diff --git a/lib/ai_helper/assistant.rb b/lib/ai_helper/assistant.rb
index 3bf198389..2fc5bcdf8 100644
--- a/lib/ai_helper/assistant.rb
+++ b/lib/ai_helper/assistant.rb
@@ -125,6 +125,11 @@ def generate_prompt(
             custom_instructions: custom_locale_instructions(user, force_default_locale),
           )
         context = attach_user_context(context, user, force_default_locale: force_default_locale)
+        context.messages.each do |msg|
+           if msg[:content].is_a?(Array)
+             msg[:content] = msg[:content].map(&:to_s).join("\n")
+           end
+        end
 
         helper_response = +""
 
@@ -248,6 +253,11 @@ def generate_image_caption(upload, user)
             ],
             custom_instructions: custom_locale_instructions(user, force_default_locale),
           )
+          context.messages.each do |msg|
+            if msg[:content].is_a?(Array)
+              msg[:content] = msg[:content].map(&:to_s).join("\n")
+            end
+          end
 
         structured_output = nil