diff --git a/lib/command/run.rb b/lib/command/run.rb
index f0af3ad9..59fd8470 100644
--- a/lib/command/run.rb
+++ b/lib/command/run.rb
@@ -207,7 +207,7 @@ def update_runner_workload # rubocop:disable Metrics/CyclomaticComplexity, Metri
         original_env_str = original_container_spec["env"]&.sort_by { |env| env["name"] }.to_s
         env_str = container_spec["env"]&.sort_by { |env| env["name"] }.to_s
         if original_env_str != env_str
-          container_spec["env"] = original_container_spec["env"]
+          container_spec["env"] = original_container_spec["env"] || []
           should_update = true
         end
 
diff --git a/spec/command/run_spec.rb b/spec/command/run_spec.rb
index 3d2d4be9..72724489 100644
--- a/spec/command/run_spec.rb
+++ b/spec/command/run_spec.rb
@@ -252,5 +252,27 @@
         expect(result[:stderr]).to include("Gemfile")
       end
     end
+
+    context "when runner workload has ENV but original workload does not" do
+      let!(:app) { dummy_test_app }
+
+      before do
+        run_cpflow_command!("apply-template", "app", "rails", "rails-runner-with-different-env", "-a", app)
+        run_cpflow_command!("build-image", "-a", app)
+        run_cpflow_command!("deploy-image", "-a", app)
+      end
+
+      after do
+        run_cpflow_command!("delete", "-a", app, "--yes")
+      end
+
+      it "updates runner workload", :slow do
+        result = run_cpflow_command("run", "-a", app, "--entrypoint", "none", "--", "ls")
+
+        expect(result[:status]).to eq(0)
+        expect(result[:stderr]).to include("Updating runner workload")
+        expect(result[:stderr]).to include("Gemfile")
+      end
+    end
   end
 end