Background Dietary patterns can impact the trajectories of healthy aging. However, dietary assessment tools can be challenging to use. With the increased use of technology in older adults, we aimed to evaluate the feasibility of older adults completing the online, Automated Self-Administered 24-h (ASA-24) dietary assessment tool. Methods We conducted a randomized, two-period, two-sequence, crossover design of twenty community-dwelling older adults (≥65 years) comparing their preference for completing the ASA-24 alone versus with a research assistant (RA). Participants were recruited via ResearchMatch.com and randomly allocated 1:1 to a sequence of completing both an ASA-24 alone or with an RA, separated by one week. After each session, participants completed an online 11-item feasibility survey (Likert-scale range of 1–5, strongly disagree to strongly agree). Mean and standard deviations were reported for each question. Results Mean age was 69 ± 3.5 years (90% females), with no differences were observed for sex, age, race, ethnicity, education, or income. Neither group felt a need for RA assistance ( p = 0.34). However, both groups felt the system was easier to follow with the help of an RA (RA: 4.4 ± 1.3, vs. SA 4.6 ± 0.5, p = 0.65), particularly when they completed the ASA-24 alone, first ( p = 0.04). When conducting the ASA-24 alone, there was less confidence the system could be learned quickly (SA 4.5 ± 0.5→3.4 ± 1.0 vs RA 3.4 ± 1.0→3.4 ± 0.7, p = 0.001). The ASA-24 was thought to be less cumbersome after repeated exposure in those concluding with the RA. Conclusion While older adults were able to complete the ASA-24 independently, the use of an RA led to improved confidence. Enhancing the sample diversity in a larger number of participants could provide helpful data to improve the science of dietary assessment.