diff --git a/index.d.ts b/index.d.ts
index 35f34c22c..83eb8f9b1 100644
--- a/index.d.ts
+++ b/index.d.ts
@@ -1,4 +1,5 @@
 import { UserDirectoryList, User } from "./src/users";
+import { CommandLineArguments } from "./src/command-line";
 import { CsrfSyncedToken } from "csrf-sync";
 
 declare global {
@@ -32,4 +33,9 @@ declare global {
      * The root directory for user data.
      */
     var DATA_ROOT: string;
+
+    /**
+     * Parsed command line arguments.
+     */
+    var COMMAND_LINE_ARGS: CommandLineArguments;
 }
diff --git a/server.js b/server.js
index 9cae3a57b..1f34b91a3 100644
--- a/server.js
+++ b/server.js
@@ -26,7 +26,6 @@ import {
     initUserStorage,
     getCookieSecret,
     getCookieSessionName,
-    getAllEnabledUsers,
     ensurePublicDirectoriesExist,
     getUserDirectoriesList,
     migrateSystemPrompts,
@@ -34,9 +33,10 @@ import {
     requireLoginMiddleware,
     setUserDataMiddleware,
     shouldRedirectToLogin,
-    tryAutoLogin,
     cleanUploads,
     getSessionCookieAge,
+    verifySecuritySettings,
+    loginPageMiddleware,
 } from './src/users.js';
 
 import getWebpackServeMiddleware from './src/middleware/webpack-serve.js';
@@ -49,7 +49,6 @@ import getCacheBusterMiddleware from './src/middleware/cacheBuster.js';
 import corsProxyMiddleware from './src/middleware/corsProxy.js';
 import {
     getVersion,
-    getConfigValue,
     color,
     removeColorFormatting,
     getSeparator,
@@ -72,6 +71,11 @@ util.inspect.defaultOptions.maxArrayLength = null;
 util.inspect.defaultOptions.maxStringLength = null;
 util.inspect.defaultOptions.depth = 4;
 
+// Set a working directory for the server
+const serverDirectory = import.meta.dirname ?? path.dirname(fileURLToPath(import.meta.url));
+console.log(`Node version: ${process.version}. Running in ${process.env.NODE_ENV} environment. Server directory: ${serverDirectory}`);
+process.chdir(serverDirectory);
+
 // Work around a node v20.0.0, v20.1.0, and v20.2.0 bug. The issue was fixed in v20.3.0.
 // https://github.com/nodejs/node/issues/47822#issuecomment-1564708870
 // Safe to remove once support for Node v20 is dropped.
@@ -80,19 +84,26 @@ if (process.versions && process.versions.node && process.versions.node.match(/20
     if (net.setDefaultAutoSelectFamily) net.setDefaultAutoSelectFamily(false);
 }
 
-const cliParser = new CommandLineParser();
-const cliArgs = cliParser.parse(process.argv);
+const cliArgs = new CommandLineParser().parse(process.argv);
 globalThis.DATA_ROOT = cliArgs.dataRoot;
+globalThis.COMMAND_LINE_ARGS = cliArgs;
 
 if (!cliArgs.enableIPv6 && !cliArgs.enableIPv4) {
     console.error('error: You can\'t disable all internet protocols: at least IPv6 or IPv4 must be enabled.');
     process.exit(1);
 }
 
-// change all relative paths
-const serverDirectory = import.meta.dirname ?? path.dirname(fileURLToPath(import.meta.url));
-console.log(`Node version: ${process.version}. Running in ${process.env.NODE_ENV} environment. Server directory: ${serverDirectory}`);
-process.chdir(serverDirectory);
+try {
+    if (cliArgs.dnsPreferIPv6) {
+        dns.setDefaultResultOrder('ipv6first');
+        console.log('Preferring IPv6 for DNS resolution');
+    } else {
+        dns.setDefaultResultOrder('ipv4first');
+        console.log('Preferring IPv4 for DNS resolution');
+    }
+} catch (error) {
+    console.warn('Failed to set DNS resolution order. Possibly unsupported in this Node version.');
+}
 
 const app = express();
 app.use(helmet({
@@ -101,19 +112,6 @@ app.use(helmet({
 app.use(compression());
 app.use(responseTime());
 
-/** @type {boolean} */
-const enableAccounts = getConfigValue('enableUserAccounts', false, 'boolean');
-
-if (cliArgs.dnsPreferIPv6) {
-    // Set default DNS resolution order to IPv6 first
-    dns.setDefaultResultOrder('ipv6first');
-    console.log('Preferring IPv6 for DNS resolution');
-} else {
-    // Set default DNS resolution order to IPv4 first
-    dns.setDefaultResultOrder('ipv4first');
-    console.log('Preferring IPv4 for DNS resolution');
-}
-
 // CORS Settings //
 const CORS = cors({
     origin: 'null',
@@ -213,24 +211,7 @@ app.get('/', getCacheBusterMiddleware(), (request, response) => {
 });
 
 // Host login page
-app.get('/login', async (request, response) => {
-    if (!enableAccounts) {
-        console.log('User accounts are disabled. Redirecting to index page.');
-        return response.redirect('/');
-    }
-
-    try {
-        const autoLogin = await tryAutoLogin(request, cliArgs.basicAuthMode);
-
-        if (autoLogin) {
-            return response.redirect('/');
-        }
-    } catch (error) {
-        console.error('Error during auto-login:', error);
-    }
-
-    return response.sendFile('login.html', { root: path.join(process.cwd(), 'public') });
-});
+app.get('/login', loginPageMiddleware);
 
 // Host frontend assets
 const webpackMiddleware = getWebpackServeMiddleware();
@@ -289,7 +270,8 @@ async function preSetupTasks() {
     await settingsInit();
     await statsInit();
 
-    const cleanupPlugins = await initializePlugins();
+    const pluginsDirectory = path.join(serverDirectory, 'plugins');
+    const cleanupPlugins = await loadPlugins(app, pluginsDirectory);
     const consoleTitle = process.title;
 
     let isExiting = false;
@@ -365,80 +347,6 @@ async function postSetupTasks(result) {
     setupLogLevel();
 }
 
-/**
- * Loads server plugins from a directory.
- * @returns {Promise<Function>} Function to be run on server exit
- */
-async function initializePlugins() {
-    try {
-        const pluginDirectory = path.join(serverDirectory, 'plugins');
-        const cleanupPlugins = await loadPlugins(app, pluginDirectory);
-        return cleanupPlugins;
-    } catch {
-        console.log('Plugin loading failed.');
-        return () => { };
-    }
-}
-
-/**
- * Prints an error message and exits the process if necessary
- * @param {string} message The error message to print
- * @returns {void}
- */
-function logSecurityAlert(message) {
-    if (cliArgs.basicAuthMode || cliArgs.whitelistMode) return; // safe!
-    console.error(color.red(message));
-    if (getConfigValue('securityOverride', false, 'boolean')) {
-        console.warn(color.red('Security has been overridden. If it\'s not a trusted network, change the settings.'));
-        return;
-    }
-    process.exit(1);
-}
-
-async function verifySecuritySettings() {
-    // Skip all security checks as listen is set to false
-    if (!cliArgs.listen) {
-        return;
-    }
-
-    if (!enableAccounts) {
-        logSecurityAlert('Your current SillyTavern configuration is insecure (listening to non-localhost). Enable whitelisting, basic authentication or user accounts.');
-    }
-
-    const users = await getAllEnabledUsers();
-    const unprotectedUsers = users.filter(x => !x.password);
-    const unprotectedAdminUsers = unprotectedUsers.filter(x => x.admin);
-
-    if (unprotectedUsers.length > 0) {
-        console.warn(color.blue('A friendly reminder that the following users are not password protected:'));
-        unprotectedUsers.map(x => `${color.yellow(x.handle)} ${color.red(x.admin ? '(admin)' : '')}`).forEach(x => console.warn(x));
-        console.log();
-        console.warn(`Consider setting a password in the admin panel or by using the ${color.blue('recover.js')} script.`);
-        console.log();
-
-        if (unprotectedAdminUsers.length > 0) {
-            logSecurityAlert('If you are not using basic authentication or whitelisting, you should set a password for all admin users.');
-        }
-    }
-
-    if (cliArgs.basicAuthMode) {
-        const perUserBasicAuth = getConfigValue('perUserBasicAuth', false, 'boolean');
-        if (perUserBasicAuth && !enableAccounts) {
-            console.error(color.red(
-                'Per-user basic authentication is enabled, but user accounts are disabled. This configuration may be insecure.',
-            ));
-        } else if (!perUserBasicAuth) {
-            const basicAuthUserName = getConfigValue('basicAuthUser.username', '');
-            const basicAuthUserPassword = getConfigValue('basicAuthUser.password', '');
-            if (!basicAuthUserName || !basicAuthUserPassword) {
-                console.warn(color.yellow(
-                    'Basic Authentication is enabled, but username or password is not set or empty!',
-                ));
-            }
-        }
-    }
-}
-
 /**
  * Registers a not-found error response if a not-found error page exists. Should only be called after all other middlewares have been registered.
  */
diff --git a/src/plugin-loader.js b/src/plugin-loader.js
index 7d7053025..f752d5201 100644
--- a/src/plugin-loader.js
+++ b/src/plugin-loader.js
@@ -38,50 +38,55 @@ const isESModule = (file) => path.extname(file) === '.mjs';
  * be called before the server shuts down.
  */
 export async function loadPlugins(app, pluginsPath) {
-    const exitHooks = [];
-    const emptyFn = () => { };
+    try {
+        const exitHooks = [];
+        const emptyFn = () => { };
 
-    // Server plugins are disabled.
-    if (!enableServerPlugins) {
-        return emptyFn;
-    }
-
-    // Plugins directory does not exist.
-    if (!fs.existsSync(pluginsPath)) {
-        return emptyFn;
-    }
-
-    const files = fs.readdirSync(pluginsPath);
-
-    // No plugins to load.
-    if (files.length === 0) {
-        return emptyFn;
-    }
-
-    await updatePlugins(pluginsPath);
-
-    for (const file of files) {
-        const pluginFilePath = path.join(pluginsPath, file);
-
-        if (fs.statSync(pluginFilePath).isDirectory()) {
-            await loadFromDirectory(app, pluginFilePath, exitHooks);
-            continue;
+        // Server plugins are disabled.
+        if (!enableServerPlugins) {
+            return emptyFn;
         }
 
-        // Not a JavaScript file.
-        if (!isCommonJS(file) && !isESModule(file)) {
-            continue;
+        // Plugins directory does not exist.
+        if (!fs.existsSync(pluginsPath)) {
+            return emptyFn;
         }
 
-        await loadFromFile(app, pluginFilePath, exitHooks);
-    }
+        const files = fs.readdirSync(pluginsPath);
 
-    if (loadedPlugins.size > 0) {
-        console.log(`${loadedPlugins.size} server plugin(s) are currently loaded. Make sure you know exactly what they do, and only install plugins from trusted sources!`);
-    }
+        // No plugins to load.
+        if (files.length === 0) {
+            return emptyFn;
+        }
 
-    // Call all plugin "exit" functions at once and wait for them to finish
-    return () => Promise.all(exitHooks.map(exitFn => exitFn()));
+        await updatePlugins(pluginsPath);
+
+        for (const file of files) {
+            const pluginFilePath = path.join(pluginsPath, file);
+
+            if (fs.statSync(pluginFilePath).isDirectory()) {
+                await loadFromDirectory(app, pluginFilePath, exitHooks);
+                continue;
+            }
+
+            // Not a JavaScript file.
+            if (!isCommonJS(file) && !isESModule(file)) {
+                continue;
+            }
+
+            await loadFromFile(app, pluginFilePath, exitHooks);
+        }
+
+        if (loadedPlugins.size > 0) {
+            console.log(`${loadedPlugins.size} server plugin(s) are currently loaded. Make sure you know exactly what they do, and only install plugins from trusted sources!`);
+        }
+
+        // Call all plugin "exit" functions at once and wait for them to finish
+        return () => Promise.all(exitHooks.map(exitFn => exitFn()));
+    } catch (error) {
+        console.error('Plugin loading failed.', error);
+        return () => { };
+    }
 }
 
 async function loadFromDirectory(app, pluginDirectoryPath, exitHooks) {
diff --git a/src/users.js b/src/users.js
index f6e383b38..da24df97c 100644
--- a/src/users.js
+++ b/src/users.js
@@ -120,6 +120,72 @@ export async function ensurePublicDirectoriesExist() {
     return directoriesList;
 }
 
+/**
+ * Prints an error message and exits the process if necessary
+ * @param {string} message The error message to print
+ * @returns {void}
+ */
+function logSecurityAlert(message) {
+    const { basicAuthMode, whitelistMode } = globalThis.COMMAND_LINE_ARGS;
+    if (basicAuthMode || whitelistMode) return; // safe!
+    console.error(color.red(message));
+    if (getConfigValue('securityOverride', false, 'boolean')) {
+        console.warn(color.red('Security has been overridden. If it\'s not a trusted network, change the settings.'));
+        return;
+    }
+    process.exit(1);
+}
+
+/**
+ * Verifies the security settings and prints warnings if necessary
+ * @returns {Promise<void>}
+ */
+export async function verifySecuritySettings() {
+    const { listen, basicAuthMode } = globalThis.COMMAND_LINE_ARGS;
+
+    // Skip all security checks as listen is set to false
+    if (!listen) {
+        return;
+    }
+
+    if (!ENABLE_ACCOUNTS) {
+        logSecurityAlert('Your current SillyTavern configuration is insecure (listening to non-localhost). Enable whitelisting, basic authentication or user accounts.');
+    }
+
+    const users = await getAllEnabledUsers();
+    const unprotectedUsers = users.filter(x => !x.password);
+    const unprotectedAdminUsers = unprotectedUsers.filter(x => x.admin);
+
+    if (unprotectedUsers.length > 0) {
+        console.warn(color.blue('A friendly reminder that the following users are not password protected:'));
+        unprotectedUsers.map(x => `${color.yellow(x.handle)} ${color.red(x.admin ? '(admin)' : '')}`).forEach(x => console.warn(x));
+        console.log();
+        console.warn(`Consider setting a password in the admin panel or by using the ${color.blue('recover.js')} script.`);
+        console.log();
+
+        if (unprotectedAdminUsers.length > 0) {
+            logSecurityAlert('If you are not using basic authentication or whitelisting, you should set a password for all admin users.');
+        }
+    }
+
+    if (basicAuthMode) {
+        const perUserBasicAuth = getConfigValue('perUserBasicAuth', false, 'boolean');
+        if (perUserBasicAuth && !ENABLE_ACCOUNTS) {
+            console.error(color.red(
+                'Per-user basic authentication is enabled, but user accounts are disabled. This configuration may be insecure.',
+            ));
+        } else if (!perUserBasicAuth) {
+            const basicAuthUserName = getConfigValue('basicAuthUser.username', '');
+            const basicAuthUserPassword = getConfigValue('basicAuthUser.password', '');
+            if (!basicAuthUserName || !basicAuthUserPassword) {
+                console.warn(color.yellow(
+                    'Basic Authentication is enabled, but username or password is not set or empty!',
+                ));
+            }
+        }
+    }
+}
+
 export function cleanUploads() {
     try {
         const uploadsPath = path.join(globalThis.DATA_ROOT, UPLOADS_DIRECTORY);
@@ -817,6 +883,31 @@ export function requireLoginMiddleware(request, response, next) {
     return next();
 }
 
+/**
+ * Middleware to host the login page.
+ * @param {import('express').Request} request Request object
+ * @param {import('express').Response} response Response object
+ */
+export async function loginPageMiddleware(request, response) {
+    if (!ENABLE_ACCOUNTS) {
+        console.log('User accounts are disabled. Redirecting to index page.');
+        return response.redirect('/');
+    }
+
+    try {
+        const { basicAuthMode } = globalThis.COMMAND_LINE_ARGS;
+        const autoLogin = await tryAutoLogin(request, basicAuthMode);
+
+        if (autoLogin) {
+            return response.redirect('/');
+        }
+    } catch (error) {
+        console.error('Error during auto-login:', error);
+    }
+
+    return response.sendFile('login.html', { root: path.join(process.cwd(), 'public') });
+}
+
 /**
  * Creates a route handler for serving files from a specific directory.
  * @param {(req: import('express').Request) => string} directoryFn A function that returns the directory path to serve files from