When Chris Brown headed to jail on Friday (March 14) after being kicked out of rehab, he probably didn't think he'd be staying too long. However, a Los Angeles judge squashed any chance of freedom when Brown's bid for release was rejected. The troubled singer is now ordered to stay in jail until April 23.

So what did Brown do to land himself in jail? According to TMZ, he violated three rules, one of which was specifically tailored for him. And that was to stay at least two feet away from any woman in the rehab facility. The other two violations involve an unauthorized outing as well as mocking therapy in the middle of a session.

But sources say that he was likely thrown out due to a sexual encounter that he had a with a female at rehab in the beginning of the month.

So once he was kicked out of rehab, Brown, whose sixth studio album, 'X,' arrives May 5, was immediately arrested. During Brown's hearing on Monday (March 17), the judge said he has an "inability to stay out of trouble." And now he's behind bars.

The crooner is also on trial for the criminal assault charge that happened in Washington, D.C., last October. The trial will take place on April 17, but it is still unsure if Brow will actually be called into court for that date.

A month in jail is a long time for someone who continues to get in trouble wherever he goes. Let's see if Chris Brown will be a free man by the time his new album arrives.