diff --git a/lib/6to5/generation/generator.js b/lib/6to5/generation/generator.js
index d2da9ac9c4..2fb74be764 100644
--- a/lib/6to5/generation/generator.js
+++ b/lib/6to5/generation/generator.js
@@ -148,10 +148,11 @@ CodeGenerator.prototype.print = function (node, parent, opts) {
   };
 
   if (this[node.type]) {
-    // only compute if this node needs parens if our parent has been changed
-    // since acorn would've wrapped us in a ParanthesizedExpression
-    var needsParens = n.needsParens(node, parent);
+    var needsCommentParens = t.isExpression(node) && node.leadingComments && node.leadingComments.length;
+    var needsParens        = needsCommentParens || n.needsParens(node, parent);
+
     if (needsParens) this.push("(");
+    if (needsCommentParens) this.indent();
 
     this.printLeadingComments(node, parent);
 
@@ -162,6 +163,10 @@ CodeGenerator.prototype.print = function (node, parent, opts) {
 
     this[node.type](node, this.buildPrint(node), parent);
 
+    if (needsCommentParens) {
+      this.newline();
+      this.dedent();
+    }
     if (needsParens) this.push(")");
 
     this.map.mark(node, "end");
diff --git a/lib/6to5/generation/node/index.js b/lib/6to5/generation/node/index.js
index 8b364bfcdb..b1ab6b7599 100644
--- a/lib/6to5/generation/node/index.js
+++ b/lib/6to5/generation/node/index.js
@@ -60,10 +60,6 @@ Node.prototype.needsParens = function () {
 
   if (!parent) return false;
 
-  if (t.isExpression(node) && node.leadingComments && node.leadingComments.length) {
-    return true;
-  }
-
   if (t.isNewExpression(parent) && parent.callee === node) {
     return t.isCallExpression(node) || _.some(node, function (val) {
       return t.isCallExpression(val);