diff --git a/app/models/attachment.rb b/app/models/attachment.rb
index 8c5750148..42ca79d6c 100644
--- a/app/models/attachment.rb
+++ b/app/models/attachment.rb
@@ -62,7 +62,12 @@ class Attachment < ApplicationRecord
   def thumb_url
     return '' unless file.attached? && image?
 
-    url_for(file.representation(resize_to_fill: [250, nil]))
+    begin
+      url_for(file.representation(resize_to_fill: [250, nil]))
+    rescue ActiveStorage::UnrepresentableError => e
+      Rails.logger.warn "Unrepresentable image attachment: #{id} (#{file.filename}) - #{e.message}"
+      ''
+    end
   end
 
   def with_attached_file?
diff --git a/spec/models/attachment_spec.rb b/spec/models/attachment_spec.rb
index 0b03a56ad..cc00eab5d 100644
--- a/spec/models/attachment_spec.rb
+++ b/spec/models/attachment_spec.rb
@@ -82,6 +82,16 @@ RSpec.describe Attachment do
 
       expect(attachment.thumb_url).to be_present
     end
+
+    it 'handles unrepresentable images gracefully' do
+      attachment = message.attachments.create!(account_id: message.account_id, file_type: :image)
+      attachment.file.attach(io: StringIO.new('fake image'), filename: 'test.jpg', content_type: 'image/jpeg')
+
+      allow(attachment.file).to receive(:representation).and_raise(ActiveStorage::UnrepresentableError.new('Cannot represent'))
+
+      expect(Rails.logger).to receive(:warn).with(/Unrepresentable image attachment: #{attachment.id}/)
+      expect(attachment.thumb_url).to eq('')
+    end
   end
 
   describe 'meta data handling' do