Indiana University-Purdue University Indianapolis (IUPUI) / Paper spray - mass spectrometry (PS-MS) has been developed as a rapid and direct ionization method for qualitative and quantitative analysis of complex samples at trace levels. In this work, different sampling devices for PS-MS were investigated to improve the assay’s simplicity and sensitivity over traditional approaches. In particular, chapter two characterizes an alternate paper substrate to enhance drug detection on surfaces like asphalt, cloth, concrete, aluminum, and glass. Analysis occurs on a single spray ticket coated with pressure-sensitive adhesive (PSA), also known as Post-it notes to detect and quantify drug residues. A PS-MS method utilizing PSA paper was developed to detect a mixture of ten drugs off of various surfaces to evaluate the qualitative and quantitative capabilities of the aforementioned substrate. After the method development on a conventional linear ion trap mass spectrometer, the assay was translated for use on a portable mass spectrometer to evaluate the suitability of the pressure-sensitive adhesive paper substrate in the field in chapter three. Chapter four introduces a sampling device combined with a snap-in solid-phase extraction (SPE) column. The new cartridge design not only inherits the functions from the first iteration SPE cartridge, including extraction and preconcentration from complex samples, but also exhibits greater flexibility in volume control and ease of use for on-site sample collection.