diff --git a/portal/setup-wizard.html b/portal/setup-wizard.html
index d7560a1..1107622 100644
--- a/portal/setup-wizard.html
+++ b/portal/setup-wizard.html
@@ -1449,8 +1449,12 @@
           // Remove loading message and start conversation flow
           document.getElementById('conversation').innerHTML = '';
 
-          // In add-menu mode, skip business info and header
-          if (config.businessId && config.menuId) {
+          // Check if any items have imageUrl - if so, offer image upload matching
+          const itemsWithImages = (config.extractedData.items || []).filter(item => item.imageUrl).length;
+          if (itemsWithImages > 0) {
+            showImageMatchingStep();
+          } else if (config.businessId && config.menuId) {
+            // In add-menu mode, skip business info and header
             showCategoriesStep();
           } else {
             showBusinessInfoStep();
@@ -1489,12 +1493,12 @@
     // Show step to upload images from saved webpage subfolder and match to items
     function showImageMatchingStep() {
       const itemCount = config.extractedData.items ? config.extractedData.items.length : 0;
-      const mappingCount = config.imageMappings.length;
+      const itemsWithImages = (config.extractedData.items || []).filter(item => item.imageUrl).length;
 
       addMessage('ai', `
-        <p>I found <strong>${itemCount} menu items</strong> and detected <strong>${mappingCount} image references</strong> in the HTML.</p>
-        <p>To add images to your menu items, upload the images from the saved webpage folder (usually named something like <code>pagename_files</code>).</p>
-        <p style="font-size:13px;color:var(--gray-500);">I'll automatically match images to items based on filenames.</p>
+        <p>I found <strong>${itemCount} menu items</strong> with <strong>${itemsWithImages} image references</strong>.</p>
+        <p>Upload the images from your saved webpage folder to add them to menu items.</p>
+        <p style="font-size:13px;color:var(--gray-500);">I'll match by Toast item ID in the filename.</p>
         <div style="margin-top:16px;">
           <input type="file" id="matchImagesInput" accept="image/*" multiple style="display:none;" onchange="handleImageMatching(event)">
           <button class="btn btn-primary" onclick="document.getElementById('matchImagesInput').click()">
@@ -1517,38 +1521,56 @@
 
       let matchedCount = 0;
       const matchResults = [];
+      const items = config.extractedData.items || [];
+
+      // Extract Toast-style item ID from filename (e.g., "item-600000000167924464_1636677556.jpg")
+      function extractToastId(str) {
+        // Match the long numeric ID pattern from Toast filenames
+        const match = str.match(/item-(\d{15,})/i);
+        return match ? match[1] : null;
+      }
+
+      // Skip duplicate sizes (_002, _003, _004 suffixes)
+      function isBaseSizeImage(filename) {
+        return !/_00[234]\.[^.]+$/i.test(filename);
+      }
 
       Array.from(files).forEach(file => {
-        const filename = file.name.toLowerCase();
+        const filename = file.name;
 
-        // Try to find a matching mapping
-        for (const mapping of config.imageMappings) {
-          const mappingFilename = mapping.filename.toLowerCase();
+        // Skip smaller size variants - only use base image
+        if (!isBaseSizeImage(filename)) {
+          return;
+        }
 
-          // Check for exact filename match or close match
-          if (filename === mappingFilename ||
-              filename.includes(mappingFilename.replace(/\.[^.]+$/, '')) ||
-              mappingFilename.includes(filename.replace(/\.[^.]+$/, ''))) {
+        // Extract Toast item ID from uploaded filename
+        const uploadedToastId = extractToastId(filename);
 
-            // Find matching item by alt text or name
-            const altText = (mapping.alt || '').toLowerCase();
-            const matchedItem = config.extractedData.items.find(item => {
-              const itemName = (item.name || '').toLowerCase();
-              const itemAlt = (item.imageAlt || '').toLowerCase();
-              return itemName === altText ||
-                     itemAlt === altText ||
-                     itemName.includes(altText) ||
-                     altText.includes(itemName) ||
-                     (itemAlt && (itemAlt.includes(altText) || altText.includes(itemAlt)));
-            });
+        // Try to match to an item
+        let matchedItem = null;
 
-            if (matchedItem) {
-              config.itemImages[matchedItem.id] = file;
-              matchedCount++;
-              matchResults.push({ item: matchedItem.name, file: file.name });
-              break;
-            }
-          }
+        if (uploadedToastId) {
+          // Match by Toast ID in imageUrl
+          matchedItem = items.find(item => {
+            if (!item.imageUrl) return false;
+            const itemToastId = extractToastId(item.imageUrl);
+            return itemToastId === uploadedToastId;
+          });
+        }
+
+        // Fallback: match by filename contained in imageUrl
+        if (!matchedItem) {
+          const filenameBase = filename.replace(/\.[^.]+$/, '').toLowerCase();
+          matchedItem = items.find(item => {
+            if (!item.imageUrl) return false;
+            return item.imageUrl.toLowerCase().includes(filenameBase);
+          });
+        }
+
+        if (matchedItem && !config.itemImages[matchedItem.id]) {
+          config.itemImages[matchedItem.id] = file;
+          matchedCount++;
+          matchResults.push({ item: matchedItem.name, file: file.name });
         }
       });