diff --git a/lib/integrations/slack/send_on_slack_service.rb b/lib/integrations/slack/send_on_slack_service.rb
index c37a152e8..0563ffd73 100644
--- a/lib/integrations/slack/send_on_slack_service.rb
+++ b/lib/integrations/slack/send_on_slack_service.rb
@@ -121,16 +121,22 @@ class Integrations::Slack::SendOnSlackService < Base::SendOnChannelService
   end
 
   def upload_file
-    return unless message.attachments.first.with_attached_file?
+    message.attachments.each do |attachment|
+      next unless attachment.with_attached_file?
 
-    result = slack_client.files_upload_v2(
-      filename: message.attachments.first.file.filename,
-      content: message.attachments.first.file.download,
-      initial_comment: 'Attached File!',
-      thread_ts: conversation.identifier,
-      channel_id: hook.reference_id
-    )
-    Rails.logger.info "slack_upload_result: #{result}"
+      begin
+        result = slack_client.files_upload_v2(
+          filename: attachment.file.filename.to_s,
+          content: attachment.file.download,
+          initial_comment: 'Attached File!',
+          thread_ts: conversation.identifier,
+          channel_id: hook.reference_id
+        )
+        Rails.logger.info "slack_upload_result: #{result}"
+      rescue Slack::Web::Api::Errors::SlackError => e
+        Rails.logger.error "Failed to upload file #{attachment.file.filename}: #{e.message}"
+      end
+    end
   end
 
   def file_type
diff --git a/spec/lib/integrations/slack/send_on_slack_service_spec.rb b/spec/lib/integrations/slack/send_on_slack_service_spec.rb
index 848a683b4..ee08a2903 100644
--- a/spec/lib/integrations/slack/send_on_slack_service_spec.rb
+++ b/spec/lib/integrations/slack/send_on_slack_service_spec.rb
@@ -163,7 +163,7 @@ describe Integrations::Slack::SendOnSlackService do
         attachment.file.attach(io: Rails.root.join('spec/assets/avatar.png').open, filename: 'avatar.png', content_type: 'image/png')
 
         expect(slack_client).to receive(:files_upload_v2).with(
-          filename: attachment.file.filename,
+          filename: attachment.file.filename.to_s,
           content: anything,
           channel_id: hook.reference_id,
           thread_ts: conversation.identifier,
@@ -178,6 +178,61 @@ describe Integrations::Slack::SendOnSlackService do
         expect(message.attachments).to be_any
       end
 
+      it 'sent multiple attachments on slack' do
+        expect(slack_client).to receive(:chat_postMessage).with(
+          channel: hook.reference_id,
+          text: message.content,
+          username: "#{message.sender.name} (Contact)",
+          thread_ts: conversation.identifier,
+          icon_url: anything,
+          unfurl_links: true
+        ).and_return(slack_message)
+
+        attachment1 = message.attachments.new(account_id: message.account_id, file_type: :image)
+        attachment1.file.attach(io: Rails.root.join('spec/assets/avatar.png').open, filename: 'avatar.png', content_type: 'image/png')
+
+        attachment2 = message.attachments.new(account_id: message.account_id, file_type: :image)
+        attachment2.file.attach(io: Rails.root.join('spec/assets/avatar.png').open, filename: 'logo.png', content_type: 'image/png')
+
+        expect(slack_client).to receive(:files_upload_v2).twice.and_return(file_attachment)
+
+        message.save!
+        builder.perform
+
+        expect(message.external_source_id_slack).to eq 'cw-origin-6789.12345'
+        expect(message.attachments.count).to eq 2
+      end
+
+      it 'handles file upload errors gracefully' do
+        expect(slack_client).to receive(:chat_postMessage).with(
+          channel: hook.reference_id,
+          text: message.content,
+          username: "#{message.sender.name} (Contact)",
+          thread_ts: conversation.identifier,
+          icon_url: anything,
+          unfurl_links: true
+        ).and_return(slack_message)
+
+        attachment = message.attachments.new(account_id: message.account_id, file_type: :image)
+        attachment.file.attach(io: Rails.root.join('spec/assets/avatar.png').open, filename: 'avatar.png', content_type: 'image/png')
+
+        expect(slack_client).to receive(:files_upload_v2).with(
+          filename: attachment.file.filename.to_s,
+          content: anything,
+          channel_id: hook.reference_id,
+          thread_ts: conversation.identifier,
+          initial_comment: 'Attached File!'
+        ).and_raise(Slack::Web::Api::Errors::SlackError.new('File upload failed'))
+
+        expect(Rails.logger).to receive(:error).with('Failed to upload file avatar.png: File upload failed')
+
+        message.save!
+
+        builder.perform
+
+        expect(message.external_source_id_slack).to eq 'cw-origin-6789.12345'
+      end
+
       it 'will not call file_upload if attachment does not have a file (e.g facebook - fallback type)' do
         expect(slack_client).to receive(:chat_postMessage).with(
           channel: hook.reference_id,