diff --git a/app/controllers/content_controller.rb b/app/controllers/content_controller.rb
index 2cbeb0df..dc138aa5 100644
--- a/app/controllers/content_controller.rb
+++ b/app/controllers/content_controller.rb
@@ -492,20 +492,32 @@ class ContentController < ApplicationController
     # Are we pinning or unpinning?
     new_pin_status = !@image.pinned
     
-    # Use update instead of update_column to trigger model callbacks
-    # The model callbacks will handle unpinning other images automatically
-    @image.update!(pinned: new_pin_status)
+    # If we're pinning this image, unpin all other images for this content first
+    # This prevents database locking issues from the model callbacks
+    if new_pin_status == true
+      # Unpin other image uploads for this content
+      ImageUpload.where(content_type: content.class.name, content_id: content.id, pinned: true)
+                .where.not(id: @image.id)
+                .update_all(pinned: false)
+      
+      # Also unpin any basil commissions for this content
+      BasilCommission.where(entity_type: content.class.name, entity_id: content.id, pinned: true)
+                     .update_all(pinned: false)
+    end
+    
+    # Now update this image's pin status (without triggering callbacks that cause locks)
+    @image.update_column(:pinned, new_pin_status)
     
     # Clear any cached images to ensure pinned images are shown
     content.instance_variable_set(:@random_image_including_private_cache, nil)
     content.instance_variable_set(:@pinned_public_image_cache, nil)
     content.instance_variable_set(:@first_public_image_cache, nil)
     
-    # Return the updated status
+    # Return the updated status (use new_pin_status since update_column might not refresh the object)
     render json: { 
       id: @image.id, 
       type: params[:image_type], 
-      pinned: @image.pinned 
+      pinned: new_pin_status 
     }
   end
 
diff --git a/app/models/basil_commission.rb b/app/models/basil_commission.rb
index d50bd6ea..b3baa767 100644
--- a/app/models/basil_commission.rb
+++ b/app/models/basil_commission.rb
@@ -52,22 +52,7 @@ class BasilCommission < ApplicationRecord
   # Use acts_as_list for ordering images
   acts_as_list scope: [:entity_type, :entity_id]
 
-  # Add callback to ensure only one pinned image per entity
-  before_save :ensure_single_pinned_image, if: -> { pinned_changed? && pinned? }
+  # Note: Pin unpinning logic is handled in the controller to prevent database locking issues
 
   private
-
-  # Ensures only one basil commission can be pinned per entity
-  def ensure_single_pinned_image
-    # Unpin other basil commissions for this entity
-    BasilCommission.where(entity_type: entity_type, entity_id: entity_id, pinned: true)
-                   .where.not(id: id)
-                   .update_all(pinned: false)
-    
-    # Also unpin any image uploads for this entity
-    if entity.respond_to?(:image_uploads)
-      ImageUpload.where(content_type: entity_type, content_id: entity_id, pinned: true)
-                 .update_all(pinned: false)
-    end
-  end
 end
diff --git a/app/models/page_data/image_upload.rb b/app/models/page_data/image_upload.rb
index 5081ba03..1deada07 100644
--- a/app/models/page_data/image_upload.rb
+++ b/app/models/page_data/image_upload.rb
@@ -38,8 +38,7 @@ class ImageUpload < ApplicationRecord
   # Use acts_as_list for ordering images
   acts_as_list scope: [:content_type, :content_id]
 
-  # Add callback to ensure only one pinned image per content
-  before_save :ensure_single_pinned_image, if: -> { pinned_changed? && pinned? }
+  # Note: Pin unpinning logic is handled in the controller to prevent database locking issues
 
   def delete_s3_image
     # todo: put this in a task for faster delete response times
@@ -47,18 +46,4 @@ class ImageUpload < ApplicationRecord
   end
 
   private
-
-  # Ensures only one image can be pinned per content item
-  def ensure_single_pinned_image
-    # Unpin other image uploads for this content
-    ImageUpload.where(content_type: content_type, content_id: content_id, pinned: true)
-              .where.not(id: id)
-              .update_all(pinned: false)
-    
-    # Also unpin any basil commissions for this content
-    if content.respond_to?(:basil_commissions)
-      BasilCommission.where(entity_type: content_type, entity_id: content_id, pinned: true)
-                     .update_all(pinned: false)
-    end
-  end
 end