diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index a27e8ba524d..6a1edbf3cc6 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -18582,6 +18582,7 @@ namespace ts {
                             }
                             return undefined;
                         case SyntaxKind.NumericLiteral:
+                            checkGrammarNumericLiteral(<NumericLiteral>e);
                             return +(<NumericLiteral>e).text;
                         case SyntaxKind.ParenthesizedExpression:
                             return evalConstant((<ParenthesizedExpression>e).expression);
@@ -21885,9 +21886,12 @@ namespace ts {
                 if (languageVersion >= ScriptTarget.ES5) {
                     diagnosticMessage = Diagnostics.Octal_literals_are_not_available_when_targeting_ECMAScript_5_and_higher_Use_the_syntax_0;
                 }
-                else if (isChildOfLiteralType(node)) {
+                else if (isChildOfNodeWithKind(node, SyntaxKind.LiteralType)) {
                     diagnosticMessage = Diagnostics.Octal_literal_types_must_use_ES2015_syntax_Use_the_syntax_0;
                 }
+                else if (isChildOfNodeWithKind(node, SyntaxKind.EnumMember)) {
+                    diagnosticMessage = Diagnostics.Octal_literals_are_not_allowed_in_enums_members_initializer_Use_the_syntax_0;
+                }
                 if (diagnosticMessage) {
                     const withMinus = isPrefixUnaryExpression(node.parent) && node.parent.operator === SyntaxKind.MinusToken;
                     const literal = `${withMinus ? "-" : ""}0o${node.text}`;
diff --git a/src/compiler/diagnosticMessages.json b/src/compiler/diagnosticMessages.json
index 7b2208e4ca1..8cf1313264f 100644
--- a/src/compiler/diagnosticMessages.json
+++ b/src/compiler/diagnosticMessages.json
@@ -3246,5 +3246,9 @@
     "Octal literal types must use ES2015 syntax. Use the syntax '{0}'.": {
         "category": "Error",
         "code": 8017
+    },
+    "Octal literals are not allowed in enums members initializer. Use the syntax '{0}'.": {
+        "category": "Error",
+        "code": 8018
     }
 }
diff --git a/src/compiler/utilities.ts b/src/compiler/utilities.ts
index edfbe639d25..3c64c4d4a34 100644
--- a/src/compiler/utilities.ts
+++ b/src/compiler/utilities.ts
@@ -732,9 +732,9 @@ namespace ts {
         return false;
     }
 
-    export function isChildOfLiteralType(node: Node): boolean {
+    export function isChildOfNodeWithKind(node: Node, kind: SyntaxKind): boolean {
         while (node) {
-            if (node.kind === SyntaxKind.LiteralType) {
+            if (node.kind === kind) {
                 return true;
             }
             node = node.parent;
diff --git a/tests/baselines/reference/es3-oldStyleOctalLiteralInEnums.errors.txt b/tests/baselines/reference/es3-oldStyleOctalLiteralInEnums.errors.txt
new file mode 100644
index 00000000000..137b76f660d
--- /dev/null
+++ b/tests/baselines/reference/es3-oldStyleOctalLiteralInEnums.errors.txt
@@ -0,0 +1,13 @@
+tests/cases/compiler/es3-oldStyleOctalLiteralInEnums.ts(2,7): error TS8018: Octal literals are not allowed in enums members initializer. Use the syntax '-0o1'.
+tests/cases/compiler/es3-oldStyleOctalLiteralInEnums.ts(3,7): error TS8018: Octal literals are not allowed in enums members initializer. Use the syntax '0o2'.
+
+
+==== tests/cases/compiler/es3-oldStyleOctalLiteralInEnums.ts (2 errors) ====
+    enum E {
+      x = -01,
+          ~~~
+!!! error TS8018: Octal literals are not allowed in enums members initializer. Use the syntax '-0o1'.
+      y = 02,
+          ~~
+!!! error TS8018: Octal literals are not allowed in enums members initializer. Use the syntax '0o2'.
+    }
\ No newline at end of file
diff --git a/tests/baselines/reference/es3-oldStyleOctalLiteralInEnums.js b/tests/baselines/reference/es3-oldStyleOctalLiteralInEnums.js
new file mode 100644
index 00000000000..0098d841f2a
--- /dev/null
+++ b/tests/baselines/reference/es3-oldStyleOctalLiteralInEnums.js
@@ -0,0 +1,12 @@
+//// [es3-oldStyleOctalLiteralInEnums.ts]
+enum E {
+  x = -01,
+  y = 02,
+}
+
+//// [es3-oldStyleOctalLiteralInEnums.js]
+var E;
+(function (E) {
+    E[E["x"] = -1] = "x";
+    E[E["y"] = 2] = "y";
+})(E || (E = {}));
diff --git a/tests/baselines/reference/es3-oldStyleOctalLiteralTypes.errors.txt b/tests/baselines/reference/es3-oldStyleOctalLiteralTypes.errors.txt
new file mode 100644
index 00000000000..5fc9843989c
--- /dev/null
+++ b/tests/baselines/reference/es3-oldStyleOctalLiteralTypes.errors.txt
@@ -0,0 +1,12 @@
+tests/cases/compiler/es3-oldStyleOctalLiteralTypes.ts(1,8): error TS8017: Octal literal types must use ES2015 syntax. Use the syntax '0o10'.
+tests/cases/compiler/es3-oldStyleOctalLiteralTypes.ts(2,8): error TS8017: Octal literal types must use ES2015 syntax. Use the syntax '-0o20'.
+
+
+==== tests/cases/compiler/es3-oldStyleOctalLiteralTypes.ts (2 errors) ====
+    let x: 010;
+           ~~~
+!!! error TS8017: Octal literal types must use ES2015 syntax. Use the syntax '0o10'.
+    let y: -020;
+           ~~~~
+!!! error TS8017: Octal literal types must use ES2015 syntax. Use the syntax '-0o20'.
+    
\ No newline at end of file
diff --git a/tests/baselines/reference/es3-oldStyleOctalLiteralTypes.js b/tests/baselines/reference/es3-oldStyleOctalLiteralTypes.js
new file mode 100644
index 00000000000..5ac915400cd
--- /dev/null
+++ b/tests/baselines/reference/es3-oldStyleOctalLiteralTypes.js
@@ -0,0 +1,8 @@
+//// [es3-oldStyleOctalLiteralTypes.ts]
+let x: 010;
+let y: -020;
+
+
+//// [es3-oldStyleOctalLiteralTypes.js]
+var x;
+var y;
diff --git a/tests/baselines/reference/es5-oldStyleOctalLiteralInEnums.errors.txt b/tests/baselines/reference/es5-oldStyleOctalLiteralInEnums.errors.txt
new file mode 100644
index 00000000000..a504568ce20
--- /dev/null
+++ b/tests/baselines/reference/es5-oldStyleOctalLiteralInEnums.errors.txt
@@ -0,0 +1,13 @@
+tests/cases/compiler/es5-oldStyleOctalLiteralInEnums.ts(2,7): error TS1085: Octal literals are not available when targeting ECMAScript 5 and higher. Use the syntax '-0o1'.
+tests/cases/compiler/es5-oldStyleOctalLiteralInEnums.ts(3,7): error TS1085: Octal literals are not available when targeting ECMAScript 5 and higher. Use the syntax '0o2'.
+
+
+==== tests/cases/compiler/es5-oldStyleOctalLiteralInEnums.ts (2 errors) ====
+    enum E {
+      x = -01,
+          ~~~
+!!! error TS1085: Octal literals are not available when targeting ECMAScript 5 and higher. Use the syntax '-0o1'.
+      y = 02,
+          ~~
+!!! error TS1085: Octal literals are not available when targeting ECMAScript 5 and higher. Use the syntax '0o2'.
+    }
\ No newline at end of file
diff --git a/tests/baselines/reference/es5-oldStyleOctalLiteralInEnums.js b/tests/baselines/reference/es5-oldStyleOctalLiteralInEnums.js
new file mode 100644
index 00000000000..71f718054fe
--- /dev/null
+++ b/tests/baselines/reference/es5-oldStyleOctalLiteralInEnums.js
@@ -0,0 +1,12 @@
+//// [es5-oldStyleOctalLiteralInEnums.ts]
+enum E {
+  x = -01,
+  y = 02,
+}
+
+//// [es5-oldStyleOctalLiteralInEnums.js]
+var E;
+(function (E) {
+    E[E["x"] = -1] = "x";
+    E[E["y"] = 2] = "y";
+})(E || (E = {}));
diff --git a/tests/cases/compiler/es3-oldStyleOctalLiteralInEnums.ts b/tests/cases/compiler/es3-oldStyleOctalLiteralInEnums.ts
new file mode 100644
index 00000000000..93489ee4820
--- /dev/null
+++ b/tests/cases/compiler/es3-oldStyleOctalLiteralInEnums.ts
@@ -0,0 +1,5 @@
+// @target: ES3
+enum E {
+  x = -01,
+  y = 02,
+}
\ No newline at end of file
diff --git a/tests/cases/compiler/oldStyleOctalLiteralTypes.ts b/tests/cases/compiler/es3-oldStyleOctalLiteralTypes.ts
similarity index 100%
rename from tests/cases/compiler/oldStyleOctalLiteralTypes.ts
rename to tests/cases/compiler/es3-oldStyleOctalLiteralTypes.ts
diff --git a/tests/cases/compiler/es5-oldStyleOctalLiteralInEnums.ts b/tests/cases/compiler/es5-oldStyleOctalLiteralInEnums.ts
new file mode 100644
index 00000000000..42a95eff2a2
--- /dev/null
+++ b/tests/cases/compiler/es5-oldStyleOctalLiteralInEnums.ts
@@ -0,0 +1,5 @@
+// @target: ES5
+enum E {
+  x = -01,
+  y = 02,
+}
\ No newline at end of file