We conducted a mixed-methods study to examine barriers to use of my Social Security (MySSA), and users’ experience of using MySSA. The quantitative phase of the study leveraged existing survey data to analyze the determinants of self-reported MySSA account use. For the qualitative phase, we interviewed 24 individuals about their views and experiences with online transactions generally and with Social Security specifically, and their perceptions of the MySSA platform as they navigated it during the interview. The quantitative analysis suggests that internet literacy and, more generally, educational levels are barriers to MySSA use. Current SSA beneficiaries and older respondents were significantly more likely to be aware of, have an account, and use MySSA. From the qualitative results, we learn that there are four key reasons for not creating a MySSA account: (1) lack of awareness of MySSA; (2) no perceived relevance/need; (3) security and privacy concerns; and (4) low internet/computer literacy. We also observe that, overall, users perceive the MySSA platform to be clear, navigable, and relevant. Nonretired, nonbeneficiary participants found the information on the platform to be particularly instructive and useful. Our findings suggest that for younger people especially, MySSA could be a potentially useful financial and retirement preparedness tool. We find that a key challenge to MySSA use is getting people to create an account in the first place and not their retention once they create an account. Further research may be warranted to address the barriers to using MySSA, increasing engagement with the platform, and realizing its potential as a key resource for retirement readiness.