Prentares Ribbon of Commendation in Archer's personnel file
The Prentares Ribbon of Commendation was an award presented to deserving Earth and Federation Starfleet personnel.
Captain Jonathan Archer was a recipient of this medal prior to his retirement from Starfleet in 2161. The medal was mentioned in the personnel file of Archer, a file in the Historical Archive: Starfleet Personnel. In the mirror universe, aboard the USS Defiant, Jonathan Archer read this file. (ENT: "In a Mirror, Darkly, Part II", production art)
Captain James T. Kirk received this award in the mid-23rd century. (TOS: "Court Martial")
Holodeck Simulation - Captain Riker
Preantares Ribbon of Commendation in Riker's service record
In 2367, while exploring a cavern on Alpha Onias III, Commander William T. Riker was rendered unconscious by gases. While unconscious, neural scanners scanned Riker's brain. The scanners used elements of Riker's reality and constructed a holodeck simulation with those elements interspersed throughout, so that it felt real to him. What Riker wanted, the scanners made possible.
In one of these simulations, on stardate 55843, Captain Riker of the USS Enterprise-D received this award for exploration of space beyond the Sargon Region. In 2383, this award was mentioned in Riker's service record that was on display in his quarters on the Enterprise-D. (TNG-R: "Future Imperfect", okudagram)