diff --git a/gemfiles/rails_7.1.gemfile.lock b/gemfiles/rails_7.1.gemfile.lock
index 5a73e5258..9f126a7ec 100644
--- a/gemfiles/rails_7.1.gemfile.lock
+++ b/gemfiles/rails_7.1.gemfile.lock
@@ -148,6 +148,7 @@ GEM
       concurrent-ruby (~> 1.1)
       webrick (~> 1.7)
       websocket-driver (~> 0.7)
+    ffi (1.17.2-x86_64-darwin)
     ffi (1.17.2-x86_64-linux-gnu)
     fiber-annotation (0.2.0)
     fiber-local (1.1.0)
@@ -224,6 +225,8 @@ GEM
     net-smtp (0.5.1)
       net-protocol
     nio4r (2.7.4)
+    nokogiri (1.18.9-x86_64-darwin)
+      racc (~> 1.4)
     nokogiri (1.18.9-x86_64-linux-gnu)
       racc (~> 1.4)
     os (1.1.4)
@@ -355,6 +358,7 @@ GEM
       simplecov (~> 0.19)
     simplecov-html (0.13.2)
     simplecov_json_formatter (0.1.4)
+    sqlite3 (2.7.3-x86_64-darwin)
     sqlite3 (2.7.3-x86_64-linux-gnu)
     stringio (3.1.7)
     thor (1.4.0)
@@ -380,6 +384,7 @@ GEM
     zeitwerk (2.7.3)
 
 PLATFORMS
+  x86_64-darwin-21
   x86_64-linux
 
 DEPENDENCIES
@@ -416,4 +421,4 @@ DEPENDENCIES
   webmock (~> 3.18)
 
 BUNDLED WITH
-   2.6.9
+   2.5.5
diff --git a/gemfiles/rails_7.2.gemfile.lock b/gemfiles/rails_7.2.gemfile.lock
index 7582f3bc4..6c7d563f2 100644
--- a/gemfiles/rails_7.2.gemfile.lock
+++ b/gemfiles/rails_7.2.gemfile.lock
@@ -142,6 +142,7 @@ GEM
       concurrent-ruby (~> 1.1)
       webrick (~> 1.7)
       websocket-driver (~> 0.7)
+    ffi (1.17.2-x86_64-darwin)
     ffi (1.17.2-x86_64-linux-gnu)
     fiber-annotation (0.2.0)
     fiber-local (1.1.0)
@@ -217,6 +218,8 @@ GEM
     net-smtp (0.5.1)
       net-protocol
     nio4r (2.7.4)
+    nokogiri (1.18.9-x86_64-darwin)
+      racc (~> 1.4)
     nokogiri (1.18.9-x86_64-linux-gnu)
       racc (~> 1.4)
     os (1.1.4)
@@ -348,6 +351,7 @@ GEM
       simplecov (~> 0.19)
     simplecov-html (0.13.2)
     simplecov_json_formatter (0.1.4)
+    sqlite3 (2.7.3-x86_64-darwin)
     sqlite3 (2.7.3-x86_64-linux-gnu)
     stringio (3.1.7)
     thor (1.4.0)
@@ -374,6 +378,7 @@ GEM
     zeitwerk (2.7.3)
 
 PLATFORMS
+  x86_64-darwin-21
   x86_64-linux
 
 DEPENDENCIES
@@ -410,4 +415,4 @@ DEPENDENCIES
   webmock (~> 3.18)
 
 BUNDLED WITH
-   2.6.9
+   2.5.5
diff --git a/gemfiles/rails_8.0.gemfile.lock b/gemfiles/rails_8.0.gemfile.lock
index e047a147d..bd7863b8f 100644
--- a/gemfiles/rails_8.0.gemfile.lock
+++ b/gemfiles/rails_8.0.gemfile.lock
@@ -142,6 +142,7 @@ GEM
       concurrent-ruby (~> 1.1)
       webrick (~> 1.7)
       websocket-driver (~> 0.7)
+    ffi (1.17.2-x86_64-darwin)
     ffi (1.17.2-x86_64-linux-gnu)
     fiber-annotation (0.2.0)
     fiber-local (1.1.0)
@@ -217,6 +218,8 @@ GEM
     net-smtp (0.5.1)
       net-protocol
     nio4r (2.7.4)
+    nokogiri (1.18.9-x86_64-darwin)
+      racc (~> 1.4)
     nokogiri (1.18.9-x86_64-linux-gnu)
       racc (~> 1.4)
     os (1.1.4)
@@ -348,6 +351,7 @@ GEM
       simplecov (~> 0.19)
     simplecov-html (0.13.2)
     simplecov_json_formatter (0.1.4)
+    sqlite3 (2.7.3-x86_64-darwin)
     sqlite3 (2.7.3-x86_64-linux-gnu)
     stringio (3.1.7)
     thor (1.4.0)
@@ -374,6 +378,7 @@ GEM
     zeitwerk (2.7.3)
 
 PLATFORMS
+  x86_64-darwin-21
   x86_64-linux
 
 DEPENDENCIES
@@ -410,4 +415,4 @@ DEPENDENCIES
   webmock (~> 3.18)
 
 BUNDLED WITH
-   2.6.9
+   2.5.5
diff --git a/lib/ruby_llm/active_record/chat_methods.rb b/lib/ruby_llm/active_record/chat_methods.rb
index fed3c4afb..352a55c36 100644
--- a/lib/ruby_llm/active_record/chat_methods.rb
+++ b/lib/ruby_llm/active_record/chat_methods.rb
@@ -286,7 +286,9 @@ def prepare_for_active_storage(attachments)
           case attachment
           when ActionDispatch::Http::UploadedFile, ActiveStorage::Blob
             attachment
-          when ActiveStorage::Attached::One, ActiveStorage::Attached::Many
+          when ActiveStorage::Attached::One
+            attachment.blob
+          when ActiveStorage::Attached::Many
             attachment.blobs
           when Hash
             attachment.values.map { |v| prepare_for_active_storage(v) }