Quantum complexity has already shed light on CFT states dual to bulk geometries containing spacelike singularities [1][2][3]. In this work, we turn our attention to the quantum complexity of CFT/quantum gravity states which are dual to bulk geometries containing a naked timelike singularity. The appearance of naked timelike singularities in semiclassical limit is allowed in string theory, particularly in the context of holography, so long as they satisfy the Gubser criterion [4, 5] -those naked timelike singularities which arise in the extremal limits of geometries containing cloaked singularities are admissible. In this work, we formulate an analogous criterion for the appearance of naked timelike singularities based on holographic complexity. We study three specific cases of naked timelike singularities, namely the negative mass Schwarzschild-AdS spacetime, the timelike Kasner-AdS [6] and Einstein-dilaton system [7]. The first two cases are outright ruled out by the Gubser criterion while the third case is more subtle -according to the Gubser criterion the singularity switches from forbidden to admissible as the parameter α is dialed in the range [0, 1] across the transition point at α = 1/ √ 3. We probe all three geometries using two holographic complexity prescriptions, namely CA and CV. We propose a simple criterion that if the holographic complexity of a geometry with naked timelike singularities is less than that of empty AdS, then that singularity cannot arise in the semiclassical limit of a UV-complete theory of quantum gravity. Our study strongly suggests that action complexity (CA) is a sensitive tool to investigate timelike singularities, being in sync with Gubser criterion in all cases. On the other hand volume complexity (CV) turns out to be not a reliable tool to probe timelike singularities.