diff --git a/app/services/gpo_confirmation_uploader.rb b/app/services/gpo_confirmation_uploader.rb
index 315c649a244..54422aba58c 100644
--- a/app/services/gpo_confirmation_uploader.rb
+++ b/app/services/gpo_confirmation_uploader.rb
@@ -43,8 +43,14 @@ def generate_export(confirmations)
   def upload_export(export)
     return unless FeatureManagement.gpo_upload_enabled?
     io = StringIO.new(export)
-    Net::SFTP.start(*sftp_config) do |sftp|
-      sftp.upload!(io, remote_path)
+
+    with_retries(
+      max_tries: 5,
+      rescue: [Net::SFTP::Exception, Net::SSH::Exception],
+    ) do
+      Net::SFTP.start(*sftp_config) do |sftp|
+        sftp.upload!(io, remote_path)
+      end
     end
   end
 
diff --git a/spec/services/gpo_confirmation_uploader_spec.rb b/spec/services/gpo_confirmation_uploader_spec.rb
index 4612d1882fc..8b95c27fb22 100644
--- a/spec/services/gpo_confirmation_uploader_spec.rb
+++ b/spec/services/gpo_confirmation_uploader_spec.rb
@@ -71,6 +71,28 @@
 
       subject
     end
+
+    context 'when an SSH error occurs' do
+      it 'retries the upload' do
+        expect(Net::SFTP).to receive(:start).twice.with(*sftp_options).and_yield(sftp_connection)
+        expect(sftp_connection).to receive(:upload!).once.and_raise(Net::SSH::ConnectionTimeout)
+        expect(sftp_connection).to receive(:upload!).once
+
+        subject
+      end
+
+      it 'raises after 5 unsuccessful retries' do
+        expect(Net::SFTP).to receive(:start).
+          exactly(5).times.
+          with(*sftp_options).
+          and_yield(sftp_connection)
+        expect(sftp_connection).to receive(:upload!).
+          exactly(5).times.
+          and_raise(Net::SSH::ConnectionTimeout)
+
+        expect { subject }.to raise_error(Net::SSH::ConnectionTimeout)
+      end
+    end
   end
 
   describe '#run' do