diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index bdf2dff585a47..87317a73b1a76 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -1828,14 +1828,19 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
     };
 
     function runWithoutResolvedSignatureCaching<T>(node: Node | undefined, fn: () => T): T {
-        const containingCall = findAncestor(node, isCallLikeExpression);
-        const containingCallResolvedSignature = containingCall && getNodeLinks(containingCall).resolvedSignature;
-        if (containingCall) {
-            getNodeLinks(containingCall).resolvedSignature = undefined;
+        const cachedSignatures = [];
+        while (node) {
+            if (isCallLikeExpression(node)) {
+                const nodeLinks = getNodeLinks(node);
+                const resolvedSignature = nodeLinks.resolvedSignature;
+                cachedSignatures.push([nodeLinks, resolvedSignature] as const);
+                nodeLinks.resolvedSignature = undefined;
+            }
+            node = node.parent;
         }
         const result = fn();
-        if (containingCall) {
-            getNodeLinks(containingCall).resolvedSignature = containingCallResolvedSignature;
+        for (const [nodeLinks, resolvedSignature] of cachedSignatures) {
+            nodeLinks.resolvedSignature = resolvedSignature;
         }
         return result;
     }
diff --git a/tests/cases/fourslash/typeErrorAfterStringCompletionsInNestedCall.ts b/tests/cases/fourslash/typeErrorAfterStringCompletionsInNestedCall.ts
new file mode 100644
index 0000000000000..6a9909c4a20e3
--- /dev/null
+++ b/tests/cases/fourslash/typeErrorAfterStringCompletionsInNestedCall.ts
@@ -0,0 +1,32 @@
+///<reference path="fourslash.ts"/>
+// @strict: true
+////
+//// type GreetingEvent =
+////   | { type: "MORNING" }
+////   | { type: "LUNCH_TIME" }
+////   | { type: "ALOHA" };
+////
+//// interface RaiseActionObject<TEvent extends { type: string }> {
+////   type: "raise";
+////   event: TEvent;
+//// }
+////
+//// declare function raise<TEvent extends { type: string }>(
+////   ev: TEvent
+//// ): RaiseActionObject<TEvent>;
+////
+//// declare function createMachine<TEvent extends { type: string }>(config: {
+////   actions: RaiseActionObject<TEvent>;
+//// }): void;
+////
+//// createMachine<GreetingEvent>({
+////   [|/*error*/actions|]: raise({ type: "ALOHA/*1*/" }),
+//// });
+
+goTo.marker("1");
+edit.insert(`x`)
+verify.completions({ exact: ["MORNING", "LUNCH_TIME", "ALOHA"] });
+verify.getSemanticDiagnostics([{
+    code: 2322,
+    message: `Type 'RaiseActionObject<{ type: "ALOHAx"; }>' is not assignable to type 'RaiseActionObject<GreetingEvent>'.\n  Type '{ type: "ALOHAx"; }' is not assignable to type 'GreetingEvent'.\n    Type '{ type: "ALOHAx"; }' is not assignable to type '{ type: "ALOHA"; }'.\n      Types of property 'type' are incompatible.\n        Type '"ALOHAx"' is not assignable to type '"ALOHA"'.`,
+}]);