diff --git a/extensions/helpers/messages.ts b/extensions/helpers/messages.ts
index c68c9d8..a9bfc54 100644
--- a/extensions/helpers/messages.ts
+++ b/extensions/helpers/messages.ts
@@ -12,14 +12,30 @@ const MESSAGES = {
   CHANGELOG: {
     message: 'Material Theme was updated. Check the release notes for more details.',
     options: {ok: 'Show me', cancel: 'Maybe later'}
+  },
+  INSTALLATION: {
+    message: 'Thank you for installing Material Theme! Would you like to enable the auto-application (with window reload when needed) of the Material Theme icons?',
+    options: {ok: 'Sure!', cancel: 'Nope :('}
   }
 };
 
 export const infoMessage = async () => {
-  if (await Window.showInformationMessage(MESSAGES.INFO.message, MESSAGES.INFO.options.ok, MESSAGES.INFO.options.cancel) === MESSAGES.INFO.options.ok) {
+  if (await Window.showInformationMessage(
+    MESSAGES.INFO.message,
+    ...MESSAGES.INFO.options as any
+  ) === MESSAGES.INFO.options.ok) {
     ThemeCommands.fixIcons();
   }
 };
 
 export const changelogMessage = async () =>
-  await Window.showInformationMessage(MESSAGES.CHANGELOG.message, MESSAGES.CHANGELOG.options.ok, MESSAGES.CHANGELOG.options.cancel) === MESSAGES.CHANGELOG.options.ok;
+  await Window.showInformationMessage(
+    MESSAGES.CHANGELOG.message,
+    ...MESSAGES.CHANGELOG.options as any
+  ) === MESSAGES.CHANGELOG.options.ok;
+
+export const installationMessage = async () =>
+  await Window.showInformationMessage(
+    MESSAGES.INSTALLATION.message,
+    ...MESSAGES.INSTALLATION.options as any
+  ) === MESSAGES.INSTALLATION.options.ok;
diff --git a/extensions/material.theme.config.ts b/extensions/material.theme.config.ts
index b603979..f13f22d 100644
--- a/extensions/material.theme.config.ts
+++ b/extensions/material.theme.config.ts
@@ -4,9 +4,9 @@ import {
 } from 'vscode';
 
 import * as ThemeCommands from './commands';
-import {isAutoApplyEnable} from './helpers/settings';
+import {isAutoApplyEnable, setCustomSetting} from './helpers/settings';
 import {onChangeConfiguration} from './helpers/configuration-change';
-import {infoMessage, changelogMessage} from './helpers/messages';
+import {infoMessage, changelogMessage, installationMessage} from './helpers/messages';
 import checkInstallation from './helpers/check-installation';
 import writeChangelog from './helpers/write-changelog';
 
@@ -24,6 +24,13 @@ export async function activate() {
     config.update('materialTheme.cache.workbench', undefined, true);
   }
 
+  if (installationType.isFirstInstall) {
+    const enableAutoApply = await installationMessage();
+    await setCustomSetting('autoApplyIcons', enableAutoApply);
+    // Set true always on new installation
+    await setCustomSetting('showReloadNotification', true);
+  }
+
   const shouldShowChangelog = (installationType.isFirstInstall || installationType.isUpdate) && await changelogMessage();
   if (shouldShowChangelog) {
     ThemeCommands.showChangelog();
diff --git a/package.json b/package.json
index 8e58291..9aa89e6 100644
--- a/package.json
+++ b/package.json
@@ -93,7 +93,12 @@
         },
         "materialTheme.autoApplyIcons": {
           "type": "boolean",
-          "description": "Enable/disable auto-apply of Material Theme icons",
+          "description": "Enable/disable auto-apply of Material Theme icons with window reload when needed",
+          "default": false
+        },
+        "materialTheme.showReloadNotification": {
+          "type": "boolean",
+          "description": "Useful when autoApplyIcons is false and you want to be asked to reload the window when needed",
           "default": true
         },
         "materialTheme.fixIconsRunning": {