Handwriting examination is becoming a captivating field nowadays, as there are numerous cases where handwriting is not written on a usual surface – i.e., paper, with a conventional writing instrument – i.e., pen. However, while it is interesting to analyze these types of handwriting samples, most forensic document examiners find it difficult due to the effect atypical surface and writing instrument have on handwriting characteristics. Thus, a systematized study has been carried out on documents prepared on unconventional surfaces such as cardboard, cloth piece, and blackboard, with uncommon writing instruments such as lipstick, kajal, and chalk. Correspondingly, studies were carried out on writing samples provided by 40 individuals using the conventional pen/paper as well as unconventional cardboard/kajal, cardboard/pen, cloth/pen, cloth/lipstick, cloth/kajal, and board/chalk combinations. Various handwriting features were examined and compared among aforementioned combinations, and changes in handwriting characteristics were reported. Those could be due to the atypical writing instruments and surfaces which conjointly impact the overall identity of the handwriting and expert’s conclusions thereon.