diff --git a/tsc/internal/parser/parser.go b/tsc/internal/parser/parser.go
index 8eef8b7a7da8d..896f567d99450 100644
--- a/tsc/internal/parser/parser.go
+++ b/tsc/internal/parser/parser.go
@@ -4263,7 +4263,8 @@ func (p *Parser) isParenthesizedArrowFunctionExpression() core.Tristate {
 }
 
 func (p *Parser) nextIsParenthesizedArrowFunctionExpression() core.Tristate {
-	if p.token == ast.KindAsyncKeyword {
+	isAsync := p.token == ast.KindAsyncKeyword
+	if isAsync {
 		p.nextToken()
 		if p.hasPrecedingLineBreak() {
 			return core.TSFalse
@@ -4277,12 +4278,12 @@ func (p *Parser) nextIsParenthesizedArrowFunctionExpression() core.Tristate {
 	if first == ast.KindOpenParenToken {
 		if second == ast.KindCloseParenToken {
 			// Simple cases: "() =>", "(): ", and "() {".
-			// This is an arrow function with no parameters.
 			// The last one is not actually an arrow function,
 			// but this is probably what the user intended.
-			third := p.nextToken()
-			switch third {
-			case ast.KindEqualsGreaterThanToken, ast.KindColonToken, ast.KindOpenBraceToken:
+			switch p.nextToken() {
+			case ast.KindColonToken:
+				return core.IfElse(isAsync, core.TSUnknown, core.TSTrue)
+			case ast.KindEqualsGreaterThanToken, ast.KindOpenBraceToken:
 				return core.TSTrue
 			}
 			return core.TSFalse
diff --git a/tsc/testdata/baselines/reference/compiler/parenthesizedAsyncArrowFunction.js b/tsc/testdata/baselines/reference/compiler/parenthesizedAsyncArrowFunction.js
index a7b6057753bcf..85e1d1e699bd0 100644
--- a/tsc/testdata/baselines/reference/compiler/parenthesizedAsyncArrowFunction.js
+++ b/tsc/testdata/baselines/reference/compiler/parenthesizedAsyncArrowFunction.js
@@ -4,6 +4,22 @@
 // Repro from #20096
 
 let foo = (async bar => bar);
+
+const a = true;
+const b = 1;
+
+function async(): number {
+    return b;
+}
+
+const f1 = a ? async() : 0;
+const f2 = a ? async() : x => x;
+const f3 = a ? a ? async() : 0 : b;
+const f4 = a ? x => async() : x => x;
+const f5 = a ? async (): Promise<number> => b : () => b;
+const f6 = a ? async (): Promise<number> => { return b; } : () => b;
+const f7 = a ? async (): Promise<number> => a ? async() : 0 : () => b;
+const f8 = a ? (): number => b : () => b;
 
 
 //// [parenthesizedAsyncArrowFunction.js]
@@ -19,3 +35,16 @@ var __awaiter = (this && this.__awaiter) || function (thisArg, _arguments, P, ge
     });
 };
 let foo = ((bar) => __awaiter(void 0, void 0, void 0, function* () { return bar; }));
+const a = true;
+const b = 1;
+function async() {
+    return b;
+}
+const f1 = a ? async() : 0;
+const f2 = a ? async() : x => x;
+const f3 = a ? a ? async() : 0 : b;
+const f4 = a ? x => async() : x => x;
+const f5 = a ? () => __awaiter(void 0, void 0, void 0, function* () { return b; }) : () => b;
+const f6 = a ? () => __awaiter(void 0, void 0, void 0, function* () { return b; }) : () => b;
+const f7 = a ? () => __awaiter(void 0, void 0, void 0, function* () { return a ? async() : 0; }) : () => b;
+const f8 = a ? () => b : () => b;
diff --git a/tsc/testdata/baselines/reference/compiler/parenthesizedAsyncArrowFunction.symbols b/tsc/testdata/baselines/reference/compiler/parenthesizedAsyncArrowFunction.symbols
index 53286f39e8465..633089a2bb1d6 100644
--- a/tsc/testdata/baselines/reference/compiler/parenthesizedAsyncArrowFunction.symbols
+++ b/tsc/testdata/baselines/reference/compiler/parenthesizedAsyncArrowFunction.symbols
@@ -8,3 +8,71 @@ let foo = (async bar => bar);
 >bar : Symbol(bar, Decl(parenthesizedAsyncArrowFunction.ts, 2, 16))
 >bar : Symbol(bar, Decl(parenthesizedAsyncArrowFunction.ts, 2, 16))
 
+const a = true;
+>a : Symbol(a, Decl(parenthesizedAsyncArrowFunction.ts, 4, 5))
+
+const b = 1;
+>b : Symbol(b, Decl(parenthesizedAsyncArrowFunction.ts, 5, 5))
+
+function async(): number {
+>async : Symbol(async, Decl(parenthesizedAsyncArrowFunction.ts, 5, 12))
+
+    return b;
+>b : Symbol(b, Decl(parenthesizedAsyncArrowFunction.ts, 5, 5))
+}
+
+const f1 = a ? async() : 0;
+>f1 : Symbol(f1, Decl(parenthesizedAsyncArrowFunction.ts, 11, 5))
+>a : Symbol(a, Decl(parenthesizedAsyncArrowFunction.ts, 4, 5))
+>async : Symbol(async, Decl(parenthesizedAsyncArrowFunction.ts, 5, 12))
+
+const f2 = a ? async() : x => x;
+>f2 : Symbol(f2, Decl(parenthesizedAsyncArrowFunction.ts, 12, 5))
+>a : Symbol(a, Decl(parenthesizedAsyncArrowFunction.ts, 4, 5))
+>async : Symbol(async, Decl(parenthesizedAsyncArrowFunction.ts, 5, 12))
+>x : Symbol(x, Decl(parenthesizedAsyncArrowFunction.ts, 12, 24))
+>x : Symbol(x, Decl(parenthesizedAsyncArrowFunction.ts, 12, 24))
+
+const f3 = a ? a ? async() : 0 : b;
+>f3 : Symbol(f3, Decl(parenthesizedAsyncArrowFunction.ts, 13, 5))
+>a : Symbol(a, Decl(parenthesizedAsyncArrowFunction.ts, 4, 5))
+>a : Symbol(a, Decl(parenthesizedAsyncArrowFunction.ts, 4, 5))
+>async : Symbol(async, Decl(parenthesizedAsyncArrowFunction.ts, 5, 12))
+>b : Symbol(b, Decl(parenthesizedAsyncArrowFunction.ts, 5, 5))
+
+const f4 = a ? x => async() : x => x;
+>f4 : Symbol(f4, Decl(parenthesizedAsyncArrowFunction.ts, 14, 5))
+>a : Symbol(a, Decl(parenthesizedAsyncArrowFunction.ts, 4, 5))
+>x : Symbol(x, Decl(parenthesizedAsyncArrowFunction.ts, 14, 14))
+>async : Symbol(async, Decl(parenthesizedAsyncArrowFunction.ts, 5, 12))
+>x : Symbol(x, Decl(parenthesizedAsyncArrowFunction.ts, 14, 29))
+>x : Symbol(x, Decl(parenthesizedAsyncArrowFunction.ts, 14, 29))
+
+const f5 = a ? async (): Promise<number> => b : () => b;
+>f5 : Symbol(f5, Decl(parenthesizedAsyncArrowFunction.ts, 15, 5))
+>a : Symbol(a, Decl(parenthesizedAsyncArrowFunction.ts, 4, 5))
+>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, --, --))
+>b : Symbol(b, Decl(parenthesizedAsyncArrowFunction.ts, 5, 5))
+>b : Symbol(b, Decl(parenthesizedAsyncArrowFunction.ts, 5, 5))
+
+const f6 = a ? async (): Promise<number> => { return b; } : () => b;
+>f6 : Symbol(f6, Decl(parenthesizedAsyncArrowFunction.ts, 16, 5))
+>a : Symbol(a, Decl(parenthesizedAsyncArrowFunction.ts, 4, 5))
+>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, --, --))
+>b : Symbol(b, Decl(parenthesizedAsyncArrowFunction.ts, 5, 5))
+>b : Symbol(b, Decl(parenthesizedAsyncArrowFunction.ts, 5, 5))
+
+const f7 = a ? async (): Promise<number> => a ? async() : 0 : () => b;
+>f7 : Symbol(f7, Decl(parenthesizedAsyncArrowFunction.ts, 17, 5))
+>a : Symbol(a, Decl(parenthesizedAsyncArrowFunction.ts, 4, 5))
+>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, --, --))
+>a : Symbol(a, Decl(parenthesizedAsyncArrowFunction.ts, 4, 5))
+>async : Symbol(async, Decl(parenthesizedAsyncArrowFunction.ts, 5, 12))
+>b : Symbol(b, Decl(parenthesizedAsyncArrowFunction.ts, 5, 5))
+
+const f8 = a ? (): number => b : () => b;
+>f8 : Symbol(f8, Decl(parenthesizedAsyncArrowFunction.ts, 18, 5))
+>a : Symbol(a, Decl(parenthesizedAsyncArrowFunction.ts, 4, 5))
+>b : Symbol(b, Decl(parenthesizedAsyncArrowFunction.ts, 5, 5))
+>b : Symbol(b, Decl(parenthesizedAsyncArrowFunction.ts, 5, 5))
+
diff --git a/tsc/testdata/baselines/reference/compiler/parenthesizedAsyncArrowFunction.types b/tsc/testdata/baselines/reference/compiler/parenthesizedAsyncArrowFunction.types
index 9f5aa33f8d645..7730643f9a392 100644
--- a/tsc/testdata/baselines/reference/compiler/parenthesizedAsyncArrowFunction.types
+++ b/tsc/testdata/baselines/reference/compiler/parenthesizedAsyncArrowFunction.types
@@ -10,3 +10,99 @@ let foo = (async bar => bar);
 >bar : any
 >bar : any
 
+const a = true;
+>a : true
+>true : true
+
+const b = 1;
+>b : 1
+>1 : 1
+
+function async(): number {
+>async : () => number
+
+    return b;
+>b : 1
+}
+
+const f1 = a ? async() : 0;
+>f1 : number
+>a ? async() : 0 : number
+>a : true
+>async() : number
+>async : () => number
+>0 : 0
+
+const f2 = a ? async() : x => x;
+>f2 : number | ((x: any) => any)
+>a ? async() : x => x : number | ((x: any) => any)
+>a : true
+>async() : number
+>async : () => number
+>x => x : (x: any) => any
+>x : any
+>x : any
+
+const f3 = a ? a ? async() : 0 : b;
+>f3 : number
+>a ? a ? async() : 0 : b : number
+>a : true
+>a ? async() : 0 : number
+>a : true
+>async() : number
+>async : () => number
+>0 : 0
+>b : 1
+
+const f4 = a ? x => async() : x => x;
+>f4 : (x: any) => any
+>a ? x => async() : x => x : (x: any) => any
+>a : true
+>x => async() : (x: any) => number
+>x : any
+>async() : number
+>async : () => number
+>x => x : (x: any) => any
+>x : any
+>x : any
+
+const f5 = a ? async (): Promise<number> => b : () => b;
+>f5 : (() => Promise<number>) | (() => number)
+>a ? async (): Promise<number> => b : () => b : (() => Promise<number>) | (() => number)
+>a : true
+>async (): Promise<number> => b : () => Promise<number>
+>b : 1
+>() => b : () => number
+>b : 1
+
+const f6 = a ? async (): Promise<number> => { return b; } : () => b;
+>f6 : (() => Promise<number>) | (() => number)
+>a ? async (): Promise<number> => { return b; } : () => b : (() => Promise<number>) | (() => number)
+>a : true
+>async (): Promise<number> => { return b; } : () => Promise<number>
+>b : 1
+>() => b : () => number
+>b : 1
+
+const f7 = a ? async (): Promise<number> => a ? async() : 0 : () => b;
+>f7 : (() => Promise<number>) | (() => number)
+>a ? async (): Promise<number> => a ? async() : 0 : () => b : (() => Promise<number>) | (() => number)
+>a : true
+>async (): Promise<number> => a ? async() : 0 : () => Promise<number>
+>a ? async() : 0 : number
+>a : true
+>async() : number
+>async : () => number
+>0 : 0
+>() => b : () => number
+>b : 1
+
+const f8 = a ? (): number => b : () => b;
+>f8 : () => number
+>a ? (): number => b : () => b : () => number
+>a : true
+>(): number => b : () => number
+>b : 1
+>() => b : () => number
+>b : 1
+
diff --git a/tsc/testdata/baselines/reference/conformance/asyncArrowFunction_allowJs.errors.txt b/tsc/testdata/baselines/reference/conformance/asyncArrowFunction_allowJs.errors.txt
index 08dc36a626764..e322798fd3804 100644
--- a/tsc/testdata/baselines/reference/conformance/asyncArrowFunction_allowJs.errors.txt
+++ b/tsc/testdata/baselines/reference/conformance/asyncArrowFunction_allowJs.errors.txt
@@ -45,4 +45,18 @@ file.js(22,12): error TS7006: Parameter 'p' implicitly has an 'any' type.
     // Error (good)
     f(async () => {
     	return 0
-    })
\ No newline at end of file
+    })
+    
+    const g = true;
+    
+    function async() {
+        return 1;
+    }
+    
+    const f1 = g ? async() : 0;
+    /** @type {number | ((x: number) => number)} */
+    const f2 = g ? async() : x => x;
+    const f3 = g ? g ? async() : 0 : 1;
+    /** @type {(x: number) => number} */
+    const f4 = g ? x => async() : x => x;
+    
\ No newline at end of file
diff --git a/tsc/testdata/baselines/reference/conformance/asyncArrowFunction_allowJs.symbols b/tsc/testdata/baselines/reference/conformance/asyncArrowFunction_allowJs.symbols
index 40bae3eb3736c..4fc7c6c17c44c 100644
--- a/tsc/testdata/baselines/reference/conformance/asyncArrowFunction_allowJs.symbols
+++ b/tsc/testdata/baselines/reference/conformance/asyncArrowFunction_allowJs.symbols
@@ -38,3 +38,41 @@ f(async () => {
 
 	return 0
 })
+
+const g = true;
+>g : Symbol(g, Decl(file.js, 28, 5))
+
+function async() {
+>async : Symbol(async, Decl(file.js, 28, 15))
+
+    return 1;
+}
+
+const f1 = g ? async() : 0;
+>f1 : Symbol(f1, Decl(file.js, 34, 5))
+>g : Symbol(g, Decl(file.js, 28, 5))
+>async : Symbol(async, Decl(file.js, 28, 15))
+
+/** @type {number | ((x: number) => number)} */
+const f2 = g ? async() : x => x;
+>f2 : Symbol(f2, Decl(file.js, 36, 5))
+>g : Symbol(g, Decl(file.js, 28, 5))
+>async : Symbol(async, Decl(file.js, 28, 15))
+>x : Symbol(x, Decl(file.js, 36, 24))
+>x : Symbol(x, Decl(file.js, 36, 24))
+
+const f3 = g ? g ? async() : 0 : 1;
+>f3 : Symbol(f3, Decl(file.js, 37, 5))
+>g : Symbol(g, Decl(file.js, 28, 5))
+>g : Symbol(g, Decl(file.js, 28, 5))
+>async : Symbol(async, Decl(file.js, 28, 15))
+
+/** @type {(x: number) => number} */
+const f4 = g ? x => async() : x => x;
+>f4 : Symbol(f4, Decl(file.js, 39, 5))
+>g : Symbol(g, Decl(file.js, 28, 5))
+>x : Symbol(x, Decl(file.js, 39, 14))
+>async : Symbol(async, Decl(file.js, 28, 15))
+>x : Symbol(x, Decl(file.js, 39, 29))
+>x : Symbol(x, Decl(file.js, 39, 29))
+
diff --git a/tsc/testdata/baselines/reference/conformance/asyncArrowFunction_allowJs.types b/tsc/testdata/baselines/reference/conformance/asyncArrowFunction_allowJs.types
index d8d3316603e0e..376d8932fec68 100644
--- a/tsc/testdata/baselines/reference/conformance/asyncArrowFunction_allowJs.types
+++ b/tsc/testdata/baselines/reference/conformance/asyncArrowFunction_allowJs.types
@@ -51,3 +51,58 @@ f(async () => {
 >0 : 0
 
 })
+
+const g = true;
+>g : true
+>true : true
+
+function async() {
+>async : () => number
+
+    return 1;
+>1 : 1
+}
+
+const f1 = g ? async() : 0;
+>f1 : number
+>g ? async() : 0 : number
+>g : true
+>async() : number
+>async : () => number
+>0 : 0
+
+/** @type {number | ((x: number) => number)} */
+const f2 = g ? async() : x => x;
+>f2 : number | ((x: number) => number)
+>g ? async() : x => x : number | ((x: number) => number)
+>g : true
+>async() : number
+>async : () => number
+>x => x : (x: number) => number
+>x : number
+>x : number
+
+const f3 = g ? g ? async() : 0 : 1;
+>f3 : number
+>g ? g ? async() : 0 : 1 : number
+>g : true
+>g ? async() : 0 : number
+>g : true
+>async() : number
+>async : () => number
+>0 : 0
+>1 : 1
+
+/** @type {(x: number) => number} */
+const f4 = g ? x => async() : x => x;
+>f4 : (x: number) => number
+>g ? x => async() : x => x : (x: number) => number
+>g : true
+>x => async() : (x: number) => number
+>x : number
+>async() : number
+>async : () => number
+>x => x : (x: number) => number
+>x : number
+>x : number
+
diff --git a/tsc/testdata/tests/cases/compiler/parenthesizedAsyncArrowFunction.ts b/tsc/testdata/tests/cases/compiler/parenthesizedAsyncArrowFunction.ts
index 057eb64c82138..8e323ebb3b172 100644
--- a/tsc/testdata/tests/cases/compiler/parenthesizedAsyncArrowFunction.ts
+++ b/tsc/testdata/tests/cases/compiler/parenthesizedAsyncArrowFunction.ts
@@ -3,3 +3,19 @@
 // Repro from #20096
 
 let foo = (async bar => bar);
+
+const a = true;
+const b = 1;
+
+function async(): number {
+    return b;
+}
+
+const f1 = a ? async() : 0;
+const f2 = a ? async() : x => x;
+const f3 = a ? a ? async() : 0 : b;
+const f4 = a ? x => async() : x => x;
+const f5 = a ? async (): Promise<number> => b : () => b;
+const f6 = a ? async (): Promise<number> => { return b; } : () => b;
+const f7 = a ? async (): Promise<number> => a ? async() : 0 : () => b;
+const f8 = a ? (): number => b : () => b;
diff --git a/tsc/testdata/tests/cases/conformance/async/es2017/asyncArrowFunction/asyncArrowFunction_allowJs.ts b/tsc/testdata/tests/cases/conformance/async/es2017/asyncArrowFunction/asyncArrowFunction_allowJs.ts
index 9f1f76100434d..39759f6cb41d8 100644
--- a/tsc/testdata/tests/cases/conformance/async/es2017/asyncArrowFunction/asyncArrowFunction_allowJs.ts
+++ b/tsc/testdata/tests/cases/conformance/async/es2017/asyncArrowFunction/asyncArrowFunction_allowJs.ts
@@ -30,4 +30,17 @@ const f = (p) => {}
 // Error (good)
 f(async () => {
 	return 0
-})
\ No newline at end of file
+})
+
+const g = true;
+
+function async() {
+    return 1;
+}
+
+const f1 = g ? async() : 0;
+/** @type {number | ((x: number) => number)} */
+const f2 = g ? async() : x => x;
+const f3 = g ? g ? async() : 0 : 1;
+/** @type {(x: number) => number} */
+const f4 = g ? x => async() : x => x;