A woman who is very familiar with the Cumberland County Sheriff’s Department and jail has been arrested again. Deputies responded recently to an area on White Hall Road to a report of a naked woman in the road. According to the arrest report, the owners of the property were able to convince 50-year-old Jean Ann Cowen to put her clothes back on. The property owner reportedly told Cowen several times not to be on the property. She was charged with criminal trespassing. According to general sessions court personnel, Cowen has been booked in the Cumberland County jail 165 times on various charges including theft, disorderly conduct, public intoxication, trespassing and DUI.