diff --git a/extensions/helpers/configuration-change.ts b/extensions/helpers/configuration-change.ts
index ef1e1aa..2ce4074 100644
--- a/extensions/helpers/configuration-change.ts
+++ b/extensions/helpers/configuration-change.ts
@@ -1,13 +1,10 @@
 import {
   ConfigurationChangeEvent
 } from 'vscode';
-import {getCustomSettings, isMaterialThemeIcons, isAutoApplyEnable, isMaterialTheme} from './settings';
+import {getCustomSettings, isMaterialThemeIcons, isMaterialTheme} from './settings';
 import {getCurrentThemeIconsID, getCurrentThemeID} from './vscode';
 
-import * as ThemeCommands from './../commands';
-import {infoMessage} from './messages';
-
-const icons = () => isAutoApplyEnable() ? ThemeCommands.fixIcons() : infoMessage();
+import handleAutoapply from './handle-autoapply';
 
 const onIconsChanged = () => {
   const customSettings = getCustomSettings();
@@ -16,27 +13,18 @@ const onIconsChanged = () => {
   }
 
   const currentIconsTheme = getCurrentThemeIconsID();
-  if (isMaterialThemeIcons(currentIconsTheme)) {
-    return icons();
-  }
+  return handleAutoapply(isMaterialThemeIcons(currentIconsTheme));
 };
 
 const onThemeChanged = () => {
   const currentTheme = getCurrentThemeID();
-  if (isMaterialTheme(currentTheme)) {
-    return icons();
-  }
+  return handleAutoapply(isMaterialTheme(currentTheme));
 };
 
 export const onChangeConfiguration = (event: ConfigurationChangeEvent) => {
   const isColorTheme = event.affectsConfiguration('workbench.colorTheme');
   const isIconTheme = event.affectsConfiguration('workbench.iconTheme');
 
-  if (isIconTheme) {
-    return onIconsChanged();
-  }
-
-  if (isColorTheme) {
-    return onThemeChanged();
-  }
+  return isIconTheme ? onIconsChanged() :
+          isColorTheme ? onThemeChanged() : null;
 };
diff --git a/extensions/helpers/handle-autoapply.ts b/extensions/helpers/handle-autoapply.ts
new file mode 100644
index 0000000..b2d914b
--- /dev/null
+++ b/extensions/helpers/handle-autoapply.ts
@@ -0,0 +1,31 @@
+import {isAutoApplyEnable, isReloadNotificationEnable, setCustomSetting} from './settings';
+import {infoMessage} from './messages';
+import {fixIcons} from '../commands';
+
+export default async (doubleCheck: boolean) => {
+  if (!doubleCheck) {
+    return;
+  }
+
+  if (isAutoApplyEnable()) {
+    return fixIcons();
+  }
+
+  if (!isReloadNotificationEnable()) {
+    return;
+  }
+
+  const result = await infoMessage();
+
+  if (result.nomore) {
+    return setCustomSetting('showReloadNotification', false);
+  }
+
+  if (result.autoreload) {
+    setCustomSetting('autoApplyIcons', true);
+  }
+
+  if (result.reload) {
+    return fixIcons();
+  }
+};
diff --git a/extensions/helpers/messages.ts b/extensions/helpers/messages.ts
index a9bfc54..470ec59 100644
--- a/extensions/helpers/messages.ts
+++ b/extensions/helpers/messages.ts
@@ -2,12 +2,10 @@ import {
   window as Window
 } from 'vscode';
 
-import * as ThemeCommands from './../commands';
-
 const MESSAGES = {
   INFO: {
     message: 'Do you want to reload to apply Material Theme Icons to enjoy the full experience?',
-    options: {ok: 'Yeah, releoad', cancel: 'No, thank you'}
+    options: {ok: 'Yeah, reload', autoreload: 'Yes and enable auto-reload', cancel: 'No, thank you', nomore: 'Never show again'}
   },
   CHANGELOG: {
     message: 'Material Theme was updated. Check the release notes for more details.',
@@ -20,22 +18,36 @@ const MESSAGES = {
 };
 
 export const infoMessage = async () => {
-  if (await Window.showInformationMessage(
+  const result = await Window.showInformationMessage(
     MESSAGES.INFO.message,
-    ...MESSAGES.INFO.options as any
-  ) === MESSAGES.INFO.options.ok) {
-    ThemeCommands.fixIcons();
+    MESSAGES.INFO.options.ok,
+    MESSAGES.INFO.options.autoreload,
+    MESSAGES.INFO.options.cancel,
+    MESSAGES.INFO.options.nomore
+  );
+
+  switch (result) {
+    case MESSAGES.INFO.options.ok:
+      return {reload: true};
+    case MESSAGES.INFO.options.autoreload:
+      return {reload: true, autoreload: true};
+    case MESSAGES.INFO.options.nomore:
+      return {nomore: true};
+    default:
+      return {};
   }
 };
 
 export const changelogMessage = async () =>
   await Window.showInformationMessage(
     MESSAGES.CHANGELOG.message,
-    ...MESSAGES.CHANGELOG.options as any
+    MESSAGES.CHANGELOG.options.ok,
+    MESSAGES.CHANGELOG.options.cancel
   ) === MESSAGES.CHANGELOG.options.ok;
 
 export const installationMessage = async () =>
   await Window.showInformationMessage(
     MESSAGES.INSTALLATION.message,
-    ...MESSAGES.INSTALLATION.options as any
+    MESSAGES.INSTALLATION.options.ok,
+    MESSAGES.INSTALLATION.options.cancel,
   ) === MESSAGES.INSTALLATION.options.ok;
diff --git a/extensions/helpers/settings.ts b/extensions/helpers/settings.ts
index 1c2073b..c726015 100644
--- a/extensions/helpers/settings.ts
+++ b/extensions/helpers/settings.ts
@@ -22,7 +22,14 @@ export function getCustomSettings(): IThemeCustomProperties {
  * Get autoApplyIcons
  */
 export function isAutoApplyEnable(): boolean {
-  return vscode.workspace.getConfiguration().get<boolean>('materialTheme.autoApplyIcons', true);
+  return vscode.workspace.getConfiguration().get<boolean>('materialTheme.autoApplyIcons');
+}
+
+/**
+ * Get showReloadNotification
+ */
+export function isReloadNotificationEnable(): boolean {
+  return vscode.workspace.getConfiguration().get<boolean>('materialTheme.showReloadNotification');
 }
 
 /**
diff --git a/extensions/material.theme.config.ts b/extensions/material.theme.config.ts
index f13f22d..900b75f 100644
--- a/extensions/material.theme.config.ts
+++ b/extensions/material.theme.config.ts
@@ -4,11 +4,12 @@ import {
 } from 'vscode';
 
 import * as ThemeCommands from './commands';
-import {isAutoApplyEnable, setCustomSetting} from './helpers/settings';
+import {setCustomSetting} from './helpers/settings';
 import {onChangeConfiguration} from './helpers/configuration-change';
-import {infoMessage, changelogMessage, installationMessage} from './helpers/messages';
+import {changelogMessage, installationMessage} from './helpers/messages';
 import checkInstallation from './helpers/check-installation';
 import writeChangelog from './helpers/write-changelog';
+import handleAutoapply from './helpers/handle-autoapply';
 
 export async function activate() {
   const config = Workspace.getConfiguration();
@@ -39,9 +40,7 @@ export async function activate() {
   // Registering commands
   Commands.registerCommand('materialTheme.setAccent', async () => {
     const wasSet = await ThemeCommands.accentsSetter();
-    if (wasSet) {
-      return isAutoApplyEnable() ? ThemeCommands.fixIcons() : infoMessage();
-    }
+    handleAutoapply(wasSet);
   });
   Commands.registerCommand('materialTheme.fixIcons', () => ThemeCommands.fixIcons());
   Commands.registerCommand('materialTheme.toggleApplyIcons', () => ThemeCommands.toggleApplyIcons());