void
+>this.props : Readonly<P>
+>this : this
+>props : Readonly<P>
+>foo : () => void
+    }
+}
+
+// Repro from #14415
+
+interface Banana {
+>Banana : Banana
+
+    color: 'yellow';
+>color : "yellow"
+}
+
+class Monkey<T extends Banana | undefined> {
+>Monkey : Monkey<T>
+>T : T
+>Banana : Banana
+
+    a: T;
+>a : T
+>T : T
+
+    render() {
+>render : () => void
+
+        if (this.a) {
+>this.a : T
+>this : this
+>a : T
+
+            this.a.color;
+>this.a.color : "yellow"
+>this.a : Banana
+>this : this
+>a : Banana
+>color : "yellow"
+        }
+    }
+}
+
+interface BigBanana extends Banana {
+>BigBanana : BigBanana
+>Banana : Banana
+}
+
+class BigMonkey extends Monkey<BigBanana> {
+>BigMonkey : BigMonkey
+>Monkey : Monkey<BigBanana>
+>BigBanana : BigBanana
+
+    render() {
+>render : () => void
+
+        if (this.a) {
+>this.a : BigBanana
+>this : this
+>a : BigBanana
+
+            this.a.color;
+>this.a.color : "yellow"
+>this.a : BigBanana
+>this : this
+>a : BigBanana
+>color : "yellow"
+        }
+    }
+}
+
+// Another repro
+
+type Item = {
+>Item : Item
+
+    (): string;
+    x: string;
+>x : string
+}
+
+function f1<T extends Item | undefined>(obj: T) {
+>f1 : <T extends Item | undefined>(obj: T) => void
+>T : T
+>Item : Item
+>obj : T
+>T : T
+
+    if (obj) {
+>obj : T
+
+        obj.x;
+>obj.x : string
+>obj : Item
+>x : string
+
+        obj["x"];
+>obj["x"] : string
+>obj : Item
+>"x" : "x"
+
+        obj();
+>obj() : string
+>obj : Item
+    }
+}
+
+function f2<T extends Item | undefined>(obj: T | undefined) {
+>f2 : <T extends Item | undefined>(obj: T | undefined) => void
+>T : T
+>Item : Item
+>obj : T | undefined
+>T : T
+
+    if (obj) {
+>obj : T | undefined
+
+        obj.x;
+>obj.x : string
+>obj : Item
+>x : string
+
+        obj["x"];
+>obj["x"] : string
+>obj : Item
+>"x" : "x"
+
+        obj();
+>obj() : string
+>obj : Item
+    }
+}
+
+function f3<T extends Item | undefined>(obj: T | null) {
+>f3 : <T extends Item | undefined>(obj: T | null) => void
+>T : T
+>Item : Item
+>obj : T | null
+>T : T
+>null : null
+
+    if (obj) {
+>obj : T | null
+
+        obj.x;
+>obj.x : string
+>obj : Item
+>x : string
+
+        obj["x"];
+>obj["x"] : string
+>obj : Item
+>"x" : "x"
+
+        obj();
+>obj() : string
+>obj : Item
+    }
+}
+
+function f4<T extends string[] | undefined>(obj: T | undefined, x: number) {
+>f4 : <T extends string[] | undefined>(obj: T | undefined, x: number) => void
+>T : T
+>obj : T | undefined
+>T : T
+>x : number
+
+    if (obj) {
+>obj : T | undefined
+
+        obj[x].length;
+>obj[x].length : number
+>obj[x] : string
+>obj : string[]
+>x : number
+>length : number
+    }
+}
+
diff --git a/tests/cases/compiler/typeVariableTypeGuards.ts b/tests/cases/compiler/typeVariableTypeGuards.ts
new file mode 100644
index 00000000000..a962fd786c7
--- /dev/null
+++ b/tests/cases/compiler/typeVariableTypeGuards.ts
@@ -0,0 +1,77 @@
+// @strict: true
+
+// Repro from #14091
+
+interface Foo {
+    foo(): void
+}
+
+class A<P extends Partial<Foo>> {
+    props: Readonly<P>
+    doSomething() {
+        this.props.foo && this.props.foo()
+    }
+}
+
+// Repro from #14415
+
+interface Banana {
+    color: 'yellow';
+}
+
+class Monkey<T extends Banana | undefined> {
+    a: T;
+    render() {
+        if (this.a) {
+            this.a.color;
+        }
+    }
+}
+
+interface BigBanana extends Banana {
+}
+
+class BigMonkey extends Monkey<BigBanana> {
+    render() {
+        if (this.a) {
+            this.a.color;
+        }
+    }
+}
+
+// Another repro
+
+type Item = {
+    (): string;
+    x: string;
+}
+
+function f1<T extends Item | undefined>(obj: T) {
+    if (obj) {
+        obj.x;
+        obj["x"];
+        obj();
+    }
+}
+
+function f2<T extends Item | undefined>(obj: T | undefined) {
+    if (obj) {
+        obj.x;
+        obj["x"];
+        obj();
+    }
+}
+
+function f3<T extends Item | undefined>(obj: T | null) {
+    if (obj) {
+        obj.x;
+        obj["x"];
+        obj();
+    }
+}
+
+function f4<T extends string[] | undefined>(obj: T | undefined, x: number) {
+    if (obj) {
+        obj[x].length;
+    }
+}