diff --git a/src/github/folderRepositoryManager.ts b/src/github/folderRepositoryManager.ts
index 9807c8a53e..6d19413919 100644
--- a/src/github/folderRepositoryManager.ts
+++ b/src/github/folderRepositoryManager.ts
@@ -495,7 +495,7 @@ export class FolderRepositoryManager extends Disposable {
 		}
 
 		const activeRemotes = await this.getActiveRemotes();
-		const isAuthenticated = this.checkForAuthMatch(activeRemotes);
+		let isAuthenticated = this.checkForAuthMatch(activeRemotes);
 		if (this.credentialStore.isAnyAuthenticated() && (activeRemotes.length === 0)) {
 			const allUnknownRemotes = await this.computeAllUnknownRemotes();
 			const areAllNeverGitHub = allUnknownRemotes.every(remote => GitHubManager.isNeverGitHub(vscode.Uri.parse(remote.normalizedHost).authority));
@@ -504,6 +504,10 @@ export class FolderRepositoryManager extends Disposable {
 				this.state = ReposManagerState.RepositoriesLoaded;
 				return true;
 			}
+			if (allUnknownRemotes.length > 0) {
+				isAuthenticated = false;
+				await vscode.commands.executeCommand('setContext', 'github:authenticated', false);
+			}
 		}
 		const repositories: GitHubRepository[] = [];
 		const resolveRemotePromises: Promise<boolean>[] = [];
diff --git a/src/test/github/folderRepositoryManager.test.ts b/src/test/github/folderRepositoryManager.test.ts
index 6e4b1b9ef4..e77be9e2a8 100644
--- a/src/test/github/folderRepositoryManager.test.ts
+++ b/src/test/github/folderRepositoryManager.test.ts
@@ -6,7 +6,7 @@
 import { default as assert } from 'assert';
 import { createSandbox, SinonSandbox } from 'sinon';
 
-import { FolderRepositoryManager, titleAndBodyFrom } from '../../github/folderRepositoryManager';
+import { FolderRepositoryManager, ReposManagerState, titleAndBodyFrom } from '../../github/folderRepositoryManager';
 import { MockRepository } from '../mocks/mockRepository';
 import { MockTelemetry } from '../mocks/mockTelemetry';
 import { MockCommandRegistry } from '../mocks/mockCommandRegistry';
@@ -20,7 +20,7 @@ import { GitApiImpl } from '../../api/api1';
 import { CredentialStore } from '../../github/credentials';
 import { MockExtensionContext } from '../mocks/mockExtensionContext';
 import { Uri } from 'vscode';
-import { GitHubServerType } from '../../common/authentication';
+import { AuthProvider, GitHubServerType } from '../../common/authentication';
 import { CreatePullRequestHelper } from '../../view/createPullRequestHelper';
 import { RepositoriesManager } from '../../github/repositoriesManager';
 import { MockThemeWatcher } from '../mocks/mockThemeWatcher';
@@ -53,6 +53,20 @@ describe('PullRequestManager', function () {
 		sinon.restore();
 	});
 
+	describe('updateRepositories', function () {
+		it('requires authentication for an unknown remote with an existing GitHub.com session', async function () {
+			const url = 'ssh://git@ghe.example.com/org/repo.git';
+			const remote = new Remote('origin', url, new Protocol(url));
+			sinon.stub(manager, 'computeAllGitHubRemotes').resolves([]);
+			sinon.stub(manager, 'computeAllUnknownRemotes').resolves([remote]);
+			sinon.stub(manager.credentialStore, 'isAuthenticated').callsFake(provider => provider === AuthProvider.github);
+
+			await manager.updateRepositories();
+
+			assert.strictEqual(manager.state, ReposManagerState.NeedsAuthentication);
+		});
+	});
+
 	describe('activePullRequest', function () {
 		it('gets and sets the active pull request', function () {
 			assert.strictEqual(manager.activePullRequest, undefined);