diff --git a/server/api/jellyfin.ts b/server/api/jellyfin.ts
index f23e9aceb..81b505f11 100644
--- a/server/api/jellyfin.ts
+++ b/server/api/jellyfin.ts
@@ -126,25 +126,31 @@ class JellyfinAPI extends ExternalAPI {
     Password?: string,
     ClientIP?: string
   ): Promise<JellyfinLoginResponse> {
-    try {
-      const headers = ClientIP
-        ? {
-            'X-Forwarded-For': ClientIP,
-          }
-        : {};
+    const authenticate = async (useHeaders: boolean) => {
+      const headers =
+        useHeaders && ClientIP ? { 'X-Forwarded-For': ClientIP } : {};
 
-      const authResponse = await this.post<JellyfinLoginResponse>(
+      return this.post<JellyfinLoginResponse>(
         '/Users/AuthenticateByName',
         {
-          Username: Username,
+          Username,
           Pw: Password,
         },
-        {
-          headers: headers,
-        }
+        { headers }
       );
+    };
 
-      return authResponse;
+    try {
+      return await authenticate(true);
+    } catch (e) {
+      logger.debug(`Failed to authenticate with headers: ${e.message}`, {
+        label: 'Jellyfin API',
+        ip: ClientIP,
+      });
+    }
+
+    try {
+      return await authenticate(false);
     } catch (e) {
       const status = e.response?.status;
 
diff --git a/server/index.ts b/server/index.ts
index b62080778..a9a746562 100644
--- a/server/index.ts
+++ b/server/index.ts
@@ -27,6 +27,7 @@ import type CacheableLookupType from 'cacheable-lookup';
 import { TypeormStore } from 'connect-typeorm/out';
 import cookieParser from 'cookie-parser';
 import csurf from 'csurf';
+import { lookup } from 'dns';
 import type { NextFunction, Request, Response } from 'express';
 import express from 'express';
 import * as OpenApiValidator from 'express-openapi-validator';
@@ -54,6 +55,19 @@ app
     const CacheableLookup = (await _importDynamic('cacheable-lookup'))
       .default as typeof CacheableLookupType;
     const cacheable = new CacheableLookup();
+
+    const originalLookup = cacheable.lookup;
+
+    // if hostname is localhost use dns.lookup instead of cacheable-lookup
+    cacheable.lookup = (...args: any) => {
+      const [hostname] = args;
+      if (hostname === 'localhost') {
+        lookup(...(args as Parameters<typeof lookup>));
+      } else {
+        originalLookup(...(args as Parameters<typeof originalLookup>));
+      }
+    };
+
     cacheable.install(http.globalAgent);
     cacheable.install(https.globalAgent);
 
diff --git a/server/routes/auth.ts b/server/routes/auth.ts
index 82c34b153..52c63ff29 100644
--- a/server/routes/auth.ts
+++ b/server/routes/auth.ts
@@ -14,6 +14,7 @@ import { ApiError } from '@server/types/error';
 import * as EmailValidator from 'email-validator';
 import { Router } from 'express';
 import gravatarUrl from 'gravatar-url';
+import net from 'net';
 
 const authRoutes = Router();
 
@@ -271,11 +272,21 @@ authRoutes.post('/jellyfin', async (req, res, next) => {
       ? jellyfinHost.slice(0, -1)
       : jellyfinHost;
 
-    const ip = req.ip ? req.ip.split(':').reverse()[0] : undefined;
+    const ip = req.ip;
+    let clientIp;
+
+    if (ip) {
+      if (net.isIPv4(ip)) {
+        clientIp = ip;
+      } else if (net.isIPv6(ip)) {
+        clientIp = ip.startsWith('::ffff:') ? ip.substring(7) : ip;
+      }
+    }
+
     const account = await jellyfinserver.login(
       body.username,
       body.password,
-      ip
+      clientIp
     );
 
     // Next let's see if the user already exists