This study examines the structure of the subtropical tropopause region over Tenerife (the Canary Islands, Spain; 28°N, 16°W) based on a 20 year (1992–2011) ozonesonde data and European Center for Medium-Range Weather Forecasts ERA-Interim potential vorticity (PV) and zonal wind speed reanalysis. High-resolution vertical profiles allowed a detailed description of the subtropical tropopause break and the associated subtropical jet stream (STJ), where models fail to properly simulate the upper troposphere–lower stratosphere (UTLS). The subtropical UTLS is revealed as a complex atmospheric region with a thickness ∼8 km, which is examined through the analysis and evaluation of four different tropopause definitions: thermal (TT), cold point, ozone (OT), and dynamical (DT) tropopauses. A novel method to determine the DT based on the vertical gradient of Lait's modified PV is presented and the concept of a second DT has been introduced for the first time. Monthly climatologies of tropopause height and potential temperature are calculated for double and single tropopause events. The 14.3 km height level is used to differentiate between tropical and extratropical UTLS regimes, intimately linked to the position of the STJ. There is fairly good consistency between all the defined tropopauses under the double tropopause scheme, except in spring, when the OT is observed at lower levels due to frequent baroclinic instabilities in the upper troposphere. As concerns to single tropopause events, the same pattern is found from April to June, reflecting the influence of analogous processes during these months. In winter, altitude differences between OT, DT, and TT resulted from poleward STJ excursions forced by blocking systems over the North Atlantic. Analysis of the tropopause inversion layer showed distinctive features for tropical and midlatitude tropopauses.