diff --git a/src/compiler/commandLineParser.ts b/src/compiler/commandLineParser.ts
index eddf40cc94b..c545cca8628 100644
--- a/src/compiler/commandLineParser.ts
+++ b/src/compiler/commandLineParser.ts
@@ -1049,19 +1049,21 @@ namespace ts {
      * Convert the json syntax tree into the json value
      */
     export function convertToObject(sourceFile: JsonSourceFile, errors: Push<Diagnostic>): any {
-        return convertToObjectWorker(sourceFile, errors, /*knownRootOptions*/ undefined, /*jsonConversionNotifier*/ undefined);
+        return convertToObjectWorker(sourceFile, errors, /*returnValue*/ true, /*knownRootOptions*/ undefined, /*jsonConversionNotifier*/ undefined);
     }
 
     /**
-     * Convert the json syntax tree into the json value
+     * Convert the json syntax tree into the json value and report errors
      */
-    function convertToObjectWorker(
+    /*@internal*/
+    export function convertToObjectWorker(
         sourceFile: JsonSourceFile,
         errors: Push<Diagnostic>,
+        returnValue: boolean,
         knownRootOptions: CommandLineOption | undefined,
         jsonConversionNotifier: JsonConversionNotifier | undefined): any {
         if (!sourceFile.statements.length) {
-            return {};
+            return returnValue ? {} : undefined;
         }
 
         return convertPropertyValueToJson(sourceFile.statements[0].expression, knownRootOptions);
@@ -1076,7 +1078,7 @@ namespace ts {
             extraKeyDiagnosticMessage: DiagnosticMessage | undefined,
             parentOption: string | undefined
         ): any {
-            const result: any = {};
+            const result: any = returnValue ? {} : undefined;
             for (const element of node.properties) {
                 if (element.kind !== SyntaxKind.PropertyAssignment) {
                     errors.push(createDiagnosticForNodeInSourceFile(sourceFile, element, Diagnostics.Property_assignment_expected));
@@ -1097,7 +1099,9 @@ namespace ts {
                 }
                 const value = convertPropertyValueToJson(element.initializer, option);
                 if (typeof keyText !== "undefined") {
-                    result[keyText] = value;
+                    if (returnValue) {
+                        result[keyText] = value;
+                    }
                     // Notify key value set, if user asked for it
                     if (jsonConversionNotifier &&
                         // Current callbacks are only on known parent option or if we are setting values in the root
@@ -1128,8 +1132,8 @@ namespace ts {
         function convertArrayLiteralExpressionToJson(
             elements: NodeArray<Expression>,
             elementOption: CommandLineOption | undefined
-        ): any[] {
-            return elements.map(element => convertPropertyValueToJson(element, elementOption));
+        ): any[] | void {
+            return (returnValue ? elements.map : elements.forEach).call(elements, (element: Expression) => convertPropertyValueToJson(element, elementOption));
         }
 
         function convertPropertyValueToJson(valueExpression: Expression, option: CommandLineOption): any {
@@ -1693,7 +1697,7 @@ namespace ts {
                 }
             }
         };
-        const json = convertToObjectWorker(sourceFile, errors, getTsconfigRootOptionsMap(), optionsIterator);
+        const json = convertToObjectWorker(sourceFile, errors, /*returnValue*/ true, getTsconfigRootOptionsMap(), optionsIterator);
         if (!typeAcquisition) {
             if (typingOptionstypeAcquisition) {
                 typeAcquisition = (typingOptionstypeAcquisition.enableAutoDiscovery !== undefined) ?
diff --git a/src/compiler/parser.ts b/src/compiler/parser.ts
index 774e9d42578..2cfc36ab911 100644
--- a/src/compiler/parser.ts
+++ b/src/compiler/parser.ts
@@ -662,6 +662,7 @@ namespace ts {
             scriptKind = ensureScriptKind(fileName, scriptKind);
             if (scriptKind === ScriptKind.JSON) {
                 const result = parseJsonText(fileName, sourceText, languageVersion, syntaxCursor, setParentNodes);
+                convertToObjectWorker(result, result.parseDiagnostics, /*returnValue*/ false, /*knownRootOptions*/ undefined, /*jsonConversionNotifier*/ undefined);
                 result.typeReferenceDirectives = emptyArray;
                 result.amdDependencies = emptyArray;
                 return result;
diff --git a/tests/baselines/reference/requireOfJsonFileWithErrors.errors.txt b/tests/baselines/reference/requireOfJsonFileWithErrors.errors.txt
new file mode 100644
index 00000000000..bac48b2f2c0
--- /dev/null
+++ b/tests/baselines/reference/requireOfJsonFileWithErrors.errors.txt
@@ -0,0 +1,19 @@
+tests/cases/compiler/b.json(2,5): error TS1327: String literal with double quotes expected.
+
+
+==== tests/cases/compiler/file1.ts (0 errors) ====
+    import b1 = require('./b.json');
+    let x = b1.a;
+    import b2 = require('./b.json');
+    if (x) {
+        let b = b2.b;
+        x = (b1.b === b);
+    }
+    
+==== tests/cases/compiler/b.json (1 errors) ====
+    {
+        'a': true,
+        ~~~
+!!! error TS1327: String literal with double quotes expected.
+        "b": "hello"
+    }
\ No newline at end of file
diff --git a/tests/baselines/reference/requireOfJsonFileWithErrors.js b/tests/baselines/reference/requireOfJsonFileWithErrors.js
new file mode 100644
index 00000000000..9f987ff3d8a
--- /dev/null
+++ b/tests/baselines/reference/requireOfJsonFileWithErrors.js
@@ -0,0 +1,32 @@
+//// [tests/cases/compiler/requireOfJsonFileWithErrors.ts] ////
+
+//// [file1.ts]
+import b1 = require('./b.json');
+let x = b1.a;
+import b2 = require('./b.json');
+if (x) {
+    let b = b2.b;
+    x = (b1.b === b);
+}
+
+//// [b.json]
+{
+    'a': true,
+    "b": "hello"
+}
+
+//// [b.json]
+{
+    'a': true,
+    "b": "hello"
+}
+//// [file1.js]
+"use strict";
+exports.__esModule = true;
+var b1 = require("./b.json");
+var x = b1.a;
+var b2 = require("./b.json");
+if (x) {
+    var b = b2.b;
+    x = (b1.b === b);
+}
diff --git a/tests/baselines/reference/requireOfJsonFileWithErrors.symbols b/tests/baselines/reference/requireOfJsonFileWithErrors.symbols
new file mode 100644
index 00000000000..43e877cbed2
--- /dev/null
+++ b/tests/baselines/reference/requireOfJsonFileWithErrors.symbols
@@ -0,0 +1,38 @@
+=== tests/cases/compiler/file1.ts ===
+import b1 = require('./b.json');
+>b1 : Symbol(b1, Decl(file1.ts, 0, 0))
+
+let x = b1.a;
+>x : Symbol(x, Decl(file1.ts, 1, 3))
+>b1.a : Symbol('a', Decl(b.json, 0, 1))
+>b1 : Symbol(b1, Decl(file1.ts, 0, 0))
+>a : Symbol('a', Decl(b.json, 0, 1))
+
+import b2 = require('./b.json');
+>b2 : Symbol(b2, Decl(file1.ts, 1, 13))
+
+if (x) {
+>x : Symbol(x, Decl(file1.ts, 1, 3))
+
+    let b = b2.b;
+>b : Symbol(b, Decl(file1.ts, 4, 7))
+>b2.b : Symbol("b", Decl(b.json, 1, 14))
+>b2 : Symbol(b2, Decl(file1.ts, 1, 13))
+>b : Symbol("b", Decl(b.json, 1, 14))
+
+    x = (b1.b === b);
+>x : Symbol(x, Decl(file1.ts, 1, 3))
+>b1.b : Symbol("b", Decl(b.json, 1, 14))
+>b1 : Symbol(b1, Decl(file1.ts, 0, 0))
+>b : Symbol("b", Decl(b.json, 1, 14))
+>b : Symbol(b, Decl(file1.ts, 4, 7))
+}
+
+=== tests/cases/compiler/b.json ===
+{
+    'a': true,
+>'a' : Symbol('a', Decl(b.json, 0, 1))
+
+    "b": "hello"
+>"b" : Symbol("b", Decl(b.json, 1, 14))
+}
diff --git a/tests/baselines/reference/requireOfJsonFileWithErrors.types b/tests/baselines/reference/requireOfJsonFileWithErrors.types
new file mode 100644
index 00000000000..35893282bee
--- /dev/null
+++ b/tests/baselines/reference/requireOfJsonFileWithErrors.types
@@ -0,0 +1,45 @@
+=== tests/cases/compiler/file1.ts ===
+import b1 = require('./b.json');
+>b1 : { 'a': boolean; "b": string; }
+
+let x = b1.a;
+>x : boolean
+>b1.a : boolean
+>b1 : { 'a': boolean; "b": string; }
+>a : boolean
+
+import b2 = require('./b.json');
+>b2 : { 'a': boolean; "b": string; }
+
+if (x) {
+>x : boolean
+
+    let b = b2.b;
+>b : string
+>b2.b : string
+>b2 : { 'a': boolean; "b": string; }
+>b : string
+
+    x = (b1.b === b);
+>x = (b1.b === b) : boolean
+>x : boolean
+>(b1.b === b) : boolean
+>b1.b === b : boolean
+>b1.b : string
+>b1 : { 'a': boolean; "b": string; }
+>b : string
+>b : string
+}
+
+=== tests/cases/compiler/b.json ===
+{
+>{    'a': true,    "b": "hello"} : { 'a': boolean; "b": string; }
+
+    'a': true,
+>'a' : boolean
+>true : true
+
+    "b": "hello"
+>"b" : string
+>"hello" : "hello"
+}
diff --git a/tests/cases/compiler/requireOfJsonFileWithErrors.ts b/tests/cases/compiler/requireOfJsonFileWithErrors.ts
new file mode 100644
index 00000000000..ad853e183b5
--- /dev/null
+++ b/tests/cases/compiler/requireOfJsonFileWithErrors.ts
@@ -0,0 +1,18 @@
+// @module: commonjs
+// @outdir: out/
+// @allowJs: true
+
+// @Filename: file1.ts
+import b1 = require('./b.json');
+let x = b1.a;
+import b2 = require('./b.json');
+if (x) {
+    let b = b2.b;
+    x = (b1.b === b);
+}
+
+// @Filename: b.json
+{
+    'a': true,
+    "b": "hello"
+}
\ No newline at end of file