After the discovery of the standard model Higgs boson, the possibility of an extended Higgs sector has become even more interesting. The speaker presents searches for heavy Higgs bosons in a MSSM-like Higgs sector at the LHC and future pp-colliders. These searches make use of associated heavy Higgs production and cover the so far unprobed intermediate and low tan beta regions for large heavy Higgs masses. The speaker shows that the complicated signatures under consideration make it necessary to introduce search strategies based on boosted decision trees (BDT).