Regarding prisons: there are a lot of difficult issues there due to the trends of the last half-century in corrections. I litigated prisoners’ rights issues in the 1980s, and it was then a mess which has only gotten worse.
By and large, people unfamiliar with these custodial environments tend to assume there’s a lot more control and supervision than there really is. I represented one fellow who had suffered grave injuries in an assault that was entirely unwitnessed by guards, and that sort of thing was pretty typical. Mostly jail security was not about supervision; it was about trying to segregate inmates from one another based upon who might be likeliest to victimize whom.
Overcrowding may have actually been worse then than it is now, though the prevalence of private prison contractors has added more wrinkles to it all. The safety of inmates is one of those things which everyone says is a paramount concern, but which nobody has the resources to actually do much about.
So, “classification,” as they call it, is the key. A rather extreme case of this sort of thing was the Northern Irish situation when matters between Republicans and Unionists were particularly awful; they’d have a whole wing for Republican prisoners, a whole wing for Unionist prisoners, and another for “Ordinary Decent Criminals.” The point of the segregation is not to disadvantage one group or another (though I am sure that there may be cases where that’s been so) but to try to afford them all mutual protection from each other. You don’t want to be the lone Unionist in a room full of IRA men, or the lone Republican in a room of Unionists.
I can say from experience that when this is done badly, it can result in seven-figure damages and years of civil rights litigation. And that’s not because it was done badly in a group-by-group sense, but because it was done badly in terms of how some individual was placed in a population.
The first cases I saw of transgender prisoners were pretty straightforward in the sense that no mind was paid to this at all. Conditions were crowded and people just got jammed in however was convenient. For obvious reasons, men’s prisons already being hotbeds of rape, a man who identified himself as a woman was ordinarily not safe in such a place.
But, women’s prisons? Yes, the man who identifies himself as a woman will be much safer there, all else being equal. But he’s not the only one whose civil rights are at issue. There’s a whole prison full of women to think of. And, of course, we are often not dealing with the highest and best of people when we are sorting prison inmates.
This is all made worse by modern corrections practice. Many inmates spend most of their time in rather large dayrooms with a lot of other prisoners. Opportunities to segregate very small numbers of inmates for their own safety or the safety of others are limited, and of course solitary confinement is not only facility-limited but also quite cruel.
Add to this the unknown and somewhat unpredictable behavior of inmates, and it’s a mess.
I raise this just to say again that nuanced accommodation is the only path forward on these things. What types of institutions, and what kinds of accommodations therein, are appropriate for particular inmates in particular gender-identity categories is not an easy question and likely has to be determined on a highly invididualized basis if it’s to be of much use; and the way that the taxpayers never want to actually fund the penal institutions, the availability and quality of that individualized judgment will always leave a great deal to be desired. No simple answers here.