We report on a pilot study investigating the influence of financial stress and technostress on users’ responses towards digital financial transactions. We developed a two factor within-subject design, where techno-unreliability as variable system response time under time pressure and perceived financial loss were manipulated in a 3x2 design. We collected psychophysiological, perceptual and behavioral data from N=15 participants while performing an adapted version of the Iowa Gambling Task. The analysis reported decreased perception of system responsiveness, financial decision quality, electrodermal activity and variable heart rate in response to both manipulated factors. We posit that these results may indicate participants’ disengagement towards the performance of a transactional digital financial task as a potential coping strategy in response to financial and technological stress. This pilot study contributes to further knowledge towards the understanding of the relationship between technology-related and financial stress.