“Prunty’s Va 14th Jany 1862” small town manuscript cancel with “Free J.W. Carter PM” on pristine cover to C.Y. Thomas, Richmond Va. Prunty’s was in Henry County (south central Virginia) with a population of only 20 souls in early 1900. This is the earliest of the recorded manuscript postmarks in the Virginia Postal History Society Catalog, although there were postmasters listed from 1849-1867. Postmasters were permitted to send free of postage letters and packages related exclusively to the business of their office. Since this letter was not sent to another post office official, it is doubtful whether it met that criteria and thus would have been illegal. CCV $150.  $150. 

Christopher Yancy Thomas detailed bio on linked page.