diff --git a/src/compiler/emitter.ts b/src/compiler/emitter.ts
index e91712d7881b7..228c58bb8a856 100644
--- a/src/compiler/emitter.ts
+++ b/src/compiler/emitter.ts
@@ -3061,11 +3061,11 @@ export function createPrinter(printerOptions: PrinterOptions = {}, handlers: Pri
                 && !stringContains(text, String.fromCharCode(CharacterCodes.e));
         }
         else if (isAccessExpression(expression)) {
-            // check if constant enum value is integer
+            // check if constant enum value is a non-negative integer
             const constantValue = getConstantValue(expression);
             // isFinite handles cases when constantValue is undefined
             return typeof constantValue === "number" && isFinite(constantValue)
-                && Math.floor(constantValue) === constantValue;
+                && constantValue >= 0 && Math.floor(constantValue) === constantValue;
         }
     }
 
diff --git a/src/compiler/transformers/ts.ts b/src/compiler/transformers/ts.ts
index 8b97637c07722..d94554c128b81 100644
--- a/src/compiler/transformers/ts.ts
+++ b/src/compiler/transformers/ts.ts
@@ -123,7 +123,6 @@ import {
     isTryStatement,
     JsxOpeningElement,
     JsxSelfClosingElement,
-    LeftHandSideExpression,
     map,
     mapDefined,
     MethodDeclaration,
@@ -2666,21 +2665,21 @@ export function transformTypeScript(context: TransformationContext) {
         return value.replace(/\*\//g, "*_/");
     }
 
-    function substituteConstantValue(node: PropertyAccessExpression | ElementAccessExpression): LeftHandSideExpression {
+    function substituteConstantValue(node: PropertyAccessExpression | ElementAccessExpression) {
         const constantValue = tryGetConstEnumValue(node);
         if (constantValue !== undefined) {
-            // track the constant value on the node for the printer in needsDotDotForPropertyAccess
+            // track the constant value on the node for the printer in mayNeedDotDotForPropertyAccess
             setConstantValue(node, constantValue);
+            const substitute = typeof constantValue === "string" ? factory.createStringLiteral(constantValue) :
+                constantValue < 0 ? factory.createPrefixUnaryExpression(SyntaxKind.MinusToken, factory.createNumericLiteral(Math.abs(constantValue))) :
+                factory.createNumericLiteral(constantValue);
 
-            const substitute = typeof constantValue === "string" ? factory.createStringLiteral(constantValue) : factory.createNumericLiteral(constantValue);
             if (!compilerOptions.removeComments) {
                 const originalNode = getOriginalNode(node, isAccessExpression);
-
                 addSyntheticTrailingComment(substitute, SyntaxKind.MultiLineCommentTrivia, ` ${safeMultiLineComment(getTextOfNode(originalNode))} `);
             }
             return substitute;
         }
-
         return node;
     }
 
diff --git a/src/testRunner/tests.ts b/src/testRunner/tests.ts
index 19474a4f4bea0..1a3da111540f4 100644
--- a/src/testRunner/tests.ts
+++ b/src/testRunner/tests.ts
@@ -34,6 +34,7 @@ import "./unittests/evaluation/asyncArrow";
 import "./unittests/evaluation/asyncGenerator";
 import "./unittests/evaluation/autoAccessors";
 import "./unittests/evaluation/awaiter";
+import "./unittests/evaluation/constEnum";
 import "./unittests/evaluation/destructuring";
 import "./unittests/evaluation/externalModules";
 import "./unittests/evaluation/esDecorators";
diff --git a/src/testRunner/unittests/evaluation/constEnum.ts b/src/testRunner/unittests/evaluation/constEnum.ts
new file mode 100644
index 0000000000000..8074c00627ff6
--- /dev/null
+++ b/src/testRunner/unittests/evaluation/constEnum.ts
@@ -0,0 +1,17 @@
+import * as evaluator from "../../_namespaces/evaluator";
+
+describe("unittests:: evaluation:: constEnum", () => {
+    it("correct order of operations for inlined negative numbers", async () => {
+        const result = evaluator.evaluateTypeScript(`
+            const enum TestEnum {
+                A = 1,
+                B = -1
+            }
+
+            export const a = typeof TestEnum.A.toString();
+            export const b = typeof TestEnum.B.toString();
+        `);
+        assert.equal(result.a, "string");
+        assert.equal(result.b, "string");
+    });
+});
diff --git a/tests/baselines/reference/constEnumPropertyAccess3.js b/tests/baselines/reference/constEnumPropertyAccess3.js
new file mode 100644
index 0000000000000..b7f184d281e5f
--- /dev/null
+++ b/tests/baselines/reference/constEnumPropertyAccess3.js
@@ -0,0 +1,33 @@
+//// [tests/cases/conformance/constEnums/constEnumPropertyAccess3.ts] ////
+
+//// [constEnumPropertyAccess3.ts]
+const enum E {
+    A = ~1,
+    B = -1,
+    C = ~(1 + 1),
+    D = -(1 + 2),
+    E = 1 - 10,
+}
+
+E.A.toString();
+E.B.toString();
+E.C.toString();
+E.D.toString();
+
+E["A"].toString();
+E["B"].toString();
+E["C"].toString();
+E["D"].toString();
+E["E"].toString();
+
+
+//// [constEnumPropertyAccess3.js]
+(-2 /* E.A */).toString();
+(-1 /* E.B */).toString();
+(-3 /* E.C */).toString();
+(-3 /* E.D */).toString();
+(-2 /* E["A"] */).toString();
+(-1 /* E["B"] */).toString();
+(-3 /* E["C"] */).toString();
+(-3 /* E["D"] */).toString();
+(-9 /* E["E"] */).toString();
diff --git a/tests/baselines/reference/constEnumPropertyAccess3.symbols b/tests/baselines/reference/constEnumPropertyAccess3.symbols
new file mode 100644
index 0000000000000..27fac59420724
--- /dev/null
+++ b/tests/baselines/reference/constEnumPropertyAccess3.symbols
@@ -0,0 +1,80 @@
+//// [tests/cases/conformance/constEnums/constEnumPropertyAccess3.ts] ////
+
+=== constEnumPropertyAccess3.ts ===
+const enum E {
+>E : Symbol(E, Decl(constEnumPropertyAccess3.ts, 0, 0))
+
+    A = ~1,
+>A : Symbol(E.A, Decl(constEnumPropertyAccess3.ts, 0, 14))
+
+    B = -1,
+>B : Symbol(E.B, Decl(constEnumPropertyAccess3.ts, 1, 11))
+
+    C = ~(1 + 1),
+>C : Symbol(E.C, Decl(constEnumPropertyAccess3.ts, 2, 11))
+
+    D = -(1 + 2),
+>D : Symbol(E.D, Decl(constEnumPropertyAccess3.ts, 3, 17))
+
+    E = 1 - 10,
+>E : Symbol(E.E, Decl(constEnumPropertyAccess3.ts, 4, 17))
+}
+
+E.A.toString();
+>E.A.toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+>E.A : Symbol(E.A, Decl(constEnumPropertyAccess3.ts, 0, 14))
+>E : Symbol(E, Decl(constEnumPropertyAccess3.ts, 0, 0))
+>A : Symbol(E.A, Decl(constEnumPropertyAccess3.ts, 0, 14))
+>toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+
+E.B.toString();
+>E.B.toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+>E.B : Symbol(E.B, Decl(constEnumPropertyAccess3.ts, 1, 11))
+>E : Symbol(E, Decl(constEnumPropertyAccess3.ts, 0, 0))
+>B : Symbol(E.B, Decl(constEnumPropertyAccess3.ts, 1, 11))
+>toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+
+E.C.toString();
+>E.C.toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+>E.C : Symbol(E.C, Decl(constEnumPropertyAccess3.ts, 2, 11))
+>E : Symbol(E, Decl(constEnumPropertyAccess3.ts, 0, 0))
+>C : Symbol(E.C, Decl(constEnumPropertyAccess3.ts, 2, 11))
+>toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+
+E.D.toString();
+>E.D.toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+>E.D : Symbol(E.D, Decl(constEnumPropertyAccess3.ts, 3, 17))
+>E : Symbol(E, Decl(constEnumPropertyAccess3.ts, 0, 0))
+>D : Symbol(E.D, Decl(constEnumPropertyAccess3.ts, 3, 17))
+>toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+
+E["A"].toString();
+>E["A"].toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+>E : Symbol(E, Decl(constEnumPropertyAccess3.ts, 0, 0))
+>"A" : Symbol(E.A, Decl(constEnumPropertyAccess3.ts, 0, 14))
+>toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+
+E["B"].toString();
+>E["B"].toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+>E : Symbol(E, Decl(constEnumPropertyAccess3.ts, 0, 0))
+>"B" : Symbol(E.B, Decl(constEnumPropertyAccess3.ts, 1, 11))
+>toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+
+E["C"].toString();
+>E["C"].toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+>E : Symbol(E, Decl(constEnumPropertyAccess3.ts, 0, 0))
+>"C" : Symbol(E.C, Decl(constEnumPropertyAccess3.ts, 2, 11))
+>toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+
+E["D"].toString();
+>E["D"].toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+>E : Symbol(E, Decl(constEnumPropertyAccess3.ts, 0, 0))
+>"D" : Symbol(E.D, Decl(constEnumPropertyAccess3.ts, 3, 17))
+>toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+
+E["E"].toString();
+>E["E"].toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+>E : Symbol(E, Decl(constEnumPropertyAccess3.ts, 0, 0))
+>"E" : Symbol(E.E, Decl(constEnumPropertyAccess3.ts, 4, 17))
+>toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+
diff --git a/tests/baselines/reference/constEnumPropertyAccess3.types b/tests/baselines/reference/constEnumPropertyAccess3.types
new file mode 100644
index 0000000000000..85d0460f9b600
--- /dev/null
+++ b/tests/baselines/reference/constEnumPropertyAccess3.types
@@ -0,0 +1,111 @@
+//// [tests/cases/conformance/constEnums/constEnumPropertyAccess3.ts] ////
+
+=== constEnumPropertyAccess3.ts ===
+const enum E {
+>E : E
+
+    A = ~1,
+>A : E.A
+>~1 : number
+>1 : 1
+
+    B = -1,
+>B : E.B
+>-1 : -1
+>1 : 1
+
+    C = ~(1 + 1),
+>C : E.C
+>~(1 + 1) : number
+>(1 + 1) : number
+>1 + 1 : number
+>1 : 1
+>1 : 1
+
+    D = -(1 + 2),
+>D : E.C
+>-(1 + 2) : number
+>(1 + 2) : number
+>1 + 2 : number
+>1 : 1
+>2 : 2
+
+    E = 1 - 10,
+>E : E.E
+>1 - 10 : number
+>1 : 1
+>10 : 10
+}
+
+E.A.toString();
+>E.A.toString() : string
+>E.A.toString : (radix?: number) => string
+>E.A : E.A
+>E : typeof E
+>A : E.A
+>toString : (radix?: number) => string
+
+E.B.toString();
+>E.B.toString() : string
+>E.B.toString : (radix?: number) => string
+>E.B : E.B
+>E : typeof E
+>B : E.B
+>toString : (radix?: number) => string
+
+E.C.toString();
+>E.C.toString() : string
+>E.C.toString : (radix?: number) => string
+>E.C : E.C
+>E : typeof E
+>C : E.C
+>toString : (radix?: number) => string
+
+E.D.toString();
+>E.D.toString() : string
+>E.D.toString : (radix?: number) => string
+>E.D : E.C
+>E : typeof E
+>D : E.C
+>toString : (radix?: number) => string
+
+E["A"].toString();
+>E["A"].toString() : string
+>E["A"].toString : (radix?: number) => string
+>E["A"] : E.A
+>E : typeof E
+>"A" : "A"
+>toString : (radix?: number) => string
+
+E["B"].toString();
+>E["B"].toString() : string
+>E["B"].toString : (radix?: number) => string
+>E["B"] : E.B
+>E : typeof E
+>"B" : "B"
+>toString : (radix?: number) => string
+
+E["C"].toString();
+>E["C"].toString() : string
+>E["C"].toString : (radix?: number) => string
+>E["C"] : E.C
+>E : typeof E
+>"C" : "C"
+>toString : (radix?: number) => string
+
+E["D"].toString();
+>E["D"].toString() : string
+>E["D"].toString : (radix?: number) => string
+>E["D"] : E.C
+>E : typeof E
+>"D" : "D"
+>toString : (radix?: number) => string
+
+E["E"].toString();
+>E["E"].toString() : string
+>E["E"].toString : (radix?: number) => string
+>E["E"] : E.E
+>E : typeof E
+>"E" : "E"
+>toString : (radix?: number) => string
+
diff --git a/tests/baselines/reference/constEnumToStringNoComments.js b/tests/baselines/reference/constEnumToStringNoComments.js
index cffb3b1cbcb61..4ab485ee16635 100644
--- a/tests/baselines/reference/constEnumToStringNoComments.js
+++ b/tests/baselines/reference/constEnumToStringNoComments.js
@@ -31,9 +31,9 @@ var y0 = 0.5.toString();
 var y1 = 0.5.toString();
 var z0 = 2..toString();
 var z1 = 2..toString();
-var a0 = -1..toString();
-var a1 = -1..toString();
-var b0 = -1.5.toString();
-var b1 = -1.5.toString();
-var c0 = -1..toString();
-var c1 = -1..toString();
+var a0 = (-1).toString();
+var a1 = (-1).toString();
+var b0 = (-1.5).toString();
+var b1 = (-1.5).toString();
+var c0 = (-1).toString();
+var c1 = (-1).toString();
diff --git a/tests/baselines/reference/constEnumToStringWithComments.js b/tests/baselines/reference/constEnumToStringWithComments.js
index 23f656658025d..22d160b033af2 100644
--- a/tests/baselines/reference/constEnumToStringWithComments.js
+++ b/tests/baselines/reference/constEnumToStringWithComments.js
@@ -31,9 +31,9 @@ var y0 = 0.5 /* Foo.Y */.toString();
 var y1 = 0.5 /* Foo["Y"] */.toString();
 var z0 = 2 /* Foo.Z */.toString();
 var z1 = 2 /* Foo["Z"] */.toString();
-var a0 = -1 /* Foo.A */.toString();
-var a1 = -1 /* Foo["A"] */.toString();
-var b0 = -1.5 /* Foo.B */.toString();
-var b1 = -1.5 /* Foo["B"] */.toString();
-var c0 = -1 /* Foo.C */.toString();
-var c1 = -1 /* Foo["C"] */.toString();
+var a0 = (-1 /* Foo.A */).toString();
+var a1 = (-1 /* Foo["A"] */).toString();
+var b0 = (-1.5 /* Foo.B */).toString();
+var b1 = (-1.5 /* Foo["B"] */).toString();
+var c0 = (-1 /* Foo.C */).toString();
+var c1 = (-1 /* Foo["C"] */).toString();
diff --git a/tests/cases/conformance/constEnums/constEnumPropertyAccess3.ts b/tests/cases/conformance/constEnums/constEnumPropertyAccess3.ts
new file mode 100644
index 0000000000000..11eaaa10cbaed
--- /dev/null
+++ b/tests/cases/conformance/constEnums/constEnumPropertyAccess3.ts
@@ -0,0 +1,18 @@
+const enum E {
+    A = ~1,
+    B = -1,
+    C = ~(1 + 1),
+    D = -(1 + 2),
+    E = 1 - 10,
+}
+
+E.A.toString();
+E.B.toString();
+E.C.toString();
+E.D.toString();
+
+E["A"].toString();
+E["B"].toString();
+E["C"].toString();
+E["D"].toString();
+E["E"].toString();