Yes

But not while it was a federal prison.

In the late 1800s, while still Army control, four prisoners who worked in
the administration office forged the commandant's signature on documents
recommending their release and then slipped the letters into the mail.

Army officials in Washington processed the recommendations and sent them
back to the commandant, who was confused, but who followed the orders.

The four prisoners were set ashore in San Francisco where they went
straight to a bar began to drink. One man soon became drunk and started to brag
about their escape. The other three quickly fled the bar in a panic.
The drunk man was recaptured and returned to the prison,
but the other three men were never heard from again.