diff --git a/app/models/attachment.rb b/app/models/attachment.rb
index a1cc062a0..c6b4e1d80 100644
--- a/app/models/attachment.rb
+++ b/app/models/attachment.rb
@@ -37,6 +37,7 @@ class Attachment < ApplicationRecord
   belongs_to :account
   belongs_to :message
   has_one_attached :file
+  before_save :set_extension
   validate :acceptable_file
   validates :external_url, length: { maximum: Limits::URL_LENGTH_LIMIT }
   enum file_type: { :image => 0, :audio => 1, :video => 2, :file => 3, :location => 4, :fallback => 5, :share => 6, :story_mention => 7,
@@ -111,6 +112,7 @@ class Attachment < ApplicationRecord
   def file_metadata
     metadata = {
       extension: extension,
+      content_type: file.content_type,
       data_url: file_url,
       thumb_url: thumb_url,
       file_size: file.byte_size,
@@ -154,6 +156,13 @@ class Attachment < ApplicationRecord
     }
   end
 
+  def set_extension
+    return unless file.attached?
+    return if extension.present?
+
+    self.extension = File.extname(file.filename.to_s).delete_prefix('.').presence
+  end
+
   def should_validate_file?
     return unless file.attached?
     # we are only limiting attachment types in case of website widget
diff --git a/spec/models/attachment_spec.rb b/spec/models/attachment_spec.rb
index a17839174..5e1dd2107 100644
--- a/spec/models/attachment_spec.rb
+++ b/spec/models/attachment_spec.rb
@@ -187,6 +187,44 @@ RSpec.describe Attachment do
     end
   end
 
+  describe 'set_extension' do
+    it 'sets extension from filename on save' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file)
+      attachment.file.attach(io: StringIO.new('fake pdf'), filename: 'test.pdf', content_type: 'application/pdf')
+      attachment.save!
+
+      expect(attachment.extension).to eq('pdf')
+    end
+
+    it 'does not overwrite extension if already set' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file, extension: 'doc')
+      attachment.file.attach(io: StringIO.new('fake pdf'), filename: 'test.pdf', content_type: 'application/pdf')
+      attachment.save!
+
+      expect(attachment.extension).to eq('doc')
+    end
+
+    it 'handles filenames without extension' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file)
+      attachment.file.attach(io: StringIO.new('fake data'), filename: 'README', content_type: 'text/plain')
+      attachment.save!
+
+      expect(attachment.extension).to be_nil
+    end
+  end
+
+  describe 'push_event_data includes extension and content_type' do
+    it 'returns extension and content_type for file attachments' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file)
+      attachment.file.attach(io: StringIO.new('fake pdf'), filename: 'test.pdf', content_type: 'application/pdf')
+      attachment.save!
+
+      event_data = attachment.push_event_data
+      expect(event_data[:extension]).to eq('pdf')
+      expect(event_data[:content_type]).to eq('application/pdf')
+    end
+  end
+
   describe 'file size validation' do
     let(:attachment) { message.attachments.new(account_id: message.account_id, file_type: :image) }