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It was reconstructed in the 14th century, during the reigns of King D. [[Denis of Portugal|Dinis]] and D. [[Ferdinand I of Portugal|Fernando]].<ref name=SIPA/>
But, following its alignment with the Kingdom of Castile during the [[1383–1385 Portuguese interregnum]], the site began to fall into disorder.<ref name=SIPA/> According to the chronicler [[Fernão Lopes]], Monsanto was a village that had been loyal to [[Beatrice of Portugal|Queen Beatrice]]. But, later however, Lopes listed the town among those aligned themselves with D. [[John I of Portugal|John]] by 1384. Beginning in the 1476, the area was reconstructed during the reign of King D. [[John I of Portugal|John I]], resulting in the construction of a barbican and protection over the well, a large {{convert|15|m|ft}} chamber that belonged to the Castro family (later identified as providing abundant water for the site).<ref name=SIPA/> By 1496, the ''[[Inquirições|Inquirição]]'' indicated 309 inhabitants.<ref name=SIPA/>
At the beginning of the 16th century, there was a graphic survey by Duarte de Armas for his [[Book of Fortresses]], designing the castle with two access gates (the oldest opened to the cliffs) and protected by two towers. In total there were four towers, a keep and cistern. The ''Torre do Pião'' (lookout tower) was in ruins at that time.<ref name=SIPA/> Supported by an alcalde, the urban nucleus included the parish of São Miguel and the parish of São Salvador. In the late 16th century, there was work performed during the reign of King D. [[Manuel I of Portugal|Manuel I]].<ref name=SIPA/>
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