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The production of three Higgs bosons at hadron colliders can be enhanced by a double-resonant effect in the ℤ2-symmetric two-real-singlet extension of the Standard Model, making it potentially observable in future LHC runs. The production rate is maximized for large scalar couplings, which prompts us to carefully reconsider the perturbativity constraints on the theory. This leads us to construct a new set of 140 benchmark points that have a triple Higgs boson production cross-section at least 100 times larger than the SM value. Furthermore, we study the dynamics of the electroweak phase transition, both analytically at leading order, and numerically without the high-temperature expansion. Both analyses indicate that a first-order phase transition is incompatible with the requirement that both singlets have a non-zero vev in the present-day vacuum, as required by doubly-enhanced triple Higgs boson production. Allowing instead one of the singlets to remain at zero field value opens up the possibility of a first-order phase transition, while di-Higgs boson production can still be enhanced by a (single) resonance.