diff --git a/tsc/internal/parser/parser.go b/tsc/internal/parser/parser.go
index 8eef8b7a7da8d..eca19fd2e97b6 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
@@ -4282,7 +4283,12 @@ func (p *Parser) nextIsParenthesizedArrowFunctionExpression() core.Tristate {
 			// but this is probably what the user intended.
 			third := p.nextToken()
 			switch third {
-			case ast.KindEqualsGreaterThanToken, ast.KindColonToken, ast.KindOpenBraceToken:
+			case ast.KindEqualsGreaterThanToken, ast.KindOpenBraceToken:
+				return core.TSTrue
+			case ast.KindColonToken:
+				if isAsync {
+					return core.TSUnknown
+				}
 				return core.TSTrue
 			}
 			return core.TSFalse
diff --git a/tsc/testdata/baselines/reference/compiler/asyncCallInConditionalExpression.js b/tsc/testdata/baselines/reference/compiler/asyncCallInConditionalExpression.js
new file mode 100644
index 0000000000000..c9907e1ad7500
--- /dev/null
+++ b/tsc/testdata/baselines/reference/compiler/asyncCallInConditionalExpression.js
@@ -0,0 +1,45 @@
+//// [tests/cases/compiler/asyncCallInConditionalExpression.ts] ////
+
+//// [a.ts]
+declare const a: boolean;
+declare function async(...args: any[]): number;
+
+const c1 = a ? async() : 0;
+const c2 = a ? async() : (x: number) => x;
+const c3 = a ? async(1) : 0;
+const c4 = a ? async() : a ? async() : 0;
+
+const f1 = async(): Promise<number> => 1;
+const f2 = async (): Promise<number> => 1;
+const f3 = a ? async(): Promise<number> => 1 : 2;
+const f4 = a ? async () => 1 : 2;
+const f5 = a ? 1 : async(): Promise<number> => 1;
+
+export {};
+
+//// [b.js]
+const t = true;
+function async() { return 1; }
+const j1 = t ? async() : 0;
+const j2 = t ? async() : x => x;
+
+export {};
+
+
+//// [a.js]
+const c1 = a ? async() : 0;
+const c2 = a ? async() : (x) => x;
+const c3 = a ? async(1) : 0;
+const c4 = a ? async() : a ? async() : 0;
+const f1 = async () => 1;
+const f2 = async () => 1;
+const f3 = a ? async () => 1 : 2;
+const f4 = a ? async () => 1 : 2;
+const f5 = a ? 1 : async () => 1;
+export {};
+//// [b.js]
+const t = true;
+function async() { return 1; }
+const j1 = t ? async() : 0;
+const j2 = t ? async() : x => x;
+export {};
diff --git a/tsc/testdata/baselines/reference/compiler/asyncCallInConditionalExpression.symbols b/tsc/testdata/baselines/reference/compiler/asyncCallInConditionalExpression.symbols
new file mode 100644
index 0000000000000..f61cf151358ab
--- /dev/null
+++ b/tsc/testdata/baselines/reference/compiler/asyncCallInConditionalExpression.symbols
@@ -0,0 +1,79 @@
+//// [tests/cases/compiler/asyncCallInConditionalExpression.ts] ////
+
+=== a.ts ===
+declare const a: boolean;
+>a : Symbol(a, Decl(a.ts, 0, 13))
+
+declare function async(...args: any[]): number;
+>async : Symbol(async, Decl(a.ts, 0, 25))
+>args : Symbol(args, Decl(a.ts, 1, 23))
+
+const c1 = a ? async() : 0;
+>c1 : Symbol(c1, Decl(a.ts, 3, 5))
+>a : Symbol(a, Decl(a.ts, 0, 13))
+>async : Symbol(async, Decl(a.ts, 0, 25))
+
+const c2 = a ? async() : (x: number) => x;
+>c2 : Symbol(c2, Decl(a.ts, 4, 5))
+>a : Symbol(a, Decl(a.ts, 0, 13))
+>async : Symbol(async, Decl(a.ts, 0, 25))
+>x : Symbol(x, Decl(a.ts, 4, 26))
+>x : Symbol(x, Decl(a.ts, 4, 26))
+
+const c3 = a ? async(1) : 0;
+>c3 : Symbol(c3, Decl(a.ts, 5, 5))
+>a : Symbol(a, Decl(a.ts, 0, 13))
+>async : Symbol(async, Decl(a.ts, 0, 25))
+
+const c4 = a ? async() : a ? async() : 0;
+>c4 : Symbol(c4, Decl(a.ts, 6, 5))
+>a : Symbol(a, Decl(a.ts, 0, 13))
+>async : Symbol(async, Decl(a.ts, 0, 25))
+>a : Symbol(a, Decl(a.ts, 0, 13))
+>async : Symbol(async, Decl(a.ts, 0, 25))
+
+const f1 = async(): Promise<number> => 1;
+>f1 : Symbol(f1, Decl(a.ts, 8, 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, --, --), Decl(lib.es2018.promise.d.ts, --, --))
+
+const f2 = async (): Promise<number> => 1;
+>f2 : Symbol(f2, Decl(a.ts, 9, 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, --, --), Decl(lib.es2018.promise.d.ts, --, --))
+
+const f3 = a ? async(): Promise<number> => 1 : 2;
+>f3 : Symbol(f3, Decl(a.ts, 10, 5))
+>a : Symbol(a, Decl(a.ts, 0, 13))
+>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, --, --))
+
+const f4 = a ? async () => 1 : 2;
+>f4 : Symbol(f4, Decl(a.ts, 11, 5))
+>a : Symbol(a, Decl(a.ts, 0, 13))
+
+const f5 = a ? 1 : async(): Promise<number> => 1;
+>f5 : Symbol(f5, Decl(a.ts, 12, 5))
+>a : Symbol(a, Decl(a.ts, 0, 13))
+>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, --, --))
+
+export {};
+
+=== b.js ===
+const t = true;
+>t : Symbol(t, Decl(b.js, 0, 5))
+
+function async() { return 1; }
+>async : Symbol(async, Decl(b.js, 0, 15))
+
+const j1 = t ? async() : 0;
+>j1 : Symbol(j1, Decl(b.js, 2, 5))
+>t : Symbol(t, Decl(b.js, 0, 5))
+>async : Symbol(async, Decl(b.js, 0, 15))
+
+const j2 = t ? async() : x => x;
+>j2 : Symbol(j2, Decl(b.js, 3, 5))
+>t : Symbol(t, Decl(b.js, 0, 5))
+>async : Symbol(async, Decl(b.js, 0, 15))
+>x : Symbol(x, Decl(b.js, 3, 24))
+>x : Symbol(x, Decl(b.js, 3, 24))
+
+export {};
+
diff --git a/tsc/testdata/baselines/reference/compiler/asyncCallInConditionalExpression.types b/tsc/testdata/baselines/reference/compiler/asyncCallInConditionalExpression.types
new file mode 100644
index 0000000000000..e143b0673baf3
--- /dev/null
+++ b/tsc/testdata/baselines/reference/compiler/asyncCallInConditionalExpression.types
@@ -0,0 +1,114 @@
+//// [tests/cases/compiler/asyncCallInConditionalExpression.ts] ////
+
+=== a.ts ===
+declare const a: boolean;
+>a : boolean
+
+declare function async(...args: any[]): number;
+>async : (...args: any[]) => number
+>args : any[]
+
+const c1 = a ? async() : 0;
+>c1 : number
+>a ? async() : 0 : number
+>a : boolean
+>async() : number
+>async : (...args: any[]) => number
+>0 : 0
+
+const c2 = a ? async() : (x: number) => x;
+>c2 : number | ((x: number) => number)
+>a ? async() : (x: number) => x : number | ((x: number) => number)
+>a : boolean
+>async() : number
+>async : (...args: any[]) => number
+>(x: number) => x : (x: number) => number
+>x : number
+>x : number
+
+const c3 = a ? async(1) : 0;
+>c3 : number
+>a ? async(1) : 0 : number
+>a : boolean
+>async(1) : number
+>async : (...args: any[]) => number
+>1 : 1
+>0 : 0
+
+const c4 = a ? async() : a ? async() : 0;
+>c4 : number
+>a ? async() : a ? async() : 0 : number
+>a : boolean
+>async() : number
+>async : (...args: any[]) => number
+>a ? async() : 0 : number
+>a : false
+>async() : number
+>async : (...args: any[]) => number
+>0 : 0
+
+const f1 = async(): Promise<number> => 1;
+>f1 : () => Promise<number>
+>async(): Promise<number> => 1 : () => Promise<number>
+>1 : 1
+
+const f2 = async (): Promise<number> => 1;
+>f2 : () => Promise<number>
+>async (): Promise<number> => 1 : () => Promise<number>
+>1 : 1
+
+const f3 = a ? async(): Promise<number> => 1 : 2;
+>f3 : 2 | (() => Promise<number>)
+>a ? async(): Promise<number> => 1 : 2 : 2 | (() => Promise<number>)
+>a : boolean
+>async(): Promise<number> => 1 : () => Promise<number>
+>1 : 1
+>2 : 2
+
+const f4 = a ? async () => 1 : 2;
+>f4 : 2 | (() => Promise<number>)
+>a ? async () => 1 : 2 : 2 | (() => Promise<number>)
+>a : boolean
+>async () => 1 : () => Promise<number>
+>1 : 1
+>2 : 2
+
+const f5 = a ? 1 : async(): Promise<number> => 1;
+>f5 : 1 | (() => Promise<number>)
+>a ? 1 : async(): Promise<number> => 1 : 1 | (() => Promise<number>)
+>a : boolean
+>1 : 1
+>async(): Promise<number> => 1 : () => Promise<number>
+>1 : 1
+
+export {};
+
+=== b.js ===
+const t = true;
+>t : true
+>true : true
+
+function async() { return 1; }
+>async : () => number
+>1 : 1
+
+const j1 = t ? async() : 0;
+>j1 : number
+>t ? async() : 0 : number
+>t : true
+>async() : number
+>async : () => number
+>0 : 0
+
+const j2 = t ? async() : x => x;
+>j2 : number | ((x: any) => any)
+>t ? async() : x => x : number | ((x: any) => any)
+>t : true
+>async() : number
+>async : () => number
+>x => x : (x: any) => any
+>x : any
+>x : any
+
+export {};
+
diff --git a/tsc/testdata/tests/cases/compiler/asyncCallInConditionalExpression.ts b/tsc/testdata/tests/cases/compiler/asyncCallInConditionalExpression.ts
new file mode 100644
index 0000000000000..d695c5021479b
--- /dev/null
+++ b/tsc/testdata/tests/cases/compiler/asyncCallInConditionalExpression.ts
@@ -0,0 +1,27 @@
+// @target: esnext
+// @allowJs: true
+// @outDir: ./out
+// @filename: a.ts
+declare const a: boolean;
+declare function async(...args: any[]): number;
+
+const c1 = a ? async() : 0;
+const c2 = a ? async() : (x: number) => x;
+const c3 = a ? async(1) : 0;
+const c4 = a ? async() : a ? async() : 0;
+
+const f1 = async(): Promise<number> => 1;
+const f2 = async (): Promise<number> => 1;
+const f3 = a ? async(): Promise<number> => 1 : 2;
+const f4 = a ? async () => 1 : 2;
+const f5 = a ? 1 : async(): Promise<number> => 1;
+
+export {};
+
+// @filename: b.js
+const t = true;
+function async() { return 1; }
+const j1 = t ? async() : 0;
+const j2 = t ? async() : x => x;
+
+export {};