diff --git a/src/compiler/transformers/ts.ts b/src/compiler/transformers/ts.ts
index e67918fd696..ba4b5fcdf52 100644
--- a/src/compiler/transformers/ts.ts
+++ b/src/compiler/transformers/ts.ts
@@ -45,6 +45,7 @@ namespace ts {
 
         const resolver = context.getEmitResolver();
         const compilerOptions = context.getCompilerOptions();
+        const strictNullChecks = typeof compilerOptions.strictNullChecks === "undefined" ? compilerOptions.strict : compilerOptions.strictNullChecks;
         const languageVersion = getEmitScriptTarget(compilerOptions);
         const moduleKind = getEmitModuleKind(compilerOptions);
 
@@ -1869,7 +1870,16 @@ namespace ts {
             // Note when updating logic here also update getEntityNameForDecoratorMetadata
             // so that aliases can be marked as referenced
             let serializedUnion: SerializedTypeNode;
-            for (const typeNode of node.types) {
+            for (let typeNode of node.types) {
+                while (typeNode.kind === SyntaxKind.ParenthesizedType) {
+                    typeNode = (typeNode as ParenthesizedTypeNode).type; // Skip parens if need be
+                }
+                if (typeNode.kind === SyntaxKind.NeverKeyword) {
+                    continue; // Always elide `never` from the union/intersection if possible
+                }
+                if (!strictNullChecks && (typeNode.kind === SyntaxKind.NullKeyword || typeNode.kind === SyntaxKind.UndefinedKeyword)) {
+                    continue; // Elide null and undefined from unions for metadata, just like what we did prior to the implementation of strict null checks
+                }
                 const serializedIndividual = serializeTypeNode(typeNode);
 
                 if (isIdentifier(serializedIndividual) && serializedIndividual.escapedText === "Object") {
@@ -1893,7 +1903,7 @@ namespace ts {
             }
 
             // If we were able to find common type, use it
-            return serializedUnion;
+            return serializedUnion || createVoidZero(); // Fallback is only hit if all union constituients are null/undefined/never
         }
 
         /**
diff --git a/tests/baselines/reference/decoratorMetadataNoStrictNull.js b/tests/baselines/reference/decoratorMetadataNoStrictNull.js
new file mode 100644
index 00000000000..dada68f0960
--- /dev/null
+++ b/tests/baselines/reference/decoratorMetadataNoStrictNull.js
@@ -0,0 +1,32 @@
+//// [decoratorMetadataNoStrictNull.ts]
+const dec = (obj: {}, prop: string) => undefined
+
+class Foo {
+  @dec public foo: string | null;
+  @dec public bar: string;
+}
+
+//// [decoratorMetadataNoStrictNull.js]
+var __decorate = (this && this.__decorate) || function (decorators, target, key, desc) {
+    var c = arguments.length, r = c < 3 ? target : desc === null ? desc = Object.getOwnPropertyDescriptor(target, key) : desc, d;
+    if (typeof Reflect === "object" && typeof Reflect.decorate === "function") r = Reflect.decorate(decorators, target, key, desc);
+    else for (var i = decorators.length - 1; i >= 0; i--) if (d = decorators[i]) r = (c < 3 ? d(r) : c > 3 ? d(target, key, r) : d(target, key)) || r;
+    return c > 3 && r && Object.defineProperty(target, key, r), r;
+};
+var __metadata = (this && this.__metadata) || function (k, v) {
+    if (typeof Reflect === "object" && typeof Reflect.metadata === "function") return Reflect.metadata(k, v);
+};
+var dec = function (obj, prop) { return undefined; };
+var Foo = /** @class */ (function () {
+    function Foo() {
+    }
+    __decorate([
+        dec,
+        __metadata("design:type", String)
+    ], Foo.prototype, "foo");
+    __decorate([
+        dec,
+        __metadata("design:type", String)
+    ], Foo.prototype, "bar");
+    return Foo;
+}());
diff --git a/tests/baselines/reference/decoratorMetadataNoStrictNull.symbols b/tests/baselines/reference/decoratorMetadataNoStrictNull.symbols
new file mode 100644
index 00000000000..32a6d08f024
--- /dev/null
+++ b/tests/baselines/reference/decoratorMetadataNoStrictNull.symbols
@@ -0,0 +1,18 @@
+=== tests/cases/compiler/decoratorMetadataNoStrictNull.ts ===
+const dec = (obj: {}, prop: string) => undefined
+>dec : Symbol(dec, Decl(decoratorMetadataNoStrictNull.ts, 0, 5))
+>obj : Symbol(obj, Decl(decoratorMetadataNoStrictNull.ts, 0, 13))
+>prop : Symbol(prop, Decl(decoratorMetadataNoStrictNull.ts, 0, 21))
+>undefined : Symbol(undefined)
+
+class Foo {
+>Foo : Symbol(Foo, Decl(decoratorMetadataNoStrictNull.ts, 0, 48))
+
+  @dec public foo: string | null;
+>dec : Symbol(dec, Decl(decoratorMetadataNoStrictNull.ts, 0, 5))
+>foo : Symbol(Foo.foo, Decl(decoratorMetadataNoStrictNull.ts, 2, 11))
+
+  @dec public bar: string;
+>dec : Symbol(dec, Decl(decoratorMetadataNoStrictNull.ts, 0, 5))
+>bar : Symbol(Foo.bar, Decl(decoratorMetadataNoStrictNull.ts, 3, 33))
+}
diff --git a/tests/baselines/reference/decoratorMetadataNoStrictNull.types b/tests/baselines/reference/decoratorMetadataNoStrictNull.types
new file mode 100644
index 00000000000..981efe6e50b
--- /dev/null
+++ b/tests/baselines/reference/decoratorMetadataNoStrictNull.types
@@ -0,0 +1,20 @@
+=== tests/cases/compiler/decoratorMetadataNoStrictNull.ts ===
+const dec = (obj: {}, prop: string) => undefined
+>dec : (obj: {}, prop: string) => any
+>(obj: {}, prop: string) => undefined : (obj: {}, prop: string) => any
+>obj : {}
+>prop : string
+>undefined : undefined
+
+class Foo {
+>Foo : Foo
+
+  @dec public foo: string | null;
+>dec : (obj: {}, prop: string) => any
+>foo : string
+>null : null
+
+  @dec public bar: string;
+>dec : (obj: {}, prop: string) => any
+>bar : string
+}
diff --git a/tests/baselines/reference/metadataOfClassFromAlias.js b/tests/baselines/reference/metadataOfClassFromAlias.js
index 307702cd7bf..77ae5c33898 100644
--- a/tests/baselines/reference/metadataOfClassFromAlias.js
+++ b/tests/baselines/reference/metadataOfClassFromAlias.js
@@ -43,7 +43,7 @@ var ClassA = /** @class */ (function () {
     }
     __decorate([
         annotation(),
-        __metadata("design:type", Object)
+        __metadata("design:type", auxiliry_1.SomeClass)
     ], ClassA.prototype, "array", void 0);
     return ClassA;
 }());
diff --git a/tests/baselines/reference/metadataOfUnionWithNull.js b/tests/baselines/reference/metadataOfUnionWithNull.js
index 80d24709b73..7bf9aeb8650 100644
--- a/tests/baselines/reference/metadataOfUnionWithNull.js
+++ b/tests/baselines/reference/metadataOfUnionWithNull.js
@@ -63,15 +63,15 @@ var B = /** @class */ (function () {
     }
     __decorate([
         PropDeco,
-        __metadata("design:type", Object)
+        __metadata("design:type", String)
     ], B.prototype, "x");
     __decorate([
         PropDeco,
-        __metadata("design:type", Object)
+        __metadata("design:type", Boolean)
     ], B.prototype, "y");
     __decorate([
         PropDeco,
-        __metadata("design:type", Object)
+        __metadata("design:type", String)
     ], B.prototype, "z");
     __decorate([
         PropDeco,
@@ -87,11 +87,11 @@ var B = /** @class */ (function () {
     ], B.prototype, "c");
     __decorate([
         PropDeco,
-        __metadata("design:type", Object)
+        __metadata("design:type", void 0)
     ], B.prototype, "d");
     __decorate([
         PropDeco,
-        __metadata("design:type", Object)
+        __metadata("design:type", typeof Symbol === "function" ? Symbol : Object)
     ], B.prototype, "e");
     __decorate([
         PropDeco,
@@ -99,15 +99,15 @@ var B = /** @class */ (function () {
     ], B.prototype, "f");
     __decorate([
         PropDeco,
-        __metadata("design:type", Object)
+        __metadata("design:type", A)
     ], B.prototype, "g");
     __decorate([
         PropDeco,
-        __metadata("design:type", Object)
+        __metadata("design:type", B)
     ], B.prototype, "h");
     __decorate([
         PropDeco,
-        __metadata("design:type", Object)
+        __metadata("design:type", typeof Symbol === "function" ? Symbol : Object)
     ], B.prototype, "j");
     return B;
 }());
diff --git a/tests/cases/compiler/decoratorMetadataNoStrictNull.ts b/tests/cases/compiler/decoratorMetadataNoStrictNull.ts
new file mode 100644
index 00000000000..4ac608ebd74
--- /dev/null
+++ b/tests/cases/compiler/decoratorMetadataNoStrictNull.ts
@@ -0,0 +1,8 @@
+// @experimentalDecorators: true
+// @emitDecoratorMetadata: true
+const dec = (obj: {}, prop: string) => undefined
+
+class Foo {
+  @dec public foo: string | null;
+  @dec public bar: string;
+}
\ No newline at end of file