diff --git a/packages/jsii-calc/lib/compliance.ts b/packages/jsii-calc/lib/compliance.ts
index b5a0a7f858..a5194ccd75 100644
--- a/packages/jsii-calc/lib/compliance.ts
+++ b/packages/jsii-calc/lib/compliance.ts
@@ -1692,3 +1692,37 @@ export class WithPrivatePropertyInConstructor {
         return this.privateField === 'Success!';
     }
 }
+
+/**
+ * Verifies that singleton enums are handled correctly
+ *
+ * https://github.com/awslabs/jsii/issues/231
+ */
+export class SingletonString {
+    private constructor() { }
+
+    public isSingletonString(value: string): boolean {
+        return value === SingletonStringEnum.SingletonString;
+    }
+}
+/** A singleton string */
+export enum SingletonStringEnum {
+    /** 1337 */
+    SingletonString = '3L1T3!'
+}
+/**
+ * Verifies that singleton enums are handled correctly
+ *
+ * https://github.com/awslabs/jsii/issues/231
+ */
+export class SingletonInt {
+    private constructor() { }
+    public isSingletonInt(value: number): boolean {
+        return value === SingletonIntEnum.SingletonInt;
+    }
+}
+/** A singleton integer. */
+export enum SingletonIntEnum {
+    /** Elite! */
+    SingletonInt = 1337
+}
diff --git a/packages/jsii-calc/test/assembly.jsii b/packages/jsii-calc/test/assembly.jsii
index 5246a4694d..23f1aa9ffe 100644
--- a/packages/jsii-calc/test/assembly.jsii
+++ b/packages/jsii-calc/test/assembly.jsii
@@ -7121,6 +7121,132 @@
       ],
       "name": "SingleInstanceTwoTypes"
     },
+    "jsii-calc.SingletonInt": {
+      "assembly": "jsii-calc",
+      "docs": {
+        "remarks": "https://github.com/awslabs/jsii/issues/231",
+        "stability": "experimental",
+        "summary": "Verifies that singleton enums are handled correctly."
+      },
+      "fqn": "jsii-calc.SingletonInt",
+      "kind": "class",
+      "locationInModule": {
+        "filename": "lib/compliance.ts",
+        "line": 1718
+      },
+      "methods": [
+        {
+          "docs": {
+            "stability": "experimental"
+          },
+          "locationInModule": {
+            "filename": "lib/compliance.ts",
+            "line": 1720
+          },
+          "name": "isSingletonInt",
+          "parameters": [
+            {
+              "name": "value",
+              "type": {
+                "primitive": "number"
+              }
+            }
+          ],
+          "returns": {
+            "type": {
+              "primitive": "boolean"
+            }
+          }
+        }
+      ],
+      "name": "SingletonInt"
+    },
+    "jsii-calc.SingletonIntEnum": {
+      "assembly": "jsii-calc",
+      "docs": {
+        "stability": "experimental",
+        "summary": "A singleton integer."
+      },
+      "fqn": "jsii-calc.SingletonIntEnum",
+      "kind": "enum",
+      "locationInModule": {
+        "filename": "lib/compliance.ts",
+        "line": 1725
+      },
+      "members": [
+        {
+          "docs": {
+            "stability": "experimental",
+            "summary": "Elite!"
+          },
+          "name": "SingletonInt"
+        }
+      ],
+      "name": "SingletonIntEnum"
+    },
+    "jsii-calc.SingletonString": {
+      "assembly": "jsii-calc",
+      "docs": {
+        "remarks": "https://github.com/awslabs/jsii/issues/231",
+        "stability": "experimental",
+        "summary": "Verifies that singleton enums are handled correctly."
+      },
+      "fqn": "jsii-calc.SingletonString",
+      "kind": "class",
+      "locationInModule": {
+        "filename": "lib/compliance.ts",
+        "line": 1701
+      },
+      "methods": [
+        {
+          "docs": {
+            "stability": "experimental"
+          },
+          "locationInModule": {
+            "filename": "lib/compliance.ts",
+            "line": 1704
+          },
+          "name": "isSingletonString",
+          "parameters": [
+            {
+              "name": "value",
+              "type": {
+                "primitive": "string"
+              }
+            }
+          ],
+          "returns": {
+            "type": {
+              "primitive": "boolean"
+            }
+          }
+        }
+      ],
+      "name": "SingletonString"
+    },
+    "jsii-calc.SingletonStringEnum": {
+      "assembly": "jsii-calc",
+      "docs": {
+        "stability": "experimental",
+        "summary": "A singleton string."
+      },
+      "fqn": "jsii-calc.SingletonStringEnum",
+      "kind": "enum",
+      "locationInModule": {
+        "filename": "lib/compliance.ts",
+        "line": 1709
+      },
+      "members": [
+        {
+          "docs": {
+            "stability": "experimental",
+            "summary": "1337."
+          },
+          "name": "SingletonString"
+        }
+      ],
+      "name": "SingletonStringEnum"
+    },
     "jsii-calc.StableClass": {
       "assembly": "jsii-calc",
       "docs": {
@@ -8648,5 +8774,5 @@
     }
   },
   "version": "0.11.2",
-  "fingerprint": "eQpFH3EHC2GlCSnThymTxnuO9HyZBFvsvddZqu1Fy+8="
+  "fingerprint": "5TwMNffhxUueZQEAGZG6+JIfS6jcTwCJWc9vixH5aLc="
 }
diff --git a/packages/jsii/lib/assembler.ts b/packages/jsii/lib/assembler.ts
index 5bf1b68990..860f752d3c 100644
--- a/packages/jsii/lib/assembler.ts
+++ b/packages/jsii/lib/assembler.ts
@@ -735,11 +735,17 @@ export class Assembler implements Emitter {
       LOG.trace(`Processing enum: ${colors.gray(ctx.namespace.join('.'))}.${colors.cyan(type.symbol.name)}`);
     }
 
-    if (_hasInternalJsDocTag(type.symbol)) {
+    // Forcefully resolving to the EnumDeclaration symbol for single-valued enums
+    const symbol: ts.Symbol = type.isLiteral() ? (type.symbol as any).parent : type.symbol;
+    if (!symbol) {
+      throw new Error(`Unable to resolve enum declaration for ${type.symbol.name}!`);
+    }
+
+    if (_hasInternalJsDocTag(symbol)) {
       return undefined;
     }
 
-    const decl = type.symbol.valueDeclaration;
+    const decl = symbol.valueDeclaration;
     const flags = ts.getCombinedModifierFlags(decl);
     // tslint:disable-next-line:no-bitwise
     if (flags & ts.ModifierFlags.Const) {
@@ -748,19 +754,20 @@ export class Assembler implements Emitter {
         `Exported enum cannot be declared 'const'`);
     }
 
-    const docs = this._visitDocumentation(type.symbol, ctx);
+    const docs = this._visitDocumentation(symbol, ctx);
 
     const typeContext = ctx.replaceStability(docs && docs.stability);
+    const members = type.isUnion() ? type.types : [type];
 
     const jsiiType: spec.EnumType = {
       assembly: this.projectInfo.name,
-      fqn: `${[this.projectInfo.name, ...ctx.namespace].join('.')}.${type.symbol.name}`,
+      fqn: `${[this.projectInfo.name, ...ctx.namespace].join('.')}.${symbol.name}`,
       kind: spec.TypeKind.Enum,
-      members: ((type as ts.UnionType).types || []).map(m => ({
+      members: members.map(m => ({
         name: m.symbol.name,
         docs: this._visitDocumentation(m.symbol, typeContext),
       })),
-      name: type.symbol.name,
+      name: symbol.name,
       namespace: ctx.namespace.length > 0 ? ctx.namespace.join('.') : undefined,
       docs
     };