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Here, dissociable Siamese nanoparticles (SIANPs) are developed for tumor cell\u2010targeted delivery of epi\u2010drug CM\u2010272 and MDSC\u2010targeted delivery of small molecule inhibitor Ibrutinib. The SIANPs are assembled via interparticle DNA annealing and detached via tumor microenvironment\u2010triggered strand separation. Such binary regulation induces endogenous retrovirus expression and immunogenic cell death in tumor cells while restraining the immunosuppressive effects of MDSCs, and synergistically promotes dendritic cell maturation and CD8<jats:sup>+<\/jats:sup> T cell activation for tumor inhibition. Significantly, immune microenvironment remodeling via SIANPs further overcomes tumor resistance to immune checkpoint blockade therapy. 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