diff --git a/services/arbiter-3.0/src/routes/auth.js b/services/arbiter-3.0/src/routes/auth.js
index 6c514fe..6a391d8 100644
--- a/services/arbiter-3.0/src/routes/auth.js
+++ b/services/arbiter-3.0/src/routes/auth.js
@@ -2,11 +2,24 @@ const express = require('express');
 const passport = require('passport');
 const router = express.Router();
 
+/**
+ * Standard Discord OAuth - redirects to admin after login
+ */
 router.get('/discord', passport.authenticate('discord'));
 
 router.get('/discord/callback', passport.authenticate('discord', {
   failureRedirect: '/'
 }), (req, res) => {
+  // Check if this was a checkout flow (tier stored in session)
+  if (req.session.pendingCheckoutTier) {
+    const tierLevel = req.session.pendingCheckoutTier;
+    delete req.session.pendingCheckoutTier; // Clean up
+    
+    // Redirect to checkout creation with Discord ID now available
+    return res.redirect(`/stripe/checkout?tier=${tierLevel}`);
+  }
+  
+  // Standard admin redirect
   res.redirect('/admin');
 });
 
diff --git a/services/arbiter-3.0/src/routes/stripe.js b/services/arbiter-3.0/src/routes/stripe.js
index eca2ac2..45f3118 100644
--- a/services/arbiter-3.0/src/routes/stripe.js
+++ b/services/arbiter-3.0/src/routes/stripe.js
@@ -3,6 +3,7 @@
  * Handles checkout sessions, webhooks, and customer portal
  * Date: April 3, 2026
  * Updated: April 6, 2026 - Added Discord role sync (Task #87)
+ * Updated: April 10, 2026 - Added /auth and /checkout routes for Discord OAuth flow
  */
 
 const express = require('express');
@@ -27,9 +28,96 @@ const corsOptions = {
 router.options('/create-checkout-session', cors(corsOptions));
 
 /**
- * CREATE CHECKOUT SESSION
+ * STRIPE AUTH - Entry point from website
+ * GET /stripe/auth?tier=X
+ * Stores tier in session, redirects to Discord OAuth
+ */
+router.get('/auth', (req, res) => {
+  const tierLevel = req.query.tier;
+  
+  if (!tierLevel || isNaN(parseInt(tierLevel))) {
+    return res.status(400).send('Invalid tier level. Please return to the subscribe page and try again.');
+  }
+  
+  // Store tier in session for after OAuth callback
+  req.session.pendingCheckoutTier = parseInt(tierLevel);
+  
+  // Redirect to Discord OAuth
+  res.redirect('/auth/discord');
+});
+
+/**
+ * CHECKOUT - Creates Stripe session after Discord OAuth
+ * GET /stripe/checkout?tier=X
+ * Called from auth callback, user is now logged in
+ */
+router.get('/checkout', async (req, res) => {
+  try {
+    // User must be authenticated
+    if (!req.user || !req.user.id) {
+      return res.redirect('/stripe/auth?tier=' + (req.query.tier || '1'));
+    }
+    
+    const tierLevel = parseInt(req.query.tier);
+    const discordId = req.user.id;
+    
+    if (!tierLevel || isNaN(tierLevel)) {
+      return res.status(400).send('Invalid tier level');
+    }
+    
+    // Get Stripe Price ID from database
+    const productResult = await db.query(
+      'SELECT stripe_price_id, tier_name, billing_type FROM stripe_products WHERE tier_level = $1',
+      [tierLevel]
+    );
+    
+    if (productResult.rows.length === 0) {
+      return res.status(404).send('Invalid tier level - product not found');
+    }
+    
+    const product = productResult.rows[0];
+    const priceId = product.stripe_price_id;
+    const billingMode = product.billing_type === 'one-time' ? 'payment' : 'subscription';
+    
+    console.log('🔍 Creating checkout session (OAuth flow):', {
+      discord_id: discordId,
+      tier_level: tierLevel,
+      tier_name: product.tier_name,
+      priceId,
+      billingMode
+    });
+    
+    // Create Stripe Checkout Session WITH client_reference_id
+    const sessionConfig = {
+      payment_method_types: ['card'],
+      line_items: [{ price: priceId, quantity: 1 }],
+      mode: billingMode,
+      client_reference_id: discordId, // 🔑 THE KEY - Discord ID for webhook
+      success_url: 'https://firefrostgaming.com/success',
+      cancel_url: 'https://firefrostgaming.com/subscribe',
+      metadata: {
+        tier_level: tierLevel.toString(),
+        tier_name: product.tier_name,
+        discord_id: discordId
+      }
+    };
+    
+    const session = await stripe.checkout.sessions.create(sessionConfig);
+    
+    // Redirect directly to Stripe Checkout
+    res.redirect(session.url);
+    
+  } catch (error) {
+    console.error('Checkout creation error:', error);
+    res.status(500).send('Failed to create checkout session. Please try again.');
+  }
+});
+
+/**
+ * CREATE CHECKOUT SESSION (Legacy API - kept for compatibility)
  * POST /stripe/create-checkout-session
  * Body: { tier_level }
+ * NOTE: This doesn't have Discord ID - use /stripe/auth flow instead
  */
 router.post('/create-checkout-session', cors(corsOptions), async (req, res) => {
   try {
@@ -53,7 +141,7 @@ router.post('/create-checkout-session', cors(corsOptions), async (req, res) => {
     const priceId = product.stripe_price_id;
     const billingMode = product.billing_type === 'one-time' ? 'payment' : 'subscription';
     
-    console.log('🔍 Creating checkout session:', {
+    console.log('🔍 Creating checkout session (legacy, no Discord ID):', {
       tier_level,
       tier_name: product.tier_name,
       priceId,