diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 05c20ffb11a..1ab76688271 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -12693,12 +12693,6 @@ namespace ts {
                 if (typeNode) {
                     return getTypeFromTypeNode(typeNode);
                 }
-                if (isInJavaScriptFile(declaration)) {
-                    const jsDocType = getTypeForDeclarationFromJSDocComment(declaration);
-                    if (jsDocType) {
-                        return jsDocType;
-                    }
-                }
                 if (declaration.kind === SyntaxKind.Parameter) {
                     const type = getContextuallyTypedParameterType(<ParameterDeclaration>declaration);
                     if (type) {
@@ -13306,6 +13300,7 @@ namespace ts {
             let patternWithComputedProperties = false;
             let hasComputedStringProperty = false;
             let hasComputedNumberProperty = false;
+            const isInJSFile = isInJavaScriptFile(node);
 
             let offset = 0;
             for (let i = 0; i < node.properties.length; i++) {
@@ -13314,6 +13309,11 @@ namespace ts {
                 if (memberDecl.kind === SyntaxKind.PropertyAssignment ||
                     memberDecl.kind === SyntaxKind.ShorthandPropertyAssignment ||
                     isObjectLiteralMethod(memberDecl)) {
+                    let jsdocType: Type;
+                    if (isInJSFile) {
+                        jsdocType = getTypeForDeclarationFromJSDocComment(memberDecl);
+                    }
+
                     let type: Type;
                     if (memberDecl.kind === SyntaxKind.PropertyAssignment) {
                         type = checkPropertyAssignment(<PropertyAssignment>memberDecl, checkMode);
@@ -13326,6 +13326,11 @@ namespace ts {
                         type = checkExpressionForMutableLocation((<ShorthandPropertyAssignment>memberDecl).name, checkMode);
                     }
 
+                    if (jsdocType) {
+                        checkTypeAssignableTo(type, jsdocType, memberDecl);
+                        type = jsdocType;
+                    }
+
                     typeFlags |= type.flags;
                     const prop = createSymbol(SymbolFlags.Property | member.flags, member.name);
                     if (inDestructuringPattern) {
diff --git a/src/compiler/utilities.ts b/src/compiler/utilities.ts
index c8827801e5e..77d1a0c6496 100644
--- a/src/compiler/utilities.ts
+++ b/src/compiler/utilities.ts
@@ -2664,11 +2664,11 @@ namespace ts {
      * Gets the effective type annotation of a variable, parameter, or property. If the node was
      * parsed in a JavaScript file, gets the type annotation from JSDoc.
      */
-    export function getEffectiveTypeAnnotationNode(node: VariableLikeDeclaration): TypeNode {
+    export function getEffectiveTypeAnnotationNode(node: VariableLikeDeclaration): TypeNode | undefined {
         if (node.type) {
             return node.type;
         }
-        if (node.flags & NodeFlags.JavaScriptFile) {
+        if (isInJavaScriptFile(node)) {
             return getJSDocType(node);
         }
     }
@@ -2677,11 +2677,11 @@ namespace ts {
      * Gets the effective return type annotation of a signature. If the node was parsed in a
      * JavaScript file, gets the return type annotation from JSDoc.
      */
-    export function getEffectiveReturnTypeNode(node: SignatureDeclaration): TypeNode {
+    export function getEffectiveReturnTypeNode(node: SignatureDeclaration): TypeNode | undefined {
         if (node.type) {
             return node.type;
         }
-        if (node.flags & NodeFlags.JavaScriptFile) {
+        if (isInJavaScriptFile(node)) {
             return getJSDocReturnType(node);
         }
     }
diff --git a/tests/baselines/reference/checkJsdocTypeTagOnObjectProperty1.js b/tests/baselines/reference/checkJsdocTypeTagOnObjectProperty1.js
new file mode 100644
index 00000000000..26f19815855
--- /dev/null
+++ b/tests/baselines/reference/checkJsdocTypeTagOnObjectProperty1.js
@@ -0,0 +1,53 @@
+//// [0.js]
+// @ts-check
+var lol = "hello Lol"
+const obj = {
+  /** @type {string|undefined} */
+  foo: undefined,
+  /** @type {string|undefined} */
+  bar: "42",
+  /** @type {function(number): number} */
+  method1(n1) {
+      return n1 + 42;
+  },
+  /** @type {string} */
+  lol,
+  /** @type {number} */
+  ['b' + 'ar1']: 42,
+  /** @type {function(number): number} */
+  arrowFunc: (num) => num + 42
+}
+obj.foo = 'string'
+obj.lol
+obj.bar = undefined;
+var k = obj.method1(0);
+obj.bar1 = "42";
+obj.arrowFunc(0);
+
+//// [0.js]
+// @ts-check
+var lol = "hello Lol";
+var obj = (_a = {
+        /** @type {string|undefined} */
+        foo: undefined,
+        /** @type {string|undefined} */
+        bar: "42",
+        /** @type {function(number): number} */
+        method1: function (n1) {
+            return n1 + 42;
+        },
+        /** @type {string} */
+        lol: lol
+    },
+    /** @type {number} */
+    _a['b' + 'ar1'] = 42,
+    /** @type {function(number): number} */
+    _a.arrowFunc = function (num) { return num + 42; },
+    _a);
+obj.foo = 'string';
+obj.lol;
+obj.bar = undefined;
+var k = obj.method1(0);
+obj.bar1 = "42";
+obj.arrowFunc(0);
+var _a;
diff --git a/tests/baselines/reference/checkJsdocTypeTagOnObjectProperty1.symbols b/tests/baselines/reference/checkJsdocTypeTagOnObjectProperty1.symbols
new file mode 100644
index 00000000000..27f70798c71
--- /dev/null
+++ b/tests/baselines/reference/checkJsdocTypeTagOnObjectProperty1.symbols
@@ -0,0 +1,68 @@
+=== tests/cases/conformance/jsdoc/0.js ===
+// @ts-check
+var lol = "hello Lol"
+>lol : Symbol(lol, Decl(0.js, 1, 3))
+
+const obj = {
+>obj : Symbol(obj, Decl(0.js, 2, 5))
+
+  /** @type {string|undefined} */
+  foo: undefined,
+>foo : Symbol(foo, Decl(0.js, 2, 13))
+>undefined : Symbol(undefined)
+
+  /** @type {string|undefined} */
+  bar: "42",
+>bar : Symbol(bar, Decl(0.js, 4, 17))
+
+  /** @type {function(number): number} */
+  method1(n1) {
+>method1 : Symbol(method1, Decl(0.js, 6, 12))
+>n1 : Symbol(n1, Decl(0.js, 8, 10))
+
+      return n1 + 42;
+>n1 : Symbol(n1, Decl(0.js, 8, 10))
+
+  },
+  /** @type {string} */
+  lol,
+>lol : Symbol(lol, Decl(0.js, 10, 4))
+
+  /** @type {number} */
+  ['b' + 'ar1']: 42,
+  /** @type {function(number): number} */
+  arrowFunc: (num) => num + 42
+>arrowFunc : Symbol(arrowFunc, Decl(0.js, 14, 20))
+>num : Symbol(num, Decl(0.js, 16, 14))
+>num : Symbol(num, Decl(0.js, 16, 14))
+}
+obj.foo = 'string'
+>obj.foo : Symbol(foo, Decl(0.js, 2, 13))
+>obj : Symbol(obj, Decl(0.js, 2, 5))
+>foo : Symbol(foo, Decl(0.js, 2, 13))
+
+obj.lol
+>obj.lol : Symbol(lol, Decl(0.js, 10, 4))
+>obj : Symbol(obj, Decl(0.js, 2, 5))
+>lol : Symbol(lol, Decl(0.js, 10, 4))
+
+obj.bar = undefined;
+>obj.bar : Symbol(bar, Decl(0.js, 4, 17))
+>obj : Symbol(obj, Decl(0.js, 2, 5))
+>bar : Symbol(bar, Decl(0.js, 4, 17))
+>undefined : Symbol(undefined)
+
+var k = obj.method1(0);
+>k : Symbol(k, Decl(0.js, 21, 3))
+>obj.method1 : Symbol(method1, Decl(0.js, 6, 12))
+>obj : Symbol(obj, Decl(0.js, 2, 5))
+>method1 : Symbol(method1, Decl(0.js, 6, 12))
+
+obj.bar1 = "42";
+>obj : Symbol(obj, Decl(0.js, 2, 5))
+
+obj.arrowFunc(0);
+>obj.arrowFunc : Symbol(arrowFunc, Decl(0.js, 14, 20))
+>obj : Symbol(obj, Decl(0.js, 2, 5))
+>arrowFunc : Symbol(arrowFunc, Decl(0.js, 14, 20))
+
diff --git a/tests/baselines/reference/checkJsdocTypeTagOnObjectProperty1.types b/tests/baselines/reference/checkJsdocTypeTagOnObjectProperty1.types
new file mode 100644
index 00000000000..72c5c55228e
--- /dev/null
+++ b/tests/baselines/reference/checkJsdocTypeTagOnObjectProperty1.types
@@ -0,0 +1,92 @@
+=== tests/cases/conformance/jsdoc/0.js ===
+// @ts-check
+var lol = "hello Lol"
+>lol : string
+>"hello Lol" : "hello Lol"
+
+const obj = {
+>obj : { [x: string]: any; foo: string | undefined; bar: string | undefined; method1(arg0: number): number; lol: string; arrowFunc: (arg0: number) => number; }
+>{  /** @type {string|undefined} */  foo: undefined,  /** @type {string|undefined} */  bar: "42",  /** @type {function(number): number} */  method1(n1) {      return n1 + 42;  },  /** @type {string} */  lol,  /** @type {number} */  ['b' + 'ar1']: 42,  /** @type {function(number): number} */  arrowFunc: (num) => num + 42} : { [x: string]: any; foo: string | undefined; bar: string | undefined; method1(arg0: number): number; lol: string; arrowFunc: (arg0: number) => number; }
+
+  /** @type {string|undefined} */
+  foo: undefined,
+>foo : string | undefined
+>undefined : undefined
+
+  /** @type {string|undefined} */
+  bar: "42",
+>bar : string | undefined
+>"42" : "42"
+
+  /** @type {function(number): number} */
+  method1(n1) {
+>method1 : (n1: any) => any
+>n1 : any
+
+      return n1 + 42;
+>n1 + 42 : any
+>n1 : any
+>42 : 42
+
+  },
+  /** @type {string} */
+  lol,
+>lol : string
+
+  /** @type {number} */
+  ['b' + 'ar1']: 42,
+>'b' + 'ar1' : string
+>'b' : "b"
+>'ar1' : "ar1"
+>42 : 42
+
+  /** @type {function(number): number} */
+  arrowFunc: (num) => num + 42
+>arrowFunc : (arg0: number) => number
+>(num) => num + 42 : (num: any) => any
+>num : any
+>num + 42 : any
+>num : any
+>42 : 42
+}
+obj.foo = 'string'
+>obj.foo = 'string' : "string"
+>obj.foo : string | undefined
+>obj : { [x: string]: any; foo: string | undefined; bar: string | undefined; method1(arg0: number): number; lol: string; arrowFunc: (arg0: number) => number; }
+>foo : string | undefined
+>'string' : "string"
+
+obj.lol
+>obj.lol : string
+>obj : { [x: string]: any; foo: string | undefined; bar: string | undefined; method1(arg0: number): number; lol: string; arrowFunc: (arg0: number) => number; }
+>lol : string
+
+obj.bar = undefined;
+>obj.bar = undefined : undefined
+>obj.bar : string | undefined
+>obj : { [x: string]: any; foo: string | undefined; bar: string | undefined; method1(arg0: number): number; lol: string; arrowFunc: (arg0: number) => number; }
+>bar : string | undefined
+>undefined : undefined
+
+var k = obj.method1(0);
+>k : number
+>obj.method1(0) : number
+>obj.method1 : (arg0: number) => number
+>obj : { [x: string]: any; foo: string | undefined; bar: string | undefined; method1(arg0: number): number; lol: string; arrowFunc: (arg0: number) => number; }
+>method1 : (arg0: number) => number
+>0 : 0
+
+obj.bar1 = "42";
+>obj.bar1 = "42" : "42"
+>obj.bar1 : any
+>obj : { [x: string]: any; foo: string | undefined; bar: string | undefined; method1(arg0: number): number; lol: string; arrowFunc: (arg0: number) => number; }
+>bar1 : any
+>"42" : "42"
+
+obj.arrowFunc(0);
+>obj.arrowFunc(0) : number
+>obj.arrowFunc : (arg0: number) => number
+>obj : { [x: string]: any; foo: string | undefined; bar: string | undefined; method1(arg0: number): number; lol: string; arrowFunc: (arg0: number) => number; }
+>arrowFunc : (arg0: number) => number
+>0 : 0
+
diff --git a/tests/baselines/reference/checkJsdocTypeTagOnObjectProperty2.errors.txt b/tests/baselines/reference/checkJsdocTypeTagOnObjectProperty2.errors.txt
new file mode 100644
index 00000000000..33c83e61172
--- /dev/null
+++ b/tests/baselines/reference/checkJsdocTypeTagOnObjectProperty2.errors.txt
@@ -0,0 +1,54 @@
+tests/cases/conformance/jsdoc/0.js(5,3): error TS2322: Type 'number' is not assignable to type 'string | undefined'.
+tests/cases/conformance/jsdoc/0.js(7,3): error TS2322: Type '(n1: any) => string' is not assignable to type '(arg0: number) => number'.
+  Type 'string' is not assignable to type 'number'.
+tests/cases/conformance/jsdoc/0.js(11,3): error TS2322: Type '(n1: any) => string' is not assignable to type '(arg0: number) => number'.
+  Type 'string' is not assignable to type 'number'.
+tests/cases/conformance/jsdoc/0.js(13,3): error TS2322: Type '(num?: string) => string' is not assignable to type '(arg0: number) => number'.
+  Types of parameters 'num' and 'arg0' are incompatible.
+    Type 'number' is not assignable to type 'string | undefined'.
+tests/cases/conformance/jsdoc/0.js(15,3): error TS2322: Type 'undefined' is not assignable to type 'string'.
+tests/cases/conformance/jsdoc/0.js(19,5): error TS2322: Type 'number' is not assignable to type 'string'.
+tests/cases/conformance/jsdoc/0.js(22,22): error TS2345: Argument of type '"0"' is not assignable to parameter of type 'number'.
+
+
+==== tests/cases/conformance/jsdoc/0.js (7 errors) ====
+    // @ts-check
+    var lol;
+    const obj = {
+      /** @type {string|undefined} */
+      bar: 42,
+      ~~~~~~~
+!!! error TS2322: Type 'number' is not assignable to type 'string | undefined'.
+      /** @type {function(number): number} */
+      method1(n1) {
+      ~~~~~~~
+!!! error TS2322: Type '(n1: any) => string' is not assignable to type '(arg0: number) => number'.
+!!! error TS2322:   Type 'string' is not assignable to type 'number'.
+          return "42";
+      },
+      /** @type {function(number): number} */
+      method2: (n1) => "lol",
+      ~~~~~~~~~~~~~~~~~~~~~~
+!!! error TS2322: Type '(n1: any) => string' is not assignable to type '(arg0: number) => number'.
+!!! error TS2322:   Type 'string' is not assignable to type 'number'.
+      /** @type {function(number): number} */
+      arrowFunc: (num="0") => num + 42,
+      ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
+!!! error TS2322: Type '(num?: string) => string' is not assignable to type '(arg0: number) => number'.
+!!! error TS2322:   Types of parameters 'num' and 'arg0' are incompatible.
+!!! error TS2322:     Type 'number' is not assignable to type 'string | undefined'.
+      /** @type {string} */
+      lol
+      ~~~
+!!! error TS2322: Type 'undefined' is not assignable to type 'string'.
+    }
+    lol = "string"
+    /** @type {string} */
+    var s = obj.method1(0);
+        ~
+!!! error TS2322: Type 'number' is not assignable to type 'string'.
+    
+    /** @type {string} */
+    var s1 = obj.method2("0");
+                         ~~~
+!!! error TS2345: Argument of type '"0"' is not assignable to parameter of type 'number'.
\ No newline at end of file
diff --git a/tests/baselines/reference/checkJsdocTypeTagOnObjectProperty2.js b/tests/baselines/reference/checkJsdocTypeTagOnObjectProperty2.js
new file mode 100644
index 00000000000..ab574fddced
--- /dev/null
+++ b/tests/baselines/reference/checkJsdocTypeTagOnObjectProperty2.js
@@ -0,0 +1,49 @@
+//// [0.js]
+// @ts-check
+var lol;
+const obj = {
+  /** @type {string|undefined} */
+  bar: 42,
+  /** @type {function(number): number} */
+  method1(n1) {
+      return "42";
+  },
+  /** @type {function(number): number} */
+  method2: (n1) => "lol",
+  /** @type {function(number): number} */
+  arrowFunc: (num="0") => num + 42,
+  /** @type {string} */
+  lol
+}
+lol = "string"
+/** @type {string} */
+var s = obj.method1(0);
+
+/** @type {string} */
+var s1 = obj.method2("0");
+
+//// [0.js]
+// @ts-check
+var lol;
+var obj = {
+    /** @type {string|undefined} */
+    bar: 42,
+    /** @type {function(number): number} */
+    method1: function (n1) {
+        return "42";
+    },
+    /** @type {function(number): number} */
+    method2: function (n1) { return "lol"; },
+    /** @type {function(number): number} */
+    arrowFunc: function (num) {
+        if (num === void 0) { num = "0"; }
+        return num + 42;
+    },
+    /** @type {string} */
+    lol: lol
+};
+lol = "string";
+/** @type {string} */
+var s = obj.method1(0);
+/** @type {string} */
+var s1 = obj.method2("0");
diff --git a/tests/cases/conformance/jsdoc/checkJsdocTypeTagOnObjectProperty1.ts b/tests/cases/conformance/jsdoc/checkJsdocTypeTagOnObjectProperty1.ts
new file mode 100644
index 00000000000..a98b0a70a2a
--- /dev/null
+++ b/tests/cases/conformance/jsdoc/checkJsdocTypeTagOnObjectProperty1.ts
@@ -0,0 +1,29 @@
+// @allowJS: true
+// @suppressOutputPathCheck: true
+// @strictNullChecks: true
+
+// @filename: 0.js
+// @ts-check
+var lol = "hello Lol"
+const obj = {
+  /** @type {string|undefined} */
+  foo: undefined,
+  /** @type {string|undefined} */
+  bar: "42",
+  /** @type {function(number): number} */
+  method1(n1) {
+      return n1 + 42;
+  },
+  /** @type {string} */
+  lol,
+  /** @type {number} */
+  ['b' + 'ar1']: 42,
+  /** @type {function(number): number} */
+  arrowFunc: (num) => num + 42
+}
+obj.foo = 'string'
+obj.lol
+obj.bar = undefined;
+var k = obj.method1(0);
+obj.bar1 = "42";
+obj.arrowFunc(0);
\ No newline at end of file
diff --git a/tests/cases/conformance/jsdoc/checkJsdocTypeTagOnObjectProperty2.ts b/tests/cases/conformance/jsdoc/checkJsdocTypeTagOnObjectProperty2.ts
new file mode 100644
index 00000000000..9bab96dee9b
--- /dev/null
+++ b/tests/cases/conformance/jsdoc/checkJsdocTypeTagOnObjectProperty2.ts
@@ -0,0 +1,27 @@
+// @allowJS: true
+// @suppressOutputPathCheck: true
+// @strictNullChecks: true
+
+// @filename: 0.js
+// @ts-check
+var lol;
+const obj = {
+  /** @type {string|undefined} */
+  bar: 42,
+  /** @type {function(number): number} */
+  method1(n1) {
+      return "42";
+  },
+  /** @type {function(number): number} */
+  method2: (n1) => "lol",
+  /** @type {function(number): number} */
+  arrowFunc: (num="0") => num + 42,
+  /** @type {string} */
+  lol
+}
+lol = "string"
+/** @type {string} */
+var s = obj.method1(0);
+
+/** @type {string} */
+var s1 = obj.method2("0");
\ No newline at end of file