Online health communities (OHCs) are important online health communication channels for older adults with diabetes to access health information. When seeking health information, they often disclose a variety of contextual information (e.g., socio-economic situations) in their questions. Selective contextual information disclosure is a type of communication strategy for users in OHCs to elicit replies from others. In this study, we adopted text analysis to investigate what contextual information older adults with diabetes disclose to articulate their information needs and used the fixed-effect Poisson model to examine the relationships between different types of contextual information disclosure and informational support receipt. Our analyses were based on a dataset of 4,505 questions and corresponding replies from an online diabetes community. The results showed that cognitive information is the most frequently disclosed contextual information, while older adults tend to disclose demographic information in their questions less. Providing demographic and situational details in questions can enhance informational support receiving, resulting in an increased number of informational supports. However, disclosing cognitive, affective, informational channels, or support information does not significantly affect the informational support receiving. These findings can contribute to extending our existing understanding of information seekers’ communication strategies in OHCs.