Chris Brown jail struggle after Karrueche Tran shares intimate moment on Instagram, Chris Worried about prison time for D.C. Assault?

Singer Chris Brown seemed upbeat after sending fans a message through his estrange girlfriend, Karrueche Tran's Instagram page, but recent reports claim that the singer is having a hard time in the Los Angeles jail.

According to Hollywoodlife, the 24-year-old singer is feeling less optimistic despite having 15 days left in jail.

"He's lost all hope. Jail has broken him," a source revealed. "He can't be upbeat or happy in jail because he doesn't have control over sh**. He can't do anything on his own and he's told what to do, when to eat, when to sleep and sh**, and people are watching over him 24/7."

The singer will be heading to D.C. for his assault case and fears that more prison time could be in his near future.

 "He wants this D.C. case behind him but he's not trying to get his hopes up," the source reveals. "He's not setting himself up for the ultimate failure. He's just playing the waiting game but he has no hopes either way because he doesn't want to be let down."

The "Loyal" singer wants to get back into his music and his fans after sending a message to "Team Breezy," which appeared to be the highlight of Brown's Monday -with the help of Tran.

"He doesn't have a voice. He's locked up, and posting that video was the least Kae could do for him," the source reveled. "It made his day that he was able to reach his fans from inside jail. It was something so small that she did but it was HUGE for him. It made him feel special and put a smile on his face. Even though she couldn't see him smile, she could feel it. She could hear his voice and how upbeat it was. She knows her man."

Will Chris change his bad boy ways once out of jail?