Fort Sill basic training writing support group sends 13 Trainees home for the holidays

By Derika UpshawJanuary 10, 2023

Stay Back Trainees have New Year's party
Stay back Trainees with Bravo Battery 1st BN 31st FA signing their names on the table during the New Year's party at with the American Red Cross who hosted the party for the Freedom Writers' organization who donated food and other party favors for the Trainees to enjoy.

Picture Credit: Petra Yahn (Photo Credit: Derika Upshaw)

FORT SILL, Okla. (Dec. 20,2022) — A writing support group comes together to donate their efforts to support Trainees during Basic Combat Training (BCT) at Fort Sill, OK, by writing to them and getting them home for the holidays.

In April 2019 while her husband attended BCT at Fort Sill, OK, Freedom Writers’ group founder Alyssa Bertram joined a Facebook family support group to help her manage expectations and navigate the world of military life. She eventually took over administration of the group in 2020, and with the help of partner Ashleigh Davis, they increased their mission to include writing to Trainees; thus, the Freedom Writers was found.

“We had one girl in (Alpha Battery 1-31st Field Artillery Battalion), who provided us the names of eight kids who didn’t have any mail coming in. Their families were not talking to them, and she asked us if there was anything we could do through our basic training support group. The mom came to me and Ashley, and we are like let us get some people to write; we have all these people. So, we just started a group to keep everybody together and then it (the concept) just took off,” recalls Bertram.

The group has volunteers ranging from teachers, Girl Scout Troops, military parents, and spouses. In November, they wrote to over 30 Trainees. Bertram receives the Trainee’s information and asks for volunteers from the group who would like to write to the Trainee. Many Trainees have formed long-lasting relationships and even got to meet their pen pals when the pen pal came for their service member’s graduation. Other Trainees credit their pen pals with providing the inspiration and motivation to continue striving for success even after personal setbacks.

“We had one mom whose 8th grade class wrote to a Trainee in Bravo Battery who had failed a graduation requirement and was not confident he was going to be able to meet the requirement in time. He received the letters from her school class, and each of them wrote one positive thought in the letter, and he (the Trainee) said “these kids believe in me, now I need to believe in me,” and he went on to pass and graduate.”

In addition to writing letters to the trainees, the group fundraises to help Trainees return home for December holiday block leave. This initiative began in 2020 during the COVID pandemic, when Trainees were unsure whether they could go home. Co-founder Ashleigh Davis was one of the first to receive assistance from the group.

“I just had that money saved up (from the Freedom Writers stationery kit sales) and I talked to the group, and I was like we have $250. Can I use this? Do you mind if I use this to pay for a partial ticket? We are trying to send (a Trainee) home and they were like, “yeah, but how about we do better than that!”

Through fundraising, the group sponsored 10 Trainees tickets home in 2020. Each year the group increased the number of people; in 2021, they sent 11 Trainees home. In 2022, they were able to raise over $9,000 and send 13 Trainees home. Additionally, the group provided funds to American Red Cross to purchase refreshments for the trainees as they waited to board the shuttles to the airports. The continuous success and growth of Freedom Writers led them to register as a nonprofit organization and expand their ability to receive donations and sponsorships.

“We just want to help. That is why I took over the Fort Sill group, to help parents who needed an outlet, they need somebody to listen to them and they always ask for anybody who needs letters. They want to know how they can help the other trainees here,” said Bertram. “I like helping the community, and this is my heart...since he (her husband) is in the reserves, there’s no FRG, there’s nothing for me to do, and I’m a stay-at-home mom, so I want to do something, and this is it.”

Bertram said she is hoping the program will continue to grow. She said she knows families want to expand, and they want to write to more Trainees.

“We just want to help as many as we can.”

If you want to know more about the Freedom Writers and how they help the Fort Sill community, you can find their Facebook page at