diff --git a/src/vs/workbench/contrib/debug/browser/debugSession.ts b/src/vs/workbench/contrib/debug/browser/debugSession.ts
index 4c6c45aa7a60f..554314b656fcb 100644
--- a/src/vs/workbench/contrib/debug/browser/debugSession.ts
+++ b/src/vs/workbench/contrib/debug/browser/debugSession.ts
@@ -139,12 +139,13 @@ export class DebugSession implements IDebugSession {
 		const parent = this._options.parentSession;
 		if (parent) {
 			toDispose.add(parent.onDidEndAdapter(() => {
-				// copy the parent repl and get a new detached repl for this child
-				if (!this.hasSeparateRepl()) {
+				// copy the parent repl and get a new detached repl for this child, and
+				// remove its parent, if it's still running
+				if (!this.hasSeparateRepl() && this.raw?.isInShutdown === false) {
 					this.repl = this.repl.clone();
 					replListener.value = this.repl.onDidChangeElements(() => this._onDidChangeREPLElements.fire());
+					this.parentSession = undefined;
 				}
-				this.parentSession = undefined;
 			}));
 		}
 	}
diff --git a/src/vs/workbench/contrib/debug/browser/rawDebugSession.ts b/src/vs/workbench/contrib/debug/browser/rawDebugSession.ts
index c9d1d4d972a36..e9db37e6855d9 100644
--- a/src/vs/workbench/contrib/debug/browser/rawDebugSession.ts
+++ b/src/vs/workbench/contrib/debug/browser/rawDebugSession.ts
@@ -172,6 +172,10 @@ export class RawDebugSession implements IDisposable {
 		this.debugAdapter.onRequest(request => this.dispatchRequest(request));
 	}
 
+	get isInShutdown() {
+		return this.inShutdown;
+	}
+
 	get onDidExitAdapter(): Event<AdapterEndEvent> {
 		return this._onDidExitAdapter.event;
 	}