diff --git a/lib/coursemology/evaluator/services/evaluate_programming_package_service.rb b/lib/coursemology/evaluator/services/evaluate_programming_package_service.rb
index 2c77142..b1af14b 100644
--- a/lib/coursemology/evaluator/services/evaluate_programming_package_service.rb
+++ b/lib/coursemology/evaluator/services/evaluate_programming_package_service.rb
@@ -106,12 +106,21 @@ def copy_archive(zip_file, tar_file, prefix = nil)
 
   def execute_package(container)
     container.start!
+    execute_package_wait(container)
+  end
+
+  # Waits for the container to exit the Running state.
+  #
+  # This will time out for long running operations, so keep retrying until we return.
+  def execute_package_wait(container)
     container_state = container.info
     while container_state.fetch('State', {}).fetch('Running', true)
       container.wait
       container.refresh!
       container_state = container.info
     end
+  rescue Docker::Error::TimeoutError
+    retry
   end
 
   def extract_result(container)
diff --git a/spec/coursemology/evaluator/services/evaluate_programming_package_service_spec.rb b/spec/coursemology/evaluator/services/evaluate_programming_package_service_spec.rb
index 5248f6a..c0d436f 100644
--- a/spec/coursemology/evaluator/services/evaluate_programming_package_service_spec.rb
+++ b/spec/coursemology/evaluator/services/evaluate_programming_package_service_spec.rb
@@ -82,6 +82,24 @@ def evaluate_result
     end
   end
 
+  describe '#execute_package_wait' do
+    let(:image) { 'python:2.7' }
+    let(:container) { subject.send(:create_container, image) }
+    after { subject.send(:destroy_container, container) }
+
+    it 'retries until the container finishes' do
+      called = 0
+      expect(container).to receive(:wait).and_wrap_original do |block, *args|
+        args.push(0.second) if called == 0
+        called += 1
+
+        block.call(*args)
+      end.at_least(:twice)
+
+      subject.send(:execute_package_wait, container)
+    end
+  end
+
   describe '#extract_result' do
     let(:image) { 'python:2.7' }
     let(:container) do