In this work, we analyse and demonstrate possible strategies to explore extended Higgs sector of the Minimal Supersymmetric Standard Model (MSSM). In particular we concentrate on heavy Higgs decays to electroweakinos. We analyse the Higgs to electroweakino decays in the allowed MSSM parameter space after taking into account 13 TeV LHC searches for supersymmetric particles and phenomenological constraints such as flavour physics, Higgs measurements and dark matter constraints. We explore some novel aspects of these Higgs decays. The final states resulting from Higgs to electroweakino decays will have backgrounds arising from the Standard Model as well as direct electroweakino production at the LHC. We demonstrate explicit kinematical differences between Higgs to electroweakino decays and associated backgrounds. Furthermore, we demonstrate for a few specific example points, optimised analysis search strategies at the high luminosity LHC (HL-LHC) run. Finally, we comment on possible search strategies for heavy Higgs decays to exotic final states, where the lightest chargino is long lived and leads to a disappearing track at the LHC.