President Trump’s personal attorney Rudolph W. Giuliani has claimed that his discussions with Ukrainian officials have been at the request of the State Department, which remained fully abreast of his dealings.

But the details of the July 25 phone call between Trump and Ukrainian President Volodymyr Zelensky raise new questions about Giuliani’s role, reinforcing the view of some U.S. officials that he operates at the president’s behest, often in a closed loop, and occasionally in contravention to the messages of diplomats in Kiev.

Technically, it is illegal for private citizens to negotiate with a foreign government on behalf of the United States under the Logan Act, but the law has rarely been enforced.

Trump is not the first president to enlist a trusted outside adviser for a sensitive international mission, but Giuliani’s interventions sparked concern among U.S. officials in Kiev who said Ukrainians told them they were unsure if Giuliani was speaking for the U.S. government, according to two officials with knowledge of the matter who sought anonymity to discuss sensitive diplomatic exchanges.

After initially declining to discuss his conversations with Ukraine, President Trump on Sept. 22 appeared to acknowledge the two leaders discussed Joe Biden. (JM Rieger/The Washington Post)

Experts said the reason such tasks are usually left up to diplomats rather than nongovernment freelancers is to ensure that a foreign government receives a consistent message across the vast U.S. federal bureaucracy.

“Clearly it should be the full-time diplomats who know Ukraine well who should be dealing with all these issues,” said Angela Stent, a former Russia hand in the George W. Bush administration.

In the rough transcript of the call released Wednesday, Trump praises Giuliani as a “highly respected man” who was a “great mayor.”

“If you could speak to him that would be great,” Trump tells Zelensky.

The president asked Zelensky to work with Giuliani and Attorney General William P. Barr to investigate Democratic presidential candidate Joe Biden, and for help in finding the Democratic National Committee computer server that U.S. officials say was hacked by Russian intelligence in the run-up to the 2016 election.

The issue of corruption is particularly sensitive in Ukraine as it has dominated discussions between Washington and Kiev in the context of development and democracy assistance, said Stent and other Ukraine watchers.

“The U.S. has been trying to tell Ukrainians for years that they have to deal with their own corrupt system and implement the rule of law, otherwise they won’t get U.S. or IMF funding,” she said, referring to the International Monetary Fund. “And having someone else coming and representing the president and giving them a different message which is ‘we want you to find as much dirt as you can on the vice president’s son’ sends a mixed message.”

For months, Giuliani has been pressing the Ukrainian government behind the scenes, gathering information about Biden and briefing Trump on his findings, Giuliani told The Washington Post.

Earlier this year, Giuliani had planned a trip to Ukraine, but it was aborted amid criticism about the propriety of his visit. Instead, he has had phone calls and meetings with Ukrainian officials in New York and Madrid.

A day before the release of the transcript, Giuliani denied that he was pursuing an alternative Ukraine agenda in a Fox News interview. “You know who I did at the request of? The State Department,” he said while holding up his cellphone, suggesting that he maintained the call logs. “I never talked to a Ukrainian official until the State Department called me and asked me to do it. And then I reported every conversation back to them.”

Giuliani has said that Kurt Volker, the U.S. special representative for Ukraine, helped secure his discussions with a top aide to Zelensky, Andriy Yermak.

A State Department official said Giuliani “does not speak on behalf of the U.S. government” and added that Volker only helped set up the meeting at Yermak’s request. Yermak’s request to meet with Giuliani came after Trump requested that Zelensky speak with the former mayor in the July call.

U.S. Embassy officials in Kiev repeatedly expressed concern about the contacts between Giuliani and Ukrainian officials. They have not been privy to most of the discussions, and at times only learned about them later from the Ukrainians, U.S. officials said.

Giuliani told The Post he has had about five conversations with Yermak this year.

Andrew Weiss, a Russia scholar at the Carnegie Endowment for International Peace, said Giuliani’s efforts to launch an investigation into Biden’s son came at a particularly sensitive time in U.S.-Ukraine relations given the surprise victory of Zelensky, a political novice and former comedian, over President Petro Poroshenko this spring.

“When the new government was being formed, U.S. officials were trying to ensure continuity with the Zelensky government, but then Giuliani throws this grenade into Ukraine’s lap and forces them to take a side in American politics and Ukrainians were worried about that,” Weiss said. “None of what Giuliani was doing was connected to core priorities of U.S. diplomacy at the time.”

In May 2019, Giuliani also met with a top Ukrainian anti-corruption prosecutor, Nazar Kholodnytsky, in Paris. Kholodnytsky — who was caught on tape advising witnesses in corruption cases how to avoid prosecution — had faced calls to step down from the U.S. ambassador to Ukraine, Marie Yovanovitch.

But the meeting came at a triumphant moment for Kholodnytsky. He was holding on to his office. Yovanovitch had been recalled from her posting early.

Kholodnytsky declined to comment on the contents of his conversation with Giuliani, which he described as that of a “prosecutor to a former prosecutor.” But he has said that he believed something didn’t add up with the 2016 release of the “black ledger” that forced Trump campaign chairman Paul Manafort to resign, and that the investigation into Burisma, the energy company of which Hunter Biden was a board member, needed to be reopened.

Giuliani, when asked about his meeting with Kholodnytsky, said: “I’m not going to tell you about that.”

Hunter Biden served for nearly five years on the board of Burisma, Ukraine’s largest private gas company, whose owner came under scrutiny by Ukrainian prosecutors for possible abuse of power and unlawful enrichment. Hunter Biden was not accused of any wrongdoing in the investigation. As vice president, Joe Biden pressured Ukraine to fire the top prosecutor, Viktor Shokin, who Biden and other Western officials said was not sufficiently pursuing corruption cases. At the time, the investigation into Burisma was dormant, according to former Ukrainian and U.S. officials.

“It’s not a new phenomenon to have politically connected people swoop in and trade on their powerful relationships with the president,” said Weiss, who served in the George H.W. Bush and Clinton administrations. “But there’s never been a sense of so much mischievous and willful spinning on the formal ways the U.S. conducts foreign policy.”

Michael Birnbaum in Kiev and Josh Dawsey in Washington contributed to this report.