In the post

app/email_new_converter.py

@@ -874,6 +874,7 @@ class EmailNewConverter:
                         return f"{parts[0]}/upload/{transformation}"
                 else:
                     # No transformations, insert them before the path
+                    # This handles both versioned URLs (v123/...) and non-versioned URLs
                     return f"{parts[0]}/upload/{transformation}/{path_part}"
         
         return cloudinary_url

app/post_process.py

@@ -256,6 +256,103 @@ def fix_unsubscribe_link(html_content: str) -> str:
     return html_content
 
 
+def fix_cloudinary_image_transformations(html_content: str) -> str:
+    """Add Cloudinary transformations to market images that are missing them.
+    
+    This ensures all market images (48px square images) have proper transformations
+    for cropping, while preserving aspect ratio for footer and top news images.
+    """
+    modified = False
+    fixed_count = 0
+    
+    # Pattern to match img tags with Cloudinary URLs
+    # Matches: <img ... src="https://res.cloudinary.com/.../upload/v123/..." ...>
+    pattern = r'(<img[^>]*src=["\'])(https://res\.cloudinary\.com/[^"\']+)(["\'][^>]*>)'
+    
+    def add_transformations(match):
+        nonlocal modified, fixed_count
+        prefix = match.group(1)
+        url = match.group(2)
+        suffix = match.group(3)
+        full_tag = match.group(0)
+        
+        # Check if URL already has transformations
+        has_transformations = "/upload/w_" in url or "/upload/c_" in url or "/upload/h_" in url
+        
+        if has_transformations:
+            return full_tag  # Already has transformations, skip
+        
+        # Check if this is a market image (48px width) vs footer/top news
+        # Market images have width="48" or style containing "width:48px"
+        is_market_image = False
+        is_footer_or_top_news = False
+        
+        # Check for width="48" attribute
+        if 'width="48"' in full_tag or "width='48'" in full_tag:
+            is_market_image = True
+        
+        # Check for style with width:48px
+        if re.search(r'width\s*:\s*48px', full_tag, re.IGNORECASE):
+            is_market_image = True
+        
+        # Check if it's a footer image (alt="Polymarket" or in footer section)
+        if 'alt="Polymarket"' in full_tag or 'alt=\'Polymarket\'' in full_tag:
+            is_footer_or_top_news = True
+        
+        # Check if it's a top news image (inside top_news_box or alt="Top news image")
+        if 'alt="Top news image"' in full_tag or 'alt=\'Top news image\'' in full_tag:
+            is_footer_or_top_news = True
+        else:
+            # Check if it's inside a top_news_box by looking for the class in nearby HTML
+            img_pos = html_content.find(full_tag)
+            if img_pos != -1:
+                # Check if there's a top_news_box before this img tag (within 1000 chars)
+                before_img = html_content[max(0, img_pos - 1000):img_pos]
+                # Look for top_news_box class (handle both quoted and unquoted, with/without spaces)
+                if re.search(r'class\s*=\s*["\']?[^"\'>]*top_news_box', before_img, re.IGNORECASE):
+                    is_footer_or_top_news = True
+        
+        # Only add transformations to market images (48px square images)
+        if is_market_image and not is_footer_or_top_news:
+            # Extract target size from width attribute or style
+            target_size = 48  # Default for market images
+            
+            # Try to extract from width attribute
+            width_match = re.search(r'width=["\'](\d+)["\']', full_tag, re.IGNORECASE)
+            if width_match:
+                target_size = int(width_match.group(1))
+            else:
+                # Try to extract from style
+                style_match = re.search(r'width\s*:\s*(\d+)px', full_tag, re.IGNORECASE)
+                if style_match:
+                    target_size = int(style_match.group(1))
+            
+            # Add transformations to the URL
+            transformation = f"w_{target_size},h_{target_size},c_fill,g_center,q_auto,f_auto"
+            
+            # Insert transformations into the URL
+            if "/upload/" in url:
+                parts = url.split("/upload/", 1)
+                if len(parts) == 2:
+                    path_part = parts[1]
+                    new_url = f"{parts[0]}/upload/{transformation}/{path_part}"
+                    modified = True
+                    fixed_count += 1
+                    return f"{prefix}{new_url}{suffix}"
+        
+        return full_tag  # No changes needed
+    
+    # Process all img tags
+    html_content = re.sub(pattern, add_transformations, html_content, flags=re.IGNORECASE)
+    
+    if modified:
+        print(f"  Fixed {fixed_count} Cloudinary image URL(s) by adding transformations")
+    else:
+        print(f"  No Cloudinary images found that need transformation fixes")
+    
+    return html_content
+
+
 def add_link_spacing(html_content: str) -> str:
     """Add spaces before specific links to ensure proper spacing in email clients.
     
@@ -336,7 +433,10 @@ def minify_html(html_content: str) -> str:
     # Step 5: Fix unsubscribe link href (update from # to {% manage_subscription_preferences_url %})
     html_content = fix_unsubscribe_link(html_content)
 
-    # Step 6: Add spaces before links (ensures proper spacing in email clients)
+    # Step 6: Fix Cloudinary image URLs (add transformations to market images)
+    html_content = fix_cloudinary_image_transformations(html_content)
+
+    # Step 7: Add spaces before links (ensures proper spacing in email clients)
     html_content = add_link_spacing(html_content)
 
     final_size = len(html_content)