diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 06395d935b7..20a4246f372 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -24740,6 +24740,12 @@ namespace ts {
                     || anyType;
             }
 
+            const contextualReturnType = getContextualReturnType(func);
+            if (contextualReturnType) {
+                return getIterationTypeOfGeneratorFunctionReturnType(IterationTypeKind.Next, contextualReturnType, isAsync)
+                    || anyType;
+            }
+
             return anyType;
         }
 
diff --git a/tests/baselines/reference/generatorTypeCheck25.types b/tests/baselines/reference/generatorTypeCheck25.types
index d0498c2da16..12dbfeaede9 100644
--- a/tests/baselines/reference/generatorTypeCheck25.types
+++ b/tests/baselines/reference/generatorTypeCheck25.types
@@ -17,15 +17,15 @@ var g3: () => Iterable<Foo> = function* () {
 >function* () {    yield;    yield new Bar;    yield new Baz;    yield *[new Bar];    yield *[new Baz];} : () => Generator<Bar | Baz, void, undefined>
 
     yield;
->yield : any
+>yield : undefined
 
     yield new Bar;
->yield new Bar : any
+>yield new Bar : undefined
 >new Bar : Bar
 >Bar : typeof Bar
 
     yield new Baz;
->yield new Baz : any
+>yield new Baz : undefined
 >new Baz : Baz
 >Baz : typeof Baz
 
diff --git a/tests/baselines/reference/generatorTypeCheck28.types b/tests/baselines/reference/generatorTypeCheck28.types
index 9cd4e5e82ce..6921c946a39 100644
--- a/tests/baselines/reference/generatorTypeCheck28.types
+++ b/tests/baselines/reference/generatorTypeCheck28.types
@@ -14,7 +14,7 @@ function* g(): IterableIterator<(x: string) => number> {
 >iterator : symbol
 
             yield x => x.length;
->yield x => x.length : any
+>yield x => x.length : undefined
 >x => x.length : (x: string) => number
 >x : string
 >x.length : number
diff --git a/tests/baselines/reference/generatorTypeCheck45.types b/tests/baselines/reference/generatorTypeCheck45.types
index cf409241947..18d3e9a5fc2 100644
--- a/tests/baselines/reference/generatorTypeCheck45.types
+++ b/tests/baselines/reference/generatorTypeCheck45.types
@@ -12,7 +12,7 @@ foo("", function* () { yield x => x.length }, p => undefined); // T is fixed, sh
 >foo : <T, U>(x: T, fun: () => Iterator<(x: T) => U, any, undefined>, fun2: (y: U) => T) => T
 >"" : ""
 >function* () { yield x => x.length } : () => Generator<(x: string) => number, void, unknown>
->yield x => x.length : any
+>yield x => x.length : undefined
 >x => x.length : (x: string) => number
 >x : string
 >x.length : number
diff --git a/tests/baselines/reference/generatorTypeCheck46.types b/tests/baselines/reference/generatorTypeCheck46.types
index cd565d55911..283188193b7 100644
--- a/tests/baselines/reference/generatorTypeCheck46.types
+++ b/tests/baselines/reference/generatorTypeCheck46.types
@@ -24,7 +24,7 @@ foo("", function* () {
 >iterator : symbol
 
             yield x => x.length
->yield x => x.length : any
+>yield x => x.length : undefined
 >x => x.length : (x: string) => number
 >x : string
 >x.length : number
diff --git a/tests/baselines/reference/generatorTypeCheck62.types b/tests/baselines/reference/generatorTypeCheck62.types
index be5635a07fc..ed957295c31 100644
--- a/tests/baselines/reference/generatorTypeCheck62.types
+++ b/tests/baselines/reference/generatorTypeCheck62.types
@@ -32,7 +32,7 @@ export function strategy<T extends StrategicState>(stratName: string, gen: (a: T
 >stratName : string
             }
             yield next;
->yield next : any
+>yield next : undefined
 >next : T
         }
     }
@@ -70,7 +70,7 @@ export const Nothing2: Strategy<State> = strategy("Nothing", function*(state: St
 >state : State
 
     yield state;
->yield state : any
+>yield state : undefined
 >state : State
 
 });
@@ -84,7 +84,7 @@ export const Nothing3: Strategy<State> = strategy("Nothing", function* (state: S
 >state : State
 
     yield ;
->yield : any
+>yield : undefined
 
     return state;
 >state : State
diff --git a/tests/baselines/reference/generatorTypeCheck63.types b/tests/baselines/reference/generatorTypeCheck63.types
index 8a1d03dcb16..64d67083e61 100644
--- a/tests/baselines/reference/generatorTypeCheck63.types
+++ b/tests/baselines/reference/generatorTypeCheck63.types
@@ -32,7 +32,7 @@ export function strategy<T extends StrategicState>(stratName: string, gen: (a: T
 >stratName : string
             }
             yield next;
->yield next : any
+>yield next : undefined
 >next : T
         }
     }
@@ -97,7 +97,7 @@ export const Nothing3: Strategy<State> = strategy("Nothing", function* (state: S
 >state : State
 
     yield state;
->yield state : any
+>yield state : undefined
 >state : State
 
     return 1;
diff --git a/tests/baselines/reference/generatorYieldContextualType.symbols b/tests/baselines/reference/generatorYieldContextualType.symbols
new file mode 100644
index 00000000000..80d20b90d75
--- /dev/null
+++ b/tests/baselines/reference/generatorYieldContextualType.symbols
@@ -0,0 +1,44 @@
+=== tests/cases/conformance/generators/generatorYieldContextualType.ts ===
+declare function f1<T, R, S>(gen: () => Generator<R, T, S>): void;
+>f1 : Symbol(f1, Decl(generatorYieldContextualType.ts, 0, 0))
+>T : Symbol(T, Decl(generatorYieldContextualType.ts, 0, 20))
+>R : Symbol(R, Decl(generatorYieldContextualType.ts, 0, 22))
+>S : Symbol(S, Decl(generatorYieldContextualType.ts, 0, 25))
+>gen : Symbol(gen, Decl(generatorYieldContextualType.ts, 0, 29))
+>Generator : Symbol(Generator, Decl(lib.es2015.generator.d.ts, --, --))
+>R : Symbol(R, Decl(generatorYieldContextualType.ts, 0, 22))
+>T : Symbol(T, Decl(generatorYieldContextualType.ts, 0, 20))
+>S : Symbol(S, Decl(generatorYieldContextualType.ts, 0, 25))
+
+f1<0, 0, 1>(function* () {
+>f1 : Symbol(f1, Decl(generatorYieldContextualType.ts, 0, 0))
+
+	const a = yield 0;
+>a : Symbol(a, Decl(generatorYieldContextualType.ts, 2, 6))
+
+	return 0;
+});
+
+declare function f2<T, R, S>(gen: () => Generator<R, T, S> | AsyncGenerator<R, T, S>): void;
+>f2 : Symbol(f2, Decl(generatorYieldContextualType.ts, 4, 3))
+>T : Symbol(T, Decl(generatorYieldContextualType.ts, 6, 20))
+>R : Symbol(R, Decl(generatorYieldContextualType.ts, 6, 22))
+>S : Symbol(S, Decl(generatorYieldContextualType.ts, 6, 25))
+>gen : Symbol(gen, Decl(generatorYieldContextualType.ts, 6, 29))
+>Generator : Symbol(Generator, Decl(lib.es2015.generator.d.ts, --, --))
+>R : Symbol(R, Decl(generatorYieldContextualType.ts, 6, 22))
+>T : Symbol(T, Decl(generatorYieldContextualType.ts, 6, 20))
+>S : Symbol(S, Decl(generatorYieldContextualType.ts, 6, 25))
+>AsyncGenerator : Symbol(AsyncGenerator, Decl(lib.es2018.asyncgenerator.d.ts, --, --))
+>R : Symbol(R, Decl(generatorYieldContextualType.ts, 6, 22))
+>T : Symbol(T, Decl(generatorYieldContextualType.ts, 6, 20))
+>S : Symbol(S, Decl(generatorYieldContextualType.ts, 6, 25))
+
+f2<0, 0, 1>(async function* () {
+>f2 : Symbol(f2, Decl(generatorYieldContextualType.ts, 4, 3))
+
+	const a = yield 0;
+>a : Symbol(a, Decl(generatorYieldContextualType.ts, 8, 6))
+
+	return 0;
+});
diff --git a/tests/baselines/reference/generatorYieldContextualType.types b/tests/baselines/reference/generatorYieldContextualType.types
new file mode 100644
index 00000000000..5caccffa933
--- /dev/null
+++ b/tests/baselines/reference/generatorYieldContextualType.types
@@ -0,0 +1,38 @@
+=== tests/cases/conformance/generators/generatorYieldContextualType.ts ===
+declare function f1<T, R, S>(gen: () => Generator<R, T, S>): void;
+>f1 : <T, R, S>(gen: () => Generator<R, T, S>) => void
+>gen : () => Generator<R, T, S>
+
+f1<0, 0, 1>(function* () {
+>f1<0, 0, 1>(function* () {	const a = yield 0;	return 0;}) : void
+>f1 : <T, R, S>(gen: () => Generator<R, T, S>) => void
+>function* () {	const a = yield 0;	return 0;} : () => Generator<0, 0, unknown>
+
+	const a = yield 0;
+>a : 1
+>yield 0 : 1
+>0 : 0
+
+	return 0;
+>0 : 0
+
+});
+
+declare function f2<T, R, S>(gen: () => Generator<R, T, S> | AsyncGenerator<R, T, S>): void;
+>f2 : <T, R, S>(gen: () => Generator<R, T, S> | AsyncGenerator<R, T, S>) => void
+>gen : () => Generator<R, T, S> | AsyncGenerator<R, T, S>
+
+f2<0, 0, 1>(async function* () {
+>f2<0, 0, 1>(async function* () {	const a = yield 0;	return 0;}) : void
+>f2 : <T, R, S>(gen: () => Generator<R, T, S> | AsyncGenerator<R, T, S>) => void
+>async function* () {	const a = yield 0;	return 0;} : () => AsyncGenerator<0, 0, unknown>
+
+	const a = yield 0;
+>a : 1
+>yield 0 : 1
+>0 : 0
+
+	return 0;
+>0 : 0
+
+});
diff --git a/tests/baselines/reference/types.asyncGenerators.es2018.1.types b/tests/baselines/reference/types.asyncGenerators.es2018.1.types
index ad35f2a796f..24da9312c15 100644
--- a/tests/baselines/reference/types.asyncGenerators.es2018.1.types
+++ b/tests/baselines/reference/types.asyncGenerators.es2018.1.types
@@ -78,7 +78,7 @@ const assignability1: () => AsyncIterableIterator<number> = async function * ()
 >async function * () {    yield 1;} : () => AsyncGenerator<number, void, unknown>
 
     yield 1;
->yield 1 : any
+>yield 1 : undefined
 >1 : 1
 
 };
@@ -87,7 +87,7 @@ const assignability2: () => AsyncIterableIterator<number> = async function * ()
 >async function * () {    yield Promise.resolve(1);} : () => AsyncGenerator<number, void, unknown>
 
     yield Promise.resolve(1);
->yield Promise.resolve(1) : any
+>yield Promise.resolve(1) : undefined
 >Promise.resolve(1) : Promise<number>
 >Promise.resolve : { <T>(value: T | PromiseLike<T>): Promise<T>; (): Promise<void>; }
 >Promise : PromiseConstructor
@@ -138,7 +138,7 @@ const assignability6: () => AsyncIterable<number> = async function * () {
 >async function * () {    yield 1;} : () => AsyncGenerator<number, void, unknown>
 
     yield 1;
->yield 1 : any
+>yield 1 : undefined
 >1 : 1
 
 };
@@ -147,7 +147,7 @@ const assignability7: () => AsyncIterable<number> = async function * () {
 >async function * () {    yield Promise.resolve(1);} : () => AsyncGenerator<number, void, unknown>
 
     yield Promise.resolve(1);
->yield Promise.resolve(1) : any
+>yield Promise.resolve(1) : undefined
 >Promise.resolve(1) : Promise<number>
 >Promise.resolve : { <T>(value: T | PromiseLike<T>): Promise<T>; (): Promise<void>; }
 >Promise : PromiseConstructor
@@ -198,7 +198,7 @@ const assignability11: () => AsyncIterator<number> = async function * () {
 >async function * () {    yield 1;} : () => AsyncGenerator<number, void, unknown>
 
     yield 1;
->yield 1 : any
+>yield 1 : undefined
 >1 : 1
 
 };
@@ -207,7 +207,7 @@ const assignability12: () => AsyncIterator<number> = async function * () {
 >async function * () {    yield Promise.resolve(1);} : () => AsyncGenerator<number, void, unknown>
 
     yield Promise.resolve(1);
->yield Promise.resolve(1) : any
+>yield Promise.resolve(1) : undefined
 >Promise.resolve(1) : Promise<number>
 >Promise.resolve : { <T>(value: T | PromiseLike<T>): Promise<T>; (): Promise<void>; }
 >Promise : PromiseConstructor
diff --git a/tests/baselines/reference/types.asyncGenerators.es2018.2.types b/tests/baselines/reference/types.asyncGenerators.es2018.2.types
index 23bf7225eb9..022ddd297a2 100644
--- a/tests/baselines/reference/types.asyncGenerators.es2018.2.types
+++ b/tests/baselines/reference/types.asyncGenerators.es2018.2.types
@@ -32,7 +32,7 @@ const assignability1: () => AsyncIterableIterator<number> = async function * ()
 >async function * () {    yield "a";} : () => AsyncGenerator<string, void, unknown>
 
     yield "a";
->yield "a" : any
+>yield "a" : undefined
 >"a" : "a"
 
 };
@@ -65,7 +65,7 @@ const assignability4: () => AsyncIterable<number> = async function * () {
 >async function * () {    yield "a";} : () => AsyncGenerator<string, void, unknown>
 
     yield "a";
->yield "a" : any
+>yield "a" : undefined
 >"a" : "a"
 
 };
@@ -98,7 +98,7 @@ const assignability7: () => AsyncIterator<number> = async function * () {
 >async function * () {    yield "a";} : () => AsyncGenerator<string, void, unknown>
 
     yield "a";
->yield "a" : any
+>yield "a" : undefined
 >"a" : "a"
 
 };
diff --git a/tests/baselines/reference/uniqueSymbols.types b/tests/baselines/reference/uniqueSymbols.types
index da2f9895218..02ededf7b1f 100644
--- a/tests/baselines/reference/uniqueSymbols.types
+++ b/tests/baselines/reference/uniqueSymbols.types
@@ -839,7 +839,7 @@ const o3: Context = {
 >method3 : () => AsyncGenerator<unique symbol, void, unknown>
 
         yield s; // yield type should not widen due to contextual type
->yield s : any
+>yield s : undefined
 >s : unique symbol
 
     },
@@ -847,7 +847,7 @@ const o3: Context = {
 >method4 : () => Generator<unique symbol, void, unknown>
 
         yield s; // yield type should not widen due to contextual type
->yield s : any
+>yield s : undefined
 >s : unique symbol
 
     },
diff --git a/tests/baselines/reference/uniqueSymbolsDeclarations.types b/tests/baselines/reference/uniqueSymbolsDeclarations.types
index b8c32385f4b..db198153153 100644
--- a/tests/baselines/reference/uniqueSymbolsDeclarations.types
+++ b/tests/baselines/reference/uniqueSymbolsDeclarations.types
@@ -832,7 +832,7 @@ const o4: Context = {
 >method3 : () => AsyncGenerator<unique symbol, void, unknown>
 
         yield s; // yield type should not widen due to contextual type
->yield s : any
+>yield s : undefined
 >s : unique symbol
 
     },
@@ -840,7 +840,7 @@ const o4: Context = {
 >method4 : () => Generator<unique symbol, void, unknown>
 
         yield s; // yield type should not widen due to contextual type
->yield s : any
+>yield s : undefined
 >s : unique symbol
 
     },
diff --git a/tests/cases/conformance/generators/generatorYieldContextualType.ts b/tests/cases/conformance/generators/generatorYieldContextualType.ts
new file mode 100644
index 00000000000..20cad6a9189
--- /dev/null
+++ b/tests/cases/conformance/generators/generatorYieldContextualType.ts
@@ -0,0 +1,14 @@
+// @target: esnext
+// @strict: true
+// @noEmit: true
+declare function f1<T, R, S>(gen: () => Generator<R, T, S>): void;
+f1<0, 0, 1>(function* () {
+	const a = yield 0;
+	return 0;
+});
+
+declare function f2<T, R, S>(gen: () => Generator<R, T, S> | AsyncGenerator<R, T, S>): void;
+f2<0, 0, 1>(async function* () {
+	const a = yield 0;
+	return 0;
+});
\ No newline at end of file