diff --git a/chat/server.js b/chat/server.js
index 22b46fe..a314a6a 100644
--- a/chat/server.js
+++ b/chat/server.js
@@ -6766,15 +6766,35 @@ async function ensureDodoCustomer(user) {
   
   // First, try to find existing customer by email
   try {
+    log('DEBUG: Looking up Dodo customer by email', {
+      userId: user.id,
+      email: email
+    });
+    
     const existingCustomers = await dodoRequest('/customers', {
       method: 'GET',
       query: { email: email }
     });
     
+    log('DEBUG: Customer lookup response', {
+      userId: user.id,
+      email: email,
+      responseKeys: Object.keys(existingCustomers || {}),
+      hasItems: !!existingCustomers?.items,
+      itemsCount: existingCustomers?.items?.length || 0,
+      rawResponse: JSON.stringify(existingCustomers).substring(0, 500)
+    });
+    
     // Check if any customers were returned
     if (existingCustomers?.items && existingCustomers.items.length > 0) {
       const existingCustomer = existingCustomers.items[0];
       const customerId = existingCustomer?.customer_id || existingCustomer?.id || '';
+      log('DEBUG: Found customer in items', {
+        userId: user.id,
+        customerId: customerId,
+        customerKeys: Object.keys(existingCustomer || {}),
+        rawCustomer: JSON.stringify(existingCustomer).substring(0, 500)
+      });
       if (customerId) {
         user.dodoCustomerId = customerId;
         await persistUsersDb();
@@ -6785,13 +6805,20 @@ async function ensureDodoCustomer(user) {
         });
         return customerId;
       }
+    } else {
+      log('DEBUG: No customers found in Dodo for email', {
+        userId: user.id,
+        email: email,
+        fullResponse: JSON.stringify(existingCustomers)
+      });
     }
   } catch (error) {
     // Log the lookup failure but continue to create new customer
     log('Failed to lookup existing Dodo customer by email', {
       userId: user.id,
       email: email,
-      error: String(error)
+      error: String(error),
+      errorStack: error.stack
     });
   }
   
@@ -12156,18 +12183,45 @@ async function handleAccountSettingsUpdate(req, res) {
     // Helper function to lookup subscription by customer
     async function lookupSubscriptionByCustomer(user) {
       try {
+        log('DEBUG: Starting subscription lookup', {
+          userId: user.id,
+          email: user.email,
+          hasDodoCustomerId: !!user.dodoCustomerId
+        });
+        
         const customerId = await ensureDodoCustomer(user);
+        
+        log('DEBUG: After ensureDodoCustomer', {
+          userId: user.id,
+          customerId: customerId,
+          hasCustomerId: !!customerId
+        });
+        
         if (!customerId) return null;
         
         // Check multiple subscription statuses: active, pending, on_hold
         const statusesToCheck = ['active', 'pending', 'on_hold'];
         
         for (const status of statusesToCheck) {
+          log('DEBUG: Querying subscriptions', {
+            userId: user.id,
+            customerId: customerId,
+            status: status
+          });
+          
           const subscriptions = await dodoRequest('/subscriptions', {
             method: 'GET',
             query: { customer_id: customerId, status: status }
           });
           
+          log('DEBUG: Subscription query response', {
+            userId: user.id,
+            status: status,
+            responseKeys: Object.keys(subscriptions || {}),
+            hasItems: !!subscriptions?.items,
+            itemsCount: subscriptions?.items?.length || 0
+          });
+          
           if (subscriptions?.items && subscriptions.items.length > 0) {
             const foundSub = subscriptions.items[0];
             log('Found missing subscription ID via Dodo lookup', {
@@ -12181,6 +12235,12 @@ async function handleAccountSettingsUpdate(req, res) {
           }
         }
         
+        log('DEBUG: No subscriptions found for customer', {
+          userId: user.id,
+          customerId: customerId,
+          checkedStatuses: statusesToCheck
+        });
+        
         return null;
       } catch (error) {
         log('Failed to lookup subscription by customer', {
@@ -12194,6 +12254,17 @@ async function handleAccountSettingsUpdate(req, res) {
 
     // If paid user is missing dodoSubscriptionId, try to look it up
     if ((isPaidToFree || isPaidToPaid) && !user.dodoSubscriptionId && PAID_PLANS.has(user.plan)) {
+      log('DEBUG: About to lookup subscription for paid user', {
+        userId: user.id,
+        email: user.email,
+        currentPlan: user.plan,
+        requestedPlan: requestedPlan,
+        isPaidToFree: isPaidToFree,
+        isPaidToPaid: isPaidToPaid,
+        hasDodoCustomerId: !!user.dodoCustomerId,
+        dodoCustomerId: user.dodoCustomerId
+      });
+      
       const foundSubscriptionId = await lookupSubscriptionByCustomer(user);
       if (foundSubscriptionId) {
         user.dodoSubscriptionId = foundSubscriptionId;