During his term at the Treasury Department, Chittenden attracted notice when he worked to the point of exhaustion in order to ensure that a bond issue required to finance the Union war effort could be issued on time. The 12,500 bond certificates needed to be sent to England by steamship so they could be sold, and each certificate required Chittenden's signature. As a result, Chittenden stayed at his desk and signed certificates continuously over three days until the task was complete, ensuring that they could be shipped on time. Chittenden injured his hand and wrist in this work, which prompted him to resign as Register.