Motivated by the coincidence of scrambling time in de Sitter and maximum lifetime given by the $textit{Trans-Planckian Censorship Conjecture}$ (TCC), we study the relation between the de Sitter complementarity and the Swampland conditions. We study thermalization in de Sitter space from different perspectives and show that TCC implies de Sitter space cannot live long enough to be considered a thermal background. We also revisit $alpha$-vacua in light of this work and show that TCC imposes multiple initial condition/fine-tuning problems on any conventional inflationary scenario.