The use of carbon nanotubes (CNTs) in the form of vertically aligned arrays or films has been of interest due to the super-compressible response and the ability to be used as electrical and thermal contacts. CNT arrays have shown the remarkable ability to react as foam-like structures and exhibit localized, coordinated buckling within specific regions. An understanding of the buckling region evolution and the resulting effects on the bulk CNT array response are important, unanswered fundamental questions necessary for the future application of CNT arrays. Here, we report on the low-cycle compression of bulk vertically aligned CNT arrays to observe initiation and growth of the buckling as a function of compressive strain and the contacting substrate material. A critical strain of ~5.5% is found above which the buckling region length increased and below which remained at or below the applied strain. The results are corroborated with nanoindentation on the surfaces, which indicate a stiffening of the near surface by 9.4%-16.5% with increasing applied strain. Also, contact substrates with different stiffness, lithium niobate and a polymer gel, were compared, which resulted in changes of ~32% in total array height after cyclic compression. Raman spectroscopy on CNT arrays before and after compressive deformation was performed observing repeatable vibrational shifts in the strained regions. Also, to observe the applicability of CNT arrays as contact sensors, electrical resistance change during compression was measured and found to increase by 4 times in the parallel versus vertical direction. Observation and results of the buckling region nature and relationship with applied strain and contacting substrates are important for applying the nanotube arrays to energy absorbing cushions, tunable dampers, thermal contacts, contact sensing, chemical sensing, or in sliding contact.