There is limited evidence of how Australian low-to-middle income (AUD $40,000–$80,000) households maintain food security. Using a sequential explanatory mixed methods methodology, this study explored and compared the food security (FS) and insecurity (FIS) experiences of these households. An initial quantitative survey categorised participants according to food security status (the 18-item United States Department of Agriculture Household Food Security Survey Module) and income level to identify and purposefully select participants to qualitatively explore food insecurity and security experiences. Of the total number of survey participants (n = 134), 42 were categorised as low-to-middle income. Of these, a subset of 16 participants (8 FIS and 8 FS) was selected, and each participant completed an in-depth interview. The interviews explored precursors, strategies to prevent or address food insecurity, and the implications of the experience. Interview data were analysed using a thematic analysis approach. Five themes emerged from the analysis: (i) food decision experiences, (ii) assets, (iii) triggers, (iv) activation of assets, and (v) consequences and emotion related to walking the food security tightrope. The leverage points across all themes were more volatile for FIS participants. Low-to-middle income Australians are facing the challenges of trying to maintain or improve their food security status, with similarities to those described in lower income groups, and should be included in approaches to prevent or address food insecurity.