diff --git a/src/_locales/en/messages.json b/src/_locales/en/messages.json
index be4275d8bb5..ec562879dfe 100644
--- a/src/_locales/en/messages.json
+++ b/src/_locales/en/messages.json
@@ -1371,5 +1371,17 @@
   },
   "desktopIntegrationVerificationText": {
     "message": "Please verify that the desktop application shows this fingerprint: "
+  },
+  "desktopIntegrationDisabledTitle": {
+    "message": "Browser integration is not enabled"
+  },
+  "desktopIntegrationDisabledDesc": {
+    "message": "Browser integration is not enabled in the Bitwarden Desktop Application. Please enable it in the settings within the desktop application."
+  },
+  "startDesktopTitle": {
+    "message": "Start the Bitwarden Desktop Application"
+  },
+  "startDesktopDesc": {
+    "message": "The bitwarden desktop application needs to be started before this function can be used."
   }
 }
diff --git a/src/background/nativeMessaging.background.ts b/src/background/nativeMessaging.background.ts
index caebdc8e277..69389358702 100644
--- a/src/background/nativeMessaging.background.ts
+++ b/src/background/nativeMessaging.background.ts
@@ -16,6 +16,7 @@ const EncryptionAlgorithm = 'sha1';
 
 export class NativeMessagingBackground {
     private connected = false;
+    private connecting: boolean;
     private port: browser.runtime.Port | chrome.runtime.Port;
 
     private resolver: any = null;
@@ -29,22 +30,54 @@ export class NativeMessagingBackground {
         private runtimeBackground: RuntimeBackground, private i18nService: I18nService, private userService: UserService,
         private messagingService: MessagingService) {}
 
-    connect() {
-        this.port = BrowserApi.connectNative('com.8bit.bitwarden');
+    async connect() {
+        return new Promise((resolve, reject) => {
+            this.port = BrowserApi.connectNative('com.8bit.bitwarden');
 
-        this.connected = true;
+            this.connecting = true;
 
-        this.port.onMessage.addListener((msg) => this.onMessage(msg));
+            this.port.onMessage.addListener((message: any) => {
+                if (message.command === 'connected') {
+                    this.connected = true;
+                    this.connecting = false;
+                    resolve();
+                } else if (message.command === 'disconnected') {
+                    if (this.connecting) {
+                        this.messagingService.send('showDialog', {
+                            text: this.i18nService.t('startDesktopDesc'),
+                            title: this.i18nService.t('startDesktopTitle'),
+                            confirmText: this.i18nService.t('ok'),
+                            type: 'error',
+                        });
+                        reject();
+                    }
+                    this.connected = false;
+                    this.port.disconnect();
+                    return;
+                }
 
-        this.port.onDisconnect.addListener(() => {
-            this.connected = false;
+                this.onMessage(message);
+            });
+
+            this.port.onDisconnect.addListener(() => {
+                if (BrowserApi.runtimeLastError().message === 'Specified native messaging host not found.') {
+                    this.messagingService.send('showDialog', {
+                        text: this.i18nService.t('desktopIntegrationDisabledDesc'),
+                        title: this.i18nService.t('desktopIntegrationDisabledTitle'),
+                        confirmText: this.i18nService.t('ok'),
+                        type: 'error',
+                    });
+                }
+                this.connected = false;
+                reject();
+            });
         });
     }
 
     async send(message: any) {
         // If not connected, try to connect
         if (!this.connected) {
-            this.connect();
+            await this.connect();
         }
 
         if (this.sharedSecret == null) {
@@ -118,7 +151,7 @@ export class NativeMessagingBackground {
         const fingerprint = (await this.cryptoService.getFingerprint(await this.userService.getUserId(), this.publicKey)).join(' ');
 
         this.messagingService.send('showDialog', {
-            html: `${this.i18nService.t('desktopIntegrationVerificationText')}<br><br><strong>${fingerprint}</strong>.`,
+            html: `${this.i18nService.t('desktopIntegrationVerificationText')}<br><br><strong>${fingerprint}</strong>`,
             title: this.i18nService.t('desktopSyncVerificationTitle'),
             confirmText: this.i18nService.t('ok'),
             type: 'warning',
@@ -129,7 +162,7 @@ export class NativeMessagingBackground {
 
     private async sendUnencrypted(message: any) {
         if (!this.connected) {
-            this.connect();
+            await this.connect();
         }
 
         message.timestamp = Date.now();
diff --git a/src/browser/browserApi.ts b/src/browser/browserApi.ts
index 1ee54a45b18..660defcca33 100644
--- a/src/browser/browserApi.ts
+++ b/src/browser/browserApi.ts
@@ -229,4 +229,12 @@ export class BrowserApi {
             return chrome.runtime.connectNative(application);
         }
     }
+
+    static runtimeLastError(): browser.runtime._LastError | chrome.runtime.LastError {
+        if (BrowserApi.isWebExtensionsApi) {
+            return browser.runtime.lastError;
+        } else if (BrowserApi.isChromeApi) {
+            return chrome.runtime.lastError;
+        }
+    }
 }