Preparing and filing taxes has become an increasingly digital task. Older adults need to file taxes to qualify for benefits, but little is known about how older adults in Canada manage tax preparation, nor about how they get help. We investigated delegation mechanisms provided by the Canada Revenue Agency, documenting workflows needed to set up delegation and identifying privacy and security risks. We conducted a semi-structured interview study (n = 19) with older adults, formal tax volunteers, and informal tax helpers to understand the challenges and experiences in tax delegation. Our results show that the CRA’s delegation mechanisms are lightweight and enable older adults to delegate tasks to others with minimal privacy and security risks. However, we found these lightweight mechanisms were not known about or used by the older adults who delegated to informal tax helpers, nor were they known about or used by any of the informal tax helpers we interviewed.