diff --git a/package.json b/package.json
index 8369697a0..d655b0d6b 100644
--- a/package.json
+++ b/package.json
@@ -328,6 +328,12 @@
             "description": "The path of the SDK to compile against (`--sdk` parameter). The default SDK is determined by the environment on macOS and Windows.",
             "order": 3
           },
+          "swift.skipCodeLLDBCheck": {
+            "type": "boolean",
+            "default": false,
+            "description": "Skip check for CodeLLDB being installed.",
+            "order": 4
+          },
           "swift.diagnostics": {
             "type": "boolean",
             "default": false,
@@ -567,9 +573,6 @@
       ]
     }
   },
-  "extensionDependencies": [
-    "vadimcn.vscode-lldb"
-  ],
   "scripts": {
     "vscode:prepublish": "npm run esbuild-base -- --minify",
     "esbuild-base": "esbuild ./src/extension.ts --bundle --outfile=dist/extension.js --external:vscode --format=cjs --platform=node --target=node16",
diff --git a/src/WorkspaceContext.ts b/src/WorkspaceContext.ts
index 6ab270309..6c5599dc0 100644
--- a/src/WorkspaceContext.ts
+++ b/src/WorkspaceContext.ts
@@ -23,7 +23,7 @@ import {
     swiftLibraryPathKey,
     getErrorDescription,
 } from "./utilities/utilities";
-import { getLLDBLibPath } from "./debugger/lldb";
+import { checkLLDBInstalled, getLLDBLibPath } from "./debugger/lldb";
 import { LanguageClientManager } from "./sourcekit-lsp/LanguageClientManager";
 import { TemporaryFolder } from "./utilities/tempFolder";
 import { SwiftToolchain } from "./toolchain/toolchain";
@@ -350,6 +350,22 @@ export class WorkspaceContext implements vscode.Disposable {
         return { dispose: () => this.observers.delete(fn) };
     }
 
+    async setupLLDB() {
+        await checkLLDBInstalled().then(
+            async result => {
+                if (result) {
+                    this.setLLDBVersion();
+                }
+            },
+            error => {
+                const errorMessage = `Error: ${getErrorDescription(error)}`;
+                vscode.window.showErrorMessage(
+                    `Failed to setup CodeLLDB for debugging of Swift code. Debugging may produce unexpected results. ${errorMessage}`
+                );
+            }
+        );
+    }
+
     /** find LLDB version and setup path in CodeLLDB */
     async setLLDBVersion() {
         const libPathResult = await getLLDBLibPath(this.toolchain);
diff --git a/src/configuration.ts b/src/configuration.ts
index 4cddcbab4..d4004d4df 100644
--- a/src/configuration.ts
+++ b/src/configuration.ts
@@ -141,6 +141,10 @@ const configuration = {
             .get<boolean>("backgroundCompilation", false);
     },
     /** output additional diagnostics */
+    get skipCodeLLDBCheck(): boolean {
+        return vscode.workspace.getConfiguration("swift").get<boolean>("skipCodeLLDBCheck", false);
+    },
+    /** output additional diagnostics */
     get diagnostics(): boolean {
         return vscode.workspace.getConfiguration("swift").get<boolean>("diagnostics", false);
     },
diff --git a/src/debugger/lldb.ts b/src/debugger/lldb.ts
index 78ac826db..92c579836 100644
--- a/src/debugger/lldb.ts
+++ b/src/debugger/lldb.ts
@@ -15,11 +15,65 @@
 // Based on code taken from CodeLLDB https://github.com/vadimcn/vscode-lldb/
 // LICENSED with MIT License
 
+import * as vscode from "vscode";
 import * as path from "path";
 import * as fs from "fs/promises";
 import { execFile } from "../utilities/utilities";
 import { Result } from "../utilities/result";
 import { SwiftToolchain } from "../toolchain/toolchain";
+import configuration from "../configuration";
+
+/**
+ * Check if CodeLLDB extension is installed and offer to install it if it is not.
+ * @returns Whether extension was installed
+ */
+export async function checkLLDBInstalled(): Promise<boolean> {
+    const lldbExtension = vscode.extensions.getExtension("vadimcn.vscode-lldb");
+    // if extension is in list return true
+    if (lldbExtension) {
+        return true;
+    }
+    // if workspace is set to ignore LLDB check then return
+    if (configuration.skipCodeLLDBCheck === true) {
+        return false;
+    }
+    // otherwise display menu asking if user wants to install it
+    return new Promise<boolean>((resolve, reject) => {
+        vscode.window
+            .showWarningMessage(
+                "Do you want to install the CodeLLDB extension?",
+                {
+                    modal: true,
+                    detail: "The Swift extension requires it to enable debugging.",
+                },
+                "Install"
+            )
+            .then(async result => {
+                switch (result) {
+                    case "Install":
+                        try {
+                            await installCodeLLDB();
+                            return resolve(true);
+                        } catch (error) {
+                            return reject(error);
+                        }
+                    case undefined:
+                        break;
+                }
+                return resolve(false);
+            });
+    });
+}
+
+/**
+ * Install CodeLLDB extension
+ */
+async function installCodeLLDB() {
+    await vscode.commands.executeCommand(
+        "workbench.extensions.installExtension",
+        "vadimcn.vscode-lldb"
+    );
+}
 
 /**
  * Get LLDB library for given LLDB executable
diff --git a/src/extension.ts b/src/extension.ts
index 54832cf45..d7352df9a 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -46,7 +46,7 @@ export async function activate(context: vscode.ExtensionContext): Promise<Api> {
         context.subscriptions.push(workspaceContext);
 
         // setup swift version of LLDB. Don't await on this as it can run in the background
-        workspaceContext.setLLDBVersion();
+        workspaceContext.setupLLDB();
 
         // listen for workspace folder changes and active text editor changes
         workspaceContext.setupEventListeners();
diff --git a/test/runTest.ts b/test/runTest.ts
index a4af7b377..7a7351171 100644
--- a/test/runTest.ts
+++ b/test/runTest.ts
@@ -12,13 +12,8 @@
 //
 //===----------------------------------------------------------------------===//
 
-import * as cp from "child_process";
 import * as path from "path";
-import {
-    runTests,
-    downloadAndUnzipVSCode,
-    resolveCliPathFromVSCodeExecutablePath,
-} from "@vscode/test-electron";
+import { runTests } from "@vscode/test-electron";
 
 async function main() {
     try {
@@ -30,22 +25,6 @@ async function main() {
         // Passed to --extensionTestsPath
         const extensionTestsPath = path.resolve(__dirname, "./suite/index");
 
-        const vscodeExecutablePath = await downloadAndUnzipVSCode();
-        const cliPath = resolveCliPathFromVSCodeExecutablePath(vscodeExecutablePath);
-
-        // Use cp.spawn / cp.exec for custom setup
-        console.log(`${cliPath} --install-extension vadimcn.vscode-lldb`);
-        const { stdout, stderr } = cp.spawnSync(
-            cliPath,
-            ["--install-extension", "vadimcn.vscode-lldb"],
-            {
-                encoding: "utf-8",
-                stdio: "inherit",
-            }
-        );
-        console.log(stdout);
-        console.log(stderr);
-
         // Download VS Code, unzip it and run the integration test
         await runTests({
             extensionDevelopmentPath,