diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index d34efcbe1bf..8f05f5f4e9f 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -7536,7 +7536,8 @@ namespace ts {
                                 return Ternary.False;
                             }
                             result &= related;
-                            if (sourceProp.flags & SymbolFlags.Optional && !(targetProp.flags & SymbolFlags.Optional)) {
+                            // When checking for comparability, be more lenient with optional properties.
+                            if (relation !== comparableRelation && sourceProp.flags & SymbolFlags.Optional && !(targetProp.flags & SymbolFlags.Optional)) {
                                 // TypeScript 1.0 spec (April 2014): 3.8.3
                                 // S is a subtype of a type T, and T is a supertype of S if ...
                                 // S' and T are object types and, for each member M in T..
diff --git a/tests/baselines/reference/optionalProperties01.js b/tests/baselines/reference/optionalProperties01.js
new file mode 100644
index 00000000000..a614b9e7e37
--- /dev/null
+++ b/tests/baselines/reference/optionalProperties01.js
@@ -0,0 +1,25 @@
+//// [optionalProperties01.ts]
+
+interface Foo {
+  required1: string;
+  required2: string;
+  optional?: string;
+}
+
+const foo1 = { required1: "hello" } as Foo;
+const foo2 = { required1: "hello", optional: "bar" } as Foo;
+
+
+//// [optionalProperties01.js]
+var foo1 = { required1: "hello" };
+var foo2 = { required1: "hello", optional: "bar" };
+
+
+//// [optionalProperties01.d.ts]
+interface Foo {
+    required1: string;
+    required2: string;
+    optional?: string;
+}
+declare const foo1: Foo;
+declare const foo2: Foo;
diff --git a/tests/baselines/reference/optionalProperties01.symbols b/tests/baselines/reference/optionalProperties01.symbols
new file mode 100644
index 00000000000..95c53626f6e
--- /dev/null
+++ b/tests/baselines/reference/optionalProperties01.symbols
@@ -0,0 +1,26 @@
+=== tests/cases/conformance/types/typeRelationships/comparable/optionalProperties01.ts ===
+
+interface Foo {
+>Foo : Symbol(Foo, Decl(optionalProperties01.ts, 0, 0))
+
+  required1: string;
+>required1 : Symbol(Foo.required1, Decl(optionalProperties01.ts, 1, 15))
+
+  required2: string;
+>required2 : Symbol(Foo.required2, Decl(optionalProperties01.ts, 2, 20))
+
+  optional?: string;
+>optional : Symbol(Foo.optional, Decl(optionalProperties01.ts, 3, 20))
+}
+
+const foo1 = { required1: "hello" } as Foo;
+>foo1 : Symbol(foo1, Decl(optionalProperties01.ts, 7, 5))
+>required1 : Symbol(required1, Decl(optionalProperties01.ts, 7, 14))
+>Foo : Symbol(Foo, Decl(optionalProperties01.ts, 0, 0))
+
+const foo2 = { required1: "hello", optional: "bar" } as Foo;
+>foo2 : Symbol(foo2, Decl(optionalProperties01.ts, 8, 5))
+>required1 : Symbol(required1, Decl(optionalProperties01.ts, 8, 14))
+>optional : Symbol(optional, Decl(optionalProperties01.ts, 8, 34))
+>Foo : Symbol(Foo, Decl(optionalProperties01.ts, 0, 0))
+
diff --git a/tests/baselines/reference/optionalProperties01.types b/tests/baselines/reference/optionalProperties01.types
new file mode 100644
index 00000000000..20d16d4071e
--- /dev/null
+++ b/tests/baselines/reference/optionalProperties01.types
@@ -0,0 +1,33 @@
+=== tests/cases/conformance/types/typeRelationships/comparable/optionalProperties01.ts ===
+
+interface Foo {
+>Foo : Foo
+
+  required1: string;
+>required1 : string
+
+  required2: string;
+>required2 : string
+
+  optional?: string;
+>optional : string | undefined
+}
+
+const foo1 = { required1: "hello" } as Foo;
+>foo1 : Foo
+>{ required1: "hello" } as Foo : Foo
+>{ required1: "hello" } : { required1: string; }
+>required1 : string
+>"hello" : "hello"
+>Foo : Foo
+
+const foo2 = { required1: "hello", optional: "bar" } as Foo;
+>foo2 : Foo
+>{ required1: "hello", optional: "bar" } as Foo : Foo
+>{ required1: "hello", optional: "bar" } : { required1: string; optional: string; }
+>required1 : string
+>"hello" : "hello"
+>optional : string
+>"bar" : "bar"
+>Foo : Foo
+
diff --git a/tests/baselines/reference/optionalProperties02.js b/tests/baselines/reference/optionalProperties02.js
new file mode 100644
index 00000000000..f632c5d67a8
--- /dev/null
+++ b/tests/baselines/reference/optionalProperties02.js
@@ -0,0 +1,18 @@
+//// [optionalProperties02.ts]
+
+interface Foo {
+    a?: string;
+    b: string;
+}
+
+<Foo>{ a: undefined };
+
+//// [optionalProperties02.js]
+({ a: undefined });
+
+
+//// [optionalProperties02.d.ts]
+interface Foo {
+    a?: string;
+    b: string;
+}
diff --git a/tests/baselines/reference/optionalProperties02.symbols b/tests/baselines/reference/optionalProperties02.symbols
new file mode 100644
index 00000000000..b88f9ad7429
--- /dev/null
+++ b/tests/baselines/reference/optionalProperties02.symbols
@@ -0,0 +1,17 @@
+=== tests/cases/conformance/types/typeRelationships/comparable/optionalProperties02.ts ===
+
+interface Foo {
+>Foo : Symbol(Foo, Decl(optionalProperties02.ts, 0, 0))
+
+    a?: string;
+>a : Symbol(Foo.a, Decl(optionalProperties02.ts, 1, 15))
+
+    b: string;
+>b : Symbol(Foo.b, Decl(optionalProperties02.ts, 2, 15))
+}
+
+<Foo>{ a: undefined };
+>Foo : Symbol(Foo, Decl(optionalProperties02.ts, 0, 0))
+>a : Symbol(a, Decl(optionalProperties02.ts, 6, 6))
+>undefined : Symbol(undefined)
+
diff --git a/tests/baselines/reference/optionalProperties02.types b/tests/baselines/reference/optionalProperties02.types
new file mode 100644
index 00000000000..05e979b3972
--- /dev/null
+++ b/tests/baselines/reference/optionalProperties02.types
@@ -0,0 +1,19 @@
+=== tests/cases/conformance/types/typeRelationships/comparable/optionalProperties02.ts ===
+
+interface Foo {
+>Foo : Foo
+
+    a?: string;
+>a : string | undefined
+
+    b: string;
+>b : string
+}
+
+<Foo>{ a: undefined };
+><Foo>{ a: undefined } : Foo
+>Foo : Foo
+>{ a: undefined } : { a: undefined; }
+>a : undefined
+>undefined : undefined
+
diff --git a/tests/cases/conformance/types/typeRelationships/comparable/optionalProperties01.ts b/tests/cases/conformance/types/typeRelationships/comparable/optionalProperties01.ts
new file mode 100644
index 00000000000..d4f04d78c80
--- /dev/null
+++ b/tests/cases/conformance/types/typeRelationships/comparable/optionalProperties01.ts
@@ -0,0 +1,11 @@
+// @strictNullChecks: true
+// @declaration: true
+
+interface Foo {
+  required1: string;
+  required2: string;
+  optional?: string;
+}
+
+const foo1 = { required1: "hello" } as Foo;
+const foo2 = { required1: "hello", optional: "bar" } as Foo;
diff --git a/tests/cases/conformance/types/typeRelationships/comparable/optionalProperties02.ts b/tests/cases/conformance/types/typeRelationships/comparable/optionalProperties02.ts
new file mode 100644
index 00000000000..21f83276d44
--- /dev/null
+++ b/tests/cases/conformance/types/typeRelationships/comparable/optionalProperties02.ts
@@ -0,0 +1,9 @@
+// @strictNullChecks: true
+// @declaration: true
+
+interface Foo {
+    a?: string;
+    b: string;
+}
+
+<Foo>{ a: undefined };
\ No newline at end of file