diff --git a/package-lock.json b/package-lock.json
index b667841bec..b1317c7b29 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -31,6 +31,7 @@
         "@typescript-eslint/eslint-plugin": "6.4.0",
         "@typescript-eslint/parser": "6.4.0",
         "@ungap/structured-clone": "1.2.0",
+        "@vscode/debugprotocol": "1.61.0",
         "@vscode/test-electron": "2.3.4",
         "@vscode/vsce": "2.20.1",
         "esbuild": "0.19.2",
@@ -1297,6 +1298,12 @@
       "integrity": "sha512-zuVdFrMJiuCDQUMCzQaD6KL28MjnqqN8XnAqiEq9PNm/hCPTSGfrXCOfwj1ow4LFb/tNymJPwsNbVePc1xFqrQ==",
       "dev": true
     },
+    "node_modules/@vscode/debugprotocol": {
+      "version": "1.61.0",
+      "resolved": "https://registry.npmjs.org/@vscode/debugprotocol/-/debugprotocol-1.61.0.tgz",
+      "integrity": "sha512-K/kF27jIStVFqlmUaGc2u+Dj8IR7YdEiSqShWr7MWhDudqpAW7uu7XMwoFwjpuC9LSaVwJMIX7EFC5OJ/RmnDQ==",
+      "dev": true
+    },
     "node_modules/@vscode/extension-telemetry": {
       "version": "0.8.2",
       "resolved": "https://registry.npmjs.org/@vscode/extension-telemetry/-/extension-telemetry-0.8.2.tgz",
@@ -6064,6 +6071,12 @@
       "integrity": "sha512-zuVdFrMJiuCDQUMCzQaD6KL28MjnqqN8XnAqiEq9PNm/hCPTSGfrXCOfwj1ow4LFb/tNymJPwsNbVePc1xFqrQ==",
       "dev": true
     },
+    "@vscode/debugprotocol": {
+      "version": "1.61.0",
+      "resolved": "https://registry.npmjs.org/@vscode/debugprotocol/-/debugprotocol-1.61.0.tgz",
+      "integrity": "sha512-K/kF27jIStVFqlmUaGc2u+Dj8IR7YdEiSqShWr7MWhDudqpAW7uu7XMwoFwjpuC9LSaVwJMIX7EFC5OJ/RmnDQ==",
+      "dev": true
+    },
     "@vscode/extension-telemetry": {
       "version": "0.8.2",
       "resolved": "https://registry.npmjs.org/@vscode/extension-telemetry/-/extension-telemetry-0.8.2.tgz",
diff --git a/package.json b/package.json
index 8125a7fbc3..00bb89705c 100644
--- a/package.json
+++ b/package.json
@@ -96,6 +96,7 @@
     "@typescript-eslint/eslint-plugin": "6.4.0",
     "@typescript-eslint/parser": "6.4.0",
     "@ungap/structured-clone": "1.2.0",
+    "@vscode/debugprotocol": "1.61.0",
     "@vscode/test-electron": "2.3.4",
     "@vscode/vsce": "2.20.1",
     "esbuild": "0.19.2",
diff --git a/src/features/DebugSession.ts b/src/features/DebugSession.ts
index 55dd794e55..884b01ee7f 100644
--- a/src/features/DebugSession.ts
+++ b/src/features/DebugSession.ts
@@ -24,6 +24,7 @@ import {
     QuickPickOptions,
     DebugConfigurationProviderTriggerKind
 } from "vscode";
+import type { DebugProtocol } from "@vscode/debugprotocol";
 import { NotificationType, RequestType } from "vscode-languageclient";
 import { LanguageClient } from "vscode-languageclient/node";
 import { LanguageClientConsumer } from "../languageClientConsumer";
@@ -375,25 +376,48 @@ export class DebugSessionFeature extends LanguageClientConsumer
             dotnetAttachConfig.processId = pid;
 
             // Ensure the .NET session stops before the PowerShell session so that the .NET debug session doesn't emit an error about the process unexpectedly terminating.
-            const startDebugEvent = debug.onDidStartDebugSession((dotnetAttachSession) => {
+            let tempConsoleDotnetAttachSession: DebugSession;
+            const startDebugEvent = debug.onDidStartDebugSession(dotnetAttachSession => {
+                if (dotnetAttachSession.configuration.name != dotnetAttachConfig.name) { return; }
+
                 // Makes the event one-time
                 // HACK: This seems like you would be calling a method on a variable not assigned yet, but it does work in the flow.
                 // The dispose shorthand demonry for making an event one-time courtesy of: https://github.com/OmniSharp/omnisharp-vscode/blob/b8b07bb12557b4400198895f82a94895cb90c461/test/integrationTests/launchConfiguration.integration.test.ts#L41-L45
                 startDebugEvent.dispose();
+
                 this.logger.writeVerbose(`Debugger session detected: ${dotnetAttachSession.name} (${dotnetAttachSession.id})`);
-                if (dotnetAttachSession.configuration.name == dotnetAttachConfig.name) {
-                    const stopDebugEvent = debug.onDidTerminateDebugSession(async (terminatedDebugSession) => {
-                        // Makes the event one-time
-                        stopDebugEvent.dispose();
 
-                        this.logger.writeVerbose(`Debugger session stopped: ${terminatedDebugSession.name} (${terminatedDebugSession.id})`);
+                tempConsoleDotnetAttachSession = dotnetAttachSession;
+
+                const stopDebugEvent = debug.onDidTerminateDebugSession(async tempConsoleSession => {
+                    if (tempConsoleDotnetAttachSession.parentSession?.id !== tempConsoleSession.id) { return; }
 
-                        if (terminatedDebugSession === session) {
-                            this.logger.writeVerbose("Terminating dotnet debugger session associated with PowerShell debug session!");
-                            await debug.stopDebugging(dotnetAttachSession);
+                    // Makes the event one-time
+                    stopDebugEvent.dispose();
+
+                    this.logger.writeVerbose(`Debugger session terminated: ${tempConsoleSession.name} (${tempConsoleSession.id})`);
+
+                    // HACK: As of 2023-08-17, there is no vscode debug API to request the C# debugger to detach, so we send it a custom DAP request instead.
+                    const disconnectRequest: DebugProtocol.DisconnectRequest = {
+                        command: "disconnect",
+                        seq: 0,
+                        type: "request",
+                        arguments: {
+                            restart: false,
+                            terminateDebuggee: false,
+                            suspendDebuggee: false
                         }
-                    });
-                }
+                    };
+
+                    try {
+                        await dotnetAttachSession.customRequest(
+                            disconnectRequest.command,
+                            disconnectRequest.arguments
+                        );
+                    } catch (err) {
+                        this.logger.writeWarning(`Disconnect request to dotnet debugger failed: ${err}`);
+                    }
+                });
             });
 
             // Start a child debug session to attach the dotnet debugger
diff --git a/test/features/DebugSession.test.ts b/test/features/DebugSession.test.ts
index 3b9b854680..60e18021cc 100644
--- a/test/features/DebugSession.test.ts
+++ b/test/features/DebugSession.test.ts
@@ -428,13 +428,16 @@ describe("DebugSessionFeature", () => {
     });
 });
 
-describe("DebugSessionFeature E2E", () => {
+describe("DebugSessionFeature E2E", function() {
+    // E2E tests can take a while to run since the debugger has to start up and attach
+    this.slow(20000);
     before(async () => {
         // Registers and warms up the debug adapter and the PowerShell Extension Terminal
         await ensureEditorServicesIsConnected();
     });
 
     it("Starts and stops a debugging session", async () => {
+
         // Inspect the debug session via the started events to ensure it is correct
         const startDebugSession = new Promise<DebugSession>((resolve) => {
             const event = debug.onDidStartDebugSession((session) => {
diff --git a/test/features/ISECompatibility.test.ts b/test/features/ISECompatibility.test.ts
index 792c3dd7bb..0f2152c1c6 100644
--- a/test/features/ISECompatibility.test.ts
+++ b/test/features/ISECompatibility.test.ts
@@ -73,6 +73,8 @@ describe("ISE compatibility feature", function () {
     });
 
     describe("Color theme interactions", function () {
+        // These tests are slow because they change the user's theme.
+        this.slow(3000);
         beforeEach(enableISEMode);
 
         function assertISESettings(): void {