diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 441a880e0e39f..56c4d8a2114c9 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -48149,8 +48149,9 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         if (enumResult) return enumResult;
         const literalValue = (type as LiteralType).value;
         return typeof literalValue === "object" ? factory.createBigIntLiteral(literalValue) :
-            typeof literalValue === "number" ? factory.createNumericLiteral(literalValue) :
-            factory.createStringLiteral(literalValue);
+            typeof literalValue === "string" ? factory.createStringLiteral(literalValue) :
+            literalValue < 0 ? factory.createPrefixUnaryExpression(SyntaxKind.MinusToken, factory.createNumericLiteral(-literalValue)) :
+            factory.createNumericLiteral(literalValue);
     }
 
     function createLiteralConstValue(node: VariableDeclaration | PropertyDeclaration | PropertySignature | ParameterDeclaration, tracker: SymbolTracker) {
diff --git a/src/compiler/factory/nodeFactory.ts b/src/compiler/factory/nodeFactory.ts
index 0de2b201803d9..907ab3833b672 100644
--- a/src/compiler/factory/nodeFactory.ts
+++ b/src/compiler/factory/nodeFactory.ts
@@ -44,6 +44,7 @@ import {
     CaseOrDefaultClause,
     cast,
     CatchClause,
+    CharacterCodes,
     ClassDeclaration,
     ClassElement,
     ClassExpression,
@@ -1254,8 +1255,10 @@ export function createNodeFactory(flags: NodeFactoryFlags, baseFactory: BaseNode
 
     // @api
     function createNumericLiteral(value: string | number, numericLiteralFlags: TokenFlags = TokenFlags.None): NumericLiteral {
+        const text = typeof value === "number" ? value + "" : value;
+        Debug.assert(text.charCodeAt(0) !== CharacterCodes.minus, "Negative numbers should be created in combination with createPrefixUnaryExpression");
         const node = createBaseDeclaration<NumericLiteral>(SyntaxKind.NumericLiteral);
-        node.text = typeof value === "number" ? value + "" : value;
+        node.text = text;
         node.numericLiteralFlags = numericLiteralFlags;
         if (numericLiteralFlags & TokenFlags.BinaryOrOctalSpecifier) node.transformFlags |= TransformFlags.ContainsES2015;
         return node;
diff --git a/src/compiler/transformers/declarations.ts b/src/compiler/transformers/declarations.ts
index 45a5df4f0b95d..0f3479133ec55 100644
--- a/src/compiler/transformers/declarations.ts
+++ b/src/compiler/transformers/declarations.ts
@@ -1798,7 +1798,11 @@ export function transformDeclarations(context: TransformationContext) {
                         if (shouldStripInternal(m)) return;
                         // Rewrite enum values to their constants, if available
                         const constValue = resolver.getConstantValue(m);
-                        return preserveJsDoc(factory.updateEnumMember(m, m.name, constValue !== undefined ? typeof constValue === "string" ? factory.createStringLiteral(constValue) : factory.createNumericLiteral(constValue) : undefined), m);
+                        const newInitializer = constValue === undefined ? undefined
+                            : typeof constValue === "string" ? factory.createStringLiteral(constValue)
+                            : constValue < 0 ? factory.createPrefixUnaryExpression(SyntaxKind.MinusToken, factory.createNumericLiteral(-constValue))
+                            : factory.createNumericLiteral(constValue);
+                        return preserveJsDoc(factory.updateEnumMember(m, m.name, newInitializer), m);
                     })),
                 ));
             }
diff --git a/src/compiler/transformers/generators.ts b/src/compiler/transformers/generators.ts
index 39f9a967e0cb3..775075a6e8f6f 100644
--- a/src/compiler/transformers/generators.ts
+++ b/src/compiler/transformers/generators.ts
@@ -2524,7 +2524,7 @@ export function transformGenerators(context: TransformationContext): (x: SourceF
                 labelExpressions = [];
             }
 
-            const expression = factory.createNumericLiteral(-1);
+            const expression = factory.createNumericLiteral(Number.MAX_SAFE_INTEGER);
             if (labelExpressions[label] === undefined) {
                 labelExpressions[label] = [expression];
             }
diff --git a/src/compiler/transformers/ts.ts b/src/compiler/transformers/ts.ts
index ac5855d72c8de..0548a5bf0da9c 100644
--- a/src/compiler/transformers/ts.ts
+++ b/src/compiler/transformers/ts.ts
@@ -1901,7 +1901,9 @@ export function transformTypeScript(context: TransformationContext) {
     function transformEnumMemberDeclarationValue(member: EnumMember): Expression {
         const value = resolver.getConstantValue(member);
         if (value !== undefined) {
-            return typeof value === "string" ? factory.createStringLiteral(value) : factory.createNumericLiteral(value);
+            return typeof value === "string" ? factory.createStringLiteral(value) :
+                value < 0 ? factory.createPrefixUnaryExpression(SyntaxKind.MinusToken, factory.createNumericLiteral(-value)) :
+                factory.createNumericLiteral(value);
         }
         else {
             enableSubstitutionForNonQualifiedEnumMembers();
@@ -2687,7 +2689,7 @@ export function transformTypeScript(context: TransformationContext) {
             // 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))) :
+                constantValue < 0 ? factory.createPrefixUnaryExpression(SyntaxKind.MinusToken, factory.createNumericLiteral(-constantValue)) :
                 factory.createNumericLiteral(constantValue);
 
             if (!compilerOptions.removeComments) {