diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 606ec5a55d4..b47410d33f9 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -22641,13 +22641,13 @@ namespace ts {
                 if (propName === undefined) {
                     return type;
                 }
-                const includesUndefined = strictNullChecks && maybeTypeOfKind(type, TypeFlags.Undefined);
-                const removeOptional = includesUndefined && isOptionalChain(access);
-                let propType = getTypeOfPropertyOfType(removeOptional ? getTypeWithFacts(type, TypeFacts.NEUndefined) : type, propName);
+                const includesNullable = strictNullChecks && maybeTypeOfKind(type, TypeFlags.Nullable);
+                const removeNullable = includesNullable && isOptionalChain(access);
+                let propType = getTypeOfPropertyOfType(removeNullable ? getTypeWithFacts(type, TypeFacts.NEUndefinedOrNull) : type, propName);
                 if (!propType) {
                     return type;
                 }
-                propType = removeOptional ? getOptionalType(propType) : propType;
+                propType = removeNullable ? getOptionalType(propType) : propType;
                 const narrowedPropType = narrowType(propType);
                 return filterType(type, t => {
                     const discriminantType = getTypeOfPropertyOrIndexSignature(t, propName);
diff --git a/tests/baselines/reference/controlFlowOptionalChain2.js b/tests/baselines/reference/controlFlowOptionalChain2.js
index 0f8478b90fa..a7cf147854b 100644
--- a/tests/baselines/reference/controlFlowOptionalChain2.js
+++ b/tests/baselines/reference/controlFlowOptionalChain2.js
@@ -17,6 +17,92 @@ function funcTwo(arg: A | B | undefined) {
   arg;
   arg?.name;
 }
+
+function funcThree(arg: A | B | null) {
+  if (arg?.type === 'B') {
+    arg; // `B`
+    return;
+  }
+
+  arg;
+  arg?.name;
+}
+
+type U = { kind: undefined, u: 'u' }
+type N = { kind: null, n: 'n' }
+type X = { kind: 'X', x: 'x' }
+
+function f1(x: X | U | undefined) {
+    if (x?.kind === undefined) {
+        x; // U | undefined
+    }
+    else {
+        x; // X
+    }
+}
+
+function f2(x: X | N | undefined) {
+    if (x?.kind === undefined) {
+        x; // undefined
+    }
+    else {
+        x; // X | N
+    }
+}
+
+function f3(x: X | U | null) {
+    if (x?.kind === undefined) {
+        x; // U | null
+    }
+    else {
+        x; // X
+    }
+}
+
+function f4(x: X | N | null) {
+    if (x?.kind === undefined) {
+        x; // null
+    }
+    else {
+        x; // X | N
+    }
+}
+
+function f5(x: X | U | undefined) {
+    if (x?.kind === null) {
+        x; // never
+    }
+    else {
+        x; // X | U | undefined
+    }
+}
+
+function f6(x: X | N | undefined) {
+    if (x?.kind === null) {
+        x; // N
+    }
+    else {
+        x; // X | undefined
+    }
+}
+
+function f7(x: X | U | null) {
+    if (x?.kind === null) {
+        x; // never
+    }
+    else {
+        x; // X | U | null
+    }
+}
+
+function f8(x: X | N | null) {
+    if (x?.kind === null) {
+        x; // N
+    }
+    else {
+        x; // X | null
+    }
+}
 
 
 //// [controlFlowOptionalChain2.js]
@@ -28,3 +114,75 @@ function funcTwo(arg) {
     arg;
     arg === null || arg === void 0 ? void 0 : arg.name;
 }
+function funcThree(arg) {
+    if ((arg === null || arg === void 0 ? void 0 : arg.type) === 'B') {
+        arg; // `B`
+        return;
+    }
+    arg;
+    arg === null || arg === void 0 ? void 0 : arg.name;
+}
+function f1(x) {
+    if ((x === null || x === void 0 ? void 0 : x.kind) === undefined) {
+        x; // U | undefined
+    }
+    else {
+        x; // X
+    }
+}
+function f2(x) {
+    if ((x === null || x === void 0 ? void 0 : x.kind) === undefined) {
+        x; // undefined
+    }
+    else {
+        x; // X | N
+    }
+}
+function f3(x) {
+    if ((x === null || x === void 0 ? void 0 : x.kind) === undefined) {
+        x; // U | null
+    }
+    else {
+        x; // X
+    }
+}
+function f4(x) {
+    if ((x === null || x === void 0 ? void 0 : x.kind) === undefined) {
+        x; // null
+    }
+    else {
+        x; // X | N
+    }
+}
+function f5(x) {
+    if ((x === null || x === void 0 ? void 0 : x.kind) === null) {
+        x; // never
+    }
+    else {
+        x; // X | U | undefined
+    }
+}
+function f6(x) {
+    if ((x === null || x === void 0 ? void 0 : x.kind) === null) {
+        x; // N
+    }
+    else {
+        x; // X | undefined
+    }
+}
+function f7(x) {
+    if ((x === null || x === void 0 ? void 0 : x.kind) === null) {
+        x; // never
+    }
+    else {
+        x; // X | U | null
+    }
+}
+function f8(x) {
+    if ((x === null || x === void 0 ? void 0 : x.kind) === null) {
+        x; // N
+    }
+    else {
+        x; // X | null
+    }
+}
diff --git a/tests/baselines/reference/controlFlowOptionalChain2.symbols b/tests/baselines/reference/controlFlowOptionalChain2.symbols
index f30a8673e45..e4b2184a889 100644
--- a/tests/baselines/reference/controlFlowOptionalChain2.symbols
+++ b/tests/baselines/reference/controlFlowOptionalChain2.symbols
@@ -42,3 +42,208 @@ function funcTwo(arg: A | B | undefined) {
 >name : Symbol(name, Decl(controlFlowOptionalChain2.ts, 1, 12))
 }
 
+function funcThree(arg: A | B | null) {
+>funcThree : Symbol(funcThree, Decl(controlFlowOptionalChain2.ts, 17, 1))
+>arg : Symbol(arg, Decl(controlFlowOptionalChain2.ts, 19, 19))
+>A : Symbol(A, Decl(controlFlowOptionalChain2.ts, 0, 0))
+>B : Symbol(B, Decl(controlFlowOptionalChain2.ts, 3, 1))
+
+  if (arg?.type === 'B') {
+>arg?.type : Symbol(type, Decl(controlFlowOptionalChain2.ts, 0, 10), Decl(controlFlowOptionalChain2.ts, 5, 10))
+>arg : Symbol(arg, Decl(controlFlowOptionalChain2.ts, 19, 19))
+>type : Symbol(type, Decl(controlFlowOptionalChain2.ts, 0, 10), Decl(controlFlowOptionalChain2.ts, 5, 10))
+
+    arg; // `B`
+>arg : Symbol(arg, Decl(controlFlowOptionalChain2.ts, 19, 19))
+
+    return;
+  }
+
+  arg;
+>arg : Symbol(arg, Decl(controlFlowOptionalChain2.ts, 19, 19))
+
+  arg?.name;
+>arg?.name : Symbol(name, Decl(controlFlowOptionalChain2.ts, 1, 12))
+>arg : Symbol(arg, Decl(controlFlowOptionalChain2.ts, 19, 19))
+>name : Symbol(name, Decl(controlFlowOptionalChain2.ts, 1, 12))
+}
+
+type U = { kind: undefined, u: 'u' }
+>U : Symbol(U, Decl(controlFlowOptionalChain2.ts, 27, 1))
+>kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 29, 10))
+>u : Symbol(u, Decl(controlFlowOptionalChain2.ts, 29, 27))
+
+type N = { kind: null, n: 'n' }
+>N : Symbol(N, Decl(controlFlowOptionalChain2.ts, 29, 36))
+>kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 30, 10))
+>n : Symbol(n, Decl(controlFlowOptionalChain2.ts, 30, 22))
+
+type X = { kind: 'X', x: 'x' }
+>X : Symbol(X, Decl(controlFlowOptionalChain2.ts, 30, 31))
+>kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 31, 10))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 31, 21))
+
+function f1(x: X | U | undefined) {
+>f1 : Symbol(f1, Decl(controlFlowOptionalChain2.ts, 31, 30))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 33, 12))
+>X : Symbol(X, Decl(controlFlowOptionalChain2.ts, 30, 31))
+>U : Symbol(U, Decl(controlFlowOptionalChain2.ts, 27, 1))
+
+    if (x?.kind === undefined) {
+>x?.kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 29, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 33, 12))
+>kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 29, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+>undefined : Symbol(undefined)
+
+        x; // U | undefined
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 33, 12))
+    }
+    else {
+        x; // X
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 33, 12))
+    }
+}
+
+function f2(x: X | N | undefined) {
+>f2 : Symbol(f2, Decl(controlFlowOptionalChain2.ts, 40, 1))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 42, 12))
+>X : Symbol(X, Decl(controlFlowOptionalChain2.ts, 30, 31))
+>N : Symbol(N, Decl(controlFlowOptionalChain2.ts, 29, 36))
+
+    if (x?.kind === undefined) {
+>x?.kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 30, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 42, 12))
+>kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 30, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+>undefined : Symbol(undefined)
+
+        x; // undefined
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 42, 12))
+    }
+    else {
+        x; // X | N
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 42, 12))
+    }
+}
+
+function f3(x: X | U | null) {
+>f3 : Symbol(f3, Decl(controlFlowOptionalChain2.ts, 49, 1))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 51, 12))
+>X : Symbol(X, Decl(controlFlowOptionalChain2.ts, 30, 31))
+>U : Symbol(U, Decl(controlFlowOptionalChain2.ts, 27, 1))
+
+    if (x?.kind === undefined) {
+>x?.kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 29, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 51, 12))
+>kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 29, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+>undefined : Symbol(undefined)
+
+        x; // U | null
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 51, 12))
+    }
+    else {
+        x; // X
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 51, 12))
+    }
+}
+
+function f4(x: X | N | null) {
+>f4 : Symbol(f4, Decl(controlFlowOptionalChain2.ts, 58, 1))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 60, 12))
+>X : Symbol(X, Decl(controlFlowOptionalChain2.ts, 30, 31))
+>N : Symbol(N, Decl(controlFlowOptionalChain2.ts, 29, 36))
+
+    if (x?.kind === undefined) {
+>x?.kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 30, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 60, 12))
+>kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 30, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+>undefined : Symbol(undefined)
+
+        x; // null
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 60, 12))
+    }
+    else {
+        x; // X | N
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 60, 12))
+    }
+}
+
+function f5(x: X | U | undefined) {
+>f5 : Symbol(f5, Decl(controlFlowOptionalChain2.ts, 67, 1))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 69, 12))
+>X : Symbol(X, Decl(controlFlowOptionalChain2.ts, 30, 31))
+>U : Symbol(U, Decl(controlFlowOptionalChain2.ts, 27, 1))
+
+    if (x?.kind === null) {
+>x?.kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 29, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 69, 12))
+>kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 29, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+
+        x; // never
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 69, 12))
+    }
+    else {
+        x; // X | U | undefined
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 69, 12))
+    }
+}
+
+function f6(x: X | N | undefined) {
+>f6 : Symbol(f6, Decl(controlFlowOptionalChain2.ts, 76, 1))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 78, 12))
+>X : Symbol(X, Decl(controlFlowOptionalChain2.ts, 30, 31))
+>N : Symbol(N, Decl(controlFlowOptionalChain2.ts, 29, 36))
+
+    if (x?.kind === null) {
+>x?.kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 30, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 78, 12))
+>kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 30, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+
+        x; // N
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 78, 12))
+    }
+    else {
+        x; // X | undefined
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 78, 12))
+    }
+}
+
+function f7(x: X | U | null) {
+>f7 : Symbol(f7, Decl(controlFlowOptionalChain2.ts, 85, 1))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 87, 12))
+>X : Symbol(X, Decl(controlFlowOptionalChain2.ts, 30, 31))
+>U : Symbol(U, Decl(controlFlowOptionalChain2.ts, 27, 1))
+
+    if (x?.kind === null) {
+>x?.kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 29, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 87, 12))
+>kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 29, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+
+        x; // never
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 87, 12))
+    }
+    else {
+        x; // X | U | null
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 87, 12))
+    }
+}
+
+function f8(x: X | N | null) {
+>f8 : Symbol(f8, Decl(controlFlowOptionalChain2.ts, 94, 1))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 96, 12))
+>X : Symbol(X, Decl(controlFlowOptionalChain2.ts, 30, 31))
+>N : Symbol(N, Decl(controlFlowOptionalChain2.ts, 29, 36))
+
+    if (x?.kind === null) {
+>x?.kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 30, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 96, 12))
+>kind : Symbol(kind, Decl(controlFlowOptionalChain2.ts, 30, 10), Decl(controlFlowOptionalChain2.ts, 31, 10))
+
+        x; // N
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 96, 12))
+    }
+    else {
+        x; // X | null
+>x : Symbol(x, Decl(controlFlowOptionalChain2.ts, 96, 12))
+    }
+}
+
diff --git a/tests/baselines/reference/controlFlowOptionalChain2.types b/tests/baselines/reference/controlFlowOptionalChain2.types
index 6e41060218e..f3b2d1cd573 100644
--- a/tests/baselines/reference/controlFlowOptionalChain2.types
+++ b/tests/baselines/reference/controlFlowOptionalChain2.types
@@ -42,3 +42,210 @@ function funcTwo(arg: A | B | undefined) {
 >name : string | undefined
 }
 
+function funcThree(arg: A | B | null) {
+>funcThree : (arg: A | B | null) => void
+>arg : A | B | null
+>null : null
+
+  if (arg?.type === 'B') {
+>arg?.type === 'B' : boolean
+>arg?.type : "A" | "B" | undefined
+>arg : A | B | null
+>type : "A" | "B" | undefined
+>'B' : "B"
+
+    arg; // `B`
+>arg : B
+
+    return;
+  }
+
+  arg;
+>arg : A | null
+
+  arg?.name;
+>arg?.name : string | undefined
+>arg : A | null
+>name : string | undefined
+}
+
+type U = { kind: undefined, u: 'u' }
+>U : U
+>kind : undefined
+>u : "u"
+
+type N = { kind: null, n: 'n' }
+>N : N
+>kind : null
+>null : null
+>n : "n"
+
+type X = { kind: 'X', x: 'x' }
+>X : X
+>kind : "X"
+>x : "x"
+
+function f1(x: X | U | undefined) {
+>f1 : (x: X | U | undefined) => void
+>x : U | X | undefined
+
+    if (x?.kind === undefined) {
+>x?.kind === undefined : boolean
+>x?.kind : "X" | undefined
+>x : U | X | undefined
+>kind : "X" | undefined
+>undefined : undefined
+
+        x; // U | undefined
+>x : U | undefined
+    }
+    else {
+        x; // X
+>x : X
+    }
+}
+
+function f2(x: X | N | undefined) {
+>f2 : (x: X | N | undefined) => void
+>x : N | X | undefined
+
+    if (x?.kind === undefined) {
+>x?.kind === undefined : boolean
+>x?.kind : "X" | null | undefined
+>x : N | X | undefined
+>kind : "X" | null | undefined
+>undefined : undefined
+
+        x; // undefined
+>x : undefined
+    }
+    else {
+        x; // X | N
+>x : N | X
+    }
+}
+
+function f3(x: X | U | null) {
+>f3 : (x: X | U | null) => void
+>x : U | X | null
+>null : null
+
+    if (x?.kind === undefined) {
+>x?.kind === undefined : boolean
+>x?.kind : "X" | undefined
+>x : U | X | null
+>kind : "X" | undefined
+>undefined : undefined
+
+        x; // U | null
+>x : U | null
+    }
+    else {
+        x; // X
+>x : X
+    }
+}
+
+function f4(x: X | N | null) {
+>f4 : (x: X | N | null) => void
+>x : N | X | null
+>null : null
+
+    if (x?.kind === undefined) {
+>x?.kind === undefined : boolean
+>x?.kind : "X" | null | undefined
+>x : N | X | null
+>kind : "X" | null | undefined
+>undefined : undefined
+
+        x; // null
+>x : null
+    }
+    else {
+        x; // X | N
+>x : N | X
+    }
+}
+
+function f5(x: X | U | undefined) {
+>f5 : (x: X | U | undefined) => void
+>x : U | X | undefined
+
+    if (x?.kind === null) {
+>x?.kind === null : boolean
+>x?.kind : "X" | undefined
+>x : U | X | undefined
+>kind : "X" | undefined
+>null : null
+
+        x; // never
+>x : never
+    }
+    else {
+        x; // X | U | undefined
+>x : U | X | undefined
+    }
+}
+
+function f6(x: X | N | undefined) {
+>f6 : (x: X | N | undefined) => void
+>x : N | X | undefined
+
+    if (x?.kind === null) {
+>x?.kind === null : boolean
+>x?.kind : "X" | null | undefined
+>x : N | X | undefined
+>kind : "X" | null | undefined
+>null : null
+
+        x; // N
+>x : N
+    }
+    else {
+        x; // X | undefined
+>x : X | undefined
+    }
+}
+
+function f7(x: X | U | null) {
+>f7 : (x: X | U | null) => void
+>x : U | X | null
+>null : null
+
+    if (x?.kind === null) {
+>x?.kind === null : boolean
+>x?.kind : "X" | undefined
+>x : U | X | null
+>kind : "X" | undefined
+>null : null
+
+        x; // never
+>x : never
+    }
+    else {
+        x; // X | U | null
+>x : U | X | null
+    }
+}
+
+function f8(x: X | N | null) {
+>f8 : (x: X | N | null) => void
+>x : N | X | null
+>null : null
+
+    if (x?.kind === null) {
+>x?.kind === null : boolean
+>x?.kind : "X" | null | undefined
+>x : N | X | null
+>kind : "X" | null | undefined
+>null : null
+
+        x; // N
+>x : N
+    }
+    else {
+        x; // X | null
+>x : X | null
+    }
+}
+
diff --git a/tests/cases/conformance/controlFlow/controlFlowOptionalChain2.ts b/tests/cases/conformance/controlFlow/controlFlowOptionalChain2.ts
index a48d627ee32..b3dc7a14561 100644
--- a/tests/cases/conformance/controlFlow/controlFlowOptionalChain2.ts
+++ b/tests/cases/conformance/controlFlow/controlFlowOptionalChain2.ts
@@ -18,3 +18,89 @@ function funcTwo(arg: A | B | undefined) {
   arg;
   arg?.name;
 }
+
+function funcThree(arg: A | B | null) {
+  if (arg?.type === 'B') {
+    arg; // `B`
+    return;
+  }
+
+  arg;
+  arg?.name;
+}
+
+type U = { kind: undefined, u: 'u' }
+type N = { kind: null, n: 'n' }
+type X = { kind: 'X', x: 'x' }
+
+function f1(x: X | U | undefined) {
+    if (x?.kind === undefined) {
+        x; // U | undefined
+    }
+    else {
+        x; // X
+    }
+}
+
+function f2(x: X | N | undefined) {
+    if (x?.kind === undefined) {
+        x; // undefined
+    }
+    else {
+        x; // X | N
+    }
+}
+
+function f3(x: X | U | null) {
+    if (x?.kind === undefined) {
+        x; // U | null
+    }
+    else {
+        x; // X
+    }
+}
+
+function f4(x: X | N | null) {
+    if (x?.kind === undefined) {
+        x; // null
+    }
+    else {
+        x; // X | N
+    }
+}
+
+function f5(x: X | U | undefined) {
+    if (x?.kind === null) {
+        x; // never
+    }
+    else {
+        x; // X | U | undefined
+    }
+}
+
+function f6(x: X | N | undefined) {
+    if (x?.kind === null) {
+        x; // N
+    }
+    else {
+        x; // X | undefined
+    }
+}
+
+function f7(x: X | U | null) {
+    if (x?.kind === null) {
+        x; // never
+    }
+    else {
+        x; // X | U | null
+    }
+}
+
+function f8(x: X | N | null) {
+    if (x?.kind === null) {
+        x; // N
+    }
+    else {
+        x; // X | null
+    }
+}