diff --git a/src/compiler/emitter.ts b/src/compiler/emitter.ts
index 3f17986359c..3afb23c6df3 100644
--- a/src/compiler/emitter.ts
+++ b/src/compiler/emitter.ts
@@ -3607,7 +3607,14 @@ export function createPrinter(printerOptions: PrinterOptions = {}, handlers: Pri
 
     function willEmitLeadingNewLine(node: Expression): boolean {
         if (!currentSourceFile) return false;
-        if (some(getLeadingCommentRanges(currentSourceFile.text, node.pos), commentWillEmitNewLine)) return true;
+        const leadingCommentRanges = getLeadingCommentRanges(currentSourceFile.text, node.pos);
+        if (leadingCommentRanges) {
+            const parseNode = getParseTreeNode(node);
+            if (parseNode && isParenthesizedExpression(parseNode.parent)) {
+                return true;
+            }
+        }
+        if (some(leadingCommentRanges, commentWillEmitNewLine)) return true;
         if (some(getSyntheticLeadingComments(node), commentWillEmitNewLine)) return true;
         if (isPartiallyEmittedExpression(node)) {
             if (node.pos !== node.expression.pos) {
diff --git a/tests/baselines/reference/commentEmitOnParenthesizedAssertionInReturnStatement.js b/tests/baselines/reference/commentEmitOnParenthesizedAssertionInReturnStatement.js
new file mode 100644
index 00000000000..bf3d947dca0
--- /dev/null
+++ b/tests/baselines/reference/commentEmitOnParenthesizedAssertionInReturnStatement.js
@@ -0,0 +1,28 @@
+//// [tests/cases/compiler/commentEmitOnParenthesizedAssertionInReturnStatement.ts] ////
+
+//// [commentEmitOnParenthesizedAssertionInReturnStatement.ts]
+export class Foo {
+  client = {
+    getThing: () => Promise.resolve('')
+  }
+
+  foo(): Promise<void> {
+    return (
+      /* TODO: Avoid using type assertions, please refactor. */ this.client
+        .getThing() as unknown as Promise<void>
+    );
+  }
+}
+
+
+//// [commentEmitOnParenthesizedAssertionInReturnStatement.js]
+export class Foo {
+    client = {
+        getThing: () => Promise.resolve('')
+    };
+    foo() {
+        return (
+        /* TODO: Avoid using type assertions, please refactor. */ this.client
+            .getThing());
+    }
+}
diff --git a/tests/baselines/reference/commentEmitOnParenthesizedAssertionInReturnStatement.symbols b/tests/baselines/reference/commentEmitOnParenthesizedAssertionInReturnStatement.symbols
new file mode 100644
index 00000000000..0a0b1f2d68d
--- /dev/null
+++ b/tests/baselines/reference/commentEmitOnParenthesizedAssertionInReturnStatement.symbols
@@ -0,0 +1,35 @@
+//// [tests/cases/compiler/commentEmitOnParenthesizedAssertionInReturnStatement.ts] ////
+
+=== commentEmitOnParenthesizedAssertionInReturnStatement.ts ===
+export class Foo {
+>Foo : Symbol(Foo, Decl(commentEmitOnParenthesizedAssertionInReturnStatement.ts, 0, 0))
+
+  client = {
+>client : Symbol(Foo.client, Decl(commentEmitOnParenthesizedAssertionInReturnStatement.ts, 0, 18))
+
+    getThing: () => Promise.resolve('')
+>getThing : Symbol(getThing, Decl(commentEmitOnParenthesizedAssertionInReturnStatement.ts, 1, 12))
+>Promise.resolve : Symbol(PromiseConstructor.resolve, Decl(lib.es2015.promise.d.ts, --, --), Decl(lib.es2015.promise.d.ts, --, --), Decl(lib.es2015.promise.d.ts, --, --))
+>Promise : Symbol(Promise, Decl(lib.es5.d.ts, --, --), Decl(lib.es2015.iterable.d.ts, --, --), Decl(lib.es2015.promise.d.ts, --, --), Decl(lib.es2015.symbol.wellknown.d.ts, --, --), Decl(lib.es2018.promise.d.ts, --, --))
+>resolve : Symbol(PromiseConstructor.resolve, Decl(lib.es2015.promise.d.ts, --, --), Decl(lib.es2015.promise.d.ts, --, --), Decl(lib.es2015.promise.d.ts, --, --))
+  }
+
+  foo(): Promise<void> {
+>foo : Symbol(Foo.foo, Decl(commentEmitOnParenthesizedAssertionInReturnStatement.ts, 3, 3))
+>Promise : Symbol(Promise, Decl(lib.es5.d.ts, --, --), Decl(lib.es2015.iterable.d.ts, --, --), Decl(lib.es2015.promise.d.ts, --, --), Decl(lib.es2015.symbol.wellknown.d.ts, --, --), Decl(lib.es2018.promise.d.ts, --, --))
+
+    return (
+      /* TODO: Avoid using type assertions, please refactor. */ this.client
+>this.client        .getThing : Symbol(getThing, Decl(commentEmitOnParenthesizedAssertionInReturnStatement.ts, 1, 12))
+>this.client : Symbol(Foo.client, Decl(commentEmitOnParenthesizedAssertionInReturnStatement.ts, 0, 18))
+>this : Symbol(Foo, Decl(commentEmitOnParenthesizedAssertionInReturnStatement.ts, 0, 0))
+>client : Symbol(Foo.client, Decl(commentEmitOnParenthesizedAssertionInReturnStatement.ts, 0, 18))
+
+        .getThing() as unknown as Promise<void>
+>getThing : Symbol(getThing, Decl(commentEmitOnParenthesizedAssertionInReturnStatement.ts, 1, 12))
+>Promise : Symbol(Promise, Decl(lib.es5.d.ts, --, --), Decl(lib.es2015.iterable.d.ts, --, --), Decl(lib.es2015.promise.d.ts, --, --), Decl(lib.es2015.symbol.wellknown.d.ts, --, --), Decl(lib.es2018.promise.d.ts, --, --))
+
+    );
+  }
+}
+
diff --git a/tests/baselines/reference/commentEmitOnParenthesizedAssertionInReturnStatement.types b/tests/baselines/reference/commentEmitOnParenthesizedAssertionInReturnStatement.types
new file mode 100644
index 00000000000..433932a4d91
--- /dev/null
+++ b/tests/baselines/reference/commentEmitOnParenthesizedAssertionInReturnStatement.types
@@ -0,0 +1,42 @@
+//// [tests/cases/compiler/commentEmitOnParenthesizedAssertionInReturnStatement.ts] ////
+
+=== commentEmitOnParenthesizedAssertionInReturnStatement.ts ===
+export class Foo {
+>Foo : Foo
+
+  client = {
+>client : { getThing: () => Promise<string>; }
+>{    getThing: () => Promise.resolve('')  } : { getThing: () => Promise<string>; }
+
+    getThing: () => Promise.resolve('')
+>getThing : () => Promise<string>
+>() => Promise.resolve('') : () => Promise<string>
+>Promise.resolve('') : Promise<string>
+>Promise.resolve : { (): Promise<void>; <T>(value: T): Promise<Awaited<T>>; <T_1>(value: T_1 | PromiseLike<T_1>): Promise<Awaited<T_1>>; }
+>Promise : PromiseConstructor
+>resolve : { (): Promise<void>; <T>(value: T): Promise<Awaited<T>>; <T_1>(value: T_1 | PromiseLike<T_1>): Promise<Awaited<T_1>>; }
+>'' : ""
+  }
+
+  foo(): Promise<void> {
+>foo : () => Promise<void>
+
+    return (
+>(      /* TODO: Avoid using type assertions, please refactor. */ this.client        .getThing() as unknown as Promise<void>    ) : Promise<void>
+
+      /* TODO: Avoid using type assertions, please refactor. */ this.client
+>this.client        .getThing() as unknown as Promise<void> : Promise<void>
+>this.client        .getThing() as unknown : unknown
+>this.client        .getThing() : Promise<string>
+>this.client        .getThing : () => Promise<string>
+>this.client : { getThing: () => Promise<string>; }
+>this : this
+>client : { getThing: () => Promise<string>; }
+
+        .getThing() as unknown as Promise<void>
+>getThing : () => Promise<string>
+
+    );
+  }
+}
+
diff --git a/tests/cases/compiler/commentEmitOnParenthesizedAssertionInReturnStatement.ts b/tests/cases/compiler/commentEmitOnParenthesizedAssertionInReturnStatement.ts
new file mode 100644
index 00000000000..042c639812a
--- /dev/null
+++ b/tests/cases/compiler/commentEmitOnParenthesizedAssertionInReturnStatement.ts
@@ -0,0 +1,17 @@
+// @strict: true
+// @lib: esnext
+// @target: esnext
+// @removeComments: false
+
+export class Foo {
+  client = {
+    getThing: () => Promise.resolve('')
+  }
+
+  foo(): Promise<void> {
+    return (
+      /* TODO: Avoid using type assertions, please refactor. */ this.client
+        .getThing() as unknown as Promise<void>
+    );
+  }
+}