The Prentares Ribbon of Commendation was an award presented to deserving Starfleet personnel in the 23rd century.
Captain Jonathan Archer was a recipient of this medal prior to his retirement from Starfleet. (ENT: "In a Mirror, Darkly, Part II")
This information appeared on the personnel file for Archer, discovered aboard the USS Defiant by his counterpart in 2155.
Captain James T. Kirk also received this award prior to his court martial in 2267. (TOS: "Court Martial")
In 2367, Barash created a holoprogram of a fictional future based on William T. Riker's thoughts and expectations. In Riker's fictional service record in the holoprogram, on stardate 55843, he was awarded the Prentares Ribbon of Commendation for exploring space beyond the Sargon Region. (TNG: "Future Imperfect")
For the remastered episode of "Future Imperfect", the original Okudagram of Riker's service record was replaced by a new graphic. This award was mentioned in that graphic.