diff --git a/R/session/vsc.R b/R/session/vsc.R
index 0b881dc4d..9561e4a76 100644
--- a/R/session/vsc.R
+++ b/R/session/vsc.R
@@ -791,3 +791,5 @@ print.hsearch <- function(x, ...) {
   registerS3method(generic, class, method, envir = parent.frame())
   invisible(NULL)
 }
+
+reg.finalizer(globalenv(), function(e) .vsc$request("detach"), onexit = TRUE)
diff --git a/src/extension.ts b/src/extension.ts
index d15bf329d..3a3de2468 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -36,6 +36,7 @@ export let enableSessionWatcher: boolean | undefined = undefined;
 export let globalHttpgdManager: httpgdViewer.HttpgdManager | undefined = undefined;
 export let rmdPreviewManager: rmarkdown.RMarkdownPreviewManager | undefined = undefined;
 export let rmdKnitManager: rmarkdown.RMarkdownKnitManager | undefined = undefined;
+export let sessionStatusBarItem: vscode.StatusBarItem | undefined = undefined;
 
 // Called (once) when the extension is activated
 export async function activate(context: vscode.ExtensionContext): Promise<apiImplementation.RExtensionImplementation> {
@@ -225,7 +226,7 @@ export async function activate(context: vscode.ExtensionContext): Promise<apiImp
 
             // create status bar item that contains info about the session watcher
             console.info('Create sessionStatusBarItem');
-            const sessionStatusBarItem = vscode.window.createStatusBarItem(vscode.StatusBarAlignment.Right, 1000);
+            sessionStatusBarItem = vscode.window.createStatusBarItem(vscode.StatusBarAlignment.Right, 1000);
             sessionStatusBarItem.command = 'r.attachActive';
             sessionStatusBarItem.text = 'R: (not attached)';
             sessionStatusBarItem.tooltip = 'Click to attach active terminal.';
diff --git a/src/rTerminal.ts b/src/rTerminal.ts
index ca8ad4966..398065548 100644
--- a/src/rTerminal.ts
+++ b/src/rTerminal.ts
@@ -9,7 +9,7 @@ import { extensionContext, homeExtDir } from './extension';
 import * as util from './util';
 import * as selection from './selection';
 import { getSelection } from './selection';
-import { removeSessionFiles } from './session';
+import { cleanupSession } from './session';
 import { config, delay, getRterm } from './util';
 import { rGuestService, isGuestSession } from './liveShare';
 import * as fs from 'fs';
@@ -162,7 +162,7 @@ export function deleteTerminal(term: vscode.Terminal): void {
     if (isDeepStrictEqual(term, rTerm)) {
         rTerm = undefined;
         if (config().get<boolean>('sessionWatcher')) {
-            removeSessionFiles();
+            cleanupSession();
         }
     }
 }
diff --git a/src/session.ts b/src/session.ts
index 34a086a81..f73793b7d 100644
--- a/src/session.ts
+++ b/src/session.ts
@@ -11,7 +11,7 @@ import { config, readContent, UriIcon } from './util';
 import { purgeAddinPickerItems, dispatchRStudioAPICall } from './rstudioapi';
 
 import { IRequest } from './liveShare/shareSession';
-import { homeExtDir, rWorkspace, globalRHelp, globalHttpgdManager, extensionContext } from './extension';
+import { homeExtDir, rWorkspace, globalRHelp, globalHttpgdManager, extensionContext, sessionStatusBarItem } from './extension';
 import { UUID, rHostService, rGuestService, isLiveShare, isHost, isGuestSession, closeBrowser, guestResDir, shareBrowser, openVirtualDoc, shareWorkspace } from './liveShare';
 
 export interface GlobalEnv {
@@ -734,6 +734,7 @@ type ISessionRequest = {
 async function updateRequest(sessionStatusBarItem: StatusBarItem) {
     console.info('[updateRequest] Started');
     console.info(`[updateRequest] requestFile: ${requestFile}`);
+
     const lockContent = await fs.readFile(requestLockFile, 'utf8');
     const newTimeStamp = Number.parseFloat(lockContent);
     if (newTimeStamp !== requestTimeStamp) {
@@ -776,6 +777,15 @@ async function updateRequest(sessionStatusBarItem: StatusBarItem) {
                         if (request.plot_url) {
                             await globalHttpgdManager?.showViewer(request.plot_url);
                         }
+                        void watchProcess(Number(pid)).then((v) => {
+                            if (v === Number(pid)) {
+                                cleanupSession();
+                            }
+                        });
+                        break;
+                    }
+                    case 'detach': {
+                        cleanupSession();
                         break;
                     }
                     case 'browser': {
@@ -815,3 +825,36 @@ async function updateRequest(sessionStatusBarItem: StatusBarItem) {
         }
     }
 }
+
+export function cleanupSession(): void {
+    if (sessionStatusBarItem) {
+        sessionStatusBarItem.text = 'R: (not attached)';
+        sessionStatusBarItem.tooltip = 'Click to attach active terminal.';
+    }
+    workspaceData.globalenv = {};
+    workspaceData.loaded_namespaces = [];
+    workspaceData.search = [];
+    rWorkspace?.refresh();
+    removeSessionFiles();
+}
+
+async function watchProcess(pid: number): Promise<number> {
+    function pidIsRunning(pid: number) {
+        try {
+            process.kill(pid, 0);
+            return true;
+        } catch (e) {
+            return false;
+        }
+    }
+
+    let res = true;
+    do {
+        res = pidIsRunning(pid);
+        await new Promise(resolve => {
+            setTimeout(resolve, 1000);
+        });
+
+    } while (res);
+    return pid;
+}