I got the impression Bonesaw thought Jack would know about the limitations of the safeguards due to having them and would be smart enough to only attack if he knew he could bypass them, rather than anyone with the safeguards being able to bypass them.
Oh yeah… that makes so much more sense.
Hm. Regent might be able to get some details out of him the same way he gathered information from Shadow Stalker, at least, so shogi might still be somewhat helpful to get past the protection, just in a different way.