diff --git a/jsconfig.json b/jsconfig.json
deleted file mode 100644
index b7caa7d0..00000000
--- a/jsconfig.json
+++ /dev/null
@@ -1,12 +0,0 @@
-{
-    "compilerOptions": {
-        "module": "commonjs",
-        "target": "es6",
-        "lib": [
-            "es6"
-        ]
-    },
-    "exclude": [
-        "node_modules"
-    ]
-}
\ No newline at end of file
diff --git a/package.json b/package.json
index b5879595..ec3202dc 100644
--- a/package.json
+++ b/package.json
@@ -365,8 +365,8 @@
     "install-local": "vsce package && code --install-extension kite-*.vsix && rm kite-*.vsix"
   },
   "dependencies": {
-    "kite-api": "=3.19.0",
-    "kite-connector": "=3.12.0",
+    "kite-api": "=3.20.0",
+    "kite-connector": "=3.14.0",
     "md5": "^2.2.0",
     "mixpanel": "^0.5.0",
     "open": "^7.3.0",
diff --git a/src/kite.js b/src/kite.js
index 5ca751c7..db57ad72 100644
--- a/src/kite.js
+++ b/src/kite.js
@@ -86,10 +86,6 @@ export const Kite = {
         vscode.workspace.getConfiguration("kite").loggingLevel.toUpperCase()
       ];
 
-    KiteAPI
-      .isKiteInstalled()
-      .catch(NotificationsManager.showKiteInstallNotification);
-
     this.setMaxFileSize();
 
     this.disposables.push(
@@ -427,6 +423,7 @@ export const Kite = {
     this.shown = {};
     this.disposables = [];
     this.attemptedToStartKite = false;
+    this.installing = false;
     this.notifications = new NotificationsManager();
     delete this.lastState;
     delete this.lastStatus;
@@ -522,12 +519,32 @@ export const Kite = {
               return state;
             }
             this.shown[state] = true;
+            if (KiteAPI.hasKiteRun()) {
+              NotificationsManager.showKiteInstallNotification();
+            } else {
+              NotificationsManager.showKiteDownloadingNotification();
+              this.installing = true;
+              KiteAPI.downloadKiteRelease({
+                install: true,
+                launchCopilot: true,
+                channel: 'vscode',
+                onRemove: () => { this.installing = false; },
+              })
+              .catch(e => {
+                console.error(e);
+                NotificationsManager.showKiteInstallErrorNotification();
+              });
+            }
             break;
           case KiteAPI.STATES.INSTALLED:
             if (
               !this.attemptedToStartKite &&
               vscode.workspace.getConfiguration("kite").startKiteEngineOnStartup
             ) {
+              if (this.installing) {
+                // Guard against running Kite before installation fully completes.
+                break;
+              }
               KiteAPI.runKiteAndWait(RUN_KITE_ATTEMPTS, RUN_KITE_INTERVAL).then(() => this.checkState(src));
               this.attemptedToStartKite = true;
             }
@@ -586,14 +603,19 @@ export const Kite = {
       this.statusBarItem.show();
       switch (state) {
         case KiteAPI.STATES.UNSUPPORTED:
+          this.statusBarItem.text = "𝕜𝕚𝕥𝕖: not supported";
           this.statusBarItem.tooltip =
             "Kite engine is currently not supported on your platform";
           this.statusBarItem.color = ERROR_COLOR();
-          this.statusBarItem.text = "𝕜𝕚𝕥𝕖: not supported";
           break;
         case KiteAPI.STATES.UNINSTALLED:
-          this.statusBarItem.text = "𝕜𝕚𝕥𝕖: not installed";
-          this.statusBarItem.tooltip = "Kite engine is not installed";
+          if (this.installing) {
+            this.statusBarItem.text = "𝕜𝕚𝕥𝕖: installing components";
+            this.statusBarItem.tooltip = "Installing components. Kite will launch automatically when ready.";
+          } else {
+            this.statusBarItem.text = "𝕜𝕚𝕥𝕖: not installed";
+            this.statusBarItem.tooltip = "Kite engine is not installed";
+          }
           this.statusBarItem.color = ERROR_COLOR();
           break;
         case KiteAPI.STATES.INSTALLED:
diff --git a/src/notifications.js b/src/notifications.js
index eb77d4cd..fd822d37 100644
--- a/src/notifications.js
+++ b/src/notifications.js
@@ -1,6 +1,5 @@
 import vscode from "vscode";
 import open from "open";
-import path from "path";
 
 import metrics from "./metrics";
 
@@ -78,22 +77,56 @@ export default class NotificationsManager {
       .then(hasDone => !hasDone && openKiteTutorial('python'));
   }
 
-  static showKiteInstallNotification(err) {
-    if (typeof err.data !== 'undefined' && err.data.state === KiteAPI.STATES.UNINSTALLED) {
-      metrics.track("vscode_kite_installer_notification_shown");
-      vscode.window
-        .showInformationMessage(
-          "Kite requires the Kite Engine backend to provide completions and documentation. Please install it to use Kite.",
-          "Install"
-        )
-        .then(item => {
-          switch (item) {
-            case "Install":
-              open("https://www.kite.com/install/?utm_medium=editor&utm_source=vscode");
-              metrics.track("vscode_kite_installer_github_link_clicked");
-              break;
-          }
-        });
-    }
+  static showKiteInstallNotification() {
+    metrics.track("vscode_kite_installer_notification_shown");
+    vscode.window
+      .showInformationMessage(
+        "Kite requires the Kite Engine backend to provide completions and documentation. Please install it to use Kite.",
+        "Install"
+      )
+      .then(item => {
+        switch (item) {
+          case "Install":
+            open("https://www.kite.com/install/?utm_medium=editor&utm_source=vscode");
+            metrics.track("vscode_kite_installer_github_link_clicked");
+            break;
+        }
+      });
+  }
+
+  static showKiteDownloadingNotification() {
+    metrics.track("vscode_kite_downloading_notification_shown");
+    vscode.window
+      .showInformationMessage(
+        "Kite ships with a standalone application called the Copilot that can show you documentation while you code. The Copilot will launch automatically after Kite is finished installing.",
+        "OK",
+        "Learn More"
+      )
+      .then(item => {
+        switch (item) {
+          case "OK":
+            break;
+          case "Learn More":
+            open("https://www.kite.com/copilot/");
+            break;
+        }
+      });
+  }
+
+  static showKiteInstallErrorNotification() {
+    metrics.track("vscode_kite_downloading_failed_notification_shown");
+    vscode.window
+      .showErrorMessage(
+        "There was an error installing the Kite Engine, which is required for Kite to provide completions and documentation. Please install it to use Kite.",
+        "Install"
+      )
+      .then(item => {
+        switch (item) {
+          case "Install":
+            open("https://www.kite.com/install/?utm_medium=editor&utm_source=vscode");
+            metrics.track("vscode_kite_installer_github_link_clicked");
+            break;
+        }
+      });
   }
 }