This research aimed to evaluate the changes induced by two thermal treatments on red beetroot and red capsicum pepper, alongside the addition of anise or fennel aqueous extracts to boost lactation. The cooking loss and yield, phytochemical profile, antioxidant activity, in vitro digestion, FT-IR investigations, and respective statistical analysis were performed for all the puree samples. Cooking loss and yield determined similar values for both vegetables used. Comparatively, between hot air and water vapor convection, the latter proved to be a milder method. By the statistical method, the samples mixed with herbal aqueous extracts presented significantly differences (p < 0.05) compared to the blank samples. Also, the samples mixed with herbal aqueous extracts were statistically significantly different from the control samples. Among the experimented samples, steamed red capsicum pepper puree enriched with aqueous anise extract (EAAA) showed the highest antioxidant activity (71.08 ± 1.9 µM Trolox/g DW). These results might mark the implementation of softer thermal methods for food preparation as well as new purposes for plants. FT-IR analysis revealed the presence of esters, glycosidic bands, pyranoid rings, and pectin, which are specific compounds for the evaluated matrices. The total phenolic content evolution was negatively affected only after the first hour of digestion. In conclusion, red beetroot and red capsicum pepper with anise or fennel aqueous extracts could contribute to improving breastfeeding. Even so, clinical tests and further analysis are necessary in order to confirm the efficacy of such products.