Jambolan (Syzygium cumini) is a native fruit from Asia that has adapted well to the tropical climate of the Amazonian region. However, due to its limited annual availability and high perishability, the jambolan fruit is still underexploited. Thus, this study aimed to preserve the jambolan through a combined process of pulsed vacuum osmotic dehydration (PVOD) and convective air-drying and to monitor the total phenolic contents (TPCs) and total monomeric anthocyanins (TMAs) during these processes. To this end, jambolan fruits were pretreated with increasing PVOD times. After monitoring of moisture loss, solid gain, weight reduction, water activity, TPC, and TMA, pretreated (PT) and non-pretreated (NPT) fruits underwent convective air-drying (50–70 °C). The PVOD reduced half of the water present in the fruits; nonetheless, PVOD decreased the TPC and TMA over time. The increase in air-drying temperature shortened the drying time for both NPT and PT jambolan, and PVOD reduced even further the drying time of the fruits. Moreover, the fruits pretreated and dried at 60 °C showed promising results, potentially being a good alternative to extend the fruit’s shelf life and make it available throughout the year.