diff --git a/extensions/eclipse-che-theia-plugin-ext/src/browser/che-github-main.ts b/extensions/eclipse-che-theia-plugin-ext/src/browser/che-github-main.ts
index 383497122..1d8e1693b 100644
--- a/extensions/eclipse-che-theia-plugin-ext/src/browser/che-github-main.ts
+++ b/extensions/eclipse-che-theia-plugin-ext/src/browser/che-github-main.ts
@@ -72,15 +72,21 @@ export class CheGithubMainImpl implements CheGithubMain {
 
   private async updateToken(): Promise<void> {
     const oAuthProvider = 'github';
-    try {
+    const authenticateAndUpdateToken: () => Promise<void> = async () => {
+      await this.oAuthUtils.authenticate(oAuthProvider, ['repo', 'user', 'write:public_key']);
       this.token = await this.oAuthUtils.getToken(oAuthProvider);
-      // Validate the GitHub token.
-      await this.getUser();
-    } catch (e) {
-      if (e.message.indexOf('Request failed with status code 401') !== -1) {
-        await this.oAuthUtils.authenticate(oAuthProvider, ['write:public_key']);
-        this.token = await this.oAuthUtils.getToken(oAuthProvider);
+    };
+    if (await this.oAuthUtils.isAuthenticated(oAuthProvider)) {
+      try {
+        // Validate the GitHub token.
+        await this.getUser();
+      } catch (e) {
+        if (/Request failed with status code 401/g.test(e.message)) {
+          await authenticateAndUpdateToken();
+        }
       }
+    } else {
+      await authenticateAndUpdateToken();
     }
   }
 }
diff --git a/extensions/eclipse-che-theia-remote-api/src/browser/oauth-utils.ts b/extensions/eclipse-che-theia-remote-api/src/browser/oauth-utils.ts
index dd81b182e..d6cc1ed4e 100644
--- a/extensions/eclipse-che-theia-remote-api/src/browser/oauth-utils.ts
+++ b/extensions/eclipse-che-theia-remote-api/src/browser/oauth-utils.ts
@@ -13,6 +13,7 @@ import { inject, injectable } from 'inversify';
 
 import { EnvVariablesServer } from '@theia/core/lib/common/env-variables';
 import { OAuthService } from '../common/oauth-service';
+import { UserService } from '../common/user-service';
 
 @injectable()
 export class OauthUtils {
@@ -27,7 +28,8 @@ export class OauthUtils {
 
   constructor(
     @inject(EnvVariablesServer) private readonly envVariableServer: EnvVariablesServer,
-    @inject(OAuthService) private readonly oAuthService: OAuthService
+    @inject(OAuthService) private readonly oAuthService: OAuthService,
+    @inject(UserService) private readonly userService: UserService
   ) {
     const onDidReceiveTokenEmitter = new Emitter<void>();
     this.onDidReceiveToken = onDidReceiveTokenEmitter.event;
@@ -57,29 +59,41 @@ export class OauthUtils {
   }
 
   async getUserToken(): Promise<string | undefined> {
-    if (this.userToken) {
-      return this.userToken;
-    } else if (this.machineToken && this.machineToken.length > 0) {
-      const timer = setTimeout(() => {
-        this.messageService.warn(
-          'Authentication is taking too long, the oauth pop-up may be blocked by your browser, ' +
-            'if so, allow popup windows for the current url and restart the workspace'
+    const updateToken: () => Promise<string | undefined> = async () => {
+      if (this.machineToken && this.machineToken.length > 0) {
+        const timer = setTimeout(() => {
+          this.messageService.warn(
+            'Authentication is taking too long, the OAuth pop-up may be blocked by your browser, ' +
+              'if so, allow pop-up windows for the current url and restart the workspace'
+          );
+        }, 10000);
+        const popup = window.open(
+          `${this.apiUrl.substring(0, this.apiUrl.indexOf('/api'))}/_app/oauth.html`,
+          'popup',
+          'toolbar=no, status=no, menubar=no, scrollbars=no, width=10, height=10, visible=none'
         );
-      }, 10000);
-      const popup = window.open(
-        `${this.apiUrl.substring(0, this.apiUrl.indexOf('/api'))}/_app/oauth.html`,
-        'popup',
-        'toolbar=no, status=no, menubar=no, scrollbars=no, width=10, height=10, visible=none'
-      );
-      if (popup) {
-        this.oAuthPopup = popup;
-      }
-      return new Promise(async resolve => {
-        this.onDidReceiveToken(() => {
-          clearTimeout(timer);
-          resolve(this.userToken);
+        if (popup) {
+          this.oAuthPopup = popup;
+        }
+        return new Promise(async resolve => {
+          this.onDidReceiveToken(() => {
+            clearTimeout(timer);
+            resolve(this.userToken);
+          });
         });
-      });
+      }
+    };
+    if (this.userToken) {
+      try {
+        await this.userService.getCurrentUser(this.userToken);
+      } catch (e) {
+        if (/Request getCurrentUser failed with message: "401"/g.test(e.message)) {
+          return updateToken();
+        }
+      }
+      return this.userToken;
+    } else {
+      return updateToken();
     }
   }
 
@@ -105,7 +119,7 @@ export class OauthUtils {
       await this.oAuthService.getOAuthToken(provider, await this.getUserToken());
       return true;
     } catch (e) {
-      return e.message.indexOf('Request failed with status code 401') > 0;
+      return new RegExp(`User \\[.*] is not associated with identity provider \\[${provider}]\\.`).test(e.message);
     }
   }
 
diff --git a/plugins/github-auth-plugin/src/github-auth-plugin.ts b/plugins/github-auth-plugin/src/github-auth-plugin.ts
index 6dfa42804..90f4fa4b0 100644
--- a/plugins/github-auth-plugin/src/github-auth-plugin.ts
+++ b/plugins/github-auth-plugin/src/github-auth-plugin.ts
@@ -23,6 +23,20 @@ export async function start(context: theia.PluginContext): Promise<void> {
     onDidChangeSessions: onDidChangeSessions.event,
     getSessions: async () => sessions,
     login: async (scopes: string[]) => {
+      if (!(await che.oAuth.isRegistered('github'))) {
+        if (
+          await theia.window.showWarningMessage(
+            'Che could not authenticate to your Github account. The setup for Github OAuth provider is not complete.',
+            'Setup instructions'
+          )
+        ) {
+          theia.commands.executeCommand(
+            'theia.open',
+            'https://www.eclipse.org/che/docs/che-7/administration-guide/configuring-authorization/#configuring-github-oauth_che'
+          );
+        }
+        return;
+      }
       const githubUser = await che.github.getUser();
       const session = {
         id: v4(),
@@ -49,22 +63,6 @@ export async function start(context: theia.PluginContext): Promise<void> {
       }
     },
   });
-  if (theia.plugins.getPlugin('github.vscode-pull-request-github')) {
-    if (sessions.length > 0) {
-      onDidChangeSessions.fire({ added: sessions.map(s => s.id), removed: [], changed: [] });
-      // TODO Remove the notification when https://github.com/eclipse-theia/theia/issues/7178 is fixed.
-    } else {
-      const signIn = 'Sign in';
-      const result = await theia.window.showInformationMessage(
-        'In order to use the Pull Requests functionality, you must sign in to GitHub',
-        signIn
-      );
-
-      if (result === signIn) {
-        theia.authentication.getSession('github', ['read:user', 'user:email', 'repo'], { createIfNone: true });
-      }
-    }
-  }
 }
 
 export function stop(): void {}