When performing endoscopic ultrasound-guided fine needle aspiration (EUS-FNA), identifying neoplasia in the setting of chronic pancreatitis can be technically challenging. The morphology of an ill-defined mass on sonography, presence of calcifications or intervening collaterals, reverberation from a biliary stent, low yield of tissue procurement, and interpretative errors in cytopathology can result in both false-negative and false-positive results. Although these challenges cannot be completely eliminated, elastography or contrast-enhanced imaging can aid in differentiating an inflammatory mass from a neoplasm. Also, performing more passes of FNA, procuring core biopsy material, performing rapid onsite evaluation, conducting ancillary pathology studies, and even repeating the procedure on a different day can aid in improving the diagnostic performance of EUS-FNA. This review provides a concise update and offers practical tips to improving the diagnostic yield of EUS-FNA when sampling solid pancreatic mass lesions in the setting of chronic pancreatitis.