diff --git a/CHANGELOG.unreleased.md b/CHANGELOG.unreleased.md
index 4e84dc42..3e144431 100644
--- a/CHANGELOG.unreleased.md
+++ b/CHANGELOG.unreleased.md
@@ -87,15 +87,26 @@ Previous versions format text with whitespace after JSX incorrectly in mdx, this
 </Hello> 123
 ```
 
-#### TypeScript/Flow: Union types inside of tuples ([#6381] by [@squidfunk])
+#### TypeScript/Flow: Union types inside tuples ([#6381] by [@squidfunk], [#6605] by [@thorn0])
 
-Previous versions would double-indent multi-line union types inside of
-tuples for TypeScipt and Flow and add a new line:
+Previous versions would double-indent multi-line union types inside
+tuples for TypeScript and Flow and add an empty line:
 
 <!-- prettier-ignore -->
 ```ts
 // Input
+type A = [
+  | AAAAAAAAAAAAAAAAAAAAAA
+  | BBBBBBBBBBBBBBBBBBBBBB
+  | CCCCCCCCCCCCCCCCCCCCCC
+  | DDDDDDDDDDDDDDDDDDDDDD
+]
+
 type B = [
+  | AAAAAAAAAAAAAAAAAAAAAA
+  | BBBBBBBBBBBBBBBBBBBBBB
+  | CCCCCCCCCCCCCCCCCCCCCC
+  | DDDDDDDDDDDDDDDDDDDDDD,
   | AAAAAAAAAAAAAAAAAAAAAA
   | BBBBBBBBBBBBBBBBBBBBBB
   | CCCCCCCCCCCCCCCCCCCCCC
@@ -108,8 +119,21 @@ type C = [
 ]
 
 // Output (Prettier stable)
+type A = [
+
+    | AAAAAAAAAAAAAAAAAAAAAA
+    | BBBBBBBBBBBBBBBBBBBBBB
+    | CCCCCCCCCCCCCCCCCCCCCC
+    | DDDDDDDDDDDDDDDDDDDDDD
+];
+
 type B = [
 
+    | AAAAAAAAAAAAAAAAAAAAAA
+    | BBBBBBBBBBBBBBBBBBBBBB
+    | CCCCCCCCCCCCCCCCCCCCCC
+    | DDDDDDDDDDDDDDDDDDDDDD,
+
     | AAAAAAAAAAAAAAAAAAAAAA
     | BBBBBBBBBBBBBBBBBBBBBB
     | CCCCCCCCCCCCCCCCCCCCCC
@@ -124,24 +148,39 @@ type C = [
           | BBBBBBBBBBBBBBBBBBBBBB
           | CCCCCCCCCCCCCCCCCCCCCC
           | DDDDDDDDDDDDDDDDDDDDDD
-    ]
+      ]
     | [
 
           | AAAAAAAAAAAAAAAAAAAAAA
           | BBBBBBBBBBBBBBBBBBBBBB
           | CCCCCCCCCCCCCCCCCCCCCC
           | DDDDDDDDDDDDDDDDDDDDDD
-    ]
+      ]
 ];
 
 // Output (Prettier master)
-type B = [
+type A = [
   | AAAAAAAAAAAAAAAAAAAAAA
   | BBBBBBBBBBBBBBBBBBBBBB
   | CCCCCCCCCCCCCCCCCCCCCC
   | DDDDDDDDDDDDDDDDDDDDDD
 ];
 
+type B = [
+  (
+    | AAAAAAAAAAAAAAAAAAAAAA
+    | BBBBBBBBBBBBBBBBBBBBBB
+    | CCCCCCCCCCCCCCCCCCCCCC
+    | DDDDDDDDDDDDDDDDDDDDDD
+  ),
+  (
+    | AAAAAAAAAAAAAAAAAAAAAA
+    | BBBBBBBBBBBBBBBBBBBBBB
+    | CCCCCCCCCCCCCCCCCCCCCC
+    | DDDDDDDDDDDDDDDDDDDDDD
+  )
+];
+
 type C = [
   | [
       | AAAAAAAAAAAAAAAAAAAAAA
@@ -813,13 +852,13 @@ Previously, the flag was not applied on html attributes.
 <div class='a-class-name'></div>
 ```
 
-#### TypeScript: Fix incorrectly removes double parentheses around types ([#6604] by [@sosukesuzuki])
+#### TypeScript: sometimes double parentheses around types were removed incorrectly ([#6604] by [@sosukesuzuki])
 
 <!-- prettier-ignore -->
 ```ts
 // Input
 type A = 0 extends ((1 extends 2  ? 3 : 4)) ? 5 : 6;
-type B = ((0 extends 1 ? 2 : 3)) extends 4 ? 5 : 6:
+type B = ((0 extends 1 ? 2 : 3)) extends 4 ? 5 : 6;
 type C = ((number | string))["toString"];
 type D = ((keyof T1))["foo"];
 
@@ -887,6 +926,7 @@ function doSmth() {
 [#6377]: https://github.com/prettier/prettier/pull/6377
 [#6604]: https://github.com/prettier/prettier/pull/6604
 [#6496]: https://github.com/prettier/prettier/pull/6496
+[#6605]: https://github.com/prettier/prettier/pull/6605
 [@brainkim]: https://github.com/brainkim
 [@duailibe]: https://github.com/duailibe
 [@gavinjoyce]: https://github.com/gavinjoyce
diff --git a/src/language-js/clean.js b/src/language-js/clean.js
index b058c8cf..ee1209be 100644
--- a/src/language-js/clean.js
+++ b/src/language-js/clean.js
@@ -60,20 +60,6 @@ function clean(ast, newObj, parent) {
     delete newObj.specifiers;
   }
 
-  // (TypeScript) bypass TSParenthesizedType
-  if (ast.type === "TSParenthesizedType") {
-    return newObj.typeAnnotation;
-  }
-
-  // (TypeScript) Bypass `& foo` and `| foo` into `foo`
-  // https://github.com/microsoft/TypeScript/issues/30995
-  if (
-    (ast.type === "TSIntersectionType" || ast.type === "TSUnionType") &&
-    ast.types.length === 1
-  ) {
-    return newObj.types[0];
-  }
-
   // We convert <div></div> to <div />
   if (ast.type === "JSXOpeningElement") {
     delete newObj.selfClosing;
diff --git a/src/language-js/needs-parens.js b/src/language-js/needs-parens.js
index d0f4b79e..0c0ec43e 100644
--- a/src/language-js/needs-parens.js
+++ b/src/language-js/needs-parens.js
@@ -380,48 +380,6 @@ function needsParens(path, options) {
           return false;
       }
 
-    case "TSParenthesizedType": {
-      const grandParent = path.getParentNode(1);
-
-      /**
-       * const foo = (): (() => void) => (): void => null;
-       *                 ^          ^
-       */
-      if (
-        getUnparenthesizedNode(node).type === "TSFunctionType" &&
-        parent.type === "TSTypeAnnotation" &&
-        grandParent.type === "ArrowFunctionExpression" &&
-        grandParent.returnType === parent
-      ) {
-        return true;
-      }
-
-      if (
-        (parent.type === "TSTypeParameter" ||
-          parent.type === "TypeParameter" ||
-          parent.type === "TSTypeAliasDeclaration" ||
-          parent.type === "TSTypeAnnotation" ||
-          parent.type === "TSParenthesizedType" ||
-          parent.type === "TSTypeParameterInstantiation") &&
-        (grandParent.type !== "TSTypeOperator" &&
-          grandParent.type !== "TSOptionalType")
-      ) {
-        return false;
-      }
-      // Delegate to inner TSParenthesizedType
-      if (
-        node.typeAnnotation.type === "TSParenthesizedType" &&
-        parent.type !== "TSArrayType" &&
-        parent.type !== "TSIndexedAccessType" &&
-        parent.type !== "TSConditionalType" &&
-        parent.type !== "TSIntersectionType" &&
-        parent.type !== "TSUnionType"
-      ) {
-        return false;
-      }
-      return true;
-    }
-
     case "SequenceExpression":
       switch (parent.type) {
         case "ReturnStatement":
@@ -486,6 +444,36 @@ function needsParens(path, options) {
           return false;
       }
 
+    case "TSConditionalType":
+      if (parent.type === "TSConditionalType" && node === parent.extendsType) {
+        return true;
+      }
+    // fallthrough
+    case "TSFunctionType":
+    case "TSConstructorType":
+      if (parent.type === "TSConditionalType" && node === parent.checkType) {
+        return true;
+      }
+    // fallthrough
+    case "TSUnionType":
+    case "TSIntersectionType":
+      if (
+        parent.type === "TSUnionType" ||
+        parent.type === "TSIntersectionType"
+      ) {
+        return true;
+      }
+    // fallthrough
+    case "TSTypeOperator":
+    case "TSInferType":
+      return (
+        parent.type === "TSArrayType" ||
+        parent.type === "TSOptionalType" ||
+        parent.type === "TSRestType" ||
+        (parent.type === "TSIndexedAccessType" && node === parent.objectType) ||
+        parent.type === "TSTypeOperator"
+      );
+
     case "ArrayTypeAnnotation":
       return parent.type === "NullableTypeAnnotation";
 
@@ -790,12 +778,6 @@ function isStatement(node) {
   );
 }
 
-function getUnparenthesizedNode(node) {
-  return node.type === "TSParenthesizedType"
-    ? getUnparenthesizedNode(node.typeAnnotation)
-    : node;
-}
-
 function endsWithRightBracket(node) {
   switch (node.type) {
     case "ObjectExpression":
diff --git a/src/language-js/postprocess.js b/src/language-js/postprocess.js
index cdd12d36..b7fcc9ed 100644
--- a/src/language-js/postprocess.js
+++ b/src/language-js/postprocess.js
@@ -2,10 +2,10 @@
 
 const { getLast } = require("../common/util");
 
-// fix unexpected locEnd caused by --no-semi style
 function postprocess(ast, options) {
   visitNode(ast, node => {
     switch (node.type) {
+      // fix unexpected locEnd caused by --no-semi style
       case "VariableDeclaration": {
         const lastDeclaration = getLast(node.declarations);
         if (lastDeclaration && lastDeclaration.init) {
@@ -13,6 +13,20 @@ function postprocess(ast, options) {
         }
         break;
       }
+      // remove redundant TypeScript nodes
+      case "TSParenthesizedType": {
+        return node.typeAnnotation;
+      }
+      case "TSUnionType":
+      case "TSIntersectionType":
+        if (node.types.length === 1) {
+          // override loc, so that comments are attached properly
+          return Object.assign({}, node.types[0], {
+            loc: node.loc,
+            range: node.range
+          });
+        }
+        break;
     }
   });
 
@@ -44,14 +58,14 @@ function postprocess(ast, options) {
   }
 }
 
-function visitNode(node, fn) {
+function visitNode(node, fn, parent, property) {
   if (!node || typeof node !== "object") {
     return;
   }
 
   if (Array.isArray(node)) {
-    for (const subNode of node) {
-      visitNode(subNode, fn);
+    for (let i = 0; i < node.length; i++) {
+      visitNode(node[i], fn, node, i);
     }
     return;
   }
@@ -61,10 +75,14 @@ function visitNode(node, fn) {
   }
 
   for (const key of Object.keys(node)) {
-    visitNode(node[key], fn);
+    visitNode(node[key], fn, node, key);
   }
 
-  fn(node);
+  const replacement = fn(node);
+
+  if (replacement) {
+    parent[property] = replacement;
+  }
 }
 
 module.exports = postprocess;
diff --git a/src/language-js/printer-estree.js b/src/language-js/printer-estree.js
index 8f78497b..23726fca 100644
--- a/src/language-js/printer-estree.js
+++ b/src/language-js/printer-estree.js
@@ -2820,32 +2820,21 @@ function printPathNoParens(path, options, print, args) {
         join(concat([line, "| "]), printed)
       ]);
 
-      let hasParens;
-
-      if (n.type === "TSUnionType") {
-        const grandParent = path.getNode(2);
-        const greatGrandParent = path.getParentNode(2);
-        const greatGreatGrandParent = path.getParentNode(3);
-
-        hasParens =
-          (parent.type === "TSParenthesizedType" &&
-            (grandParent.type === "TSAsExpression" ||
-              grandParent.type === "TSUnionType" ||
-              grandParent.type === "TSIntersectionType" ||
-              grandParent.type === "TSTypeOperator" ||
-              grandParent.type === "TSArrayType" ||
-              grandParent.type === "TSTupleType")) ||
-          (greatGrandParent &&
-            greatGrandParent.type === "TSParenthesizedType" &&
-            greatGreatGrandParent &&
-            (greatGreatGrandParent.type === "TSUnionType" ||
-              greatGreatGrandParent.type === "TSIntersectionType"));
-      } else {
-        hasParens = pathNeedsParens(path, options);
+      if (pathNeedsParens(path, options)) {
+        return group(concat([indent(code), softline]));
       }
 
-      if (hasParens) {
-        return group(concat([indent(code), softline]));
+      if (
+        (parent.type === "TupleTypeAnnotation" && parent.types.length > 1) ||
+        (parent.type === "TSTupleType" && parent.elementTypes.length > 1)
+      ) {
+        return group(
+          concat([
+            indent(concat([ifBreak(concat(["(", softline])), code])),
+            softline,
+            ifBreak(")")
+          ])
+        );
       }
 
       return group(shouldIndent ? indent(code) : code);
@@ -3173,9 +3162,6 @@ function printPathNoParens(path, options, print, args) {
       ]);
     case "TSTypeQuery":
       return concat(["typeof ", path.call(print, "exprName")]);
-    case "TSParenthesizedType": {
-      return path.call(print, "typeAnnotation");
-    }
     case "TSIndexSignature": {
       const parent = path.getParentNode();
 
diff --git a/src/main/comments.js b/src/main/comments.js
index 3f5d776d..895dce48 100644
--- a/src/main/comments.js
+++ b/src/main/comments.js
@@ -320,8 +320,8 @@ function breakTies(tiesToBreak, text, options) {
     assert.strictEqual(comment.precedingNode, precedingNode);
     assert.strictEqual(comment.followingNode, followingNode);
 
-    const gap = text.slice(options.locEnd(comment), gapEndPos).trim();
-    if (gap === "" || /^\(+$/.test(gap)) {
+    const gap = text.slice(options.locEnd(comment), gapEndPos);
+    if (/^[\s(]*$/.test(gap)) {
       gapEndPos = options.locStart(comment);
     } else {
       // The gap string contained something other than whitespace or open
diff --git a/tests/typescript/conformance/types/union/__snapshots__/jsfmt.spec.js.snap b/tests/typescript/conformance/types/union/__snapshots__/jsfmt.spec.js.snap
index 1271da85..e9e5c74a 100644
--- a/tests/typescript/conformance/types/union/__snapshots__/jsfmt.spec.js.snap
+++ b/tests/typescript/conformance/types/union/__snapshots__/jsfmt.spec.js.snap
@@ -469,7 +469,6 @@ printWidth: 80
 class C { }
 class D extends C { foo() { } }
 var x: C;
-var x: | C;
 var x : C | D;
 
 // A | B is equivalent to B | A.
@@ -492,7 +491,6 @@ class D extends C {
   foo() {}
 }
 var x: C;
-var x: C;
 var x: C | D;
 
 // A | B is equivalent to B | A.
diff --git a/tests/typescript/conformance/types/union/unionTypeEquivalence.ts b/tests/typescript/conformance/types/union/unionTypeEquivalence.ts
index b9c78c75..821eb35d 100644
--- a/tests/typescript/conformance/types/union/unionTypeEquivalence.ts
+++ b/tests/typescript/conformance/types/union/unionTypeEquivalence.ts
@@ -2,7 +2,6 @@
 class C { }
 class D extends C { foo() { } }
 var x: C;
-var x: | C;
 var x : C | D;
 
 // A | B is equivalent to B | A.
diff --git a/tests/typescript_conditional_types/__snapshots__/jsfmt.spec.js.snap b/tests/typescript_conditional_types/__snapshots__/jsfmt.spec.js.snap
index 34f70876..e06f96ae 100644
--- a/tests/typescript_conditional_types/__snapshots__/jsfmt.spec.js.snap
+++ b/tests/typescript_conditional_types/__snapshots__/jsfmt.spec.js.snap
@@ -33,6 +33,16 @@ type Type06 = ((0 extends 1 ? 2 : 3)) extends 4 ? 5 : 6;
 type Type07 = (((0 extends 1 ? 2 : 3))) extends 4 ? 5 : 6;
 type Type08 = ((((0 extends 1 ? 2 : 3)))) extends 4 ? 5 : 6;
 
+type T1 = () => void extends T ? U : V;
+type T1a = () => (void extends T ? U : V);
+type T1b = () => (void) extends T ? U : V;
+type T2 = (() => void) extends T ? U : V;
+
+type U1 = new () => X extends T ? U : V;
+type U1a = new () => (X extends T ? U : V);
+type U1b = new () => (X) extends T ? U : V;
+type U2 = (new () => X) extends T ? U : V;
+
 =====================================output=====================================
 export type DeepReadonly<T> = T extends any[]
   ? DeepReadonlyArray<T[number]>
@@ -71,6 +81,16 @@ type Type06 = (0 extends 1 ? 2 : 3) extends 4 ? 5 : 6;
 type Type07 = (0 extends 1 ? 2 : 3) extends 4 ? 5 : 6;
 type Type08 = (0 extends 1 ? 2 : 3) extends 4 ? 5 : 6;
 
+type T1 = () => void extends T ? U : V;
+type T1a = () => void extends T ? U : V;
+type T1b = () => void extends T ? U : V;
+type T2 = (() => void) extends T ? U : V;
+
+type U1 = new () => X extends T ? U : V;
+type U1a = new () => X extends T ? U : V;
+type U1b = new () => X extends T ? U : V;
+type U2 = (new () => X) extends T ? U : V;
+
 ================================================================================
 `;
 
@@ -82,6 +102,12 @@ printWidth: 80
 =====================================input======================================
 type TestReturnType<T extends (...args: any[]) => any> = T extends (...args: any[]) => infer R ? R : any;
 
+type Unpacked<T> =
+  T extends (infer U)[] ? U :
+  T extends (...args: any[]) => infer U ? U :
+  T extends Promise<infer U> ? U :
+  T;
+
 =====================================output=====================================
 type TestReturnType<T extends (...args: any[]) => any> = T extends (
   ...args: any[]
@@ -89,5 +115,13 @@ type TestReturnType<T extends (...args: any[]) => any> = T extends (
   ? R
   : any;
 
+type Unpacked<T> = T extends (infer U)[]
+  ? U
+  : T extends (...args: any[]) => infer U
+  ? U
+  : T extends Promise<infer U>
+  ? U
+  : T;
+
 ================================================================================
 `;
diff --git a/tests/typescript_conditional_types/conditonal-types.ts b/tests/typescript_conditional_types/conditonal-types.ts
index e5147c52..b2ce6ad0 100644
--- a/tests/typescript_conditional_types/conditonal-types.ts
+++ b/tests/typescript_conditional_types/conditonal-types.ts
@@ -24,3 +24,13 @@ type Type05 = (0 extends 1 ? 2 : 3) extends 4 ? 5 : 6;
 type Type06 = ((0 extends 1 ? 2 : 3)) extends 4 ? 5 : 6;
 type Type07 = (((0 extends 1 ? 2 : 3))) extends 4 ? 5 : 6;
 type Type08 = ((((0 extends 1 ? 2 : 3)))) extends 4 ? 5 : 6;
+
+type T1 = () => void extends T ? U : V;
+type T1a = () => (void extends T ? U : V);
+type T1b = () => (void) extends T ? U : V;
+type T2 = (() => void) extends T ? U : V;
+
+type U1 = new () => X extends T ? U : V;
+type U1a = new () => (X extends T ? U : V);
+type U1b = new () => (X) extends T ? U : V;
+type U2 = (new () => X) extends T ? U : V;
diff --git a/tests/typescript_conditional_types/infer-type.ts b/tests/typescript_conditional_types/infer-type.ts
index ed8e81c8..eb20f81c 100644
--- a/tests/typescript_conditional_types/infer-type.ts
+++ b/tests/typescript_conditional_types/infer-type.ts
@@ -1 +1,7 @@
 type TestReturnType<T extends (...args: any[]) => any> = T extends (...args: any[]) => infer R ? R : any;
+
+type Unpacked<T> =
+  T extends (infer U)[] ? U :
+  T extends (...args: any[]) => infer U ? U :
+  T extends Promise<infer U> ? U :
+  T;
diff --git a/tests/typescript_intersection/__snapshots__/jsfmt.spec.js.snap b/tests/typescript_intersection/__snapshots__/jsfmt.spec.js.snap
index 4a1fd0b2..8c7b31db 100644
--- a/tests/typescript_intersection/__snapshots__/jsfmt.spec.js.snap
+++ b/tests/typescript_intersection/__snapshots__/jsfmt.spec.js.snap
@@ -11,12 +11,90 @@ type B = ((number | string)) & boolean;
 type C = (((number | string))) & boolean;
 type D = ((((number | string)))) & boolean;
 
+let b1 : C;
+let b2 : & C;
+let b3 : (& C);
+let b4 : & (C);
+let b5 : (& (C));
+let b6 : /*1*/ & C;
+let b7 : /*1*/ & (C);
+let b8 : /*1*/ (& C);
+let b9 : (/*1*/ & C);
+let b10: /*1*/ & /*2*/ C;
+let b11: /*1*/ (& /*2*/ C);
+
+let bb1: /*1*/ & /*2*/ C & D;
+let bb2: /*1*/ & /*2*/ C & /*3*/ D;
+let bb3: /*1*/ & /*2*/ C & /*3*/ D /*5*/;
+
+type B2  = & C;
+type B3  = (& C);
+type B4  = & (C);
+type B5  = (& (C));
+type B6  = /*1*/ & C;
+type B7  = /*1*/ & (C);
+type B8  = /*1*/ (& C);
+type B9  = (/*1*/ & C);
+type B10 = /*1*/ & /*2*/ C;
+type B11 = /*1*/ (& /*2*/ C);
+type B12 = /*1*/ & ( (C));
+
+type Bb1 = /*1*/ & /*2*/ C & D;
+type Bb2 = /*1*/ & /*2*/ C & /*3*/ D;
+type Bb3 = /*1*/ & /*2*/ C & /*3*/ D /*4*/;
+
+type D1 = /*1*/ | a & b;
+type D2 = /*1*/ | a & (b);
+type D3 = /*1*/ | a & (| b);
+type D4 = /*1*/ | (a & b);
+type D5 = /*1*/ (| a & b);
+type D6 /*0*/ = /*1*/ (| a & b);
+
 =====================================output=====================================
 type A = (number | string) & boolean;
 type B = (number | string) & boolean;
 type C = (number | string) & boolean;
 type D = (number | string) & boolean;
 
+let b1: C;
+let b2: C;
+let b3: C;
+let b4: C;
+let b5: C;
+let b6: /*1*/ C;
+let b7: /*1*/ C;
+let b8: /*1*/ C;
+let b9: /*1*/ C;
+let b10: /*1*/ /*2*/ C;
+let b11: /*1*/ /*2*/ C;
+
+let bb1: /*1*/ /*2*/ C & D;
+let bb2: /*1*/ /*2*/ C & /*3*/ D;
+let bb3: /*1*/ /*2*/ C & /*3*/ D /*5*/;
+
+type B2 = C;
+type B3 = C;
+type B4 = C;
+type B5 = C;
+type B6 = /*1*/ C;
+type B7 = /*1*/ C;
+type B8 = /*1*/ C;
+type B9 = /*1*/ C;
+type B10 = /*1*/ /*2*/ C;
+type B11 = /*1*/ /*2*/ C;
+type B12 = /*1*/ C;
+
+type Bb1 = /*1*/ /*2*/ C & D;
+type Bb2 = /*1*/ /*2*/ C & /*3*/ D;
+type Bb3 = /*1*/ /*2*/ C & /*3*/ D /*4*/;
+
+type D1 = /*1*/ a & b;
+type D2 = /*1*/ a & b;
+type D3 = /*1*/ a & b;
+type D4 = /*1*/ a & b;
+type D5 = /*1*/ a & b;
+type D6 /*0*/ = /*1*/ a & b;
+
 ================================================================================
 `;
 
@@ -32,11 +110,89 @@ type B = ((number | string)) & boolean;
 type C = (((number | string))) & boolean;
 type D = ((((number | string)))) & boolean;
 
+let b1 : C;
+let b2 : & C;
+let b3 : (& C);
+let b4 : & (C);
+let b5 : (& (C));
+let b6 : /*1*/ & C;
+let b7 : /*1*/ & (C);
+let b8 : /*1*/ (& C);
+let b9 : (/*1*/ & C);
+let b10: /*1*/ & /*2*/ C;
+let b11: /*1*/ (& /*2*/ C);
+
+let bb1: /*1*/ & /*2*/ C & D;
+let bb2: /*1*/ & /*2*/ C & /*3*/ D;
+let bb3: /*1*/ & /*2*/ C & /*3*/ D /*5*/;
+
+type B2  = & C;
+type B3  = (& C);
+type B4  = & (C);
+type B5  = (& (C));
+type B6  = /*1*/ & C;
+type B7  = /*1*/ & (C);
+type B8  = /*1*/ (& C);
+type B9  = (/*1*/ & C);
+type B10 = /*1*/ & /*2*/ C;
+type B11 = /*1*/ (& /*2*/ C);
+type B12 = /*1*/ & ( (C));
+
+type Bb1 = /*1*/ & /*2*/ C & D;
+type Bb2 = /*1*/ & /*2*/ C & /*3*/ D;
+type Bb3 = /*1*/ & /*2*/ C & /*3*/ D /*4*/;
+
+type D1 = /*1*/ | a & b;
+type D2 = /*1*/ | a & (b);
+type D3 = /*1*/ | a & (| b);
+type D4 = /*1*/ | (a & b);
+type D5 = /*1*/ (| a & b);
+type D6 /*0*/ = /*1*/ (| a & b);
+
 =====================================output=====================================
 type A = (number | string) & boolean
 type B = (number | string) & boolean
 type C = (number | string) & boolean
 type D = (number | string) & boolean
 
+let b1: C
+let b2: C
+let b3: C
+let b4: C
+let b5: C
+let b6: /*1*/ C
+let b7: /*1*/ C
+let b8: /*1*/ C
+let b9: /*1*/ C
+let b10: /*1*/ /*2*/ C
+let b11: /*1*/ /*2*/ C
+
+let bb1: /*1*/ /*2*/ C & D
+let bb2: /*1*/ /*2*/ C & /*3*/ D
+let bb3: /*1*/ /*2*/ C & /*3*/ D /*5*/
+
+type B2 = C
+type B3 = C
+type B4 = C
+type B5 = C
+type B6 = /*1*/ C
+type B7 = /*1*/ C
+type B8 = /*1*/ C
+type B9 = /*1*/ C
+type B10 = /*1*/ /*2*/ C
+type B11 = /*1*/ /*2*/ C
+type B12 = /*1*/ C
+
+type Bb1 = /*1*/ /*2*/ C & D
+type Bb2 = /*1*/ /*2*/ C & /*3*/ D
+type Bb3 = /*1*/ /*2*/ C & /*3*/ D /*4*/
+
+type D1 = /*1*/ a & b
+type D2 = /*1*/ a & b
+type D3 = /*1*/ a & b
+type D4 = /*1*/ a & b
+type D5 = /*1*/ a & b
+type D6 /*0*/ = /*1*/ a & b
+
 ================================================================================
 `;
diff --git a/tests/typescript_intersection/intersection-parens.ts b/tests/typescript_intersection/intersection-parens.ts
index a6077856..b19671ac 100644
--- a/tests/typescript_intersection/intersection-parens.ts
+++ b/tests/typescript_intersection/intersection-parens.ts
@@ -2,3 +2,42 @@ type A = (number | string) & boolean;
 type B = ((number | string)) & boolean;
 type C = (((number | string))) & boolean;
 type D = ((((number | string)))) & boolean;
+
+let b1 : C;
+let b2 : & C;
+let b3 : (& C);
+let b4 : & (C);
+let b5 : (& (C));
+let b6 : /*1*/ & C;
+let b7 : /*1*/ & (C);
+let b8 : /*1*/ (& C);
+let b9 : (/*1*/ & C);
+let b10: /*1*/ & /*2*/ C;
+let b11: /*1*/ (& /*2*/ C);
+
+let bb1: /*1*/ & /*2*/ C & D;
+let bb2: /*1*/ & /*2*/ C & /*3*/ D;
+let bb3: /*1*/ & /*2*/ C & /*3*/ D /*5*/;
+
+type B2  = & C;
+type B3  = (& C);
+type B4  = & (C);
+type B5  = (& (C));
+type B6  = /*1*/ & C;
+type B7  = /*1*/ & (C);
+type B8  = /*1*/ (& C);
+type B9  = (/*1*/ & C);
+type B10 = /*1*/ & /*2*/ C;
+type B11 = /*1*/ (& /*2*/ C);
+type B12 = /*1*/ & ( (C));
+
+type Bb1 = /*1*/ & /*2*/ C & D;
+type Bb2 = /*1*/ & /*2*/ C & /*3*/ D;
+type Bb3 = /*1*/ & /*2*/ C & /*3*/ D /*4*/;
+
+type D1 = /*1*/ | a & b;
+type D2 = /*1*/ | a & (b);
+type D3 = /*1*/ | a & (| b);
+type D4 = /*1*/ | (a & b);
+type D5 = /*1*/ (| a & b);
+type D6 /*0*/ = /*1*/ (| a & b);
diff --git a/tests/typescript_optional_type/__snapshots__/jsfmt.spec.js.snap b/tests/typescript_optional_type/__snapshots__/jsfmt.spec.js.snap
index 01af5d6b..fcf68d50 100644
--- a/tests/typescript_optional_type/__snapshots__/jsfmt.spec.js.snap
+++ b/tests/typescript_optional_type/__snapshots__/jsfmt.spec.js.snap
@@ -7,9 +7,11 @@ printWidth: 80
                                                                                 | printWidth
 =====================================input======================================
 type T = [("a" | "b")?];
+type TupleWithOptional = [number, (1 extends 2 ? string[] : number[])?];
 
 =====================================output=====================================
 type T = [("a" | "b")?];
+type TupleWithOptional = [number, (1 extends 2 ? string[] : number[])?];
 
 ================================================================================
 `;
diff --git a/tests/typescript_optional_type/complex.ts b/tests/typescript_optional_type/complex.ts
index f5c170a3..b6cda8b4 100644
--- a/tests/typescript_optional_type/complex.ts
+++ b/tests/typescript_optional_type/complex.ts
@@ -1 +1,2 @@
 type T = [("a" | "b")?];
+type TupleWithOptional = [number, (1 extends 2 ? string[] : number[])?];
diff --git a/tests/typescript_rest_type/__snapshots__/jsfmt.spec.js.snap b/tests/typescript_rest_type/__snapshots__/jsfmt.spec.js.snap
index fef6f895..1334dc24 100644
--- a/tests/typescript_rest_type/__snapshots__/jsfmt.spec.js.snap
+++ b/tests/typescript_rest_type/__snapshots__/jsfmt.spec.js.snap
@@ -1,5 +1,19 @@
 // Jest Snapshot v1, https://goo.gl/fbAQLP
 
+exports[`complex.ts 1`] = `
+====================================options=====================================
+parsers: ["typescript"]
+printWidth: 80
+                                                                                | printWidth
+=====================================input======================================
+type TupleWithRest = [number, ...(1 extends 2 ? string[] : number[])];
+
+=====================================output=====================================
+type TupleWithRest = [number, ...(1 extends 2 ? string[] : number[])];
+
+================================================================================
+`;
+
 exports[`simple.ts 1`] = `
 ====================================options=====================================
 parsers: ["typescript"]
diff --git a/tests/typescript_rest_type/complex.ts b/tests/typescript_rest_type/complex.ts
new file mode 100644
index 00000000..db303842
--- /dev/null
+++ b/tests/typescript_rest_type/complex.ts
@@ -0,0 +1 @@
+type TupleWithRest = [number, ...(1 extends 2 ? string[] : number[])];
diff --git a/tests/typescript_union/__snapshots__/jsfmt.spec.js.snap b/tests/typescript_union/__snapshots__/jsfmt.spec.js.snap
index 2cf4944c..2bb487bd 100644
--- a/tests/typescript_union/__snapshots__/jsfmt.spec.js.snap
+++ b/tests/typescript_union/__snapshots__/jsfmt.spec.js.snap
@@ -138,7 +138,7 @@ type State = {
 } & (
   | { discriminant: "FOO"; foo: any }
   | { discriminant: "BAR"; bar: any }
-  | { discriminant: "BAZ"; baz: any } 
+  | { discriminant: "BAZ"; baz: any }
 );
 
 const foo = [abc, def, ghi, jkl, mno, pqr, stu, vwx, yz] as (
@@ -169,6 +169,49 @@ const foo:
       | DDDDDDDDDDDDDDDDDDDDDD
     ) = bar;
 
+let a1 : C;
+let a2 : | C;
+let a3 : (| C);
+let a4 : | (C);
+let a5 : (| (C));
+let a6 : /*1*/ | C;
+let a7 : /*1*/ | (C);
+let a8 : /*1*/ (| C);
+let a9 : (/*1*/ | C);
+let a10: /*1*/ | /*2*/ C;
+let a11: /*1*/ (| /*2*/ C);
+
+let aa1: /*1*/ | /*2*/ C | D;
+let aa2: /*1*/ | /*2*/ C | /*3*/ D;
+let aa3: /*1*/ | /*2*/ C | /*3*/ D /*4*/;
+
+type A1  = C;
+type A2  = | C;
+type A3  = (| C);
+type A4  = | (C);
+type A5  = (| (C));
+type A6  = /*1*/ | C;
+type A7  = /*1*/ | (C);
+type A8  = /*1*/ (| C);
+type A9  = (/*1*/ | C);
+type A10 = /*1*/ | /*2*/ C;
+type A11 = /*1*/ (| /*2*/ C);
+type A12 = /*1*/ | ( (C));
+type A13 = /*1*/ ( (C));
+
+type Aa1 = /*1*/ | /*2*/ C | D;
+type Aa2 = /*1*/ | /*2*/ C | /*3*/ D;
+type Aa3 = /*1*/ | /*2*/ C | /*3*/ D /*4*/;
+
+type C1 = /*1*/ & a | b;
+type C2 = /*1*/ & a | (b);
+type C3 = /*1*/ & a | (& b);
+type C4 = /*1*/ & (a | b);
+type C5 = /*1*/ (& a | b);
+type C6 /*0*/ = /*1*/ (& a | b);
+
+type Ctor = (new () => X) | Y;
+
 =====================================output=====================================
 export type A =
   | aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
@@ -236,6 +279,49 @@ const foo:
       | DDDDDDDDDDDDDDDDDDDDDD
     ) = bar;
 
+let a1: C;
+let a2: C;
+let a3: C;
+let a4: C;
+let a5: C;
+let a6: /*1*/ C;
+let a7: /*1*/ C;
+let a8: /*1*/ C;
+let a9: /*1*/ C;
+let a10: /*1*/ /*2*/ C;
+let a11: /*1*/ /*2*/ C;
+
+let aa1: /*1*/ /*2*/ C | D;
+let aa2: /*1*/ /*2*/ C | /*3*/ D;
+let aa3: /*1*/ /*2*/ C | /*3*/ D /*4*/;
+
+type A1 = C;
+type A2 = C;
+type A3 = C;
+type A4 = C;
+type A5 = C;
+type A6 = /*1*/ C;
+type A7 = /*1*/ C;
+type A8 = /*1*/ C;
+type A9 = /*1*/ C;
+type A10 = /*1*/ /*2*/ C;
+type A11 = /*1*/ /*2*/ C;
+type A12 = /*1*/ C;
+type A13 = /*1*/ C;
+
+type Aa1 = /*1*/ /*2*/ C | D;
+type Aa2 = /*1*/ /*2*/ C | /*3*/ D;
+type Aa3 = /*1*/ /*2*/ C | /*3*/ D /*4*/;
+
+type C1 = /*1*/ a | b;
+type C2 = /*1*/ a | b;
+type C3 = /*1*/ a | b;
+type C4 = /*1*/ a | b;
+type C5 = /*1*/ a | b;
+type C6 /*0*/ = /*1*/ a | b;
+
+type Ctor = (new () => X) | Y;
+
 ================================================================================
 `;
 
@@ -284,6 +370,15 @@ type B = [
   | DDDDDDDDDDDDDDDDDDDDDD
 ]
 
+type B1 = [
+  (
+    | AAAAAAAAAAAAAAAAAAAAAA
+    | BBBBBBBBBBBBBBBBBBBBBB
+    | CCCCCCCCCCCCCCCCCCCCCC
+    | DDDDDDDDDDDDDDDDDDDDDD
+  )
+]
+
 type C = [
   | [AAAAAAAAAAAAAAAAAAAAAA | BBBBBBBBBBBBBBBBBBBBBB | CCCCCCCCCCCCCCCCCCCCCC | DDDDDDDDDDDDDDDDDDDDDD]
   | [AAAAAAAAAAAAAAAAAAAAAA | BBBBBBBBBBBBBBBBBBBBBB | CCCCCCCCCCCCCCCCCCCCCC | DDDDDDDDDDDDDDDDDDDDDD]
@@ -294,7 +389,7 @@ type D = [
   (AAAAAAAAAAAAAAAAAAAAAA | BBBBBBBBBBBBBBBBBBBBBB | CCCCCCCCCCCCCCCCCCCCCC | DDDDDDDDDDDDDDDDDDDDDD)
 ]
 
-type E = [
+type D1 = [
   (
     | AAAAAAAAAAAAAAAAAAAAAA
     | BBBBBBBBBBBBBBBBBBBBBB
@@ -308,6 +403,29 @@ type E = [
     | DDDDDDDDDDDDDDDDDDDDDD
   )
 ]
+
+type D2 = [
+  | AAAAAAAAAAAAAAAAAAAAAA
+  | BBBBBBBBBBBBBBBBBBBBBB
+  | CCCCCCCCCCCCCCCCCCCCCC
+  | DDDDDDDDDDDDDDDDDDDDDD,
+  | AAAAAAAAAAAAAAAAAAAAAA
+  | BBBBBBBBBBBBBBBBBBBBBB
+  | CCCCCCCCCCCCCCCCCCCCCC
+  | DDDDDDDDDDDDDDDDDDDDDD
+]
+
+type E = [ AA | BB, AA | BB ]
+
+type F = [
+  | AAAAAAAAAAAAAAAAAAAAAA
+  | BBBBBBBBBBBBBBBBBBBBBB
+  | CCCCCCCCCCCCCCCCCCCCCC
+  | DDDDDDDDDDDDDDDDDDDDDD,
+  | AAAAAAAAAAAAAAAAAAAAAA
+  | BBBBBBBBBBBBBBBBBBBBBB
+]
+
 =====================================output=====================================
 type A = [
   | AAAAAAAAAAAAAAAAAAAAAA
@@ -323,6 +441,13 @@ type B = [
   | DDDDDDDDDDDDDDDDDDDDDD
 ];
 
+type B1 = [
+  | AAAAAAAAAAAAAAAAAAAAAA
+  | BBBBBBBBBBBBBBBBBBBBBB
+  | CCCCCCCCCCCCCCCCCCCCCC
+  | DDDDDDDDDDDDDDDDDDDDDD
+];
+
 type C = [
   | [
       | AAAAAAAAAAAAAAAAAAAAAA
@@ -353,7 +478,7 @@ type D = [
   )
 ];
 
-type E = [
+type D1 = [
   (
     | AAAAAAAAAAAAAAAAAAAAAA
     | BBBBBBBBBBBBBBBBBBBBBB
@@ -368,5 +493,32 @@ type E = [
   )
 ];
 
+type D2 = [
+  (
+    | AAAAAAAAAAAAAAAAAAAAAA
+    | BBBBBBBBBBBBBBBBBBBBBB
+    | CCCCCCCCCCCCCCCCCCCCCC
+    | DDDDDDDDDDDDDDDDDDDDDD
+  ),
+  (
+    | AAAAAAAAAAAAAAAAAAAAAA
+    | BBBBBBBBBBBBBBBBBBBBBB
+    | CCCCCCCCCCCCCCCCCCCCCC
+    | DDDDDDDDDDDDDDDDDDDDDD
+  )
+];
+
+type E = [AA | BB, AA | BB];
+
+type F = [
+  (
+    | AAAAAAAAAAAAAAAAAAAAAA
+    | BBBBBBBBBBBBBBBBBBBBBB
+    | CCCCCCCCCCCCCCCCCCCCCC
+    | DDDDDDDDDDDDDDDDDDDDDD
+  ),
+  AAAAAAAAAAAAAAAAAAAAAA | BBBBBBBBBBBBBBBBBBBBBB
+];
+
 ================================================================================
 `;
diff --git a/tests/typescript_union/union-parens.ts b/tests/typescript_union/union-parens.ts
index ddc8e10b..6b9c086f 100644
--- a/tests/typescript_union/union-parens.ts
+++ b/tests/typescript_union/union-parens.ts
@@ -36,7 +36,7 @@ type State = {
 } & (
   | { discriminant: "FOO"; foo: any }
   | { discriminant: "BAR"; bar: any }
-  | { discriminant: "BAZ"; baz: any } 
+  | { discriminant: "BAZ"; baz: any }
 );
 
 const foo = [abc, def, ghi, jkl, mno, pqr, stu, vwx, yz] as (
@@ -66,3 +66,46 @@ const foo:
       | CCCCCCCCCCCCCCCCCCCCCC
       | DDDDDDDDDDDDDDDDDDDDDD
     ) = bar;
+
+let a1 : C;
+let a2 : | C;
+let a3 : (| C);
+let a4 : | (C);
+let a5 : (| (C));
+let a6 : /*1*/ | C;
+let a7 : /*1*/ | (C);
+let a8 : /*1*/ (| C);
+let a9 : (/*1*/ | C);
+let a10: /*1*/ | /*2*/ C;
+let a11: /*1*/ (| /*2*/ C);
+
+let aa1: /*1*/ | /*2*/ C | D;
+let aa2: /*1*/ | /*2*/ C | /*3*/ D;
+let aa3: /*1*/ | /*2*/ C | /*3*/ D /*4*/;
+
+type A1  = C;
+type A2  = | C;
+type A3  = (| C);
+type A4  = | (C);
+type A5  = (| (C));
+type A6  = /*1*/ | C;
+type A7  = /*1*/ | (C);
+type A8  = /*1*/ (| C);
+type A9  = (/*1*/ | C);
+type A10 = /*1*/ | /*2*/ C;
+type A11 = /*1*/ (| /*2*/ C);
+type A12 = /*1*/ | ( (C));
+type A13 = /*1*/ ( (C));
+
+type Aa1 = /*1*/ | /*2*/ C | D;
+type Aa2 = /*1*/ | /*2*/ C | /*3*/ D;
+type Aa3 = /*1*/ | /*2*/ C | /*3*/ D /*4*/;
+
+type C1 = /*1*/ & a | b;
+type C2 = /*1*/ & a | (b);
+type C3 = /*1*/ & a | (& b);
+type C4 = /*1*/ & (a | b);
+type C5 = /*1*/ (& a | b);
+type C6 /*0*/ = /*1*/ (& a | b);
+
+type Ctor = (new () => X) | Y;
diff --git a/tests/typescript_union/within-tuple.ts b/tests/typescript_union/within-tuple.ts
index 12f40cb3..7539bc9d 100644
--- a/tests/typescript_union/within-tuple.ts
+++ b/tests/typescript_union/within-tuple.ts
@@ -7,6 +7,15 @@ type B = [
   | DDDDDDDDDDDDDDDDDDDDDD
 ]
 
+type B1 = [
+  (
+    | AAAAAAAAAAAAAAAAAAAAAA
+    | BBBBBBBBBBBBBBBBBBBBBB
+    | CCCCCCCCCCCCCCCCCCCCCC
+    | DDDDDDDDDDDDDDDDDDDDDD
+  )
+]
+
 type C = [
   | [AAAAAAAAAAAAAAAAAAAAAA | BBBBBBBBBBBBBBBBBBBBBB | CCCCCCCCCCCCCCCCCCCCCC | DDDDDDDDDDDDDDDDDDDDDD]
   | [AAAAAAAAAAAAAAAAAAAAAA | BBBBBBBBBBBBBBBBBBBBBB | CCCCCCCCCCCCCCCCCCCCCC | DDDDDDDDDDDDDDDDDDDDDD]
@@ -17,7 +26,7 @@ type D = [
   (AAAAAAAAAAAAAAAAAAAAAA | BBBBBBBBBBBBBBBBBBBBBB | CCCCCCCCCCCCCCCCCCCCCC | DDDDDDDDDDDDDDDDDDDDDD)
 ]
 
-type E = [
+type D1 = [
   (
     | AAAAAAAAAAAAAAAAAAAAAA
     | BBBBBBBBBBBBBBBBBBBBBB
@@ -30,4 +39,26 @@ type E = [
     | CCCCCCCCCCCCCCCCCCCCCC
     | DDDDDDDDDDDDDDDDDDDDDD
   )
-]
\ No newline at end of file
+]
+
+type D2 = [
+  | AAAAAAAAAAAAAAAAAAAAAA
+  | BBBBBBBBBBBBBBBBBBBBBB
+  | CCCCCCCCCCCCCCCCCCCCCC
+  | DDDDDDDDDDDDDDDDDDDDDD,
+  | AAAAAAAAAAAAAAAAAAAAAA
+  | BBBBBBBBBBBBBBBBBBBBBB
+  | CCCCCCCCCCCCCCCCCCCCCC
+  | DDDDDDDDDDDDDDDDDDDDDD
+]
+
+type E = [ AA | BB, AA | BB ]
+
+type F = [
+  | AAAAAAAAAAAAAAAAAAAAAA
+  | BBBBBBBBBBBBBBBBBBBBBB
+  | CCCCCCCCCCCCCCCCCCCCCC
+  | DDDDDDDDDDDDDDDDDDDDDD,
+  | AAAAAAAAAAAAAAAAAAAAAA
+  | BBBBBBBBBBBBBBBBBBBBBB
+]