diff --git a/src/TestExplorer/TestRunner.ts b/src/TestExplorer/TestRunner.ts
index e6cccbd15..6309dcdaf 100644
--- a/src/TestExplorer/TestRunner.ts
+++ b/src/TestExplorer/TestRunner.ts
@@ -449,6 +449,8 @@ export class TestRunner {
     private testArgs: TestRunArguments;
     private xcTestOutputParser: IXCTestOutputParser;
     private swiftTestOutputParser: SwiftTestingOutputParser;
+    private debugSessionTerminatedEmitter = new vscode.EventEmitter<void>();
+    public onDebugSessionTerminated: vscode.Event<void>;
     private static CANCELLATION_ERROR = "Test run cancelled.";
 
     /**
@@ -487,6 +489,7 @@ export class TestRunner {
             this.testRun.addParameterizedTestCase,
             this.testRun.addAttachment
         );
+        this.onDebugSessionTerminated = this.debugSessionTerminatedEmitter.event;
     }
 
     /**
@@ -1158,8 +1161,13 @@ export class TestRunner {
                             LoggingDebugAdapterTracker.setDebugSessionCallback(
                                 session,
                                 this.workspaceContext.logger,
-                                output => {
-                                    outputHandler(output);
+                                output => outputHandler(output),
+                                exitCode => {
+                                    // Debug session is stopped with exitCode 9 (SIGKILL)
+                                    // when the user terminates it manually.
+                                    if (exitCode === 9) {
+                                        this.debugSessionTerminatedEmitter.fire();
+                                    }
                                 }
                             );
 
diff --git a/src/commands/testMultipleTimes.ts b/src/commands/testMultipleTimes.ts
index a6f3dad99..9986e0638 100644
--- a/src/commands/testMultipleTimes.ts
+++ b/src/commands/testMultipleTimes.ts
@@ -59,6 +59,10 @@ export async function runTestMultipleTimes(
         token.token
     );
 
+    // If the user terminates a debugging session we want
+    // to cancel the remaining iterations.
+    const terminationListener = runner.onDebugSessionTerminated(() => token.cancel());
+
     testExplorer.onDidCreateTestRunEmitter.fire(runner.testRun);
 
     const testRunState = new TestRunnerTestRunState(runner.testRun);
@@ -91,6 +95,7 @@ export async function runTestMultipleTimes(
         }
     }
     await runner.testRun.end();
+    terminationListener.dispose();
 
     return runStates;
 }
diff --git a/src/debugger/logTracker.ts b/src/debugger/logTracker.ts
index df6004c96..548bf3649 100644
--- a/src/debugger/logTracker.ts
+++ b/src/debugger/logTracker.ts
@@ -30,6 +30,7 @@ export class LoggingDebugAdapterTrackerFactory implements vscode.DebugAdapterTra
 interface OutputEventBody {
     category: string;
     output: string;
+    exitCode: number | undefined;
 }
 
 interface DebugMessage {
@@ -68,7 +69,9 @@ export class LoggingDebugAdapterTracker implements vscode.DebugAdapterTracker {
     private static debugSessionIdMap: { [id: string]: LoggingDebugAdapterTracker } = {};
 
     private cb?: (output: string) => void;
+    private exitHandler?: (exitCode: number) => void;
     private output: string[] = [];
+    private exitCode: number | undefined;
 
     constructor(public id: string) {
         LoggingDebugAdapterTracker.debugSessionIdMap[id] = this;
@@ -77,41 +80,54 @@ export class LoggingDebugAdapterTracker implements vscode.DebugAdapterTracker {
     static setDebugSessionCallback(
         session: vscode.DebugSession,
         logger: SwiftLogger,
-        cb: (log: string) => void
+        cb: (log: string) => void,
+        exitHandler: (exitCode: number) => void
     ) {
         const loggingDebugAdapter = this.debugSessionIdMap[session.id];
         if (loggingDebugAdapter) {
-            loggingDebugAdapter.cb = cb;
+            loggingDebugAdapter.setCallbacks(cb, exitHandler);
             for (const o of loggingDebugAdapter.output) {
                 cb(o);
             }
+            if (loggingDebugAdapter.exitCode) {
+                exitHandler(loggingDebugAdapter.exitCode);
+            }
             loggingDebugAdapter.output = [];
+            loggingDebugAdapter.exitCode = undefined;
         } else {
             logger.error("Could not find debug adapter for session: " + session.id);
         }
     }
 
+    setCallbacks(handleOutput: (output: string) => void, handleExit: (exitCode: number) => void) {
+        this.cb = handleOutput;
+        this.exitHandler = handleExit;
+    }
+
     /**
      * The debug adapter has sent a Debug Adapter Protocol message to the editor. Check
      * it is a output message and is not being sent to the console
      */
     onDidSendMessage(message: unknown): void {
         const debugMessage = message as DebugMessage;
-        if (
-            !(
-                debugMessage &&
-                debugMessage.type === "event" &&
-                debugMessage.event === "output" &&
-                debugMessage.body.category !== "console"
-            )
-        ) {
+        if (!debugMessage) {
             return;
         }
-        const output = debugMessage.body.output;
-        if (this.cb) {
-            this.cb(output);
-        } else {
-            this.output.push(output);
+
+        if (debugMessage.event === "exited" && debugMessage.body.exitCode) {
+            this.exitCode = debugMessage.body.exitCode;
+            this.exitHandler?.(debugMessage.body.exitCode);
+        } else if (
+            debugMessage.type === "event" &&
+            debugMessage.event === "output" &&
+            debugMessage.body.category !== "console"
+        ) {
+            const output = debugMessage.body.output;
+            if (this.cb) {
+                this.cb(output);
+            } else {
+                this.output.push(output);
+            }
         }
     }
 
@@ -119,7 +135,7 @@ export class LoggingDebugAdapterTracker implements vscode.DebugAdapterTracker {
      * The debug adapter session is about to be stopped. Delete the session from
      * the tracker
      */
-    onWillStopSession?(): void {
+    onWillStopSession(): void {
         delete LoggingDebugAdapterTracker.debugSessionIdMap[this.id];
     }
 }