The proper classification of tobacco products is very important for regulatory and taxation purposes. Cigar products present a special problem because of a wide variation in sizes, blends and additives used in the tobacco filler, and the nature of the wrapper and binder (if used). Proper classification of little cigars (also known as small cigars or cigarillos) can present problems because of their similarity to some cigarette products. However, attempts to use routine chemical and non-routine measures (e.g., LC-MS-MS) to distinguish cigars from cigarettes based on levels of certain analytes have not been fully satisfactory. Consequently, we characterized several varieties of little cigars with two GC-MS scan techniques: 1) the Direct Silylation Scan ( in situ silylation of tobacco before analysis), which provides identifications and semi-quantitative data, on acids, humectants, sugars, and certain other compounds (Moldoveanu et al., 46th TCRC, Paper #28); and 2) the HFP Scan ( in situ extraction of tobacco with hexafluoroisopropanol before analysis), which allows the analysis of the semivolatile compounds ranging, from low molecular-weight ketones to neophytadiene and some sterols (Dong et al., 47th TCRC, Paper #16). Both GC-MS techniques were performed on an Agilent 6890 GC coupled with an Agilent 5972 MS. A DB-5MS capillary GC column (25 m x 0.25 µm film thickness and 0.25 mm ID) was used. The data from our analyses allowed us to distinguish between little cigars with blends typical of large cigars from little cigars containing flue-cured tobaccos and little cigars containing added sugars and/or humectants. Comparisons will also be made with typical cigarette tobaccos