diff --git a/packages/@aws-cdk/cdk/lib/token.ts b/packages/@aws-cdk/cdk/lib/token.ts
index d7d64df131c61..bc4f3dca4e971 100644
--- a/packages/@aws-cdk/cdk/lib/token.ts
+++ b/packages/@aws-cdk/cdk/lib/token.ts
@@ -93,16 +93,16 @@ export class Token {
    * on the string.
    */
   public toString(): string {
-    const valueType = typeof this.valueOrFunction;
     // Optimization: if we can immediately resolve this, don't bother
-    // registering a Token.
-    if (valueType === 'string' || valueType === 'number' || valueType === 'boolean') {
-      return this.valueOrFunction.toString();
+    // registering a Token (unless it's already a token).
+    if (typeof(this.valueOrFunction) === 'string') {
+      return this.valueOrFunction;
     }
 
     if (this.tokenStringification === undefined) {
       this.tokenStringification = TokenMap.instance().registerString(this, this.displayName);
     }
+
     return this.tokenStringification;
   }
 
@@ -139,9 +139,8 @@ export class Token {
    * is constructing a `FnJoin` or a `FnSelect` on it.
    */
   public toList(): string[] {
-    const valueType = typeof this.valueOrFunction;
-    if (valueType === 'string' || valueType === 'number' || valueType === 'boolean') {
-      throw this.newError('Got a literal Token value; only intrinsics can ever evaluate to lists.');
+    if (Array.isArray(this.valueOrFunction)) {
+      return this.valueOrFunction;
     }
 
     if (this.tokenListification === undefined) {
@@ -160,14 +159,13 @@ export class Token {
    * other operations can and probably will destroy the token-ness of the value.
    */
   public toNumber(): number {
+    // Optimization: if we can immediately resolve this, don't bother
+    // registering a Token.
+    if (typeof(this.valueOrFunction) === 'number') {
+      return this.valueOrFunction;
+    }
+
     if (this.tokenNumberification === undefined) {
-      const valueType = typeof this.valueOrFunction;
-      // Optimization: if we can immediately resolve this, don't bother
-      // registering a Token.
-      if (valueType === 'number') { return this.valueOrFunction; }
-      if (valueType !== 'function') {
-        throw this.newError(`Token value is not number or lazy, can't represent as number: ${this.valueOrFunction}`);
-      }
       this.tokenNumberification = TokenMap.instance().registerNumber(this);
     }
 
diff --git a/packages/@aws-cdk/cdk/test/test.tokens.ts b/packages/@aws-cdk/cdk/test/test.tokens.ts
index 1ea25183712e6..40cf95d468bf0 100644
--- a/packages/@aws-cdk/cdk/test/test.tokens.ts
+++ b/packages/@aws-cdk/cdk/test/test.tokens.ts
@@ -3,6 +3,7 @@ import { App as Root, findTokens, Fn, Stack, Token } from '../lib';
 import { createTokenDouble, extractTokenDouble } from '../lib/encoding';
 import { TokenMap } from '../lib/token-map';
 import { evaluateCFN } from './evaluate-cfn';
+import { func } from 'fast-check/*';
 
 export = {
   'resolve a plain old object should just return the object'(test: Test) {
@@ -467,7 +468,6 @@ export = {
 
     'can number-encode and resolve Token objects'(test: Test) {
       // GIVEN
-      const stack = new Stack();
       const x = new Token(() => 123);
 
       // THEN
@@ -475,7 +475,7 @@ export = {
       test.equal(true, Token.isToken(encoded), 'encoded number does not test as token');
 
       // THEN
-      const resolved = stack.node.resolve({ value: encoded });
+      const resolved = resolve({ value: encoded });
       test.deepEqual(resolved, { value: 123 });
 
       test.done();
@@ -522,6 +522,91 @@ export = {
     const token = fn1();
     test.throws(() => token.throwError('message!'), /Token created:/);
     test.done();
+  },
+
+  'type coercion': (() => {
+    const tests: any = { };
+
+    const inputs = [
+      () => 'lazy',
+      'a string',
+      1234,
+      { an_object: 1234 },
+      [ 1, 2, 3 ],
+      false
+    ];
+
+    for (const input of inputs) {
+      // GIVEN
+      const stringToken = new Token(input).toString();
+      const numberToken = new Token(input).toNumber();
+      const listToken = new Token(input).toList();
+
+      // THEN
+      const expected = typeof(input) === 'function' ? input() : input;
+
+      tests[`${input}<string>.toNumber()`] = (test: Test) => {
+        test.deepEqual(resolve(new Token(stringToken).toNumber()), expected);
+        test.done();
+      };
+
+      tests[`${input}<list>.toNumber()`] = (test: Test) => {
+        test.deepEqual(resolve(new Token(listToken).toNumber()), expected);
+        test.done();
+      };
+
+      tests[`${input}<number>.toNumber()`] = (test: Test) => {
+        test.deepEqual(resolve(new Token(numberToken).toNumber()), expected);
+        test.done();
+      };
+
+      tests[`${input}<string>.toString()`] = (test: Test) => {
+        test.deepEqual(resolve(new Token(stringToken).toString()), expected);
+        test.done();
+      };
+
+      tests[`${input}<list>.toString()`] = (test: Test) => {
+        test.deepEqual(resolve(new Token(listToken).toString()), expected);
+        test.done();
+      };
+
+      tests[`${input}<number>.toString()`] = (test: Test) => {
+        test.deepEqual(resolve(new Token(numberToken).toString()), expected);
+        test.done();
+      };
+
+      tests[`${input}<string>.toList()`] = (test: Test) => {
+        test.deepEqual(resolve(new Token(stringToken).toList()), expected);
+        test.done();
+      };
+
+      tests[`${input}<list>.toList()`] = (test: Test) => {
+        test.deepEqual(resolve(new Token(listToken).toList()), expected);
+        test.done();
+      };
+
+      tests[`${input}<number>.toList()`] = (test: Test) => {
+        test.deepEqual(resolve(new Token(numberToken).toList()), expected);
+        test.done();
+      };
+    }
+
+    return tests;
+  })(),
+
+  'toXxx short circuts if the input is of the same type': {
+    'toNumber(number)'(test: Test) {
+      test.deepEqual(new Token(123).toNumber(), 123);
+      test.done();
+    },
+    'toList(list)'(test: Test) {
+      test.deepEqual(new Token([1, 2, 3]).toList(), [1, 2, 3]);
+      test.done();
+    },
+    'toString(string)'(test: Test) {
+      test.deepEqual(new Token('string').toString(), 'string'),
+      test.done();
+    }
   }
 };