NEW YORK (JTA) – Here’s a riddle: If a transgender Jew shows up at an Orthodox synagogue, on which side of the mechitzah barrier separating the sexes should the person be seated?

That’s an easy one compared to more complex Jewish legal questions raised by people who don’t identify as the gender suggested by their physical anatomy at birth.

Is a woman who transitioned to male required to put on tefillin daily? Can a man who becomes a woman marry under Orthodox law? What about someone whose gender identity doesn’t fit binary categories? Can the circumcision requirement of conversion be waived if the convert is male but has no penis?

With the growing visibility of transgender people, these are no longer theoretical questions.

While American society generally grapples with how and how much to accommodate trans preferences, Jewish religious denominations are doing some unique grappling of their own.

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The more liberal movements have been the most progressive on transgender issues. But even in the Orthodox world, which presents the most barriers to transgender acceptance, both culturally and in Jewish law, some community figures are talking about the need to find a place for trans Jews.

“It’s something that has to be dealt with,” Rabbi Tzvi Hersh Weinreb, executive vice president emeritus of the Orthodox Union, told JTA. “I’ve read a lot about it and offered a range of opinions along with a plea for compassion. These are people who are going through difficulties. How do we reach out to them compassionately as human beings, as fellow Jews, as people we don’t want to lose from the Orthodox community?”

Last November, the Union for Reform Judaism passed a landmark resolution affirming transgender equality. It called on Reform institutions to adopt changes to embrace trans individuals without impediment: referring to them by their chosen identity, providing gender-neutral bathrooms, instituting sensitivity training for staff and community members, and making liturgical language more gender neutral. The trans equality resolution went further than any major religious denomination in America has gone – Jewish or non-Jewish.

In the Conservative movement, the Rabbinical Assembly’s Committee on Jewish Law and Standards is nearing a vote about what constitutes sufficient grounds in Jewish law for someone to change their gender: Is it enough to “present” in the new gender identity, or must there be at least hormonal change, or is sex reassignment surgery required?

There are practical implications to this question. Even in egalitarian Conservative Judaism, gender determines how one is prepared for burial, what kind of wedding ceremony one has (same-sex or traditional) and whether one must undergo a circumcision in order to convert.

The new proposed Conservative rule, drafted by Rabbi Leonard Sharzer, argues that gender identity should be broadly defined.

“A person with male anatomy who identifies as female and is presenting to the world as female in terms of dress and action, even if there has been no hormonal therapy or surgery, then in most situations we should apply halachah as it applies to their adopted gender,” Sharzer said, using the Hebrew term for Jewish law.

Meanwhile, the movement is making trans-friendly changes. The Jewish Theological Seminary recently designated two all-gender bathrooms, and the school’s application form has been changed so applicants can define their gender any way they choose rather than checking off boxes labeled male or female. Some rituals, too, have been adapted. For example, individuals may be called to the Torah without the traditional gender-specific language “son of” or “daughter of.” Instead, the person is identified as “of the family of.”

“We’ve tried to help students who do not want to identify according to strict binary categories,” said Rabbi Daniel Nevins, dean of the JTS rabbinical school. “I won’t claim we’ve got it all down. They have discreet needs that we’re trying our best to understand – and to embrace them, which is what we really want.”

Though most but not all Orthodox authorities who have considered the issue say the hallmarks of transgender identity – cross-dressing, hormonal treatment, sex reassignment surgery – are forbidden, that still leaves two key questions. One, if someone has surgically altered their anatomy, what gender are they according to Jewish law? And two, how should Orthodox communities strive to treat trans Jews?

READ: How ‘Transparent’ is reshaping views of transgender Jews

To be sure, in most Orthodox communities these are still largely theoretical questions, and there is no shortage of Orthodox Jews who don’t want to talk about or see transgender Jews in their shuls. And most Orthodox Jews who do come out as trans tend to leave Orthodoxy.

“Most people who are trans probably won’t feel comfortable remaining in the Orthodox community, which is sad but for the moment I think is a fact of life,” said Rabbi Mark Dratch, executive vice president of the Rabbinical Council of America, the nation’s main centrist Orthodox rabbinical association. “On the other hand, for those who want to stay Orthodox, there are the challenges of creating a safe space in a community where there’s lots of misunderstanding, prejudice and concerns about halachic complications.”

Dana Friedman, a 51-year-old trans Orthodox Jew, is familiar with many of those complications. She grew up modern Orthodox, left the community amid transitioning three decades ago and returned to Orthodox observance in 2008, when she felt things had changed enough for her to be accepted.

“It’s been eight years and nobody’s made a public fuss,” said Friedman, an information technology consultant in New York who dabbles in “Ortho tranny” standup comedy (it’s a very small genre). “Nobody has asked me to leave anyplace. And I have not heard that anybody has a real problem with me being in the women’s section.”

Rabbi Jeffrey Fox, the head at Yeshivat Maharat, a religious seminary for Orthodox women co-founded by the liberal-minded Rabbi Avi Weiss of Riverdale, has researched trans-related questions of Jewish law. Since he started lecturing publicly about the subject three years ago, he says he has been contacted by some 30 trans Jews in the Orthodox community.

“How can we help them have a meaningful Jewish life? I don’t think the answer is to tell them you just don’t belong in my shul,” Fox said. “This means we’re confronting questions we could never have imagined before.”

At first glance, Orthodox Jewish law might seem pretty clear-cut on gender transitions. Cross-dressing is explicitly prohibited in the Bible, and the Torah’s ban on castrating animals generally is understood to apply to humans, too. From the perspective of Jewish law, according to Weinreb, a Jew’s gender is unchangeable and determined solely by anatomy at birth, regardless of surgery or hormonal treatments.

However, there is ample rabbinic discourse about men who have lost their genitalia – once a more common happenstance due to warfare, accidents, disease and the prevalence of eunuchs. The Talmud also debates Jewish law as it relates to those born with both male and female physical characteristics, and those who appear to have neither.

In fact, the authoritative Code of Jewish Law known as the Shulchan Aruch makes clear that a prospective convert whose penis has been amputated may convert without circumcision.

Rabbi Eliezer Waldenberg, a leading Israeli Orthodox rabbinic figure known as the Tzitz Eliezer who died in 2006, suggested that a person’s gender was determined by their current anatomy. He ruled that a married person whose genitalia were surgically altered to that of the opposite sex would not require a get, or religious writ, to consummate divorce, since same-sex marriage is impossible according to Orthodox Jewish law. Many of the rulings by Waldenberg, who served as an Orthodox rabbinic authority for Jerusalem’s Shaare Zedek hospital, were not consensus views, however.

Fox said there are instances when Jewish law may support helping someone make a gender transition – namely, in cases where an individual is so distressed by gender dysphoria as to be suicidal. That’s actually quite common, Fox said, noting that the commandment of pikuach nefesh – saving a human life – should supersede restrictions against castration or cross-dressing.

If someone surgically alters their anatomy even in contravention of Jewish law, the question of what gender they are – and therefore what Jewish rituals they are required to observe – depends on which rabbinic opinion one follows.

In any case, most trans Jews are not asking rabbis for permission to undergo hormonal therapy or surgery, Fox noted. They’re making changes on their own, and are concerned about being welcomed in the community. The question, then, is how rabbis and Orthodox communities react.

“When you’re dealing with life and death issues, the question of whether you count in a minyan is secondary,” Fox said. “We have to make sure these people are safe and are welcomed.”

The quandary of how Orthodox communities should relate to people who have contravened Jewish law is not unique to transgender issues. Generations ago, Orthodox rabbis debated how to treat Jews known to violate the Sabbath or kosher laws, and whether they could be counted toward a minyan. More recently, Orthodox communities have been grappling with how to treat openly gay individuals.

Trans Jews should be treated just as sympathetically, said Rabbi Asher Lopatin, president of Yeshivat Chovevei Torah, the “open” Orthodox rabbinical school also started by Weiss. He recalled helping an observant trans congregant at the Chicago synagogue he led for two decades figure out which side of the mechitzah to sit on. The community’s own comfort level figured into the decision, he said.

“These things are not always as binary and clear-cut as people think,” Lopatin told JTA. “LGBTQ issues at least have to get us to start thinking and being creative.”