Elon Musk had more extensive – and more friendly – communications with the financier and sex offender Jeffrey Epstein than previously publicly known, according to documents released on Friday by the Department of Justice. Emails in the files appear to show the two cordially messaging each other on two separate occasions to make plans for Musk to visit Epstein’s island.

The documents include Musk and Epstein emailing in both 2012 and 2013 to determine when Musk should make the trip to Little St James. Neither exchanges appear to have resulted in Musk visiting the island, due to logistical issues.

“Will be in the BVI/St Bart’s area over the holidays. Is there a good time to visit?” Musk states on 13 December 2013.

“any day 1st - 8th . play it by ear if you want. always space for you,” Epstein replies.

Musk then sends several emails relaying his schedule, and the two settle on 2 January as a date for the visit. The email exchange ends with Epstein telling Musk that he would need to remain in New York and sending his regrets that they could not meet.

“Bad news- Unfortunately , my schedule will keep me in New York . I was really looking forward to finally spending some time together with just fun as the agenda. so i am very disappointed. Hopefully we can schedule another time in the near future,” Epstein wrote.

In November 2012, Epstein sent Musk an email asking “how many people will you be for the heli to island”.

“Probably just Talulah and me. What day/night will be the wildest party on your island?” Musk replied. On 2 January 2013, Musk sent Epstein an email suggesting that the visit wouldn’t take place saying: “Logistics won’t work this time around.”

Musk has been harshly critical of those linked to Epstein, but the newly released emails appear to contradict his own longstanding denial of any ties of his own. The Tesla CEO told Vanity Fair in 2019 that Epstein was “obviously a creep” and claimed that Epstein “tried repeatedly to get me to visit his island. I declined.” The emails between the two moguls come years after Epstein was convicted in 2008 of soliciting prostitution from a minor in Florida. Authorities later arrested Epstein in 2019 on federal sex-trafficking charges.

A separate email in the documents shows Epstein’s longtime assistant Lesley Groff appearing to make plans for Epstein to have lunch at SpaceX in 2013, stating: “Elon Musk appreciates the invitation to the Ranch but has commitments… Lunch on Monday Feb.25th at 1pm at Space X is confirmed”. It is unclear whether the lunch took place or whether Musk was in attendance. Yet another series of exchanges from March 2013 features Epstein and Musk emailing back and forth after Epstein sends him congratulations a day after a SpaceX rocket launch.

A representative for Musk and his artificial intelligence company, xAI, did not immediately return a request for comment.

The newly released emails between Musk and Epstein, who was found dead in his prison cell in 2019 and for years has been the subject of speculation over his connections to some of the world’s most powerful people, are part of a tranche of 3 million documents that the justice department made public on Friday.

Musk has faced pressure to address any potential connection to Epstein in the past, including after an earlier justice department release of documents related to the investigation mentioned his name. House Democrats last year released a copy of Epstein’s daily schedule, which showed a calendar entry from 2014 that states “Reminder: Elon Musk to island Dec. 6 (is this still happening?)”. No other information was included, and Musk denied making plans for the visit in a post on X.

“This is false,” he wrote in response to a post that mentioned the allegations.

Musk has also denied knowing Epstein’s longtime co-conspirator Ghislaine Maxwell, claiming that a much-circulated photo of the two of them together at an event was because she “photobombed” him at a Vanity Fair party. Musk stated that he once visited Epstein’s Manhattan apartment “for about 30 minutes” with his ex-wife Talulah Riley as part of research for a book she was writing, but did not specify an exact date.

While he has denied a personal connection to Epstein, Musk has invoked the sex offender’s name to attack others. He claimed during his public falling-out with Donald Trump last year that the president’s name was in the Epstein files. He later appeared to delete his posts on X accusing Trump of ties to Epstein. Musk also insulted fellow tech mogul Bill Gates in May over the Microsoft founder’s relationship with Epstein, lashing out after Gates criticized him for cuts to humanitarian aid.

“Who does Bill Gates think he is to make comments about the welfare of children given that he frequented Jeffrey Epstein?” Musk said.