Paul and Timothy are almost inseparable. The letters to Philemon and the Philippians are addressed from both Paul and Timothy and appear to be sent from prison. This makes most sense if both are in prison, especially given the risk inherent in naming an accomplice who remains free. And when Paul is in prison, Timothy is not sent anywhere. Could it be that Timothy was in prison alongside Paul? The personal tone and content of both letters nonetheless reflect concern only for Paul, what he has done and what will happen to him. No one cares about Timothy, so Timothy is probably not in prison.