diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 4f76f46bd11c4..879be1c6fbf58 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -14586,14 +14586,18 @@ namespace ts {
             }
             // TypeScript 1.0 spec (April 2014): 4.15.4
             // The instanceof operator requires the left operand to be of type Any, an object type, or a type parameter type,
-            // and the right operand to be of type Any or a subtype of the 'Function' interface type.
+            // and the right operand to be of type Any, a subtype of the 'Function' interface type, or have a call or construct signature.
             // The result is always of the Boolean primitive type.
             // NOTE: do not raise error if leftType is unknown as related error was already reported
             if (isTypeOfKind(leftType, TypeFlags.Primitive)) {
                 error(left, Diagnostics.The_left_hand_side_of_an_instanceof_expression_must_be_of_type_any_an_object_type_or_a_type_parameter);
             }
             // NOTE: do not raise error if right is unknown as related error was already reported
-            if (!(isTypeAny(rightType) || isTypeSubtypeOf(rightType, globalFunctionType))) {
+            if (!(isTypeAny(rightType) ||
+                  rightType.flags & TypeFlags.Nullable ||
+                  getSignaturesOfType(rightType, SignatureKind.Call).length ||
+                  getSignaturesOfType(rightType, SignatureKind.Construct).length ||
+                  isTypeSubtypeOf(rightType, globalFunctionType))) {
                 error(right, Diagnostics.The_right_hand_side_of_an_instanceof_expression_must_be_of_type_any_or_of_a_type_assignable_to_the_Function_interface_type);
             }
             return booleanType;
diff --git a/tests/baselines/reference/instanceofOperatorWithInvalidStaticToString.js b/tests/baselines/reference/instanceofOperatorWithInvalidStaticToString.js
new file mode 100644
index 0000000000000..bf5a6f7bce132
--- /dev/null
+++ b/tests/baselines/reference/instanceofOperatorWithInvalidStaticToString.js
@@ -0,0 +1,34 @@
+//// [instanceofOperatorWithInvalidStaticToString.ts]
+declare class StaticToString {
+    static toString(): void;
+}
+
+function foo(staticToString: StaticToString) {
+    return staticToString instanceof StaticToString;
+}
+
+declare class StaticToNumber {
+    static toNumber(): void;
+}
+function bar(staticToNumber: StaticToNumber) {
+    return staticToNumber instanceof StaticToNumber;
+}
+
+declare class NormalToString {
+    toString(): void;
+}
+function baz(normal: NormalToString) {
+    return normal instanceof NormalToString;
+}
+
+
+//// [instanceofOperatorWithInvalidStaticToString.js]
+function foo(staticToString) {
+    return staticToString instanceof StaticToString;
+}
+function bar(staticToNumber) {
+    return staticToNumber instanceof StaticToNumber;
+}
+function baz(normal) {
+    return normal instanceof NormalToString;
+}
diff --git a/tests/baselines/reference/instanceofOperatorWithInvalidStaticToString.symbols b/tests/baselines/reference/instanceofOperatorWithInvalidStaticToString.symbols
new file mode 100644
index 0000000000000..4f4dbda611a0c
--- /dev/null
+++ b/tests/baselines/reference/instanceofOperatorWithInvalidStaticToString.symbols
@@ -0,0 +1,50 @@
+=== tests/cases/conformance/expressions/binaryOperators/instanceofOperator/instanceofOperatorWithInvalidStaticToString.ts ===
+declare class StaticToString {
+>StaticToString : Symbol(StaticToString, Decl(instanceofOperatorWithInvalidStaticToString.ts, 0, 0))
+
+    static toString(): void;
+>toString : Symbol(StaticToString.toString, Decl(instanceofOperatorWithInvalidStaticToString.ts, 0, 30))
+}
+
+function foo(staticToString: StaticToString) {
+>foo : Symbol(foo, Decl(instanceofOperatorWithInvalidStaticToString.ts, 2, 1))
+>staticToString : Symbol(staticToString, Decl(instanceofOperatorWithInvalidStaticToString.ts, 4, 13))
+>StaticToString : Symbol(StaticToString, Decl(instanceofOperatorWithInvalidStaticToString.ts, 0, 0))
+
+    return staticToString instanceof StaticToString;
+>staticToString : Symbol(staticToString, Decl(instanceofOperatorWithInvalidStaticToString.ts, 4, 13))
+>StaticToString : Symbol(StaticToString, Decl(instanceofOperatorWithInvalidStaticToString.ts, 0, 0))
+}
+
+declare class StaticToNumber {
+>StaticToNumber : Symbol(StaticToNumber, Decl(instanceofOperatorWithInvalidStaticToString.ts, 6, 1))
+
+    static toNumber(): void;
+>toNumber : Symbol(StaticToNumber.toNumber, Decl(instanceofOperatorWithInvalidStaticToString.ts, 8, 30))
+}
+function bar(staticToNumber: StaticToNumber) {
+>bar : Symbol(bar, Decl(instanceofOperatorWithInvalidStaticToString.ts, 10, 1))
+>staticToNumber : Symbol(staticToNumber, Decl(instanceofOperatorWithInvalidStaticToString.ts, 11, 13))
+>StaticToNumber : Symbol(StaticToNumber, Decl(instanceofOperatorWithInvalidStaticToString.ts, 6, 1))
+
+    return staticToNumber instanceof StaticToNumber;
+>staticToNumber : Symbol(staticToNumber, Decl(instanceofOperatorWithInvalidStaticToString.ts, 11, 13))
+>StaticToNumber : Symbol(StaticToNumber, Decl(instanceofOperatorWithInvalidStaticToString.ts, 6, 1))
+}
+
+declare class NormalToString {
+>NormalToString : Symbol(NormalToString, Decl(instanceofOperatorWithInvalidStaticToString.ts, 13, 1))
+
+    toString(): void;
+>toString : Symbol(NormalToString.toString, Decl(instanceofOperatorWithInvalidStaticToString.ts, 15, 30))
+}
+function baz(normal: NormalToString) {
+>baz : Symbol(baz, Decl(instanceofOperatorWithInvalidStaticToString.ts, 17, 1))
+>normal : Symbol(normal, Decl(instanceofOperatorWithInvalidStaticToString.ts, 18, 13))
+>NormalToString : Symbol(NormalToString, Decl(instanceofOperatorWithInvalidStaticToString.ts, 13, 1))
+
+    return normal instanceof NormalToString;
+>normal : Symbol(normal, Decl(instanceofOperatorWithInvalidStaticToString.ts, 18, 13))
+>NormalToString : Symbol(NormalToString, Decl(instanceofOperatorWithInvalidStaticToString.ts, 13, 1))
+}
+
diff --git a/tests/baselines/reference/instanceofOperatorWithInvalidStaticToString.types b/tests/baselines/reference/instanceofOperatorWithInvalidStaticToString.types
new file mode 100644
index 0000000000000..11efa0cffc386
--- /dev/null
+++ b/tests/baselines/reference/instanceofOperatorWithInvalidStaticToString.types
@@ -0,0 +1,53 @@
+=== tests/cases/conformance/expressions/binaryOperators/instanceofOperator/instanceofOperatorWithInvalidStaticToString.ts ===
+declare class StaticToString {
+>StaticToString : StaticToString
+
+    static toString(): void;
+>toString : () => void
+}
+
+function foo(staticToString: StaticToString) {
+>foo : (staticToString: StaticToString) => boolean
+>staticToString : StaticToString
+>StaticToString : StaticToString
+
+    return staticToString instanceof StaticToString;
+>staticToString instanceof StaticToString : boolean
+>staticToString : StaticToString
+>StaticToString : typeof StaticToString
+}
+
+declare class StaticToNumber {
+>StaticToNumber : StaticToNumber
+
+    static toNumber(): void;
+>toNumber : () => void
+}
+function bar(staticToNumber: StaticToNumber) {
+>bar : (staticToNumber: StaticToNumber) => boolean
+>staticToNumber : StaticToNumber
+>StaticToNumber : StaticToNumber
+
+    return staticToNumber instanceof StaticToNumber;
+>staticToNumber instanceof StaticToNumber : boolean
+>staticToNumber : StaticToNumber
+>StaticToNumber : typeof StaticToNumber
+}
+
+declare class NormalToString {
+>NormalToString : NormalToString
+
+    toString(): void;
+>toString : () => void
+}
+function baz(normal: NormalToString) {
+>baz : (normal: NormalToString) => boolean
+>normal : NormalToString
+>NormalToString : NormalToString
+
+    return normal instanceof NormalToString;
+>normal instanceof NormalToString : boolean
+>normal : NormalToString
+>NormalToString : typeof NormalToString
+}
+
diff --git a/tests/cases/conformance/expressions/binaryOperators/instanceofOperator/instanceofOperatorWithInvalidStaticToString.ts b/tests/cases/conformance/expressions/binaryOperators/instanceofOperator/instanceofOperatorWithInvalidStaticToString.ts
new file mode 100644
index 0000000000000..b99f8d71141dd
--- /dev/null
+++ b/tests/cases/conformance/expressions/binaryOperators/instanceofOperator/instanceofOperatorWithInvalidStaticToString.ts
@@ -0,0 +1,21 @@
+declare class StaticToString {
+    static toString(): void;
+}
+
+function foo(staticToString: StaticToString) {
+    return staticToString instanceof StaticToString;
+}
+
+declare class StaticToNumber {
+    static toNumber(): void;
+}
+function bar(staticToNumber: StaticToNumber) {
+    return staticToNumber instanceof StaticToNumber;
+}
+
+declare class NormalToString {
+    toString(): void;
+}
+function baz(normal: NormalToString) {
+    return normal instanceof NormalToString;
+}