  After orientifold projection, the conifold singularity in hypermultiplet
moduli space of Calabi-Yau compactifications cannot be avoided by geometric
deformations. We study the non-perturbative fate of this singularity in a local
model involving O6-planes and D6-branes wrapping the deformed conifold in Type
IIA string theory. We classify possible A-type orientifolds of the deformed
conifold and find that they cannot all be continued to the small resolution.
When passing through the singularity on the deformed side, the O-plane charge
generally jumps by the class of the vanishing cycle. To decide which classical
configurations are dynamically connected, we construct the quantum moduli space
by lifting the orientifold to M-theory as well as by looking at the
superpotential. We find a rich pattern of smooth and phase transitions
depending on the total sixbrane charge. Non-BPS states from branes wrapped on
non-supersymmetric bolts are responsible for a phase transition. We also
clarify the nature of a Z_2 valued D0-brane charge in the 6-brane background.
Along the way, we obtain a new metric of G_2 holonomy corresponding to an
O6-plane on the three sphere of the deformed conifold.
