diff --git a/site/src/api/api.ts b/site/src/api/api.ts
index 1c0a6d77b8..303042f2cc 100644
--- a/site/src/api/api.ts
+++ b/site/src/api/api.ts
@@ -101,9 +101,19 @@ export const logout = async (): Promise<void> => {
   await axios.post("/api/v2/users/logout")
 }
 
-export const getUser = async (): Promise<TypesGen.User> => {
-  const response = await axios.get<TypesGen.User>("/api/v2/users/me")
-  return response.data
+export const getAuthenticatedUser = async (): Promise<
+  TypesGen.User | undefined
+> => {
+  try {
+    const response = await axios.get<TypesGen.User>("/api/v2/users/me")
+    return response.data
+  } catch (error) {
+    if (axios.isAxiosError(error) && error.response?.status === 401) {
+      return undefined
+    }
+
+    throw error
+  }
 }
 
 export const getAuthMethods = async (): Promise<TypesGen.AuthMethods> => {
diff --git a/site/src/components/RequireAuth/RequireAuth.tsx b/site/src/components/RequireAuth/RequireAuth.tsx
index a4716b517f..b82335dab3 100644
--- a/site/src/components/RequireAuth/RequireAuth.tsx
+++ b/site/src/components/RequireAuth/RequireAuth.tsx
@@ -13,9 +13,12 @@ export const RequireAuth: FC = () => {
 
   if (authState.matches("signedOut")) {
     return <Navigate to={navigateTo} state={{ isRedirect: !isHomePage }} />
-  } else if (authState.matches("waitingForTheFirstUser")) {
+  } else if (authState.matches("configuringTheFirstUser")) {
     return <Navigate to="/setup" />
-  } else if (authState.hasTag("loading")) {
+  } else if (
+    authState.matches("loadingInitialAuthData") ||
+    authState.matches("signingOut")
+  ) {
     return <FullScreenLoader />
   } else {
     return <Outlet />
diff --git a/site/src/components/SignInForm/OAuthSignInForm.tsx b/site/src/components/SignInForm/OAuthSignInForm.tsx
index 8978259a6b..ca958ab09e 100644
--- a/site/src/components/SignInForm/OAuthSignInForm.tsx
+++ b/site/src/components/SignInForm/OAuthSignInForm.tsx
@@ -9,7 +9,7 @@ import { FC } from "react"
 import { makeStyles } from "@material-ui/core/styles"
 
 type OAuthSignInFormProps = {
-  isLoading: boolean
+  isSigningIn: boolean
   redirectTo: string
   authMethods?: AuthMethods
 }
@@ -22,7 +22,7 @@ const useStyles = makeStyles((theme) => ({
 }))
 
 export const OAuthSignInForm: FC<OAuthSignInFormProps> = ({
-  isLoading,
+  isSigningIn,
   redirectTo,
   authMethods,
 }) => {
@@ -39,7 +39,7 @@ export const OAuthSignInForm: FC<OAuthSignInFormProps> = ({
         >
           <Button
             startIcon={<GitHubIcon className={styles.buttonIcon} />}
-            disabled={isLoading}
+            disabled={isSigningIn}
             fullWidth
             type="submit"
             variant="outlined"
@@ -68,7 +68,7 @@ export const OAuthSignInForm: FC<OAuthSignInFormProps> = ({
                 <KeyIcon className={styles.buttonIcon} />
               )
             }
-            disabled={isLoading}
+            disabled={isSigningIn}
             fullWidth
             type="submit"
             variant="outlined"
diff --git a/site/src/components/SignInForm/PasswordSignInForm.tsx b/site/src/components/SignInForm/PasswordSignInForm.tsx
index 3ef5c6b491..01c3ca6b06 100644
--- a/site/src/components/SignInForm/PasswordSignInForm.tsx
+++ b/site/src/components/SignInForm/PasswordSignInForm.tsx
@@ -1,26 +1,23 @@
 import { Stack } from "../Stack/Stack"
-import { AlertBanner } from "../AlertBanner/AlertBanner"
 import TextField from "@material-ui/core/TextField"
 import { getFormHelpers, onChangeTrimmed } from "../../util/formUtils"
 import { LoadingButton } from "../LoadingButton/LoadingButton"
-import { Language, LoginErrors } from "./SignInForm"
+import { Language } from "./SignInForm"
 import { FormikContextType, FormikTouched, useFormik } from "formik"
 import * as Yup from "yup"
 import { FC } from "react"
 import { BuiltInAuthFormValues } from "./SignInForm.types"
 
 type PasswordSignInFormProps = {
-  loginErrors: Partial<Record<LoginErrors, Error | unknown>>
   onSubmit: (credentials: { email: string; password: string }) => void
   initialTouched?: FormikTouched<BuiltInAuthFormValues>
-  isLoading: boolean
+  isSigningIn: boolean
 }
 
 export const PasswordSignInForm: FC<PasswordSignInFormProps> = ({
-  loginErrors,
   onSubmit,
   initialTouched,
-  isLoading,
+  isSigningIn,
 }) => {
   const validationSchema = Yup.object({
     email: Yup.string()
@@ -37,33 +34,14 @@ export const PasswordSignInForm: FC<PasswordSignInFormProps> = ({
         password: "",
       },
       validationSchema,
-      // The email field has an autoFocus, but users may log in with a button click.
-      // This is set to `false` in order to keep the autoFocus, validateOnChange
-      // and Formik experience friendly. Validation will kick in onChange (any
-      // field), or after a submission attempt.
-      validateOnBlur: false,
       onSubmit,
       initialTouched,
     })
-  const getFieldHelpers = getFormHelpers<BuiltInAuthFormValues>(
-    form,
-    loginErrors.authError,
-  )
+  const getFieldHelpers = getFormHelpers<BuiltInAuthFormValues>(form)
 
   return (
     <form onSubmit={form.handleSubmit}>
       <Stack>
-        {Object.keys(loginErrors).map(
-          (errorKey: string) =>
-            Boolean(loginErrors[errorKey as LoginErrors]) && (
-              <AlertBanner
-                key={errorKey}
-                severity="error"
-                error={loginErrors[errorKey as LoginErrors]}
-                text={Language.errorMessages[errorKey as LoginErrors]}
-              />
-            ),
-        )}
         <TextField
           {...getFieldHelpers("email")}
           onChange={onChangeTrimmed(form)}
@@ -85,12 +63,12 @@ export const PasswordSignInForm: FC<PasswordSignInFormProps> = ({
         />
         <div>
           <LoadingButton
-            loading={isLoading}
+            loading={isSigningIn}
             fullWidth
             type="submit"
             variant="outlined"
           >
-            {isLoading ? "" : Language.passwordSignIn}
+            {isSigningIn ? "" : Language.passwordSignIn}
           </LoadingButton>
         </div>
       </Stack>
diff --git a/site/src/components/SignInForm/SignInForm.tsx b/site/src/components/SignInForm/SignInForm.tsx
index 2303f860bb..b3c7470254 100644
--- a/site/src/components/SignInForm/SignInForm.tsx
+++ b/site/src/components/SignInForm/SignInForm.tsx
@@ -11,24 +11,11 @@ import Button from "@material-ui/core/Button"
 import EmailIcon from "@material-ui/icons/EmailOutlined"
 import { AlertBanner } from "components/AlertBanner/AlertBanner"
 
-export enum LoginErrors {
-  AUTH_ERROR = "authError",
-  GET_USER_ERROR = "getUserError",
-  CHECK_PERMISSIONS_ERROR = "checkPermissionsError",
-  GET_METHODS_ERROR = "getMethodsError",
-}
-
 export const Language = {
   emailLabel: "Email",
   passwordLabel: "Password",
   emailInvalid: "Please enter a valid email address.",
   emailRequired: "Please enter an email address.",
-  errorMessages: {
-    [LoginErrors.AUTH_ERROR]: "Incorrect email or password.",
-    [LoginErrors.GET_USER_ERROR]: "Failed to fetch user details.",
-    [LoginErrors.CHECK_PERMISSIONS_ERROR]: "Unable to fetch user permissions.",
-    [LoginErrors.GET_METHODS_ERROR]: "Unable to fetch auth methods.",
-  },
   passwordSignIn: "Sign In",
   githubSignIn: "GitHub",
   oidcSignIn: "OpenID Connect",
@@ -49,6 +36,9 @@ const useStyles = makeStyles((theme) => ({
       fontWeight: 600,
     },
   },
+  error: {
+    marginBottom: theme.spacing(4),
+  },
   divider: {
     paddingTop: theme.spacing(3),
     paddingBottom: theme.spacing(3),
@@ -75,9 +65,9 @@ const useStyles = makeStyles((theme) => ({
 }))
 
 export interface SignInFormProps {
-  isLoading: boolean
+  isSigningIn: boolean
   redirectTo: string
-  loginErrors: Partial<Record<LoginErrors, Error | unknown>>
+  error?: unknown
   authMethods?: AuthMethods
   onSubmit: (credentials: { email: string; password: string }) => void
   // initialTouched is only used for testing the error state of the form.
@@ -87,8 +77,8 @@ export interface SignInFormProps {
 export const SignInForm: FC<React.PropsWithChildren<SignInFormProps>> = ({
   authMethods,
   redirectTo,
-  isLoading,
-  loginErrors,
+  isSigningIn,
+  error,
   onSubmit,
   initialTouched,
 }) => {
@@ -96,11 +86,9 @@ export const SignInForm: FC<React.PropsWithChildren<SignInFormProps>> = ({
     authMethods?.github.enabled || authMethods?.oidc.enabled,
   )
   const passwordEnabled = authMethods?.password.enabled ?? true
-
   // Hide password auth by default if any OAuth method is enabled
   const [showPasswordAuth, setShowPasswordAuth] = useState(!oAuthEnabled)
   const styles = useStyles()
-
   const commonTranslation = useTranslation("common")
   const loginPageTranslation = useTranslation("loginPage")
 
@@ -110,12 +98,16 @@ export const SignInForm: FC<React.PropsWithChildren<SignInFormProps>> = ({
         {loginPageTranslation.t("signInTo")}{" "}
         <strong>{commonTranslation.t("coder")}</strong>
       </h1>
+      <Maybe condition={error !== undefined}>
+        <div className={styles.error}>
+          <AlertBanner severity="error" error={error} />
+        </div>
+      </Maybe>
       <Maybe condition={passwordEnabled && showPasswordAuth}>
         <PasswordSignInForm
-          loginErrors={loginErrors}
           onSubmit={onSubmit}
           initialTouched={initialTouched}
-          isLoading={isLoading}
+          isSigningIn={isSigningIn}
         />
       </Maybe>
       <Maybe condition={passwordEnabled && showPasswordAuth && oAuthEnabled}>
@@ -127,7 +119,7 @@ export const SignInForm: FC<React.PropsWithChildren<SignInFormProps>> = ({
       </Maybe>
       <Maybe condition={oAuthEnabled}>
         <OAuthSignInForm
-          isLoading={isLoading}
+          isSigningIn={isSigningIn}
           redirectTo={redirectTo}
           authMethods={authMethods}
         />
diff --git a/site/src/hooks/useMe.ts b/site/src/hooks/useMe.ts
index 00677d66a9..bd0ac6bf59 100644
--- a/site/src/hooks/useMe.ts
+++ b/site/src/hooks/useMe.ts
@@ -1,14 +1,14 @@
 import { User } from "api/typesGenerated"
 import { useAuth } from "components/AuthProvider/AuthProvider"
-import { selectUser } from "xServices/auth/authSelectors"
+import { isAuthenticated } from "xServices/auth/authXService"
 
 export const useMe = (): User => {
   const [authState] = useAuth()
-  const me = selectUser(authState)
+  const { data } = authState.context
 
-  if (!me) {
-    throw new Error("User not found.")
+  if (isAuthenticated(data)) {
+    return data.user
   }
 
-  return me
+  throw new Error("User is not authenticated")
 }
diff --git a/site/src/hooks/useOrganizationId.ts b/site/src/hooks/useOrganizationId.ts
index 05c58f4c3a..9f1c382c0e 100644
--- a/site/src/hooks/useOrganizationId.ts
+++ b/site/src/hooks/useOrganizationId.ts
@@ -1,13 +1,13 @@
 import { useAuth } from "components/AuthProvider/AuthProvider"
-import { selectOrgId } from "../xServices/auth/authSelectors"
+import { isAuthenticated } from "xServices/auth/authXService"
 
 export const useOrganizationId = (): string => {
   const [authState] = useAuth()
-  const organizationId = selectOrgId(authState)
+  const { data } = authState.context
 
-  if (!organizationId) {
-    throw new Error("No organization ID found")
+  if (isAuthenticated(data)) {
+    return data.user.organization_ids[0]
   }
 
-  return organizationId
+  throw new Error("User is not authenticated")
 }
diff --git a/site/src/hooks/usePermissions.ts b/site/src/hooks/usePermissions.ts
index 9b3955c200..75e86c1dfc 100644
--- a/site/src/hooks/usePermissions.ts
+++ b/site/src/hooks/usePermissions.ts
@@ -1,13 +1,13 @@
 import { useAuth } from "components/AuthProvider/AuthProvider"
-import { AuthContext } from "xServices/auth/authXService"
+import { isAuthenticated, Permissions } from "xServices/auth/authXService"
 
-export const usePermissions = (): NonNullable<AuthContext["permissions"]> => {
+export const usePermissions = (): Permissions => {
   const [authState] = useAuth()
-  const { permissions } = authState.context
+  const { data } = authState.context
 
-  if (!permissions) {
-    throw new Error("Permissions are not loaded yet.")
+  if (isAuthenticated(data)) {
+    return data.permissions
   }
 
-  return permissions
+  throw new Error("User is not authenticated.")
 }
diff --git a/site/src/pages/LoginPage/LoginPage.test.tsx b/site/src/pages/LoginPage/LoginPage.test.tsx
index d5f5bcff25..2054e65136 100644
--- a/site/src/pages/LoginPage/LoginPage.test.tsx
+++ b/site/src/pages/LoginPage/LoginPage.test.tsx
@@ -36,13 +36,11 @@ describe("LoginPage", () => {
 
   it("shows an error message if SignIn fails", async () => {
     // Given
+    const apiErrorMessage = "Something wrong happened"
     server.use(
       // Make login fail
       rest.post("/api/v2/users/login", async (req, res, ctx) => {
-        return res(
-          ctx.status(500),
-          ctx.json({ message: Language.errorMessages.authError }),
-        )
+        return res(ctx.status(500), ctx.json({ message: apiErrorMessage }))
       }),
     )
 
@@ -57,30 +55,10 @@ describe("LoginPage", () => {
     const signInButton = await screen.findByText(Language.passwordSignIn)
     fireEvent.click(signInButton)
 
-    // Then
-    const errorMessage = await screen.findByText(
-      Language.errorMessages.authError,
-    )
-    expect(errorMessage).toBeDefined()
-    expect(history.location.pathname).toEqual("/login")
-  })
-
-  it("shows an error if fetching auth methods fails", async () => {
-    // Given
-    const apiErrorMessage = "Unable to fetch methods"
-    server.use(
-      // Make login fail
-      rest.get("/api/v2/users/authmethods", async (req, res, ctx) => {
-        return res(ctx.status(500), ctx.json({ message: apiErrorMessage }))
-      }),
-    )
-
-    // When
-    render(<LoginPage />)
-
     // Then
     const errorMessage = await screen.findByText(apiErrorMessage)
     expect(errorMessage).toBeDefined()
+    expect(history.location.pathname).toEqual("/login")
   })
 
   it("shows github authentication when enabled", async () => {
diff --git a/site/src/pages/LoginPage/LoginPage.tsx b/site/src/pages/LoginPage/LoginPage.tsx
index fd737b5c4c..8574f8e2b6 100644
--- a/site/src/pages/LoginPage/LoginPage.tsx
+++ b/site/src/pages/LoginPage/LoginPage.tsx
@@ -15,7 +15,7 @@ export const LoginPage: FC = () => {
 
   if (authState.matches("signedIn")) {
     return <Navigate to={redirectTo} replace />
-  } else if (authState.matches("waitingForTheFirstUser")) {
+  } else if (authState.matches("configuringTheFirstUser")) {
     return <Navigate to="/setup" />
   } else {
     return (
@@ -27,7 +27,8 @@ export const LoginPage: FC = () => {
         </Helmet>
         <LoginPageView
           context={authState.context}
-          isLoading={authState.hasTag("loading")}
+          isLoading={authState.matches("loadingInitialAuthData")}
+          isSigningIn={authState.matches("signingIn")}
           onSignIn={({ email, password }) => {
             authSend({ type: "SIGN_IN", email, password })
           }}
diff --git a/site/src/pages/LoginPage/LoginPageView.stories.tsx b/site/src/pages/LoginPage/LoginPageView.stories.tsx
index 057e4760ad..23034508db 100644
--- a/site/src/pages/LoginPage/LoginPageView.stories.tsx
+++ b/site/src/pages/LoginPage/LoginPageView.stories.tsx
@@ -1,5 +1,6 @@
 import { action } from "@storybook/addon-actions"
 import { ComponentMeta, Story } from "@storybook/react"
+import { MockAuthMethods } from "testHelpers/entities"
 import { LoginPageView, LoginPageViewProps } from "./LoginPageView"
 
 export default {
@@ -15,18 +16,44 @@ export const Example = Template.bind({})
 Example.args = {
   isLoading: false,
   onSignIn: action("onSignIn"),
-  context: {},
+  context: {
+    data: {
+      authMethods: MockAuthMethods,
+      hasFirstUser: false,
+    },
+  },
 }
 
-const err = new Error(
-  "You are signed out or your session has expired. Please sign in again to continue.",
-)
+const err = new Error("Username or email are wrong.")
 
 export const AuthError = Template.bind({})
 AuthError.args = {
   isLoading: false,
   onSignIn: action("onSignIn"),
   context: {
-    authError: err,
+    error: err,
+    data: {
+      authMethods: MockAuthMethods,
+      hasFirstUser: false,
+    },
+  },
+}
+
+export const LoadingInitialData = Template.bind({})
+LoadingInitialData.args = {
+  isLoading: true,
+  onSignIn: action("onSignIn"),
+  context: {},
+}
+
+export const SigningIn = Template.bind({})
+SigningIn.args = {
+  isSigningIn: true,
+  onSignIn: action("onSignIn"),
+  context: {
+    data: {
+      authMethods: MockAuthMethods,
+      hasFirstUser: false,
+    },
   },
 }
diff --git a/site/src/pages/LoginPage/LoginPageView.tsx b/site/src/pages/LoginPage/LoginPageView.tsx
index d2cf1cfdd1..ceff95d381 100644
--- a/site/src/pages/LoginPage/LoginPageView.tsx
+++ b/site/src/pages/LoginPage/LoginPageView.tsx
@@ -2,34 +2,28 @@ import { makeStyles } from "@material-ui/core/styles"
 import { FullScreenLoader } from "components/Loader/FullScreenLoader"
 import { FC } from "react"
 import { useLocation } from "react-router-dom"
-import { AuthContext } from "xServices/auth/authXService"
-import { LoginErrors, SignInForm } from "components/SignInForm/SignInForm"
+import { AuthContext, UnauthenticatedData } from "xServices/auth/authXService"
+import { SignInForm } from "components/SignInForm/SignInForm"
 import { retrieveRedirect } from "util/redirect"
 import { CoderIcon } from "components/Icons/CoderIcon"
 
-interface LocationState {
-  isRedirect: boolean
-}
-
 export interface LoginPageViewProps {
   context: AuthContext
   isLoading: boolean
+  isSigningIn: boolean
   onSignIn: (credentials: { email: string; password: string }) => void
 }
 
 export const LoginPageView: FC<LoginPageViewProps> = ({
   context,
   isLoading,
+  isSigningIn,
   onSignIn,
 }) => {
   const location = useLocation()
   const redirectTo = retrieveRedirect(location.search)
-  const locationState = location.state
-    ? (location.state as LocationState)
-    : null
-  const isRedirected = locationState ? locationState.isRedirect : false
-  const { authError, getUserError, checkPermissionsError, getMethodsError } =
-    context
+  const { error } = context
+  const data = context.data as UnauthenticatedData
   const styles = useStyles()
 
   return isLoading ? (
@@ -39,15 +33,10 @@ export const LoginPageView: FC<LoginPageViewProps> = ({
       <div className={styles.container}>
         <CoderIcon fill="white" opacity={1} className={styles.icon} />
         <SignInForm
-          authMethods={context.methods}
+          authMethods={data.authMethods}
           redirectTo={redirectTo}
-          isLoading={isLoading}
-          loginErrors={{
-            [LoginErrors.AUTH_ERROR]: authError,
-            [LoginErrors.GET_USER_ERROR]: isRedirected ? getUserError : null,
-            [LoginErrors.CHECK_PERMISSIONS_ERROR]: checkPermissionsError,
-            [LoginErrors.GET_METHODS_ERROR]: getMethodsError,
-          }}
+          isSigningIn={isSigningIn}
+          error={error}
           onSubmit={onSignIn}
         />
         <footer className={styles.footer}>
diff --git a/site/src/pages/UserSettingsPage/AccountPage/AccountPage.tsx b/site/src/pages/UserSettingsPage/AccountPage/AccountPage.tsx
index b377d94d06..820b5f86c5 100644
--- a/site/src/pages/UserSettingsPage/AccountPage/AccountPage.tsx
+++ b/site/src/pages/UserSettingsPage/AccountPage/AccountPage.tsx
@@ -2,6 +2,8 @@ import { FC } from "react"
 import { Section } from "../../../components/SettingsLayout/Section"
 import { AccountForm } from "../../../components/SettingsAccountForm/SettingsAccountForm"
 import { useAuth } from "components/AuthProvider/AuthProvider"
+import { useMe } from "hooks/useMe"
+import { usePermissions } from "hooks/usePermissions"
 
 export const Language = {
   title: "Account",
@@ -9,13 +11,11 @@ export const Language = {
 
 export const AccountPage: FC = () => {
   const [authState, authSend] = useAuth()
-  const { me, permissions, updateProfileError } = authState.context
+  const me = useMe()
+  const permissions = usePermissions()
+  const { updateProfileError } = authState.context
   const canEditUsers = permissions && permissions.updateUsers
 
-  if (!me) {
-    throw new Error("No current user found")
-  }
-
   return (
     <Section title={Language.title} description="Update your account info">
       <AccountForm
diff --git a/site/src/xServices/auth/authSelectors.ts b/site/src/xServices/auth/authSelectors.ts
deleted file mode 100644
index 60848d9489..0000000000
--- a/site/src/xServices/auth/authSelectors.ts
+++ /dev/null
@@ -1,18 +0,0 @@
-import { StateFrom } from "xstate"
-import { AuthContext, authMachine } from "./authXService"
-
-type AuthState = StateFrom<typeof authMachine>
-
-export const selectOrgId = (state: AuthState): string | undefined => {
-  return state.context.me?.organization_ids[0]
-}
-
-export const selectPermissions = (
-  state: AuthState,
-): AuthContext["permissions"] => {
-  return state.context.permissions
-}
-
-export const selectUser = (state: AuthState): AuthContext["me"] => {
-  return state.context.me
-}
diff --git a/site/src/xServices/auth/authXService.ts b/site/src/xServices/auth/authXService.ts
index e1c663fb31..de3d367459 100644
--- a/site/src/xServices/auth/authXService.ts
+++ b/site/src/xServices/auth/authXService.ts
@@ -78,24 +78,102 @@ export const permissionsToCheck = {
 
 export type Permissions = Record<keyof typeof permissionsToCheck, boolean>
 
+export type AuthenticatedData = {
+  user: TypesGen.User
+  permissions: Permissions
+}
+export type UnauthenticatedData = {
+  hasFirstUser: boolean
+  authMethods: TypesGen.AuthMethods
+}
+export type AuthData = AuthenticatedData | UnauthenticatedData
+
+export const isAuthenticated = (data?: AuthData): data is AuthenticatedData =>
+  data !== undefined && "user" in data
+
+const loadInitialAuthData = async (): Promise<AuthData> => {
+  const authenticatedUser = await API.getAuthenticatedUser()
+
+  if (authenticatedUser) {
+    const permissions = (await API.checkAuthorization({
+      checks: permissionsToCheck,
+    })) as Permissions
+    return {
+      user: authenticatedUser,
+      permissions,
+    }
+  }
+
+  const [hasFirstUser, authMethods] = await Promise.all([
+    API.hasFirstUser(),
+    API.getAuthMethods(),
+  ])
+
+  return {
+    hasFirstUser,
+    authMethods,
+  }
+}
+
+const signIn = async (
+  email: string,
+  password: string,
+): Promise<AuthenticatedData> => {
+  await API.login(email, password)
+  const [user, permissions] = await Promise.all([
+    API.getAuthenticatedUser(),
+    API.checkAuthorization({
+      checks: permissionsToCheck,
+    }),
+  ])
+
+  return {
+    user: user as TypesGen.User,
+    permissions: permissions as Permissions,
+  }
+}
+
+const signOut = async () => {
+  // Get app hostname so we can see if we need to log out of app URLs.
+  // We need to load this before we log out of the API as this is an
+  // authenticated endpoint.
+  const appHost = await API.getApplicationsHost()
+  const [authMethods] = await Promise.all([
+    API.getAuthMethods(), // Antecipate and load the auth methods
+    API.logout(),
+  ])
+
+  // Logout the app URLs
+  if (appHost.host !== "") {
+    const { protocol, host } = window.location
+    const redirect_uri = encodeURIComponent(`${protocol}//${host}/login`)
+    // The path doesn't matter but we use /api because the dev server
+    // proxies /api to the backend.
+    const uri = `${protocol}//${appHost.host.replace(
+      "*",
+      "coder-logout",
+    )}/api/logout?redirect_uri=${redirect_uri}`
+
+    return {
+      redirectUrl: uri,
+    }
+  }
+
+  return {
+    hasFirstUser: true,
+    authMethods,
+  } as UnauthenticatedData
+}
 export interface AuthContext {
-  getUserError?: Error | unknown
-  // The getMethods API call does not return an ApiError.
-  // It can only error out in a generic fashion.
-  getMethodsError?: Error | unknown
-  authError?: Error | unknown
+  error?: Error | unknown
   updateProfileError?: Error | unknown
-  me?: TypesGen.User
-  methods?: TypesGen.AuthMethods
-  permissions?: Permissions
-  checkPermissionsError?: Error | unknown
+  data?: AuthData
 }
 
 export type AuthEvent =
   | { type: "SIGN_OUT" }
   | { type: "SIGN_IN"; email: string; password: string }
   | { type: "UPDATE_PROFILE"; data: TypesGen.UpdateUserProfileRequest }
-  | { type: "GET_AUTH_METHODS" }
 
 export const authMachine =
   /** @xstate-layout N4IgpgJg5mDOIC5QEMCuAXAFgZXc9YAdLAJZQB2kA8hgMTYCSA4gHID6DLioADgPal0JPuW4gAHogBsATimEAzDIAcAFgUB2VTJ26ANCACeiAIwaADKsLKFtu-dsBfRwbRZc+IqQolyUBuS0ECJEvgBufADWXmTkAWL8gsKiSBKICubKhKpSyhoArAbGCGaqGoRSlVXVlfnOrhg4eATEsb7+gWAATl18XYQ8ADb4AGZ9ALatFPGpiSRCImKSCLLySmqa2ro6RaYFAEzWDscK9SBuTZ6EMOhCfgCqsN1BIYThUUQ3ALJgCQLzySW6Uy2VyBV2JXyUhMFRqcLqLnOjQ8LRudygj2e3V6-SGowm1zA6B+fySi1Sy32MnyhHyyksYK2ug0EJM1IURxO9jOFxRnyJ6IACt1xiRYKQRLAXpQ3uQItFCABjTBgRWRYVdUXi5LwWb-BYpUDLZRScygvKFIyIGQaQ4FHnI5r827tDVaiXkKXYvoDYboMaapUqtVusUe3W8fWAimIE1mnIW1l0rImOE1BENdxOwkuvw-LB8CBS4Iy94K75EzCFiMgOYGoEIZRUwgyVT5BQmfaW4omGxZGxcuwOrNXNHtfNVou0b24v0ByYVgtF0kA8lG2PN1vtzvd0zszmD06I3nZ7yUCABAa9EYkQahCB32j3QUAEQAggAVACibEFACUqAAMQYAAZL8V3rGMSjbGQKihLsISkOlaWHS4WjPSBLx4a9byIVAeAgfBXRwx8S1COUPkIE8rgwi9yCvPgbzvQh8MIoUSLABB3kVIiRAAbXMABdCDo3XaD8lgpCpAQq0EA0eTUL5KZzywjiWIIoi-EFDjpx6H08X9AlqPQ2JMPo7DGNw9S2OIyy7y4iieINAThL1MlDTScTJPg3dGxkfZFNPUy6OIWBMDeB8wFoJgvw-NhsGwAAJNgAGkvwATREtdPM7VQrE0XyTF7coB0PQKaOCy9xXCsc-ASxKUrAQxpXI+UiGMmIKDM0KaoFdp6sawwHIiJzkhcrKPOWIqkOscFZNTfYOXtY9HQqrqQuqnN0QGprdJxX18UDDrlO6zbaqgHahu43jyHGtzV0m0x9jyxQ5p7ExzBhUrB3Kkz1qqsLCEGPhkAgSAIsfP8vxilgvz-T8f3q1KMomht9g+8ocnMGQCtZDRZAPLkMyREc-pU+jNuB0HwcVEQb01S6-zAGBKC6TxaAAYTfFgOa-EC2ChmG4YR+KkuRzL7sgsT0bMQhzCUcxpMK20vsPBRieO2iAfCqmwYgJU6ZIBmksGpmWe6dmOaoFhgL-L4Behr9Yfh79ReStKJcjdy0Yx0Fsdx+b23MX7OvJnqgZBvXCC6ZmwFZzSLpN3ayNlNqqNWsnTsB3XwZj822e2pOrscm67q9h6GzMBQrDy7cZJ7DR1ZQlbSdDrOdcj3PY-jwuGt2mcDsMo6M7bjbs87-W87ji3e8G4a+FG-ihNRqCq5rtsO3r0wpG0ZvMzQ0eqtVVAunmQwIai5931d7Avw5+4-wYD9PdrKNsqmsoOQyBM3sQZ6pBDidDax9T7oHPqxBO2AQFnxaqnSimtKoU2gWA6ykDkHFxGqXZektRI5U-ooBkiZZIKFyHvEmB8gFH0VCfM+qDtroL2vpOcRkR6UKQdQ0B4CNL0I4Wfeei9brYPLlLPBjcCE-18m2KwGtWFa0CIwVgbAqD3A-CvaWWgYSEN-iUDIZpUxpiqBoQBZ52g0HQLAssoczFqM8k2WCW5N6+X2OYeShMTgyNbspUxdAB4GXnMpaxOD35-w0XLCRrJ0ZWH0QYqQRiW4UOVKqSI7RAJG1gOgTEXQLEUQVMdRJaoUlpIyU8Lo-CsGuWEbg5YmhCD7B3nU-YA5lA6HVhCZxYjoRshyDvJQ+NVCAIAO7IABH4QCfQPwqlSV0dJmT6DMHYJwGx1Sm7Yx0I3SwziTBOLqWaLQdIpC2HyKoLZ5gESInIIWOAYgEHrUCZU4JJRsY0iIT2akZoPEUJMX4GY9zHoIDbIcdGLzt4qFhDEpCgDzqZKWYgVQ+xWSyCyOC2okK+paRFGGHUML-mmnNNorZbIwUxI+Upc6E5qzYq2LUuQwKSitnymrI8+8lJyIYkxe8zELlfj0l0bFVcaRlCklvRspzjGILZVZEgkVCAzj5Y3AV+MfIQjyEy8hLLxUWXZRfOVRVsiKqVhCRuhxtgaBVY3A5MgxX-XMmpCB7E7K-CCX8oq+RnnaIKJa+J6rrUSrvHykwHZZq+X2bScwYbzUSTUBCr1QUfWbSlX6p1lctlusKp2Q4JLY1hzOmixOfdii-MrlIiotKPpyCtdm8e1N9YJsdYWqCmyshyH9vigoVhkWxIre3CO1aDbkHpuMRm3cZ51tft7BtqhzAZoVga+aGhexuOOJmtalaO69qnj3fqRc+UKHpIQIq87S25GXZnMea69Y7qhPuswxVCptnKNsOQ7Z2xUhPYfCmYV-WBtLVOjkJqzUkP6TGldp10EX0IFynlcroRywsI4iEu6ArAdPVQmhKDa0yqg0m1e+NNFwZ3BCNswdkPvuIGB2tcqakuPlgR4h2MWzMgAxartwDeEoLtf1dB-rXVBoQyQljqHOFfq+q2v9jHG7mqUKqm55N-UuN4-NT6DGdD5C0Gp-Ypq31eL8HcsdFcG0yA+rB5QtHijOKOYoNWgD8nJNGUU6F2GxK9LlvSTIcLGn5C2ZUNpLj5CxIUFSD6XmuyDOGeiMZXQJlgCmTMkp2LGm1OUFCHQORGkyEVqoZQbTNly2-poaERy6kh0pYl5LrZpLNIy1l2Sm5dAkPRs4wz+NlDOGcEAA */
@@ -108,46 +186,47 @@ export const authMachine =
         context: {} as AuthContext,
         events: {} as AuthEvent,
         services: {} as {
-          getMe: {
-            data: TypesGen.User
-          }
-          getMethods: {
-            data: TypesGen.AuthMethods
+          loadInitialAuthData: {
+            data: Awaited<ReturnType<typeof loadInitialAuthData>>
           }
           signIn: {
-            data: TypesGen.LoginWithPasswordResponse
+            data: Awaited<ReturnType<typeof signIn>>
           }
           updateProfile: {
             data: TypesGen.User
           }
-          updateSecurity: {
-            data: undefined
-          }
-          checkPermissions: {
-            data: TypesGen.AuthorizationResponse
-          }
-          hasFirstUser: {
-            data: boolean
-          }
           signOut: {
-            data:
-              | {
-                  redirectUrl: string
-                }
-              | undefined
+            data: Awaited<ReturnType<typeof signOut>>
           }
         },
       },
-      context: {
-        me: undefined,
-        getUserError: undefined,
-        authError: undefined,
-        updateProfileError: undefined,
-        methods: undefined,
-        getMethodsError: undefined,
-      },
-      initial: "gettingUser",
+      initial: "loadingInitialAuthData",
       states: {
+        loadingInitialAuthData: {
+          invoke: {
+            src: "loadInitialAuthData",
+            onDone: [
+              {
+                target: "signedIn",
+                actions: ["assignData", "clearError"],
+                cond: "isAuthenticated",
+              },
+              {
+                target: "configuringTheFirstUser",
+                actions: ["assignData", "clearError"],
+                cond: "needSetup",
+              },
+              {
+                target: "signedOut",
+                actions: ["assignData", "clearError"],
+              },
+            ],
+            onError: {
+              target: "signedOut",
+              actions: ["assignError"],
+            },
+          },
+        },
         signedOut: {
           on: {
             SIGN_IN: {
@@ -156,85 +235,31 @@ export const authMachine =
           },
         },
         signingIn: {
-          entry: "clearAuthError",
+          entry: "clearError",
           invoke: {
             src: "signIn",
             id: "signIn",
             onDone: [
               {
-                target: "gettingUser",
-              },
-            ],
-            onError: [
-              {
-                actions: "assignAuthError",
-                target: "signedOut",
-              },
-            ],
-          },
-          tags: "loading",
-        },
-        gettingUser: {
-          entry: "clearGetUserError",
-          invoke: {
-            src: "getMe",
-            id: "getMe",
-            onDone: [
-              {
-                actions: "assignMe",
-                target: "gettingPermissions",
-              },
-            ],
-            onError: [
-              {
-                actions: "assignGetUserError",
-                target: "checkingFirstUser",
-              },
-            ],
-          },
-          tags: "loading",
-        },
-        gettingPermissions: {
-          entry: "clearGetPermissionsError",
-          invoke: {
-            src: "checkPermissions",
-            id: "checkPermissions",
-            onDone: [
-              {
-                actions: "assignPermissions",
                 target: "signedIn",
+                actions: "assignData",
               },
             ],
             onError: [
               {
-                actions: "assignGetPermissionsError",
+                actions: "assignError",
                 target: "signedOut",
               },
             ],
           },
-          tags: "loading",
-        },
-        gettingMethods: {
-          invoke: {
-            src: "getMethods",
-            id: "getMethods",
-            onDone: [
-              {
-                actions: ["assignMethods", "clearGetMethodsError"],
-                target: "signedOut",
-              },
-            ],
-            onError: [
-              {
-                actions: "assignGetMethodsError",
-                target: "signedOut",
-              },
-            ],
-          },
-          tags: "loading",
         },
         signedIn: {
           type: "parallel",
+          on: {
+            SIGN_OUT: {
+              target: "signingOut",
+            },
+          },
           states: {
             profile: {
               initial: "idle",
@@ -257,7 +282,7 @@ export const authMachine =
                     src: "updateProfile",
                     onDone: [
                       {
-                        actions: ["assignMe", "notifySuccessProfileUpdate"],
+                        actions: ["updateUser", "notifySuccessProfileUpdate"],
                         target: "#authState.signedIn.profile.idle.noError",
                       },
                     ],
@@ -271,41 +296,6 @@ export const authMachine =
                 },
               },
             },
-            methods: {
-              initial: "idle",
-              states: {
-                idle: {
-                  on: {
-                    GET_AUTH_METHODS: {
-                      target: "gettingMethods",
-                    },
-                  },
-                },
-                gettingMethods: {
-                  entry: "clearGetMethodsError",
-                  invoke: {
-                    src: "getMethods",
-                    onDone: [
-                      {
-                        actions: ["assignMethods", "clearGetMethodsError"],
-                        target: "idle",
-                      },
-                    ],
-                    onError: [
-                      {
-                        actions: "assignGetMethodsError",
-                        target: "idle",
-                      },
-                    ],
-                  },
-                },
-              },
-            },
-          },
-          on: {
-            SIGN_OUT: {
-              target: "signingOut",
-            },
           },
         },
         signingOut: {
@@ -314,40 +304,23 @@ export const authMachine =
             id: "signOut",
             onDone: [
               {
-                actions: ["unassignMe", "clearAuthError", "redirect"],
+                actions: ["clearData", "clearError", "redirect"],
                 cond: "hasRedirectUrl",
               },
               {
-                actions: ["unassignMe", "clearAuthError"],
-                target: "gettingMethods",
+                actions: ["clearData", "clearError"],
+                target: "signedOut",
               },
             ],
             onError: [
               {
-                actions: "assignAuthError",
+                actions: "assignError",
                 target: "signedIn",
               },
             ],
           },
-          tags: "loading",
         },
-        checkingFirstUser: {
-          invoke: {
-            src: "hasFirstUser",
-            onDone: [
-              {
-                cond: "isTrue",
-                target: "gettingMethods",
-              },
-              {
-                target: "waitingForTheFirstUser",
-              },
-            ],
-            onError: "signedOut",
-          },
-          tags: "loading",
-        },
-        waitingForTheFirstUser: {
+        configuringTheFirstUser: {
           on: {
             SIGN_IN: {
               target: "signingIn",
@@ -358,82 +331,46 @@ export const authMachine =
     },
     {
       services: {
-        signIn: async (_, event) => {
-          return await API.login(event.email, event.password)
-        },
-        signOut: async () => {
-          // Get app hostname so we can see if we need to log out of app URLs.
-          // We need to load this before we log out of the API as this is an
-          // authenticated endpoint.
-          const appHost = await API.getApplicationsHost()
-          await API.logout()
-
-          if (appHost.host !== "") {
-            const { protocol, host } = window.location
-            const redirect_uri = encodeURIComponent(
-              `${protocol}//${host}/login`,
-            )
-            // The path doesn't matter but we use /api because the dev server
-            // proxies /api to the backend.
-            const uri = `${protocol}//${appHost.host.replace(
-              "*",
-              "coder-logout",
-            )}/api/logout?redirect_uri=${redirect_uri}`
-
-            return {
-              redirectUrl: uri,
-            }
-          }
-        },
-        getMe: API.getUser,
-        getMethods: API.getAuthMethods,
-        updateProfile: async (context, event) => {
-          if (!context.me) {
-            throw new Error("No current user found")
+        loadInitialAuthData,
+        signIn: (_, { email, password }) => signIn(email, password),
+        signOut,
+        updateProfile: async ({ data }, event) => {
+          if (!data) {
+            throw new Error("Authenticated data is not loaded yet")
           }
 
-          return API.updateProfile(context.me.id, event.data)
+          if (isAuthenticated(data)) {
+            return API.updateProfile(data.user.id, event.data)
+          }
+
+          throw new Error("User not authenticated")
         },
-        checkPermissions: async () => {
-          return API.checkAuthorization({
-            checks: permissionsToCheck,
-          })
-        },
-        // First user
-        hasFirstUser: () => API.hasFirstUser(),
       },
       actions: {
-        assignMe: assign({
-          me: (_, event) => event.data,
+        assignData: assign({
+          data: (_, { data }) => data,
         }),
-        unassignMe: assign((context: AuthContext) => ({
-          ...context,
-          me: undefined,
-        })),
-        assignMethods: assign({
-          methods: (_, event) => event.data,
+        clearData: assign({
+          data: (_) => undefined,
         }),
-        assignGetMethodsError: assign({
-          getMethodsError: (_, event) => event.data,
+        assignError: assign({
+          error: (_, event) => event.data,
         }),
-        clearGetMethodsError: assign((context: AuthContext) => ({
-          ...context,
-          getMethodsError: undefined,
-        })),
-        assignGetUserError: assign({
-          getUserError: (_, event) => event.data,
+        clearError: assign({
+          error: (_) => undefined,
         }),
-        clearGetUserError: assign((context: AuthContext) => ({
-          ...context,
-          getUserError: undefined,
-        })),
-        assignAuthError: assign({
-          authError: (_, event) => event.data,
+        updateUser: assign({
+          data: (context, event) => {
+            if (!context.data) {
+              throw new Error("No authentication data loaded")
+            }
+
+            return {
+              ...context.data,
+              user: event.data,
+            }
+          },
         }),
-        clearAuthError: assign((context: AuthContext) => ({
-          ...context,
-          authError: undefined,
-        })),
         assignUpdateProfileError: assign({
           updateProfileError: (_, event) => event.data,
         }),
@@ -443,20 +380,8 @@ export const authMachine =
         clearUpdateProfileError: assign({
           updateProfileError: (_) => undefined,
         }),
-        assignPermissions: assign({
-          // Setting event.data as Permissions to be more stricted. So we know
-          // what permissions we asked for.
-          permissions: (_, event) => event.data as Permissions,
-        }),
-        assignGetPermissionsError: assign({
-          checkPermissionsError: (_, event) => event.data,
-        }),
-        clearGetPermissionsError: assign({
-          checkPermissionsError: (_) => undefined,
-        }),
         redirect: (_, { data }) => {
-          // eslint-disable-next-line @typescript-eslint/no-unnecessary-condition -- data can be undefined
-          if (!data) {
+          if (!("redirectUrl" in data)) {
             throw new Error(
               "Redirect only should be called with data.redirectUrl",
             )
@@ -466,7 +391,9 @@ export const authMachine =
         },
       },
       guards: {
-        isTrue: (_, event) => event.data,
+        isAuthenticated: (_, { data }) => isAuthenticated(data),
+        needSetup: (_, { data }) =>
+          !isAuthenticated(data) && !data.hasFirstUser,
         hasRedirectUrl: (_, { data }) => Boolean(data),
       },
     },