diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 91346429b1774..101947565e916 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -32422,29 +32422,28 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         if (!(type.flags & TypeFlags.Union)) {
             return getContextualCallSignature(type, node);
         }
-        let signatureList: Signature[] | undefined;
-        const types = (type as UnionType).types;
-        for (const current of types) {
-            const signature = getContextualCallSignature(current, node);
-            if (signature) {
-                if (!signatureList) {
-                    // This signature will contribute to contextual union signature
-                    signatureList = [signature];
-                }
-                else if (!compareSignaturesIdentical(signatureList[0], signature, /*partialMatch*/ false, /*ignoreThisTypes*/ true, /*ignoreReturnTypes*/ true, compareTypesIdentical)) {
-                    // Signatures aren't identical, do not use
-                    return undefined;
-                }
-                else {
-                    // Use this signature for contextual union signature
-                    signatureList.push(signature);
-                }
+
+        let signatures = mapDefined((type as UnionType).types, t => getContextualCallSignature(t, node));
+        const functionFlags = getFunctionFlags(node);
+        if (functionFlags & FunctionFlags.Generator) {
+            signatures = filter(signatures, s => checkGeneratorInstantiationAssignabilityToReturnType(getReturnTypeOfSignature(s), functionFlags, /*errorNode*/ undefined));
+        }
+        else if (functionFlags & FunctionFlags.Async) {
+            signatures = filter(signatures, s => !!getAwaitedTypeOfPromise(getReturnTypeOfSignature(s)));
+        }
+        signatures.sort((s1, s2) => getMinArgumentCount(s1) - getMinArgumentCount(s2));
+        if (!signatures.length) {
+            return;
+        }
+
+        for (let i = 1; i < signatures.length; i++) {
+            if (!compareSignaturesIdentical(signatures[0], signatures[i], /*partialMatch*/ true, /*ignoreThisTypes*/ true, /*ignoreReturnTypes*/ true, compareTypesSubtypeOf)) {
+                // Signatures aren't identical, do not use
+                return undefined;
             }
         }
         // Result is union of signatures collected (return type is union of return types of this signature set)
-        if (signatureList) {
-            return signatureList.length === 1 ? signatureList[0] : createUnionSignature(signatureList[0], signatureList);
-        }
+        return signatures.length === 1 ? signatures[0] : createUnionSignature(signatures[0], signatures);
     }
 
     function checkGrammarRegularExpressionLiteral(node: RegularExpressionLiteral) {
diff --git a/tests/baselines/reference/contextualSignatureWithExtraParameters.symbols b/tests/baselines/reference/contextualSignatureWithExtraParameters.symbols
new file mode 100644
index 0000000000000..0016764e832c5
--- /dev/null
+++ b/tests/baselines/reference/contextualSignatureWithExtraParameters.symbols
@@ -0,0 +1,229 @@
+//// [tests/cases/compiler/contextualSignatureWithExtraParameters.ts] ////
+
+=== contextualSignatureWithExtraParameters.ts ===
+// https://github.com/microsoft/TypeScript/issues/59309
+function f1(
+>f1 : Symbol(f1, Decl(contextualSignatureWithExtraParameters.ts, 0, 0))
+
+    cb: ((item: number) => void) | ((item: number, extra: string) => void),
+>cb : Symbol(cb, Decl(contextualSignatureWithExtraParameters.ts, 1, 12))
+>item : Symbol(item, Decl(contextualSignatureWithExtraParameters.ts, 2, 10))
+>item : Symbol(item, Decl(contextualSignatureWithExtraParameters.ts, 2, 37))
+>extra : Symbol(extra, Decl(contextualSignatureWithExtraParameters.ts, 2, 50))
+
+  ) {}
+  
+f1((item) => {});
+>f1 : Symbol(f1, Decl(contextualSignatureWithExtraParameters.ts, 0, 0))
+>item : Symbol(item, Decl(contextualSignatureWithExtraParameters.ts, 5, 4))
+
+function f2<T>(
+>f2 : Symbol(f2, Decl(contextualSignatureWithExtraParameters.ts, 5, 17))
+>T : Symbol(T, Decl(contextualSignatureWithExtraParameters.ts, 7, 12))
+
+    arr: T[],
+>arr : Symbol(arr, Decl(contextualSignatureWithExtraParameters.ts, 7, 15))
+>T : Symbol(T, Decl(contextualSignatureWithExtraParameters.ts, 7, 12))
+
+    cb: ((item: T) => void) | ((item: T, extra: unknown) => void),
+>cb : Symbol(cb, Decl(contextualSignatureWithExtraParameters.ts, 8, 13))
+>item : Symbol(item, Decl(contextualSignatureWithExtraParameters.ts, 9, 10))
+>T : Symbol(T, Decl(contextualSignatureWithExtraParameters.ts, 7, 12))
+>item : Symbol(item, Decl(contextualSignatureWithExtraParameters.ts, 9, 32))
+>T : Symbol(T, Decl(contextualSignatureWithExtraParameters.ts, 7, 12))
+>extra : Symbol(extra, Decl(contextualSignatureWithExtraParameters.ts, 9, 40))
+
+  ) {}
+  
+f2([1, 2, 3], (item) => {});
+>f2 : Symbol(f2, Decl(contextualSignatureWithExtraParameters.ts, 5, 17))
+>item : Symbol(item, Decl(contextualSignatureWithExtraParameters.ts, 12, 15))
+
+export interface AsyncResultCallback<T, E = Error> {
+>AsyncResultCallback : Symbol(AsyncResultCallback, Decl(contextualSignatureWithExtraParameters.ts, 12, 28))
+>T : Symbol(T, Decl(contextualSignatureWithExtraParameters.ts, 14, 37))
+>E : Symbol(E, Decl(contextualSignatureWithExtraParameters.ts, 14, 39))
+>Error : Symbol(Error, Decl(lib.es5.d.ts, --, --), Decl(lib.es5.d.ts, --, --), Decl(lib.es2022.error.d.ts, --, --))
+
+    (err?: E | null, result?: T): void;
+>err : Symbol(err, Decl(contextualSignatureWithExtraParameters.ts, 15, 5))
+>E : Symbol(E, Decl(contextualSignatureWithExtraParameters.ts, 14, 39))
+>result : Symbol(result, Decl(contextualSignatureWithExtraParameters.ts, 15, 20))
+>T : Symbol(T, Decl(contextualSignatureWithExtraParameters.ts, 14, 37))
+}
+
+export interface AsyncResultIterator<T, R, E = Error> {
+>AsyncResultIterator : Symbol(AsyncResultIterator, Decl(contextualSignatureWithExtraParameters.ts, 16, 1))
+>T : Symbol(T, Decl(contextualSignatureWithExtraParameters.ts, 18, 37))
+>R : Symbol(R, Decl(contextualSignatureWithExtraParameters.ts, 18, 39))
+>E : Symbol(E, Decl(contextualSignatureWithExtraParameters.ts, 18, 42))
+>Error : Symbol(Error, Decl(lib.es5.d.ts, --, --), Decl(lib.es5.d.ts, --, --), Decl(lib.es2022.error.d.ts, --, --))
+
+    (item: T, callback: AsyncResultCallback<R, E>): void;
+>item : Symbol(item, Decl(contextualSignatureWithExtraParameters.ts, 19, 5))
+>T : Symbol(T, Decl(contextualSignatureWithExtraParameters.ts, 18, 37))
+>callback : Symbol(callback, Decl(contextualSignatureWithExtraParameters.ts, 19, 13))
+>AsyncResultCallback : Symbol(AsyncResultCallback, Decl(contextualSignatureWithExtraParameters.ts, 12, 28))
+>R : Symbol(R, Decl(contextualSignatureWithExtraParameters.ts, 18, 39))
+>E : Symbol(E, Decl(contextualSignatureWithExtraParameters.ts, 18, 42))
+}
+export interface AsyncResultIteratorPromise<T, R> {
+>AsyncResultIteratorPromise : Symbol(AsyncResultIteratorPromise, Decl(contextualSignatureWithExtraParameters.ts, 20, 1))
+>T : Symbol(T, Decl(contextualSignatureWithExtraParameters.ts, 21, 44))
+>R : Symbol(R, Decl(contextualSignatureWithExtraParameters.ts, 21, 46))
+
+    (item: T): Promise<R>;
+>item : Symbol(item, Decl(contextualSignatureWithExtraParameters.ts, 22, 5))
+>T : Symbol(T, Decl(contextualSignatureWithExtraParameters.ts, 21, 44))
+>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, --, --))
+>R : Symbol(R, Decl(contextualSignatureWithExtraParameters.ts, 21, 46))
+}
+
+declare function mapLimit<T, R, E = Error>(
+>mapLimit : Symbol(mapLimit, Decl(contextualSignatureWithExtraParameters.ts, 23, 1))
+>T : Symbol(T, Decl(contextualSignatureWithExtraParameters.ts, 25, 26))
+>R : Symbol(R, Decl(contextualSignatureWithExtraParameters.ts, 25, 28))
+>E : Symbol(E, Decl(contextualSignatureWithExtraParameters.ts, 25, 31))
+>Error : Symbol(Error, Decl(lib.es5.d.ts, --, --), Decl(lib.es5.d.ts, --, --), Decl(lib.es2022.error.d.ts, --, --))
+
+    arr: T[],
+>arr : Symbol(arr, Decl(contextualSignatureWithExtraParameters.ts, 25, 43))
+>T : Symbol(T, Decl(contextualSignatureWithExtraParameters.ts, 25, 26))
+
+    limit: number,
+>limit : Symbol(limit, Decl(contextualSignatureWithExtraParameters.ts, 26, 13))
+
+    iterator:  AsyncResultIteratorPromise<T, R> | AsyncResultIterator<T, R, E>,
+>iterator : Symbol(iterator, Decl(contextualSignatureWithExtraParameters.ts, 27, 18))
+>AsyncResultIteratorPromise : Symbol(AsyncResultIteratorPromise, Decl(contextualSignatureWithExtraParameters.ts, 20, 1))
+>T : Symbol(T, Decl(contextualSignatureWithExtraParameters.ts, 25, 26))
+>R : Symbol(R, Decl(contextualSignatureWithExtraParameters.ts, 25, 28))
+>AsyncResultIterator : Symbol(AsyncResultIterator, Decl(contextualSignatureWithExtraParameters.ts, 16, 1))
+>T : Symbol(T, Decl(contextualSignatureWithExtraParameters.ts, 25, 26))
+>R : Symbol(R, Decl(contextualSignatureWithExtraParameters.ts, 25, 28))
+>E : Symbol(E, Decl(contextualSignatureWithExtraParameters.ts, 25, 31))
+
+): Promise<R[]>;
+>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, --, --))
+>R : Symbol(R, Decl(contextualSignatureWithExtraParameters.ts, 25, 28))
+
+mapLimit([1,2,3], 3, async (n) => {
+>mapLimit : Symbol(mapLimit, Decl(contextualSignatureWithExtraParameters.ts, 23, 1))
+>n : Symbol(n, Decl(contextualSignatureWithExtraParameters.ts, 31, 28))
+
+    return n ** 2;
+>n : Symbol(n, Decl(contextualSignatureWithExtraParameters.ts, 31, 28))
+
+});
+
+function f3(
+>f3 : Symbol(f3, Decl(contextualSignatureWithExtraParameters.ts, 33, 3))
+
+    cb: ((a: string, b?: string) => void) | ((a: string, ...rest: string[]) => void)
+>cb : Symbol(cb, Decl(contextualSignatureWithExtraParameters.ts, 35, 12))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 36, 10))
+>b : Symbol(b, Decl(contextualSignatureWithExtraParameters.ts, 36, 20))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 36, 46))
+>rest : Symbol(rest, Decl(contextualSignatureWithExtraParameters.ts, 36, 56))
+
+  ) {}
+  
+f3((a) => {});
+>f3 : Symbol(f3, Decl(contextualSignatureWithExtraParameters.ts, 33, 3))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 39, 4))
+
+f3((a, b) => {});
+>f3 : Symbol(f3, Decl(contextualSignatureWithExtraParameters.ts, 33, 3))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 40, 4))
+>b : Symbol(b, Decl(contextualSignatureWithExtraParameters.ts, 40, 6))
+
+function f4(
+>f4 : Symbol(f4, Decl(contextualSignatureWithExtraParameters.ts, 40, 17))
+
+    cb: ((a: string, b: string) => void) | ((a: string, ...rest: string[]) => void)
+>cb : Symbol(cb, Decl(contextualSignatureWithExtraParameters.ts, 42, 12))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 43, 10))
+>b : Symbol(b, Decl(contextualSignatureWithExtraParameters.ts, 43, 20))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 43, 45))
+>rest : Symbol(rest, Decl(contextualSignatureWithExtraParameters.ts, 43, 55))
+
+  ) {}
+  
+f4((a) => {});
+>f4 : Symbol(f4, Decl(contextualSignatureWithExtraParameters.ts, 40, 17))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 46, 4))
+
+f4((a, b) => {});
+>f4 : Symbol(f4, Decl(contextualSignatureWithExtraParameters.ts, 40, 17))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 47, 4))
+>b : Symbol(b, Decl(contextualSignatureWithExtraParameters.ts, 47, 6))
+
+function f5(
+>f5 : Symbol(f5, Decl(contextualSignatureWithExtraParameters.ts, 47, 17))
+
+    cb: ((a: string, b: string) => void) | ((...rest: string[]) => void)
+>cb : Symbol(cb, Decl(contextualSignatureWithExtraParameters.ts, 49, 12))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 50, 10))
+>b : Symbol(b, Decl(contextualSignatureWithExtraParameters.ts, 50, 20))
+>rest : Symbol(rest, Decl(contextualSignatureWithExtraParameters.ts, 50, 45))
+
+  ) {}
+  
+f5((a) => {});
+>f5 : Symbol(f5, Decl(contextualSignatureWithExtraParameters.ts, 47, 17))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 53, 4))
+
+f5((a, b) => {});
+>f5 : Symbol(f5, Decl(contextualSignatureWithExtraParameters.ts, 47, 17))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 54, 4))
+>b : Symbol(b, Decl(contextualSignatureWithExtraParameters.ts, 54, 6))
+
+function f6(
+>f6 : Symbol(f6, Decl(contextualSignatureWithExtraParameters.ts, 54, 17))
+
+  cb: ((a: string) => string) | ((a: "a" | "b") => Promise<"a" | "b">)
+>cb : Symbol(cb, Decl(contextualSignatureWithExtraParameters.ts, 56, 12))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 57, 8))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 57, 34))
+>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, --, --))
+
+) {}
+
+f6(async (a) => a);
+>f6 : Symbol(f6, Decl(contextualSignatureWithExtraParameters.ts, 54, 17))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 60, 10))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 60, 10))
+
+function f7(
+>f7 : Symbol(f7, Decl(contextualSignatureWithExtraParameters.ts, 60, 19))
+
+  cb: ((a: string) => string) | ((a: number) => Generator<number, void, unknown>)
+>cb : Symbol(cb, Decl(contextualSignatureWithExtraParameters.ts, 62, 12))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 63, 8))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 63, 34))
+>Generator : Symbol(Generator, Decl(lib.es2015.generator.d.ts, --, --))
+
+) {}
+
+f7(function* generator(a) {yield 0});
+>f7 : Symbol(f7, Decl(contextualSignatureWithExtraParameters.ts, 60, 19))
+>generator : Symbol(generator, Decl(contextualSignatureWithExtraParameters.ts, 66, 3))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 66, 23))
+
+function f8(
+>f8 : Symbol(f8, Decl(contextualSignatureWithExtraParameters.ts, 66, 37))
+
+  cb: ((a: string) => string) | ((a: number) => AsyncGenerator<number, void, unknown>)
+>cb : Symbol(cb, Decl(contextualSignatureWithExtraParameters.ts, 68, 12))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 69, 8))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 69, 34))
+>AsyncGenerator : Symbol(AsyncGenerator, Decl(lib.es2018.asyncgenerator.d.ts, --, --))
+
+) {}
+
+f8(async function* generator(a) {yield 0});
+>f8 : Symbol(f8, Decl(contextualSignatureWithExtraParameters.ts, 66, 37))
+>generator : Symbol(generator, Decl(contextualSignatureWithExtraParameters.ts, 72, 3))
+>a : Symbol(a, Decl(contextualSignatureWithExtraParameters.ts, 72, 29))
+
+
diff --git a/tests/baselines/reference/contextualSignatureWithExtraParameters.types b/tests/baselines/reference/contextualSignatureWithExtraParameters.types
new file mode 100644
index 0000000000000..7b4eea10094be
--- /dev/null
+++ b/tests/baselines/reference/contextualSignatureWithExtraParameters.types
@@ -0,0 +1,342 @@
+//// [tests/cases/compiler/contextualSignatureWithExtraParameters.ts] ////
+
+=== contextualSignatureWithExtraParameters.ts ===
+// https://github.com/microsoft/TypeScript/issues/59309
+function f1(
+>f1 : (cb: ((item: number) => void) | ((item: number, extra: string) => void)) => void
+>   : ^  ^^                                                                  ^^^^^^^^^
+
+    cb: ((item: number) => void) | ((item: number, extra: string) => void),
+>cb : ((item: number) => void) | ((item: number, extra: string) => void)
+>   : ^^    ^^      ^^^^^    ^^^^^^    ^^      ^^     ^^      ^^^^^    ^
+>item : number
+>     : ^^^^^^
+>item : number
+>     : ^^^^^^
+>extra : string
+>      : ^^^^^^
+
+  ) {}
+  
+f1((item) => {});
+>f1((item) => {}) : void
+>                 : ^^^^
+>f1 : (cb: ((item: number) => void) | ((item: number, extra: string) => void)) => void
+>   : ^  ^^                                                                  ^^^^^^^^^
+>(item) => {} : (item: number) => void
+>             : ^    ^^^^^^^^^^^^^^^^^
+>item : number
+>     : ^^^^^^
+
+function f2<T>(
+>f2 : <T>(arr: T[], cb: ((item: T) => void) | ((item: T, extra: unknown) => void)) => void
+>   : ^ ^^   ^^   ^^  ^^                                                         ^^^^^^^^^
+
+    arr: T[],
+>arr : T[]
+>    : ^^^
+
+    cb: ((item: T) => void) | ((item: T, extra: unknown) => void),
+>cb : ((item: T) => void) | ((item: T, extra: unknown) => void)
+>   : ^^    ^^ ^^^^^    ^^^^^^    ^^ ^^     ^^       ^^^^^    ^
+>item : T
+>     : ^
+>item : T
+>     : ^
+>extra : unknown
+>      : ^^^^^^^
+
+  ) {}
+  
+f2([1, 2, 3], (item) => {});
+>f2([1, 2, 3], (item) => {}) : void
+>                            : ^^^^
+>f2 : <T>(arr: T[], cb: ((item: T) => void) | ((item: T, extra: unknown) => void)) => void
+>   : ^ ^^   ^^   ^^  ^^                                                         ^^^^^^^^^
+>[1, 2, 3] : number[]
+>          : ^^^^^^^^
+>1 : 1
+>  : ^
+>2 : 2
+>  : ^
+>3 : 3
+>  : ^
+>(item) => {} : (item: number) => void
+>             : ^    ^^^^^^^^^^^^^^^^^
+>item : number
+>     : ^^^^^^
+
+export interface AsyncResultCallback<T, E = Error> {
+    (err?: E | null, result?: T): void;
+>err : E | null | undefined
+>    : ^^^^^^^^^^^^^^^^^^^^
+>result : T | undefined
+>       : ^^^^^^^^^^^^^
+}
+
+export interface AsyncResultIterator<T, R, E = Error> {
+    (item: T, callback: AsyncResultCallback<R, E>): void;
+>item : T
+>     : ^
+>callback : AsyncResultCallback<R, E>
+>         : ^^^^^^^^^^^^^^^^^^^^^^^^^
+}
+export interface AsyncResultIteratorPromise<T, R> {
+    (item: T): Promise<R>;
+>item : T
+>     : ^
+}
+
+declare function mapLimit<T, R, E = Error>(
+>mapLimit : <T, R, E = Error>(arr: T[], limit: number, iterator: AsyncResultIteratorPromise<T, R> | AsyncResultIterator<T, R, E>) => Promise<R[]>
+>         : ^ ^^ ^^ ^^^^^^^^^^   ^^   ^^     ^^      ^^        ^^                                                               ^^^^^            
+
+    arr: T[],
+>arr : T[]
+>    : ^^^
+
+    limit: number,
+>limit : number
+>      : ^^^^^^
+
+    iterator:  AsyncResultIteratorPromise<T, R> | AsyncResultIterator<T, R, E>,
+>iterator : AsyncResultIteratorPromise<T, R> | AsyncResultIterator<T, R, E>
+>         : ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+
+): Promise<R[]>;
+
+mapLimit([1,2,3], 3, async (n) => {
+>mapLimit([1,2,3], 3, async (n) => {    return n ** 2;}) : Promise<number[]>
+>                                                        : ^^^^^^^^^^^^^^^^^
+>mapLimit : <T, R, E = Error>(arr: T[], limit: number, iterator: AsyncResultIteratorPromise<T, R> | AsyncResultIterator<T, R, E>) => Promise<R[]>
+>         : ^ ^^ ^^ ^^^^^^^^^^   ^^   ^^     ^^      ^^        ^^                                                               ^^^^^            
+>[1,2,3] : number[]
+>        : ^^^^^^^^
+>1 : 1
+>  : ^
+>2 : 2
+>  : ^
+>3 : 3
+>  : ^
+>3 : 3
+>  : ^
+>async (n) => {    return n ** 2;} : (n: number) => Promise<number>
+>                                  : ^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+>n : number
+>  : ^^^^^^
+
+    return n ** 2;
+>n ** 2 : number
+>       : ^^^^^^
+>n : number
+>  : ^^^^^^
+>2 : 2
+>  : ^
+
+});
+
+function f3(
+>f3 : (cb: ((a: string, b?: string) => void) | ((a: string, ...rest: string[]) => void)) => void
+>   : ^  ^^                                                                            ^^^^^^^^^
+
+    cb: ((a: string, b?: string) => void) | ((a: string, ...rest: string[]) => void)
+>cb : ((a: string, b?: string) => void) | ((a: string, ...rest: string[]) => void)
+>   : ^^ ^^      ^^ ^^^      ^^^^^    ^^^^^^ ^^      ^^^^^    ^^        ^^^^^    ^
+>a : string
+>  : ^^^^^^
+>b : string | undefined
+>  : ^^^^^^^^^^^^^^^^^^
+>a : string
+>  : ^^^^^^
+>rest : string[]
+>     : ^^^^^^^^
+
+  ) {}
+  
+f3((a) => {});
+>f3((a) => {}) : void
+>              : ^^^^
+>f3 : (cb: ((a: string, b?: string) => void) | ((a: string, ...rest: string[]) => void)) => void
+>   : ^  ^^                                                                            ^^^^^^^^^
+>(a) => {} : (a: string) => void
+>          : ^ ^^^^^^^^^^^^^^^^^
+>a : string
+>  : ^^^^^^
+
+f3((a, b) => {});
+>f3((a, b) => {}) : void
+>                 : ^^^^
+>f3 : (cb: ((a: string, b?: string) => void) | ((a: string, ...rest: string[]) => void)) => void
+>   : ^  ^^                                                                            ^^^^^^^^^
+>(a, b) => {} : (a: string, b: string | undefined) => void
+>             : ^ ^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+>a : string
+>  : ^^^^^^
+>b : string | undefined
+>  : ^^^^^^^^^^^^^^^^^^
+
+function f4(
+>f4 : (cb: ((a: string, b: string) => void) | ((a: string, ...rest: string[]) => void)) => void
+>   : ^  ^^                                                                           ^^^^^^^^^
+
+    cb: ((a: string, b: string) => void) | ((a: string, ...rest: string[]) => void)
+>cb : ((a: string, b: string) => void) | ((a: string, ...rest: string[]) => void)
+>   : ^^ ^^      ^^ ^^      ^^^^^    ^^^^^^ ^^      ^^^^^    ^^        ^^^^^    ^
+>a : string
+>  : ^^^^^^
+>b : string
+>  : ^^^^^^
+>a : string
+>  : ^^^^^^
+>rest : string[]
+>     : ^^^^^^^^
+
+  ) {}
+  
+f4((a) => {});
+>f4((a) => {}) : void
+>              : ^^^^
+>f4 : (cb: ((a: string, b: string) => void) | ((a: string, ...rest: string[]) => void)) => void
+>   : ^  ^^                                                                           ^^^^^^^^^
+>(a) => {} : (a: string) => void
+>          : ^ ^^^^^^^^^^^^^^^^^
+>a : string
+>  : ^^^^^^
+
+f4((a, b) => {});
+>f4((a, b) => {}) : void
+>                 : ^^^^
+>f4 : (cb: ((a: string, b: string) => void) | ((a: string, ...rest: string[]) => void)) => void
+>   : ^  ^^                                                                           ^^^^^^^^^
+>(a, b) => {} : (a: string, b: string) => void
+>             : ^ ^^^^^^^^^^ ^^^^^^^^^^^^^^^^^
+>a : string
+>  : ^^^^^^
+>b : string
+>  : ^^^^^^
+
+function f5(
+>f5 : (cb: ((a: string, b: string) => void) | ((...rest: string[]) => void)) => void
+>   : ^  ^^                                                                ^^^^^^^^^
+
+    cb: ((a: string, b: string) => void) | ((...rest: string[]) => void)
+>cb : ((a: string, b: string) => void) | ((...rest: string[]) => void)
+>   : ^^ ^^      ^^ ^^      ^^^^^    ^^^^^^^^^    ^^        ^^^^^    ^
+>a : string
+>  : ^^^^^^
+>b : string
+>  : ^^^^^^
+>rest : string[]
+>     : ^^^^^^^^
+
+  ) {}
+  
+f5((a) => {});
+>f5((a) => {}) : void
+>              : ^^^^
+>f5 : (cb: ((a: string, b: string) => void) | ((...rest: string[]) => void)) => void
+>   : ^  ^^                                                                ^^^^^^^^^
+>(a) => {} : (a: string) => void
+>          : ^ ^^^^^^^^^^^^^^^^^
+>a : string
+>  : ^^^^^^
+
+f5((a, b) => {});
+>f5((a, b) => {}) : void
+>                 : ^^^^
+>f5 : (cb: ((a: string, b: string) => void) | ((...rest: string[]) => void)) => void
+>   : ^  ^^                                                                ^^^^^^^^^
+>(a, b) => {} : (a: string, b: string) => void
+>             : ^ ^^^^^^^^^^ ^^^^^^^^^^^^^^^^^
+>a : string
+>  : ^^^^^^
+>b : string
+>  : ^^^^^^
+
+function f6(
+>f6 : (cb: ((a: string) => string) | ((a: "a" | "b") => Promise<"a" | "b">)) => void
+>   : ^  ^^                                                                ^^^^^^^^^
+
+  cb: ((a: string) => string) | ((a: "a" | "b") => Promise<"a" | "b">)
+>cb : ((a: string) => string) | ((a: "a" | "b") => Promise<"a" | "b">)
+>   : ^^ ^^      ^^^^^      ^^^^^^ ^^         ^^^^^                  ^
+>a : string
+>  : ^^^^^^
+>a : "a" | "b"
+>  : ^^^^^^^^^
+
+) {}
+
+f6(async (a) => a);
+>f6(async (a) => a) : void
+>                   : ^^^^
+>f6 : (cb: ((a: string) => string) | ((a: "a" | "b") => Promise<"a" | "b">)) => void
+>   : ^  ^^                                                                ^^^^^^^^^
+>async (a) => a : (a: "a" | "b") => Promise<"a" | "b">
+>               : ^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+>a : "a" | "b"
+>  : ^^^^^^^^^
+>a : "a" | "b"
+>  : ^^^^^^^^^
+
+function f7(
+>f7 : (cb: ((a: string) => string) | ((a: number) => Generator<number, void, unknown>)) => void
+>   : ^  ^^                                                                           ^^^^^^^^^
+
+  cb: ((a: string) => string) | ((a: number) => Generator<number, void, unknown>)
+>cb : ((a: string) => string) | ((a: number) => Generator<number, void, unknown>)
+>   : ^^ ^^      ^^^^^      ^^^^^^ ^^      ^^^^^                                ^
+>a : string
+>  : ^^^^^^
+>a : number
+>  : ^^^^^^
+
+) {}
+
+f7(function* generator(a) {yield 0});
+>f7(function* generator(a) {yield 0}) : void
+>                                     : ^^^^
+>f7 : (cb: ((a: string) => string) | ((a: number) => Generator<number, void, unknown>)) => void
+>   : ^  ^^                                                                           ^^^^^^^^^
+>function* generator(a) {yield 0} : (a: number) => Generator<number, void, unknown>
+>                                 : ^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+>generator : (a: number) => Generator<number, void, unknown>
+>          : ^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+>a : number
+>  : ^^^^^^
+>yield 0 : unknown
+>        : ^^^^^^^
+>0 : 0
+>  : ^
+
+function f8(
+>f8 : (cb: ((a: string) => string) | ((a: number) => AsyncGenerator<number, void, unknown>)) => void
+>   : ^  ^^                                                                                ^^^^^^^^^
+
+  cb: ((a: string) => string) | ((a: number) => AsyncGenerator<number, void, unknown>)
+>cb : ((a: string) => string) | ((a: number) => AsyncGenerator<number, void, unknown>)
+>   : ^^ ^^      ^^^^^      ^^^^^^ ^^      ^^^^^                                     ^
+>a : string
+>  : ^^^^^^
+>a : number
+>  : ^^^^^^
+
+) {}
+
+f8(async function* generator(a) {yield 0});
+>f8(async function* generator(a) {yield 0}) : void
+>                                           : ^^^^
+>f8 : (cb: ((a: string) => string) | ((a: number) => AsyncGenerator<number, void, unknown>)) => void
+>   : ^  ^^                                                                                ^^^^^^^^^
+>async function* generator(a) {yield 0} : (a: number) => AsyncGenerator<number, void, unknown>
+>                                       : ^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+>generator : (a: number) => AsyncGenerator<number, void, unknown>
+>          : ^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+>a : number
+>  : ^^^^^^
+>yield 0 : unknown
+>        : ^^^^^^^
+>0 : 0
+>  : ^
+
+
diff --git a/tests/cases/compiler/contextualSignatureWithExtraParameters.ts b/tests/cases/compiler/contextualSignatureWithExtraParameters.ts
new file mode 100644
index 0000000000000..a5382c0c4dc96
--- /dev/null
+++ b/tests/cases/compiler/contextualSignatureWithExtraParameters.ts
@@ -0,0 +1,79 @@
+// @strict: true
+// @target: esnext
+// @lib: esnext
+// @noEmit: true
+
+// https://github.com/microsoft/TypeScript/issues/59309
+function f1(
+    cb: ((item: number) => void) | ((item: number, extra: string) => void),
+  ) {}
+  
+f1((item) => {});
+
+function f2<T>(
+    arr: T[],
+    cb: ((item: T) => void) | ((item: T, extra: unknown) => void),
+  ) {}
+  
+f2([1, 2, 3], (item) => {});
+
+export interface AsyncResultCallback<T, E = Error> {
+    (err?: E | null, result?: T): void;
+}
+
+export interface AsyncResultIterator<T, R, E = Error> {
+    (item: T, callback: AsyncResultCallback<R, E>): void;
+}
+export interface AsyncResultIteratorPromise<T, R> {
+    (item: T): Promise<R>;
+}
+
+declare function mapLimit<T, R, E = Error>(
+    arr: T[],
+    limit: number,
+    iterator:  AsyncResultIteratorPromise<T, R> | AsyncResultIterator<T, R, E>,
+): Promise<R[]>;
+
+mapLimit([1,2,3], 3, async (n) => {
+    return n ** 2;
+});
+
+function f3(
+    cb: ((a: string, b?: string) => void) | ((a: string, ...rest: string[]) => void)
+  ) {}
+  
+f3((a) => {});
+f3((a, b) => {});
+
+function f4(
+    cb: ((a: string, b: string) => void) | ((a: string, ...rest: string[]) => void)
+  ) {}
+  
+f4((a) => {});
+f4((a, b) => {});
+
+function f5(
+    cb: ((a: string, b: string) => void) | ((...rest: string[]) => void)
+  ) {}
+  
+f5((a) => {});
+f5((a, b) => {});
+
+function f6(
+  cb: ((a: string) => string) | ((a: "a" | "b") => Promise<"a" | "b">)
+) {}
+
+f6(async (a) => a);
+
+function f7(
+  cb: ((a: string) => string) | ((a: number) => Generator<number, void, unknown>)
+) {}
+
+f7(function* generator(a) {yield 0});
+
+function f8(
+  cb: ((a: string) => string) | ((a: number) => AsyncGenerator<number, void, unknown>)
+) {}
+
+f8(async function* generator(a) {yield 0});
+