diff --git a/src/gitProviders/GitHubContactServiceProvider.ts b/src/gitProviders/GitHubContactServiceProvider.ts
index bc3973cfef..1d88f69a8e 100644
--- a/src/gitProviders/GitHubContactServiceProvider.ts
+++ b/src/gitProviders/GitHubContactServiceProvider.ts
@@ -125,7 +125,7 @@ export class GitHubContactServiceProvider implements ContactServiceProvider {
 		}
 		const origin = await this.pullRequestManager.folderManagers[0]?.getOrigin();
 		if (origin) {
-			const currentUser = origin.hub.currentUser ? await origin.hub.currentUser : undefined;
+			const currentUser = await origin.getAuthenticatedUser();
 			if (currentUser) {
 				return currentUser.login;
 			}
diff --git a/src/github/credentials.ts b/src/github/credentials.ts
index e1e9ae9ee1..e5d42b8c4d 100644
--- a/src/github/credentials.ts
+++ b/src/github/credentials.ts
@@ -551,19 +551,25 @@ export class CredentialStore extends Disposable {
 	}
 
 	public async isCurrentUser(authProviderId: AuthProvider, username: string): Promise<boolean> {
-		const api = authProviderId === AuthProvider.github ? this._githubAPI : this._githubEnterpriseAPI;
-		return (await api?.currentUser)?.login === username;
+		return (await this.getCurrentUser(authProviderId))?.login === username;
 	}
 
 	public async getIsEmu(authProviderId: AuthProvider): Promise<boolean> {
 		const github = this.getHub(authProviderId);
+		this.ensureCurrentUser(github);
 		return !!(await github?.isEmu);
 	}
 
 	public getCurrentUser(authProviderId: AuthProvider): Promise<IAccount> {
 		const github = this.getHub(authProviderId);
-		const octokit = github?.octokit;
-		return (octokit && github?.currentUser)!;
+		this.ensureCurrentUser(github);
+		return github?.currentUser!;
+	}
+
+	private ensureCurrentUser(github: GitHub | undefined): void {
+		if (github && (!github.currentUser || !github.isEmu)) {
+			this.setCurrentUser(github);
+		}
 	}
 
 	private setCurrentUser(github: GitHub): void {
@@ -577,8 +583,27 @@ export class CredentialStore extends Disposable {
 				reject(e);
 			});
 		});
-		github.currentUser = getUser.then(result => convertRESTUserToAccount(result.data));
-		github.isEmu = getUser.then(result => result.data.plan?.name === 'emu_user');
+		let currentUser: Promise<IAccount>;
+		let isEmu: Promise<boolean>;
+		const clearFailedRequest = () => {
+			if (github.currentUser === currentUser && github.isEmu === isEmu) {
+				github.currentUser = undefined;
+				github.isEmu = undefined;
+			}
+		};
+		currentUser = getUser.then(result => convertRESTUserToAccount(result.data), e => {
+			clearFailedRequest();
+			throw e;
+		});
+		isEmu = getUser.then(result => result.data.plan?.name === 'emu_user', e => {
+			clearFailedRequest();
+			throw e;
+		});
+		github.currentUser = currentUser;
+		github.isEmu = isEmu;
+
+		void currentUser.catch(() => undefined);
+		void isEmu.catch(() => undefined);
 	}
 
 	private async getSession(authProviderId: AuthProvider, getAuthSessionOptions: vscode.AuthenticationGetSessionOptions, scopes: string[], requireScopes: boolean): Promise<{ session: vscode.AuthenticationSession | undefined, isNew: boolean, scopes: string[] }> {
diff --git a/src/github/githubRepository.ts b/src/github/githubRepository.ts
index fb6abd413d..7ed48ec22f 100644
--- a/src/github/githubRepository.ts
+++ b/src/github/githubRepository.ts
@@ -424,7 +424,7 @@ export class GitHubRepository extends Disposable {
 			repo
 		});
 		Logger.debug(`Fetch metadata for repo ${owner}/${repo} - done`, this.id);
-		const metadata = { ...result.data, currentUser: await this._hub?.currentUser };
+		const metadata = { ...result.data, currentUser: await this.getAuthenticatedUser() };
 		return metadata;
 	}
 
@@ -437,15 +437,22 @@ export class GitHubRepository extends Disposable {
 
 		Logger.debug(`Fetch metadata - enter`, this.id);
 		const { remote } = await this.ensure();
-		this._metadata = this.getMetadataForRepo(remote.owner, remote.repositoryName).catch(e => {
-			if ((getErrorCode(e) === '404') && !isSamlError(e) && !this._isInaccessible) {
-				this._isInaccessible = true;
-				Logger.warn(`Repository ${remote.owner}/${remote.repositoryName} from remote ${remote.remoteName} in workspace folder ${this.rootUri.fsPath} returned HTTP 404 and will be skipped for this session.`, this.id);
+		const metadata = this.getMetadataForRepo(remote.owner, remote.repositoryName).catch(e => {
+			if (this._metadata === metadata) {
+				if ((getErrorCode(e) === '404') && !isSamlError(e)) {
+					if (!this._isInaccessible) {
+						this._isInaccessible = true;
+						Logger.warn(`Repository ${remote.owner}/${remote.repositoryName} from remote ${remote.remoteName} in workspace folder ${this.rootUri.fsPath} returned HTTP 404 and will be skipped for this session.`, this.id);
+					}
+				} else {
+					this._metadata = undefined;
+				}
 			}
 			throw e;
 		});
+		this._metadata = metadata;
 		Logger.debug(`Fetch metadata ${remote.owner}/${remote.repositoryName} - done`, this.id);
-		return this._metadata;
+		return metadata;
 	}
 
 	/**
diff --git a/src/github/pullRequestOverview.ts b/src/github/pullRequestOverview.ts
index c39e55f05d..3b8d07f7fc 100644
--- a/src/github/pullRequestOverview.ts
+++ b/src/github/pullRequestOverview.ts
@@ -44,6 +44,12 @@ import { asPromise, formatError } from '../common/utils';
 import { IRequestMessage, PULL_REQUEST_OVERVIEW_VIEW_TYPE } from '../common/webview';
 import { toCheckRunLogUri } from '../view/checkRunLogContentProvider';
 
+function withErrorContext<T>(operation: string, promise: Promise<T>): Promise<T> {
+	return promise.catch(e => {
+		throw new Error(`${operation} failed: ${formatError(e)}`);
+	});
+}
+
 export class PullRequestOverviewPanel extends IssueOverviewPanel<PullRequestModel> {
 	public static override ID: string = 'PullRequestOverviewPanel';
 	public static override readonly viewType = PULL_REQUEST_OVERVIEW_VIEW_TYPE;
@@ -344,27 +350,27 @@ export class PullRequestOverviewPanel extends IssueOverviewPanel<PullRequestMode
 
 		try {
 			const updatingPromise = Promise.all([
-				this._folderRepositoryManager.resolvePullRequest(
+				withErrorContext('Resolving pull request', this._folderRepositoryManager.resolvePullRequest(
 					pullRequestModel.remote.owner,
 					pullRequestModel.remote.repositoryName,
 					pullRequestModel.number,
-				),
-				pullRequestModel.getTimelineEvents(),
-				this._folderRepositoryManager.getPullRequestRepositoryDefaultBranch(pullRequestModel),
-				pullRequestModel.getStatusChecks(),
-				pullRequestModel.getReviewRequests(),
-				this._folderRepositoryManager.getPullRequestRepositoryAccessAndMergeMethods(pullRequestModel),
-				this._folderRepositoryManager.getBranchNameForPullRequest(pullRequestModel),
-				this._folderRepositoryManager.getCurrentUser(pullRequestModel.githubRepository),
-				pullRequestModel.canEdit(),
-				this._folderRepositoryManager.getOrgTeamsCount(pullRequestModel.githubRepository),
-				this._folderRepositoryManager.mergeQueueMethodForBranch(pullRequestModel.base.ref, pullRequestModel.remote.owner, pullRequestModel.remote.repositoryName),
-				this._folderRepositoryManager.isHeadUpToDateWithBase(pullRequestModel),
-				pullRequestModel.getMergeability(),
-				this._folderRepositoryManager.getPreferredEmail(pullRequestModel),
-				pullRequestModel.getCoAuthors(),
-				pullRequestModel.validateDraftMode(),
-				this._folderRepositoryManager.getAssignableUsers()
+				)),
+				withErrorContext('Fetching timeline events', pullRequestModel.getTimelineEvents()),
+				withErrorContext('Fetching the repository default branch', this._folderRepositoryManager.getPullRequestRepositoryDefaultBranch(pullRequestModel)),
+				withErrorContext('Fetching status checks', pullRequestModel.getStatusChecks()),
+				withErrorContext('Fetching review requests', pullRequestModel.getReviewRequests()),
+				withErrorContext('Fetching repository access and merge methods', this._folderRepositoryManager.getPullRequestRepositoryAccessAndMergeMethods(pullRequestModel)),
+				withErrorContext('Fetching the pull request branch', this._folderRepositoryManager.getBranchNameForPullRequest(pullRequestModel)),
+				withErrorContext('Fetching current user', this._folderRepositoryManager.getCurrentUser(pullRequestModel.githubRepository)),
+				withErrorContext('Checking edit permission', pullRequestModel.canEdit()),
+				withErrorContext('Fetching organization teams', this._folderRepositoryManager.getOrgTeamsCount(pullRequestModel.githubRepository)),
+				withErrorContext('Fetching the merge queue method', this._folderRepositoryManager.mergeQueueMethodForBranch(pullRequestModel.base.ref, pullRequestModel.remote.owner, pullRequestModel.remote.repositoryName)),
+				withErrorContext('Checking whether the branch is up to date', this._folderRepositoryManager.isHeadUpToDateWithBase(pullRequestModel)),
+				withErrorContext('Fetching mergeability', pullRequestModel.getMergeability()),
+				withErrorContext('Fetching the preferred email', this._folderRepositoryManager.getPreferredEmail(pullRequestModel)),
+				withErrorContext('Fetching co-authors', pullRequestModel.getCoAuthors()),
+				withErrorContext('Validating draft mode', pullRequestModel.validateDraftMode()),
+				withErrorContext('Fetching assignable users', this._folderRepositoryManager.getAssignableUsers())
 			]);
 			const clearingPromise = updatingPromise.finally(() => {
 				if (this._updatingPromise === clearingPromise) {
@@ -482,7 +488,7 @@ export class PullRequestOverviewPanel extends IssueOverviewPanel<PullRequestMode
 				this._folderRepositoryManager.checkBranchUpToDate(pullRequest, true);
 			}
 		} catch (e) {
-			vscode.window.showErrorMessage(`Error updating pull request description: ${formatError(e)}`);
+			vscode.window.showErrorMessage(`Error updating pull request: ${formatError(e)}`);
 		}
 	}
 
diff --git a/src/test/github/credentials.test.ts b/src/test/github/credentials.test.ts
index 14718f7e4b..0b2683d1d3 100644
--- a/src/test/github/credentials.test.ts
+++ b/src/test/github/credentials.test.ts
@@ -3,10 +3,15 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { strictEqual, deepStrictEqual } from 'assert';
+import { deepStrictEqual, rejects, strictEqual } from 'assert';
+import { Octokit } from '@octokit/rest';
+import { SinonSandbox, createSandbox } from 'sinon';
 import * as vscode from 'vscode';
 import { AuthProvider } from '../../common/authentication';
-import { findExistingSession } from '../../github/credentials';
+import { CredentialStore, findExistingSession, GitHub } from '../../github/credentials';
+import { LoggingApolloClient, LoggingOctokit, RateLogger } from '../../github/loggingOctokit';
+import { MockExtensionContext } from '../mocks/mockExtensionContext';
+import { MockTelemetry } from '../mocks/mockTelemetry';
 
 const oldestScopes = ['read:user', 'user:email', 'repo'];
 const defaultScopes = [...oldestScopes, 'workflow'];
@@ -29,6 +34,16 @@ function createSession(id: string, accountId: string, scopes: string[]): vscode.
 }
 
 describe('CredentialStore', function () {
+	let sinon: SinonSandbox;
+
+	beforeEach(function () {
+		sinon = createSandbox();
+	});
+
+	afterEach(function () {
+		sinon.restore();
+	});
+
 	describe('findExistingSession', function () {
 		it('keeps broader scope lookup on the preferred account', async function () {
 			const firstAccountAdditional = createSession('first-additional', 'first', additionalScopes);
@@ -99,4 +114,50 @@ describe('CredentialStore', function () {
 			deepStrictEqual(additionalResult?.scopes, additionalScopes);
 		});
 	});
+
+	it('retries a shared current user request after a failure', async function () {
+		const telemetry = new MockTelemetry();
+		const credentialStore = new CredentialStore(telemetry, new MockExtensionContext());
+		const github: GitHub = {
+			octokit: new LoggingOctokit(new Octokit(), new RateLogger(telemetry, false)),
+			graphql: {} as LoggingApolloClient,
+		};
+		sinon.stub(credentialStore, 'getHub').returns(github);
+		const getAuthenticatedUser = sinon.stub(github.octokit, 'call');
+		const error = new Error('Connect Timeout Error');
+		getAuthenticatedUser.onFirstCall().rejects(error);
+		getAuthenticatedUser.onSecondCall().resolves({
+			data: {
+				login: 'octocat',
+				node_id: 'MDQ6VXNlcjE=',
+				html_url: 'https://github.com/octocat',
+				avatar_url: 'https://github.com/images/error/octocat_happy.gif',
+				type: 'User',
+				plan: { name: 'emu_user' },
+			}
+		});
+
+		await rejects(Promise.all([
+			credentialStore.getCurrentUser(AuthProvider.github),
+			credentialStore.getIsEmu(AuthProvider.github),
+		]), candidate => candidate === error);
+		strictEqual(getAuthenticatedUser.callCount, 1);
+
+		const [currentUser, isEmu] = await Promise.all([
+			credentialStore.getCurrentUser(AuthProvider.github),
+			credentialStore.getIsEmu(AuthProvider.github),
+		]);
+
+		deepStrictEqual({
+			requests: getAuthenticatedUser.callCount,
+			login: currentUser.login,
+			isEmu,
+		}, {
+			requests: 2,
+			login: 'octocat',
+			isEmu: true,
+		});
+		strictEqual(await credentialStore.isCurrentUser(AuthProvider.github, 'octocat'), true);
+		strictEqual(getAuthenticatedUser.callCount, 2);
+	});
 });
diff --git a/src/test/github/githubRepository.test.ts b/src/test/github/githubRepository.test.ts
index 946c2f7c54..515a93764a 100644
--- a/src/test/github/githubRepository.test.ts
+++ b/src/test/github/githubRepository.test.ts
@@ -56,6 +56,25 @@ describe('GitHubRepository', function () {
 		});
 	});
 
+	describe('getMetadata', function () {
+		it('retries after a transient failure and caches the successful result', async function () {
+			const url = 'https://github.com/some/repo';
+			const remote = new GitHubRemote('origin', url, new Protocol(url), GitHubServerType.GitHubDotCom);
+			const repo = new GitHubRepository(1, remote, Uri.file('/workspaces/repo'), credentialStore, telemetry);
+			sinon.stub(repo, 'ensure').resolves(repo);
+			const fetchMetadata = sinon.stub(repo as any, 'getMetadataForRepo');
+			const error = new Error('Connect Timeout Error');
+			const metadata = { name: 'repo', owner: { login: 'some' } };
+			fetchMetadata.onFirstCall().rejects(error);
+			fetchMetadata.onSecondCall().resolves(metadata);
+
+			await assert.rejects(repo.getMetadata(), candidate => candidate === error);
+			assert.strictEqual(await repo.getMetadata(), metadata);
+			assert.strictEqual(await repo.getMetadata(), metadata);
+			assert.strictEqual(fetchMetadata.callCount, 2);
+		});
+	});
+
 	describe('resolveRemote', function () {
 		beforeEach(function () {
 			sinon.stub(credentialStore, 'isAuthenticated').returns(true);
diff --git a/src/test/github/pullRequestOverview.test.ts b/src/test/github/pullRequestOverview.test.ts
index d0469014fa..a7afa1d237 100644
--- a/src/test/github/pullRequestOverview.test.ts
+++ b/src/test/github/pullRequestOverview.test.ts
@@ -99,6 +99,27 @@ describe('PullRequestOverview', function () {
 			assert.notStrictEqual(PullRequestOverviewPanel.findPanel('aaa', 'bbb', 1000), undefined);
 		});
 
+		it('identifies the operation that failed while updating', async function () {
+			repo.addGraphQLPullRequest(builder => {
+				builder.pullRequest(response => {
+					response.repository(r => {
+						r.pullRequest(pr => pr.number(1000));
+					});
+				});
+			});
+
+			const prItem = convertRESTPullRequestToRawPullRequest(new PullRequestBuilder().number(1000).build(), repo);
+			const prModel = new PullRequestModel(credentialStore, telemetry, repo, remote, prItem);
+			const identity = { owner: prModel.remote.owner, repo: prModel.remote.repositoryName, number: prModel.number };
+			sinon.stub(pullRequestManager, 'getCurrentUser').rejects(new Error('Connect Timeout Error'));
+			const showErrorMessage = sinon.stub(vscode.window, 'showErrorMessage');
+
+			await PullRequestOverviewPanel.createOrShow(telemetry, EXTENSION_URI, pullRequestManager, identity, prModel);
+
+			assert.strictEqual(showErrorMessage.callCount, 1);
+			assert.strictEqual(showErrorMessage.firstCall.args[0], 'Error updating pull request: Fetching current user failed: Connect Timeout Error');
+		});
+
 		it('reveals an existing panel for the same PR', async function () {
 			const createWebviewPanel = sinon.spy(vscode.window, 'createWebviewPanel');