On Monday, Tesla and SpaceX joined some 130 other companies mostly from tech on a legal brief opposing the ban. Their additions to a list that already included Apple, Google, Facebook, and Microsoft were significant because their founder, Elon Musk, serves on Trump’s advisory business council.

The brief argues Trump’s order “violates the immigration laws and the Constitution” and “inflicts significant harm on American business, innovation and growth.” (There were also some notable holdouts, including Oracle, IBM, and Cisco.) Meanwhile, over 200 tech investors and entrepreneurs are planning to send Trump a letter today that looks past the ban, calling the order and a likely forthcoming crackdown on foreign worker visas “morally and economically misguided,” adding it will “inflict irreversible harm on the startup community and America’s ability to compete globally.”

Looking back, last year’s Republican primary offered plenty of signs that a breach between the industry and Trump was inevitable. The billionaire real estate developer was alone among the GOP frontrunners in declining to court the tech elite’s approval. While Jeb Bush called himself a “disruptor” and touted his Apple fanboy credentials, and Marco Rubio gave economic speeches at the Washington offices of tech giants like Google and Uber, Trump took the opposite tack, striking an actively hostile pose.

When Apple CEO Tim Cook resisted FBI pressure to help crack the San Bernardino attacker’s phone, Trump said he would have come down so hard on the executive, “his head would be spinning all of the way back to Silicon Valley.” That was after Trump said if elected, he’d force the company to “start building their damn computers and things in this country instead of in other countries.”

Other tech luminaries got their share of abuse, too: Trump singled out Amazon’s tax avoidance strategies, for example, proclaiming at one point, “if I become president, oh, do they have problems. They’re going to have such problems.”

Industry insiders took some heart when investor Peter Thiel joined Trump’s transition team, guaranteeing that the then-incoming president would at least be hearing from someone who spoke their language. But on the immigration debate that’s powered tech’s budding feud with the new administration, it’s not clear Thiel is an ally. Though Thiel himself is an immigrant, having arrived in the U.S. from Germany with his family in the 1970s, back in 2008 he reportedly donated $1 million to NumbersUSA, a group dedicated to reducing immigration to pre-1965 levels.

He’s declined to criticize the ban—though he hasn’t exactly endorsed it, either. And Palantir, a data-mining firm he cofounded that works with US Customs and Border Protection, didn’t join its industry brethren on the legal brief. Tech has other channels into the White House. Musk now looks to be the sector’s self-appointed ambassador to Trumpworld. And insiders say Trump son-in-law and senior advisor Jared Kushner has been solicitous. What fraying ties remain will soon be tested by the rollout of Trump’s new restrictions on visas for skilled foreign workers.