diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 84b111555df7e..4afe02a324d17 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -25695,10 +25695,16 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                 inferToMultipleTypes(source, (target as UnionOrIntersectionType).types, target.flags);
             }
             else if (source.flags & TypeFlags.Union) {
-                // Source is a union or intersection type, infer from each constituent type
-                const sourceTypes = (source as UnionOrIntersectionType).types;
-                for (const sourceType of sourceTypes) {
-                    inferFromTypes(sourceType, target);
+                const singleSignature = getSingleCallOrConstructSignature(source);
+                if (singleSignature) {
+                    inferFromTypes(getOrCreateTypeFromSignature(singleSignature), target);
+                }
+                else {
+                    // Source is a union type, infer from each constituent type
+                    const sourceTypes = (source as UnionType).types;
+                    for (const sourceType of sourceTypes) {
+                        inferFromTypes(sourceType, target);
+                    }
                 }
             }
             else if (target.flags & TypeFlags.TemplateLiteral) {
@@ -33946,8 +33952,8 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
     }
 
     function getSingleSignature(type: Type, kind: SignatureKind, allowMembers: boolean): Signature | undefined {
-        if (type.flags & TypeFlags.Object) {
-            const resolved = resolveStructuredTypeMembers(type as ObjectType);
+        if (type.flags & TypeFlags.StructuredType) {
+            const resolved = resolveStructuredTypeMembers(type as StructuredType);
             if (allowMembers || resolved.properties.length === 0 && resolved.indexInfos.length === 0) {
                 if (kind === SignatureKind.Call && resolved.callSignatures.length === 1 && resolved.constructSignatures.length === 0) {
                     return resolved.callSignatures[0];
diff --git a/tests/baselines/reference/inferenceFromUnionCombinedSingleSignature1.symbols b/tests/baselines/reference/inferenceFromUnionCombinedSingleSignature1.symbols
new file mode 100644
index 0000000000000..e34449bcf8cb2
--- /dev/null
+++ b/tests/baselines/reference/inferenceFromUnionCombinedSingleSignature1.symbols
@@ -0,0 +1,29 @@
+//// [tests/cases/compiler/inferenceFromUnionCombinedSingleSignature1.ts] ////
+
+=== inferenceFromUnionCombinedSingleSignature1.ts ===
+// https://github.com/microsoft/TypeScript/issues/58468
+
+declare const fn: (() => void) | ((a: number) => void);
+>fn : Symbol(fn, Decl(inferenceFromUnionCombinedSingleSignature1.ts, 2, 13))
+>a : Symbol(a, Decl(inferenceFromUnionCombinedSingleSignature1.ts, 2, 35))
+
+declare const x: number;
+>x : Symbol(x, Decl(inferenceFromUnionCombinedSingleSignature1.ts, 4, 13))
+
+declare const y: any;
+>y : Symbol(y, Decl(inferenceFromUnionCombinedSingleSignature1.ts, 5, 13))
+
+fn.call(null, x);
+>fn.call : Symbol(CallableFunction.call, Decl(lib.es5.d.ts, --, --))
+>fn : Symbol(fn, Decl(inferenceFromUnionCombinedSingleSignature1.ts, 2, 13))
+>call : Symbol(CallableFunction.call, Decl(lib.es5.d.ts, --, --))
+>x : Symbol(x, Decl(inferenceFromUnionCombinedSingleSignature1.ts, 4, 13))
+
+fn.call(null, y);
+>fn.call : Symbol(CallableFunction.call, Decl(lib.es5.d.ts, --, --))
+>fn : Symbol(fn, Decl(inferenceFromUnionCombinedSingleSignature1.ts, 2, 13))
+>call : Symbol(CallableFunction.call, Decl(lib.es5.d.ts, --, --))
+>y : Symbol(y, Decl(inferenceFromUnionCombinedSingleSignature1.ts, 5, 13))
+
+export {};
+
diff --git a/tests/baselines/reference/inferenceFromUnionCombinedSingleSignature1.types b/tests/baselines/reference/inferenceFromUnionCombinedSingleSignature1.types
new file mode 100644
index 0000000000000..55a8783f88d1f
--- /dev/null
+++ b/tests/baselines/reference/inferenceFromUnionCombinedSingleSignature1.types
@@ -0,0 +1,43 @@
+//// [tests/cases/compiler/inferenceFromUnionCombinedSingleSignature1.ts] ////
+
+=== inferenceFromUnionCombinedSingleSignature1.ts ===
+// https://github.com/microsoft/TypeScript/issues/58468
+
+declare const fn: (() => void) | ((a: number) => void);
+>fn : (() => void) | ((a: number) => void)
+>   : ^^^^^^^    ^^^^^^ ^^      ^^^^^    ^
+>a : number
+>  : ^^^^^^
+
+declare const x: number;
+>x : number
+>  : ^^^^^^
+
+declare const y: any;
+>y : any
+
+fn.call(null, x);
+>fn.call(null, x) : void
+>                 : ^^^^
+>fn.call : <T, A extends any[], R>(this: (this: T, ...args: A) => R, thisArg: T, ...args: A) => R
+>        : ^ ^^ ^^^^^^^^^^^^^^^^ ^^    ^^                          ^^       ^^ ^^^^^    ^^ ^^^^^^
+>fn : (() => void) | ((a: number) => void)
+>   : ^^^^^^^^^^^^^^^^^ ^^      ^^^^^^^^^^
+>call : <T, A extends any[], R>(this: (this: T, ...args: A) => R, thisArg: T, ...args: A) => R
+>     : ^ ^^ ^^^^^^^^^^^^^^^^ ^^    ^^                          ^^       ^^ ^^^^^    ^^ ^^^^^^
+>x : number
+>  : ^^^^^^
+
+fn.call(null, y);
+>fn.call(null, y) : void
+>                 : ^^^^
+>fn.call : <T, A extends any[], R>(this: (this: T, ...args: A) => R, thisArg: T, ...args: A) => R
+>        : ^ ^^ ^^^^^^^^^^^^^^^^ ^^    ^^                          ^^       ^^ ^^^^^    ^^ ^^^^^^
+>fn : (() => void) | ((a: number) => void)
+>   : ^^^^^^^^^^^^^^^^^ ^^      ^^^^^^^^^^
+>call : <T, A extends any[], R>(this: (this: T, ...args: A) => R, thisArg: T, ...args: A) => R
+>     : ^ ^^ ^^^^^^^^^^^^^^^^ ^^    ^^                          ^^       ^^ ^^^^^    ^^ ^^^^^^
+>y : any
+
+export {};
+
diff --git a/tests/baselines/reference/jsDeclarationsGetterSetter.js b/tests/baselines/reference/jsDeclarationsGetterSetter.js
index 90a1a35f8a873..994dd0e63ebb5 100644
--- a/tests/baselines/reference/jsDeclarationsGetterSetter.js
+++ b/tests/baselines/reference/jsDeclarationsGetterSetter.js
@@ -280,5 +280,5 @@ export class L {
     set x(value: any);
 }
 export class M {
-    set x(value: any);
+    set x(value: boolean);
 }
diff --git a/tests/baselines/reference/neverIntersectionNotCallable.types b/tests/baselines/reference/neverIntersectionNotCallable.types
index fab7840e6b7ea..e2baf29c4c67b 100644
--- a/tests/baselines/reference/neverIntersectionNotCallable.types
+++ b/tests/baselines/reference/neverIntersectionNotCallable.types
@@ -12,8 +12,8 @@ declare const f: { (x: string): number, a: "" } & { a: number }
 >  : ^^^^^^
 
 f()
->f() : any
->    : ^^^
+>f() : number
+>    : ^^^^^^
 >f : never
 >  : ^^^^^
 
diff --git a/tests/cases/compiler/inferenceFromUnionCombinedSingleSignature1.ts b/tests/cases/compiler/inferenceFromUnionCombinedSingleSignature1.ts
new file mode 100644
index 0000000000000..ab13ce7c1d909
--- /dev/null
+++ b/tests/cases/compiler/inferenceFromUnionCombinedSingleSignature1.ts
@@ -0,0 +1,14 @@
+// @strict: true
+// @noEmit: true
+
+// https://github.com/microsoft/TypeScript/issues/58468
+
+declare const fn: (() => void) | ((a: number) => void);
+
+declare const x: number;
+declare const y: any;
+
+fn.call(null, x);
+fn.call(null, y);
+
+export {};