Hi DanDanTheIceCreamMan, I have experienced this in the past; I don't think you can actually delete messages that you send to yourself. I recall having he same issue a number of weeks ago on my buyer account. However, all messages are automatically deleted from your inbox after 1 / 2 months, but these are kept (encrypted) on the Silk Road servers for 3 months in order to deal with any issues that may arise. Thread locked as resolved. Libertas