diff --git a/packages/core/src/common/disposable.ts b/packages/core/src/common/disposable.ts
index 1920343c9073e..cfb07b03166b0 100644
--- a/packages/core/src/common/disposable.ts
+++ b/packages/core/src/common/disposable.ts
@@ -133,3 +133,28 @@ export function disposableTimeout(...args: Parameters<typeof setTimeout>): Dispo
     const handle = setTimeout(...args);
     return { dispose: () => clearTimeout(handle) };
 }
+
+/**
+ * Wrapper for a {@link Disposable} that is not available immediately.
+ */
+export class DisposableWrapper implements Disposable {
+
+    private disposed = false;
+    private disposable: Disposable | undefined = undefined;
+
+    set(disposable: Disposable): void {
+        if (this.disposed) {
+            disposable.dispose();
+        } else {
+            this.disposable = disposable;
+        }
+    }
+
+    dispose(): void {
+        this.disposed = true;
+        if (this.disposable) {
+            this.disposable.dispose();
+            this.disposable = undefined;
+        }
+    }
+}
diff --git a/packages/core/src/common/message-rpc/rpc-protocol.ts b/packages/core/src/common/message-rpc/rpc-protocol.ts
index 9ebd529c4a3ed..f3f51decb3270 100644
--- a/packages/core/src/common/message-rpc/rpc-protocol.ts
+++ b/packages/core/src/common/message-rpc/rpc-protocol.ts
@@ -16,7 +16,7 @@
 /* eslint-disable @typescript-eslint/no-explicit-any */
 
 import { CancellationToken, CancellationTokenSource } from '../cancellation';
-import { Disposable, DisposableCollection } from '../disposable';
+import { DisposableWrapper, Disposable, DisposableCollection } from '../disposable';
 import { Emitter, Event } from '../event';
 import { Deferred } from '../promise-util';
 import { Channel } from './channel';
@@ -57,6 +57,7 @@ export class RpcProtocol {
     static readonly CANCELLATION_TOKEN_KEY = 'add.cancellation.token';
 
     protected readonly pendingRequests: Map<number, Deferred<any>> = new Map();
+    protected readonly pendingRequestCancellationEventListeners: Map<number, DisposableWrapper> = new Map();
 
     protected nextMessageId: number = 0;
 
@@ -80,6 +81,8 @@ export class RpcProtocol {
         channel.onClose(event => {
             this.pendingRequests.forEach(pending => pending.reject(new Error(event.reason)));
             this.pendingRequests.clear();
+            this.pendingRequestCancellationEventListeners.forEach(disposable => disposable.dispose());
+            this.pendingRequestCancellationEventListeners.clear();
             this.toDispose.dispose();
         });
         this.toDispose.push(channel.onMessage(readBuffer => this.handleMessage(this.decoder.parse(readBuffer()))));
@@ -131,6 +134,7 @@ export class RpcProtocol {
         } else {
             throw new Error(`No reply handler for reply with id: ${id}`);
         }
+        this.disposeCancellationEventListener(id);
     }
 
     protected handleReplyErr(id: number, error: any): void {
@@ -141,6 +145,15 @@ export class RpcProtocol {
         } else {
             throw new Error(`No reply handler for error reply with id: ${id}`);
         }
+        this.disposeCancellationEventListener(id);
+    }
+
+    protected disposeCancellationEventListener(id: number): void {
+        const toDispose = this.pendingRequestCancellationEventListeners.get(id);
+        if (toDispose) {
+            this.pendingRequestCancellationEventListeners.delete(id);
+            toDispose.dispose();
+        }
     }
 
     sendRequest<T>(method: string, args: any[]): Promise<T> {
@@ -157,6 +170,10 @@ export class RpcProtocol {
 
         this.pendingRequests.set(id, reply);
 
+        // register disposable before output.commit() even when not available yet
+        const disposableWrapper = new DisposableWrapper();
+        this.pendingRequestCancellationEventListeners.set(id, disposableWrapper);
+
         const output = this.channel.getWriteBuffer();
         this.encoder.request(output, id, method, args);
         output.commit();
@@ -164,7 +181,10 @@ export class RpcProtocol {
         if (cancellationToken?.isCancellationRequested) {
             this.sendCancel(id);
         } else {
-            cancellationToken?.onCancellationRequested(() => this.sendCancel(id));
+            const disposable = cancellationToken?.onCancellationRequested(() => this.sendCancel(id));
+            if (disposable) {
+                disposableWrapper.set(disposable);
+            }
         }
 
         return reply.promise;