I think I figured out why some ships with reckless officers won't engage. If the difference in firepower is too heavily in favor of the enemy, reckless ships won't engage.
I noticed this when testing Hyperion builds. Lighter weapon builds refuse to engage multiple enemies, whereas heavier weapon builds will engage.
In the simulator the enemy fleet I used was 1 dominator, one medusa, two sunders, two hammerheads, and one mule. The loadouts are the following. The first is Heavy needler, pulse laser, and mining blaster with armored weapon mounts built in. It will not engage the enemy even with a reckless officer. The second loadout is Mining blaster, thumper, and ion pulser, with expanded mags built in. It will engage the enemy with a reckless officer.
While the second loadout has more officer skills, I don't think that is the issue as neither will properly engage a lone onslaught. When engaging an onslaught, both teleport onto it, and then immediately start retreating regardless of flux level. The onslaught of course has a significantly higher firepower than any lone ship in the above fleet, which is why I suspect it's an issue of the A.I. overcompensating when going against overwhelming firepower.
It should be noted this wasn't an issue last patch, and while it could be an artifact of removing safety overrides, I doubt it because other people are reporting similar issues.