Motivated by the Swampland Program, which addresses the difficulty of realizing de Sitter solutions in string compactifications, we study a toy de Sitter No-Scale Supergravity model and show that for particular choices of parameters it can be consistent with the Refined de Sitter Conjecture and the Trans-Planckian Censorship Conjecture. Then we add rolling dynamics and show that the theory can become stable along the imaginary direction, where it would otherwise be unstable. We then generalize to the case of multi-field rolling and de Sitter fields, finding the parameter space where they can be compatible with the Refined de Sitter Conjecture. The modified models with rolling fields can be used to construct Quintessence models to accommodate the accelerating expansion of the Universe.