  The collimation and evolution of relativistic outflows in $\gamma$-ray bursts
(GRBs) are determined by their interaction with the stellar envelope through
which they travel before reaching the much larger distance where the energy is
dissipated and $\gamma$-rays are produced. We consider the case of a Poynting
flux dominated relativistic outflow and show that it suffers strong
inverse-Compton (IC) scattering drag near the stellar surface and the jet is
slowed down to sub-relativistic speed if its initial magnetization parameter
($\sigma_0$) is larger than about 10$^5$. If the temperature of the cocoon
surrounding the jet were to be larger than about 10 keV, then an optically
thick layer of electrons and positrons forms at the interface of the cocoon and
the jet, and one might expect this pair screen to protect the interior of the
jet from IC drag. However, the pair screen turns out to be ephemeral, and
instead of shielding the jet it speeds up the IC drag on it. Although a high
$\sigma_0$ jet might not survive its passage through the star, a fraction of
its energy is converted to 1-100 MeV radiation that escapes the star and
appears as a bright flash lasting for about 10 s.
