Occupational therapists use a variety of approaches during intervention to address handwriting legibility, including therapeutic practice, sensorimotor approaches, and practice using iPad apps. The purpose of this pilot study was to compare the effectiveness of three interventions implemented in small groups to improve handwriting legibility: handwriting practice on iPad apps alone, handwriting practice using iPads combined with a traditional OT multisensory approach, or a traditional OT multisensory approach alone with handwriting practice. A pretest-posttest design with random assignment was employed in the current study. Although all of the mean group scores improved, a Kruskal-Wallis H test revealed no statistically significant differences in THS-R scores between the three groups after the intervention, X[superscript 2](2) = 4.63, p = 0.09. A blinded qualitative analysis of handwriting samples from each group revealed observable improvements in the letter formation in the iPad only group as compared to the other two intervention groups.