diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 93f559c1faa79..4fca657a214e1 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -37307,7 +37307,9 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                 return nullWideningType;
             case SyntaxKind.NoSubstitutionTemplateLiteral:
             case SyntaxKind.StringLiteral:
-                return getFreshTypeOfLiteralType(getStringLiteralType((node as StringLiteralLike).text));
+                return hasSkipDirectInferenceFlag(node) ?
+                    anyType :
+                    getFreshTypeOfLiteralType(getStringLiteralType((node as StringLiteralLike).text));
             case SyntaxKind.NumericLiteral:
                 checkGrammarNumericLiteral(node as NumericLiteral);
                 return getFreshTypeOfLiteralType(getNumberLiteralType(+(node as NumericLiteral).text));
diff --git a/tests/cases/fourslash/completionsForStringDependingOnContexSensitiveSignature.ts b/tests/cases/fourslash/completionsForStringDependingOnContexSensitiveSignature.ts
new file mode 100644
index 0000000000000..e80c014546d73
--- /dev/null
+++ b/tests/cases/fourslash/completionsForStringDependingOnContexSensitiveSignature.ts
@@ -0,0 +1,41 @@
+/// <reference path="fourslash.ts" />
+// @strict: true
+////
+//// type ActorRef<TEvent extends { type: string }> = {
+////   send: (ev: TEvent) => void
+//// }
+//// 
+//// type Action<TContext> = {
+////   (ctx: TContext): void
+//// }
+//// 
+//// type Config<TContext> = {
+////   entry: Action<TContext>
+//// }
+//// 
+//// declare function createMachine<TContext>(config: Config<TContext>): void
+//// 
+//// type EventFrom<T> = T extends ActorRef<infer TEvent> ? TEvent : never
+//// 
+//// declare function sendTo<
+////   TContext,
+////   TActor extends ActorRef<any>
+//// >(
+////   actor: ((ctx: TContext) => TActor),
+////   event: EventFrom<TActor>
+//// ): Action<TContext>
+//// 
+//// createMachine<{
+////   child: ActorRef<{ type: "EVENT" }>;
+//// }>({
+////   entry: sendTo((ctx) => ctx.child, { type: /*1*/ }),
+//// });
+////
+//// createMachine<{
+////   child: ActorRef<{ type: "EVENT" }>;
+//// }>({
+////   entry: sendTo((ctx) => ctx.child, { type: "/*2*/" }),
+//// });
+
+verify.completions({ marker: "1", includes: [`"EVENT"`] })
+verify.completions({ marker: "2", exact: [`EVENT`] })
\ No newline at end of file