diff --git a/src/localization/en.json b/src/localization/en.json
index 268ab2be..4f4c7394 100644
--- a/src/localization/en.json
+++ b/src/localization/en.json
@@ -2612,7 +2612,9 @@
             "account_removed": "Account removed.",
             "auto_login_success": "Automatically logged in.",
             "auto_login_failed": "Failed to login automatically.",
-            "offline": "You're offline."
+            "offline": "You're offline.",
+            "login_network_issue_hint_title": "Having trouble signing in?",
+            "login_network_issue_hint_description": "Several recent sign-in attempts failed. If your credentials are correct, this may be caused by a network, proxy, VPN, or regional access issue."
         },
         "vrcx_updater": {
             "failed": "Failed to check for update, {message}",
diff --git a/src/shared/constants/link.js b/src/shared/constants/link.js
index 0bf88c93..da2c2723 100644
--- a/src/shared/constants/link.js
+++ b/src/shared/constants/link.js
@@ -1,5 +1,7 @@
 const links = {
     wiki: 'https://github.com/vrcx-team/VRCX/wiki',
+    troubleshootingAuthUserConnectionIssues:
+        'https://github.com/vrcx-team/VRCX/wiki/Troubleshooting#401-authuser--connection-issues',
     github: 'https://github.com/vrcx-team/VRCX',
     discord: 'https://vrcx.app/discord'
 };
diff --git a/src/stores/__tests__/authLoginFailureToast.test.js b/src/stores/__tests__/authLoginFailureToast.test.js
new file mode 100644
index 00000000..7efe0599
--- /dev/null
+++ b/src/stores/__tests__/authLoginFailureToast.test.js
@@ -0,0 +1,467 @@
+import { afterEach, beforeEach, describe, expect, test, vi } from 'vitest';
+import { createPinia, setActivePinia } from 'pinia';
+import { nextTick, reactive } from 'vue';
+
+import { links } from '../../shared/constants/link';
+
+const mockWatchState = reactive({
+    isLoggedIn: false,
+    isFriendsLoaded: false,
+    isFavoritesLoaded: false
+});
+
+const mocks = vi.hoisted(() => ({
+    toast: {
+        dismiss: vi.fn(),
+        error: vi.fn(),
+        info: vi.fn(),
+        success: vi.fn(),
+        warning: vi.fn()
+    },
+    request: vi.fn(),
+    authRequest: {
+        getConfig: vi.fn()
+    },
+    runLoginSuccessFlow: vi.fn(),
+    runLogoutFlow: vi.fn(),
+    runHandleAutoLoginFlow: vi.fn(),
+    getCurrentUser: vi.fn(),
+    initWebsocket: vi.fn(),
+    advancedSettingsStore: {
+        enablePrimaryPassword: false,
+        setEnablePrimaryPassword: vi.fn(),
+        setEnablePrimaryPasswordConfigRepository: vi.fn(),
+        runAvatarAutoCleanup: vi.fn()
+    },
+    generalSettingsStore: {
+        autoLoginDelayEnabled: false,
+        autoLoginDelaySeconds: 0
+    },
+    modalStore: {
+        prompt: vi.fn(),
+        otpPrompt: vi.fn(),
+        confirm: vi.fn(),
+        alert: vi.fn()
+    },
+    updateLoopStore: {
+        setNextCurrentUserRefresh: vi.fn(),
+        setIpcTimeout: vi.fn()
+    },
+    userStore: {
+        currentUser: {
+            id: 'usr_me',
+            displayName: 'Tester'
+        },
+        setUserDialogVisible: vi.fn()
+    },
+    vrcxStore: {
+        waitForDatabaseInit: vi.fn().mockResolvedValue(true)
+    },
+    configRepository: {
+        getString: vi.fn(),
+        getBool: vi.fn(),
+        setString: vi.fn(),
+        setBool: vi.fn(),
+        remove: vi.fn()
+    },
+    webApiService: {
+        clearCookies: vi.fn().mockResolvedValue(undefined),
+        getCookies: vi.fn().mockResolvedValue([]),
+        setCookies: vi.fn().mockResolvedValue(undefined)
+    },
+    security: {
+        encrypt: vi.fn(),
+        decrypt: vi.fn()
+    },
+    notyShow: vi.fn(),
+    appDebug: {
+        endpointDomain: '',
+        websocketDomain: '',
+        endpointDomainVrchat: 'https://vrchat.com',
+        websocketDomainVrchat: 'wss://pubsub.vrchat.com',
+        errorNoty: null
+    }
+}));
+
+vi.mock('vue-sonner', () => ({
+    toast: mocks.toast
+}));
+
+vi.mock('noty', () => ({
+    default: vi.fn().mockImplementation(function NotyMock() {
+        this.show = (...args) => mocks.notyShow(...args);
+    })
+}));
+
+vi.mock('vue-i18n', () => ({
+    useI18n: () => ({
+        t: (key) => key
+    })
+}));
+
+vi.mock('../../services/request', () => ({
+    request: (...args) => mocks.request(...args)
+}));
+
+vi.mock('../../api', () => ({
+    authRequest: mocks.authRequest
+}));
+
+vi.mock('../../coordinators/authCoordinator', () => ({
+    runLoginSuccessFlow: (...args) => mocks.runLoginSuccessFlow(...args),
+    runLogoutFlow: (...args) => mocks.runLogoutFlow(...args)
+}));
+
+vi.mock('../../coordinators/authAutoLoginCoordinator', () => ({
+    runHandleAutoLoginFlow: (...args) => mocks.runHandleAutoLoginFlow(...args)
+}));
+
+vi.mock('../../coordinators/userCoordinator', () => ({
+    getCurrentUser: (...args) => mocks.getCurrentUser(...args)
+}));
+
+vi.mock('../../services/appConfig', () => ({
+    AppDebug: mocks.appDebug,
+    isApiLogSuppressed: vi.fn(() => true),
+    logWebRequest: vi.fn()
+}));
+
+vi.mock('../../shared/utils', () => ({
+    escapeTag: (value) => value
+}));
+
+vi.mock('../../services/database', () => ({
+    database: new Proxy(
+        {},
+        {
+            get: (_target, prop) => {
+                if (prop === '__esModule') return false;
+                return vi.fn().mockResolvedValue(undefined);
+            }
+        }
+    )
+}));
+
+vi.mock('../../services/security', () => ({
+    default: mocks.security
+}));
+
+vi.mock('../../services/webapi', () => ({
+    default: mocks.webApiService
+}));
+
+vi.mock('../../services/watchState', () => ({
+    watchState: mockWatchState
+}));
+
+vi.mock('../../services/config', () => ({
+    default: mocks.configRepository
+}));
+
+vi.mock('../../services/websocket', () => ({
+    initWebsocket: (...args) => mocks.initWebsocket(...args),
+    closeWebSocket: vi.fn()
+}));
+
+vi.mock('../../stores/settings/advanced', () => ({
+    useAdvancedSettingsStore: () => mocks.advancedSettingsStore
+}));
+
+vi.mock('../../stores/settings/general', () => ({
+    useGeneralSettingsStore: () => mocks.generalSettingsStore
+}));
+
+vi.mock('../../stores/modal', () => ({
+    useModalStore: () => mocks.modalStore
+}));
+
+vi.mock('../../stores/updateLoop', () => ({
+    useUpdateLoopStore: () => mocks.updateLoopStore
+}));
+
+vi.mock('../../stores/user', () => ({
+    useUserStore: () => mocks.userStore
+}));
+
+vi.mock('../../stores/vrcx', () => ({
+    useVrcxStore: () => mocks.vrcxStore
+}));
+
+vi.mock('worker-timers', () => ({
+    setTimeout: vi.fn()
+}));
+
+function flushPromises() {
+    return Promise.resolve().then(() => Promise.resolve());
+}
+
+function makeAuthError(message, status = 401) {
+    const err = new Error(message);
+    err.status = status;
+    err.endpoint = 'auth/user';
+    return err;
+}
+
+async function createAuthStore() {
+    setActivePinia(createPinia());
+    const { useAuthStore } = await import('../auth');
+    const store = useAuthStore();
+    await flushPromises();
+    return store;
+}
+
+async function failManualLogin(store, error) {
+    mocks.authRequest.getConfig.mockResolvedValueOnce({ json: {} });
+    mocks.request.mockRejectedValueOnce(error);
+    await store.login().catch(() => {});
+    await flushPromises();
+}
+
+async function failSavedAccountLogin(store, error, overrides = {}) {
+    const savedUser = {
+        user: { id: 'usr_saved', displayName: 'Saved User' },
+        loginParams: {
+            username: 'saved@example.com',
+            password: 'password',
+            endpoint: '',
+            websocket: '',
+            ...overrides
+        }
+    };
+    mocks.authRequest.getConfig.mockResolvedValueOnce({ json: {} });
+    mocks.request.mockRejectedValueOnce(error);
+    await store.relogin(savedUser).catch(() => {});
+    await flushPromises();
+}
+
+async function succeedManualLogin(store) {
+    mocks.authRequest.getConfig.mockResolvedValueOnce({ json: {} });
+    mocks.request.mockResolvedValueOnce({
+        id: 'usr_me',
+        displayName: 'Tester'
+    });
+    await store.login().catch(() => {});
+    mockWatchState.isLoggedIn = true;
+    await nextTick();
+    await flushPromises();
+}
+
+describe('useAuthStore login failure toast policy', () => {
+    beforeEach(() => {
+        vi.useFakeTimers();
+        vi.setSystemTime(new Date('2026-03-23T00:00:00.000Z'));
+        vi.clearAllMocks();
+
+        mocks.configRepository.getString.mockImplementation(
+            (_key, defaultValue = '') => Promise.resolve(defaultValue)
+        );
+        mocks.configRepository.getBool.mockImplementation(
+            (_key, defaultValue = false) => Promise.resolve(defaultValue)
+        );
+        mocks.configRepository.setString.mockResolvedValue(undefined);
+        mocks.configRepository.setBool.mockResolvedValue(undefined);
+        mocks.configRepository.remove.mockResolvedValue(undefined);
+        mocks.authRequest.getConfig.mockResolvedValue({ json: {} });
+        mocks.request.mockReset();
+        mocks.request.mockResolvedValue({});
+        mocks.toast.warning.mockReturnValue('login-network-issue-toast');
+        mocks.runLoginSuccessFlow.mockReset();
+        mocks.runLogoutFlow.mockReset();
+        mocks.runHandleAutoLoginFlow.mockReset();
+        mocks.getCurrentUser.mockReset();
+        mocks.initWebsocket.mockReset();
+        mocks.notyShow.mockReset();
+        mocks.toast.warning.mockReset();
+        mocks.toast.warning.mockReturnValue('login-network-issue-toast');
+        mocks.toast.success.mockReset();
+        mocks.toast.error.mockReset();
+        mocks.toast.info.mockReset();
+        mocks.toast.dismiss.mockReset();
+        mocks.advancedSettingsStore.enablePrimaryPassword = false;
+        mockWatchState.isLoggedIn = false;
+        mockWatchState.isFriendsLoaded = false;
+        mockWatchState.isFavoritesLoaded = false;
+        mocks.userStore.currentUser = {
+            id: 'usr_me',
+            displayName: 'Tester'
+        };
+        mocks.vrcxStore.waitForDatabaseInit.mockResolvedValue(true);
+
+        globalThis.AppApi = {
+            CheckGameRunning: vi.fn(),
+            FlashWindow: vi.fn(),
+            IPCAnnounceStart: vi.fn(),
+            OpenLink: vi.fn()
+        };
+    });
+
+    afterEach(() => {
+        vi.useRealTimers();
+    });
+
+    test('shows a single warning toast on the third manual login failure inside 90 seconds', async () => {
+        const store = await createAuthStore();
+        store.loginForm.username = 'tester@example.com';
+        store.loginForm.password = 'password';
+
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+        vi.setSystemTime(new Date('2026-03-23T00:00:30.000Z'));
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+
+        expect(mocks.toast.warning).not.toHaveBeenCalled();
+
+        vi.setSystemTime(new Date('2026-03-23T00:01:00.000Z'));
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+
+        expect(mocks.toast.warning).toHaveBeenCalledTimes(1);
+        expect(mocks.toast.warning).toHaveBeenCalledWith(
+            'message.auth.login_network_issue_hint_title',
+            expect.objectContaining({
+                description: 'message.auth.login_network_issue_hint_description',
+                duration: Infinity,
+                action: expect.objectContaining({
+                    label: 'common.actions.open',
+                    onClick: expect.any(Function)
+                })
+            })
+        );
+        mocks.toast.warning.mock.calls[0][1].action.onClick();
+        expect(globalThis.AppApi.OpenLink).toHaveBeenCalledWith(
+            links.troubleshootingAuthUserConnectionIssues
+        );
+    });
+
+    test('does not count explicit password errors toward the warning threshold', async () => {
+        const store = await createAuthStore();
+        store.loginForm.username = 'tester@example.com';
+        store.loginForm.password = 'password';
+
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+        vi.setSystemTime(new Date('2026-03-23T00:00:20.000Z'));
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+        vi.setSystemTime(new Date('2026-03-23T00:00:40.000Z'));
+        await failManualLogin(
+            store,
+            makeAuthError('Invalid Username/Email or Password', 401)
+        );
+
+        expect(mocks.toast.warning).not.toHaveBeenCalled();
+    });
+
+    test('does not trigger the warning during auto-login retries', async () => {
+        const store = await createAuthStore();
+        store.setAttemptingAutoLogin(true);
+
+        const savedUser = {
+            user: { id: 'usr_me', displayName: 'Tester' },
+            loginParams: {
+                username: 'tester@example.com',
+                password: 'password',
+                endpoint: '',
+                websocket: ''
+            }
+        };
+
+        mocks.authRequest.getConfig.mockResolvedValue({ json: {} });
+        mocks.request.mockRejectedValueOnce(makeAuthError('Unauthorized', 401));
+        await store.relogin(savedUser).catch(() => {});
+        await flushPromises();
+
+        expect(mocks.toast.warning).not.toHaveBeenCalled();
+        expect(mocks.runHandleAutoLoginFlow).not.toHaveBeenCalled();
+    });
+
+    test('counts saved-account relogin failures together with manual login failures', async () => {
+        const store = await createAuthStore();
+        store.loginForm.username = 'tester@example.com';
+        store.loginForm.password = 'password';
+
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+        vi.setSystemTime(new Date('2026-03-23T00:00:30.000Z'));
+        await failSavedAccountLogin(store, makeAuthError('Unauthorized', 401), {
+            username: 'tester@example.com'
+        });
+
+        expect(mocks.toast.warning).not.toHaveBeenCalled();
+
+        vi.setSystemTime(new Date('2026-03-23T00:01:00.000Z'));
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+
+        expect(mocks.toast.warning).toHaveBeenCalledTimes(1);
+    });
+
+    test('resets the failure window after a successful login', async () => {
+        const store = await createAuthStore();
+        store.loginForm.username = 'tester@example.com';
+        store.loginForm.password = 'password';
+
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+        vi.setSystemTime(new Date('2026-03-23T00:00:30.000Z'));
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+        vi.setSystemTime(new Date('2026-03-23T00:01:00.000Z'));
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+
+        expect(mocks.toast.warning).toHaveBeenCalledTimes(1);
+
+        vi.setSystemTime(new Date('2026-03-23T00:01:05.000Z'));
+        await succeedManualLogin(store);
+        expect(mocks.toast.dismiss).toHaveBeenCalledWith(
+            'login-network-issue-toast'
+        );
+
+        mocks.toast.warning.mockClear();
+        mocks.toast.dismiss.mockClear();
+
+        mockWatchState.isLoggedIn = false;
+        await nextTick();
+
+        vi.setSystemTime(new Date('2026-03-23T00:01:10.000Z'));
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+        vi.setSystemTime(new Date('2026-03-23T00:01:30.000Z'));
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+
+        expect(mocks.toast.warning).not.toHaveBeenCalled();
+    });
+
+    test('resets the failure window when the user edits the login form', async () => {
+        const store = await createAuthStore();
+        store.loginForm.username = 'tester@example.com';
+        store.loginForm.password = 'password';
+
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+        vi.setSystemTime(new Date('2026-03-23T00:00:20.000Z'));
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+        expect(mocks.toast.warning).not.toHaveBeenCalled();
+
+        store.loginForm.username = 'tester2@example.com';
+        await nextTick();
+
+        vi.setSystemTime(new Date('2026-03-23T00:00:35.000Z'));
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+
+        expect(mocks.toast.warning).not.toHaveBeenCalled();
+    });
+
+    test('dismisses the sticky warning when credentials change before the next submit', async () => {
+        const store = await createAuthStore();
+        store.loginForm.username = 'tester@example.com';
+        store.loginForm.password = 'password';
+
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+        vi.setSystemTime(new Date('2026-03-23T00:00:30.000Z'));
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+        vi.setSystemTime(new Date('2026-03-23T00:01:00.000Z'));
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+
+        expect(mocks.toast.warning).toHaveBeenCalledTimes(1);
+
+        store.loginForm.password = 'new-password';
+        vi.setSystemTime(new Date('2026-03-23T00:01:10.000Z'));
+        await failManualLogin(store, makeAuthError('Unauthorized', 401));
+
+        expect(mocks.toast.dismiss).toHaveBeenCalledWith(
+            'login-network-issue-toast'
+        );
+        expect(mocks.toast.warning).toHaveBeenCalledTimes(1);
+    });
+});
diff --git a/src/stores/auth.js b/src/stores/auth.js
index b8e04170..1b742b3c 100644
--- a/src/stores/auth.js
+++ b/src/stores/auth.js
@@ -13,6 +13,7 @@ import { AppDebug } from '../services/appConfig';
 import { authRequest } from '../api';
 import { database } from '../services/database';
 import { escapeTag } from '../shared/utils';
+import { links } from '../shared/constants/link';
 import { initWebsocket } from '../services/websocket';
 import { request } from '../services/request';
 import { runHandleAutoLoginFlow } from '../coordinators/authAutoLoginCoordinator';
@@ -73,12 +74,21 @@ export const useAuthStore = defineStore('Auth', () => {
     const enableCustomEndpoint = ref(false);
 
     const attemptingAutoLogin = ref(false);
+    const loginNetworkIssueHintState = reactive({
+        hinted: false,
+        timestamps: [],
+        lastAttemptFingerprint: ''
+    });
+    const loginNetworkIssueHintToastId = ref(null);
+    const loginNetworkIssueHintWindowMs = 90000;
+    const loginNetworkIssueHintThreshold = 3;
 
     watch(
         [() => watchState.isLoggedIn, () => userStore.currentUser],
         ([isLoggedIn, currentUser]) => {
             twoFactorAuthDialogVisible.value = false;
             if (isLoggedIn) {
+                resetLoginNetworkIssueHintState();
                 updateStoredUser(currentUser);
                 new Noty({
                     type: 'success',
@@ -91,6 +101,11 @@ export const useAuthStore = defineStore('Auth', () => {
         { flush: 'sync' }
     );
 
+    watch(
+        [() => loginForm.value.username, () => loginForm.value.password],
+        resetLoginNetworkIssueHintState
+    );
+
     watch(
         () => watchState.isFriendsLoaded,
         (isFriendsLoaded) => {
@@ -225,7 +240,9 @@ export const useAuthStore = defineStore('Auth', () => {
             );
             if (user) {
                 delete user.cookies;
-                await relogin(user);
+                await relogin(user, {
+                    shouldTrackLoginNetworkIssueHint: false
+                });
             }
         }
     }
@@ -241,7 +258,9 @@ export const useAuthStore = defineStore('Auth', () => {
             if (user) {
                 await webApiService.clearCookies();
                 delete user.cookies;
-                relogin(user).then(() => {
+                relogin(user, {
+                    shouldTrackLoginNetworkIssueHint: false
+                }).then(() => {
                     toast.success(t('message.auth.email_2fa_resent'));
                 });
                 return;
@@ -250,6 +269,102 @@ export const useAuthStore = defineStore('Auth', () => {
         toast.error(t('message.auth.email_2fa_no_credentials'));
     }
 
+    /**
+     *
+     */
+    function resetLoginNetworkIssueHintState() {
+        if (loginNetworkIssueHintToastId.value) {
+            toast.dismiss(loginNetworkIssueHintToastId.value);
+            loginNetworkIssueHintToastId.value = null;
+        }
+        loginNetworkIssueHintState.hinted = false;
+        loginNetworkIssueHintState.timestamps = [];
+        loginNetworkIssueHintState.lastAttemptFingerprint = '';
+    }
+
+    /**
+     *
+     * @param {{ username?: string, password?: string, endpoint?: string, websocket?: string }} [params]
+     * @returns {string}
+     */
+    function buildLoginNetworkIssueAttemptFingerprint(params = {}) {
+        return [
+            params.username ?? '',
+            params.password ?? '',
+            params.endpoint ?? '',
+            params.websocket ?? ''
+        ].join('\u0000');
+    }
+
+    /**
+     *
+     * @param {{ username?: string, password?: string, endpoint?: string, websocket?: string }} params
+     */
+    function resetLoginNetworkIssueHintStateIfCredentialsChanged(params) {
+        const fingerprint = buildLoginNetworkIssueAttemptFingerprint(params);
+        if (
+            loginNetworkIssueHintState.lastAttemptFingerprint &&
+            loginNetworkIssueHintState.lastAttemptFingerprint !== fingerprint
+        ) {
+            resetLoginNetworkIssueHintState();
+        }
+        loginNetworkIssueHintState.lastAttemptFingerprint = fingerprint;
+    }
+
+    /**
+     *
+     * @param {Error & {status?: number, endpoint?: string}} err
+     * @returns {boolean}
+     */
+    function shouldCountLoginFailureForNetworkHint(err) {
+        if (!err || err.endpoint !== 'auth/user') {
+            return false;
+        }
+        if (
+            typeof err.message === 'string' &&
+            err.message.includes('Invalid Username/Email or Password')
+        ) {
+            return false;
+        }
+        return [401].includes(err.status);
+    }
+
+    /**
+     *
+     */
+    function maybeShowLoginNetworkIssueHint() {
+        const now = Date.now();
+        loginNetworkIssueHintState.timestamps =
+            loginNetworkIssueHintState.timestamps.filter(
+                (timestamp) => timestamp > now - loginNetworkIssueHintWindowMs
+            );
+        loginNetworkIssueHintState.timestamps.push(now);
+        if (
+            loginNetworkIssueHintState.hinted ||
+            loginNetworkIssueHintState.timestamps.length <
+                loginNetworkIssueHintThreshold
+        ) {
+            return;
+        }
+        loginNetworkIssueHintState.hinted = true;
+        loginNetworkIssueHintToastId.value = toast.warning(
+            t('message.auth.login_network_issue_hint_title'),
+            {
+                description: t(
+                    'message.auth.login_network_issue_hint_description'
+                ),
+                duration: Infinity,
+                action: {
+                    label: t('common.actions.open'),
+                    onClick: () =>
+                        AppApi.OpenLink(
+                            links.troubleshootingAuthUserConnectionIssues
+                        )
+                }
+            }
+        );
+    }
+
     /**
      *
      */
@@ -471,7 +586,10 @@ export const useAuthStore = defineStore('Auth', () => {
      *
      * @param user
      */
-    async function relogin(user) {
+    async function relogin(
+        user,
+        { shouldTrackLoginNetworkIssueHint = !attemptingAutoLogin.value } = {}
+    ) {
         const { loginParams } = user;
         if (user.cookies) {
             await webApiService.setCookies(user.cookies);
@@ -488,6 +606,14 @@ export const useAuthStore = defineStore('Auth', () => {
         loginForm.value.loading = true;
         try {
             let password = loginParams.password;
+            if (shouldTrackLoginNetworkIssueHint) {
+                resetLoginNetworkIssueHintStateIfCredentialsChanged({
+                    username: loginParams.username,
+                    password,
+                    endpoint: loginParams.endpoint,
+                    websocket: loginParams.websocket
+                });
+            }
             if (advancedSettingsStore.enablePrimaryPassword) {
                 try {
                     password = await checkPrimaryPassword(loginParams);
@@ -506,6 +632,12 @@ export const useAuthStore = defineStore('Auth', () => {
                     websocket: loginParams.websocket
                 });
             } catch (err) {
+                if (
+                    shouldTrackLoginNetworkIssueHint &&
+                    shouldCountLoginFailureForNetworkHint(err)
+                ) {
+                    maybeShowLoginNetworkIssueHint();
+                }
                 await handleLogoutEvent();
                 throw err;
             }
@@ -549,6 +681,12 @@ export const useAuthStore = defineStore('Auth', () => {
         await webApiService.clearCookies();
         if (!loginForm.value.loading) {
             loginForm.value.loading = true;
+            resetLoginNetworkIssueHintStateIfCredentialsChanged({
+                username: loginForm.value.username,
+                password: loginForm.value.password,
+                endpoint: loginForm.value.endpoint,
+                websocket: loginForm.value.websocket
+            });
             if (loginForm.value.endpoint) {
                 AppDebug.endpointDomain = loginForm.value.endpoint;
                 AppDebug.websocketDomain = loginForm.value.websocket;
@@ -589,27 +727,43 @@ export const useAuthStore = defineStore('Auth', () => {
                                 loginForm.value.password,
                                 value
                             );
-                            await authLogin({
-                                username: loginForm.value.username,
-                                password: loginForm.value.password,
-                                endpoint: loginForm.value.endpoint,
-                                websocket: loginForm.value.websocket,
-                                saveCredentials:
-                                    loginForm.value.saveCredentials,
-                                cipher: pwd
-                            });
+                            try {
+                                await authLogin({
+                                    username: loginForm.value.username,
+                                    password: loginForm.value.password,
+                                    endpoint: loginForm.value.endpoint,
+                                    websocket: loginForm.value.websocket,
+                                    saveCredentials:
+                                        loginForm.value.saveCredentials,
+                                    cipher: pwd
+                                });
+                            } catch (err) {
+                                if (
+                                    shouldCountLoginFailureForNetworkHint(err)
+                                ) {
+                                    maybeShowLoginNetworkIssueHint();
+                                }
+                                throw err;
+                            }
                         }
                     } catch {
                         // prompt cancelled or crypto failed
                     }
                 } else {
-                    await authLogin({
-                        username: loginForm.value.username,
-                        password: loginForm.value.password,
-                        endpoint: loginForm.value.endpoint,
-                        websocket: loginForm.value.websocket,
-                        saveCredentials: loginForm.value.saveCredentials
-                    });
+                    try {
+                        await authLogin({
+                            username: loginForm.value.username,
+                            password: loginForm.value.password,
+                            endpoint: loginForm.value.endpoint,
+                            websocket: loginForm.value.websocket,
+                            saveCredentials: loginForm.value.saveCredentials
+                        });
+                    } catch (err) {
+                        if (shouldCountLoginFailureForNetworkHint(err)) {
+                            maybeShowLoginNetworkIssueHint();
+                        }
+                        throw err;
+                    }
                 }
             } finally {
                 loginForm.value.loading = false;