diff --git a/internal/printer/emitcontext.go b/internal/printer/emitcontext.go
index 68467e25d3a..24e0c43a98b 100644
--- a/internal/printer/emitcontext.go
+++ b/internal/printer/emitcontext.go
@@ -900,6 +900,19 @@ func (c *EmitContext) AddInitializationStatement(node *ast.Node) {
 	scope.initializationStatements = append(scope.initializationStatements, node)
 }
 
+func (c *EmitContext) ConvertToFunctionBlock(node *ast.Node, multiLine bool) *ast.Node {
+	if ast.IsBlock(node) {
+		return node
+	}
+	returnStatement := c.Factory.NewReturnStatement(node)
+	returnStatement.Loc = node.Loc
+	statements := c.Factory.NewNodeList([]*ast.Node{returnStatement})
+	statements.Loc = node.Loc
+	block := c.Factory.NewBlock(statements, multiLine)
+	block.Loc = node.Loc
+	return block
+}
+
 func (c *EmitContext) VisitFunctionBody(node *ast.BlockOrExpression, visitor *ast.NodeVisitor) *ast.BlockOrExpression {
 	// !!! c.resumeVariableEnvironment()
 	updated := visitor.VisitNode(node)
@@ -913,8 +926,13 @@ func (c *EmitContext) VisitFunctionBody(node *ast.BlockOrExpression, visitor *as
 	}
 
 	if !ast.IsBlock(updated) {
-		statements := c.MergeEnvironment([]*ast.Statement{c.Factory.NewReturnStatement(updated)}, declarations)
-		return c.Factory.NewBlock(c.Factory.NewNodeList(statements), false /*multiLine*/)
+		c.AddEmitFlags(updated, EFNoComments)
+		block := c.ConvertToFunctionBlock(updated, false /*multiLine*/)
+		return c.Factory.UpdateBlock(
+			block.AsBlock(),
+			c.MergeEnvironmentList(block.StatementList(), declarations),
+			block.AsBlock().MultiLine,
+		)
 	}
 
 	return c.Factory.UpdateBlock(
diff --git a/internal/transformers/estransforms/async.go b/internal/transformers/estransforms/async.go
index a7c2d0b7250..0097159ee02 100644
--- a/internal/transformers/estransforms/async.go
+++ b/internal/transformers/estransforms/async.go
@@ -841,7 +841,10 @@ func (tx *asyncTransformer) transformAsyncFunctionBody(node *ast.Node, outerPara
 		)
 
 		if captureLexicalArguments && tx.lexicalArguments.used {
-			block := tx.convertToFunctionBlock(result)
+			block := tx.EmitContext().ConvertToFunctionBlock(result, true /*multiLine*/)
+			if !ast.IsBlock(result) {
+				tx.EmitContext().SetOriginal(block.StatementList().Nodes[0], result)
+			}
 			result = tx.Factory().UpdateBlock(
 				block.AsBlock(),
 				tx.EmitContext().MergeEnvironmentList(block.StatementList(), []*ast.Node{tx.createCaptureArgumentsStatement()}),
@@ -889,20 +892,6 @@ func (tx *asyncTransformer) transformAsyncFunctionBodyWorker(body *ast.Node) *as
 	return block
 }
 
-func (tx *asyncTransformer) convertToFunctionBlock(node *ast.Node) *ast.Node {
-	if ast.IsBlock(node) {
-		return node
-	}
-	ret := tx.Factory().NewReturnStatement(node)
-	ret.Loc = node.Loc
-	tx.EmitContext().SetOriginal(ret, node)
-	list := tx.Factory().NewNodeList([]*ast.Node{ret})
-	list.Loc = node.Loc
-	block := tx.Factory().NewBlock(list, true)
-	block.Loc = node.Loc
-	return block
-}
-
 // assignmentTargetContainsSuperProperty checks top-down whether an assignment target
 // expression contains a super property or element access (super.x or super[x]).
 // This avoids relying on parent pointers (IsAssignmentTarget) which may not be set
diff --git a/testdata/baselines/reference/compiler/optionalChainingArrowFunctionCommentEs2018.js b/testdata/baselines/reference/compiler/optionalChainingArrowFunctionCommentEs2018.js
new file mode 100644
index 00000000000..466d090cf07
--- /dev/null
+++ b/testdata/baselines/reference/compiler/optionalChainingArrowFunctionCommentEs2018.js
@@ -0,0 +1,40 @@
+//// [tests/cases/compiler/optionalChainingArrowFunctionCommentEs2018.ts] ////
+
+//// [optionalChainingArrowFunctionCommentEs2018.ts]
+const thing = { nested: { condition: true } };
+
+const wat = () =>
+    // explanatory comment
+    thing?.nested?.condition ? "pass" : "fail";
+
+const watInline = () => /* inline explanatory comment */ thing?.nested?.condition ? "pass" : "fail";
+
+const watInlineMultiline = () => /* inline
+explanatory comment */ thing?.nested?.condition ? "pass" : "fail";
+
+const watInlineThenLeading = () => /* inline explanatory comment */
+    // leading explanatory comment
+    thing?.nested?.condition ? "pass" : "fail";
+
+declare const o: { a?: number[] };
+
+export const f = () =>
+    // comment
+    o.a?.length;
+
+
+//// [optionalChainingArrowFunctionCommentEs2018.js]
+const thing = { nested: { condition: true } };
+const wat = () => { var _a; 
+// explanatory comment
+return ((_a = thing === null || thing === void 0 ? void 0 : thing.nested) === null || _a === void 0 ? void 0 : _a.condition) ? "pass" : "fail"; };
+const watInline = () => /* inline explanatory comment */ { var _a; /* inline explanatory comment */ return ((_a = thing === null || thing === void 0 ? void 0 : thing.nested) === null || _a === void 0 ? void 0 : _a.condition) ? "pass" : "fail"; };
+const watInlineMultiline = () => /* inline
+explanatory comment */ { var _a; /* inline
+explanatory comment */ return ((_a = thing === null || thing === void 0 ? void 0 : thing.nested) === null || _a === void 0 ? void 0 : _a.condition) ? "pass" : "fail"; };
+const watInlineThenLeading = () => /* inline explanatory comment */ { var _a; /* inline explanatory comment */ 
+// leading explanatory comment
+return ((_a = thing === null || thing === void 0 ? void 0 : thing.nested) === null || _a === void 0 ? void 0 : _a.condition) ? "pass" : "fail"; };
+export const f = () => { var _a; 
+// comment
+return (_a = o.a) === null || _a === void 0 ? void 0 : _a.length; };
diff --git a/testdata/baselines/reference/compiler/optionalChainingArrowFunctionCommentEs2018.symbols b/testdata/baselines/reference/compiler/optionalChainingArrowFunctionCommentEs2018.symbols
new file mode 100644
index 00000000000..3f296faf1a9
--- /dev/null
+++ b/testdata/baselines/reference/compiler/optionalChainingArrowFunctionCommentEs2018.symbols
@@ -0,0 +1,63 @@
+//// [tests/cases/compiler/optionalChainingArrowFunctionCommentEs2018.ts] ////
+
+=== optionalChainingArrowFunctionCommentEs2018.ts ===
+const thing = { nested: { condition: true } };
+>thing : Symbol(thing, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 5))
+>nested : Symbol(nested, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 15))
+>condition : Symbol(condition, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 25))
+
+const wat = () =>
+>wat : Symbol(wat, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 2, 5))
+
+    // explanatory comment
+    thing?.nested?.condition ? "pass" : "fail";
+>thing?.nested?.condition : Symbol(condition, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 25))
+>thing?.nested : Symbol(nested, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 15))
+>thing : Symbol(thing, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 5))
+>nested : Symbol(nested, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 15))
+>condition : Symbol(condition, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 25))
+
+const watInline = () => /* inline explanatory comment */ thing?.nested?.condition ? "pass" : "fail";
+>watInline : Symbol(watInline, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 6, 5))
+>thing?.nested?.condition : Symbol(condition, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 25))
+>thing?.nested : Symbol(nested, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 15))
+>thing : Symbol(thing, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 5))
+>nested : Symbol(nested, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 15))
+>condition : Symbol(condition, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 25))
+
+const watInlineMultiline = () => /* inline
+>watInlineMultiline : Symbol(watInlineMultiline, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 8, 5))
+
+explanatory comment */ thing?.nested?.condition ? "pass" : "fail";
+>thing?.nested?.condition : Symbol(condition, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 25))
+>thing?.nested : Symbol(nested, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 15))
+>thing : Symbol(thing, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 5))
+>nested : Symbol(nested, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 15))
+>condition : Symbol(condition, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 25))
+
+const watInlineThenLeading = () => /* inline explanatory comment */
+>watInlineThenLeading : Symbol(watInlineThenLeading, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 11, 5))
+
+    // leading explanatory comment
+    thing?.nested?.condition ? "pass" : "fail";
+>thing?.nested?.condition : Symbol(condition, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 25))
+>thing?.nested : Symbol(nested, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 15))
+>thing : Symbol(thing, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 5))
+>nested : Symbol(nested, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 15))
+>condition : Symbol(condition, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 0, 25))
+
+declare const o: { a?: number[] };
+>o : Symbol(o, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 15, 13))
+>a : Symbol(a, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 15, 18))
+
+export const f = () =>
+>f : Symbol(f, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 17, 12))
+
+    // comment
+    o.a?.length;
+>o.a?.length : Symbol(Array.length, Decl(lib.es5.d.ts, --, --))
+>o.a : Symbol(a, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 15, 18))
+>o : Symbol(o, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 15, 13))
+>a : Symbol(a, Decl(optionalChainingArrowFunctionCommentEs2018.ts, 15, 18))
+>length : Symbol(Array.length, Decl(lib.es5.d.ts, --, --))
+
diff --git a/testdata/baselines/reference/compiler/optionalChainingArrowFunctionCommentEs2018.types b/testdata/baselines/reference/compiler/optionalChainingArrowFunctionCommentEs2018.types
new file mode 100644
index 00000000000..5aabfba66c3
--- /dev/null
+++ b/testdata/baselines/reference/compiler/optionalChainingArrowFunctionCommentEs2018.types
@@ -0,0 +1,83 @@
+//// [tests/cases/compiler/optionalChainingArrowFunctionCommentEs2018.ts] ////
+
+=== optionalChainingArrowFunctionCommentEs2018.ts ===
+const thing = { nested: { condition: true } };
+>thing : { nested: { condition: boolean; }; }
+>{ nested: { condition: true } } : { nested: { condition: boolean; }; }
+>nested : { condition: boolean; }
+>{ condition: true } : { condition: boolean; }
+>condition : boolean
+>true : true
+
+const wat = () =>
+>wat : () => "fail" | "pass"
+>() =>    // explanatory comment    thing?.nested?.condition ? "pass" : "fail" : () => "fail" | "pass"
+
+    // explanatory comment
+    thing?.nested?.condition ? "pass" : "fail";
+>thing?.nested?.condition ? "pass" : "fail" : "fail" | "pass"
+>thing?.nested?.condition : boolean
+>thing?.nested : { condition: boolean; }
+>thing : { nested: { condition: boolean; }; }
+>nested : { condition: boolean; }
+>condition : boolean
+>"pass" : "pass"
+>"fail" : "fail"
+
+const watInline = () => /* inline explanatory comment */ thing?.nested?.condition ? "pass" : "fail";
+>watInline : () => "fail" | "pass"
+>() => /* inline explanatory comment */ thing?.nested?.condition ? "pass" : "fail" : () => "fail" | "pass"
+>thing?.nested?.condition ? "pass" : "fail" : "fail" | "pass"
+>thing?.nested?.condition : boolean
+>thing?.nested : { condition: boolean; }
+>thing : { nested: { condition: boolean; }; }
+>nested : { condition: boolean; }
+>condition : boolean
+>"pass" : "pass"
+>"fail" : "fail"
+
+const watInlineMultiline = () => /* inline
+>watInlineMultiline : () => "fail" | "pass"
+>() => /* inlineexplanatory comment */ thing?.nested?.condition ? "pass" : "fail" : () => "fail" | "pass"
+
+explanatory comment */ thing?.nested?.condition ? "pass" : "fail";
+>thing?.nested?.condition ? "pass" : "fail" : "fail" | "pass"
+>thing?.nested?.condition : boolean
+>thing?.nested : { condition: boolean; }
+>thing : { nested: { condition: boolean; }; }
+>nested : { condition: boolean; }
+>condition : boolean
+>"pass" : "pass"
+>"fail" : "fail"
+
+const watInlineThenLeading = () => /* inline explanatory comment */
+>watInlineThenLeading : () => "fail" | "pass"
+>() => /* inline explanatory comment */    // leading explanatory comment    thing?.nested?.condition ? "pass" : "fail" : () => "fail" | "pass"
+
+    // leading explanatory comment
+    thing?.nested?.condition ? "pass" : "fail";
+>thing?.nested?.condition ? "pass" : "fail" : "fail" | "pass"
+>thing?.nested?.condition : boolean
+>thing?.nested : { condition: boolean; }
+>thing : { nested: { condition: boolean; }; }
+>nested : { condition: boolean; }
+>condition : boolean
+>"pass" : "pass"
+>"fail" : "fail"
+
+declare const o: { a?: number[] };
+>o : { a?: number[]; }
+>a : number[] | undefined
+
+export const f = () =>
+>f : () => number | undefined
+>() =>    // comment    o.a?.length : () => number | undefined
+
+    // comment
+    o.a?.length;
+>o.a?.length : number | undefined
+>o.a : number[] | undefined
+>o : { a?: number[]; }
+>a : number[] | undefined
+>length : number | undefined
+
diff --git a/testdata/tests/cases/compiler/optionalChainingArrowFunctionCommentEs2018.ts b/testdata/tests/cases/compiler/optionalChainingArrowFunctionCommentEs2018.ts
new file mode 100644
index 00000000000..f3d5d571e02
--- /dev/null
+++ b/testdata/tests/cases/compiler/optionalChainingArrowFunctionCommentEs2018.ts
@@ -0,0 +1,22 @@
+// @target: es2018
+
+const thing = { nested: { condition: true } };
+
+const wat = () =>
+    // explanatory comment
+    thing?.nested?.condition ? "pass" : "fail";
+
+const watInline = () => /* inline explanatory comment */ thing?.nested?.condition ? "pass" : "fail";
+
+const watInlineMultiline = () => /* inline
+explanatory comment */ thing?.nested?.condition ? "pass" : "fail";
+
+const watInlineThenLeading = () => /* inline explanatory comment */
+    // leading explanatory comment
+    thing?.nested?.condition ? "pass" : "fail";
+
+declare const o: { a?: number[] };
+
+export const f = () =>
+    // comment
+    o.a?.length;