diff --git a/packages/vscode-typescript/src/client.ts b/packages/vscode-typescript/src/client.ts
index b8bd17df8540a..68729770dbf21 100644
--- a/packages/vscode-typescript/src/client.ts
+++ b/packages/vscode-typescript/src/client.ts
@@ -314,9 +314,8 @@ export class Client implements vscode.Disposable {
             logLevelListener,
             serverTelemetryListener,
             registerSourceDefinitionFeature(this.client),
-            registerOnAutoInsertFeature(this.documentSelector, this.client),
         );
-        // Register the selector-scoped custom providers (hover, multi-document highlight). These start
+        // Register the selector-scoped custom providers (hover, multi-document highlight, on-auto-insert). These start
         // scoped to the static jsTs selector and expand as content-mapped extensions register.
         this.registerSelectorScopedFeatures();
     }
@@ -383,6 +382,7 @@ export class Client implements vscode.Disposable {
         this.selectorScopedFeatures.push(
             registerMultiDocumentHighlightFeature(selector, this.client),
             registerHoverFeature(selector, this.client),
+            registerOnAutoInsertFeature(selector, this.client),
         );
     }
 
diff --git a/packages/vscode-typescript/src/languageFeatures/util/dependentRegistration.ts b/packages/vscode-typescript/src/languageFeatures/util/dependentRegistration.ts
index 2c9608c2ae14f..e119bac392b60 100644
--- a/packages/vscode-typescript/src/languageFeatures/util/dependentRegistration.ts
+++ b/packages/vscode-typescript/src/languageFeatures/util/dependentRegistration.ts
@@ -3,14 +3,15 @@ import * as vscode from "vscode";
 export class Condition {
     private _value: boolean;
     private isDisposed = false;
+    private readonly updateListener: vscode.Disposable;
 
     constructor(
         private readonly getValue: () => boolean,
-        onUpdate: (handler: () => void) => void,
+        onUpdate: (handler: () => void) => vscode.Disposable,
     ) {
         this._value = this.getValue();
 
-        onUpdate(() => {
+        this.updateListener = onUpdate(() => {
             const newValue = this.getValue();
             if (newValue !== this._value) {
                 this._value = newValue;
@@ -31,6 +32,7 @@ export class Condition {
             return;
         }
         this.isDisposed = true;
+        this.updateListener.dispose();
         this._onDidChange.dispose();
     }
 }