The files also reveal how Uber's relationship with one of Europe's top officials, European Commission vice-president Neelie Kroes, began significantly earlier and ran deeper than previously was known, putting her in an apparent breach of rules governing commissioners' conduct.
They reveal she was in talks to join Uber's advisory board before she even left her last European post in November 2014.
EU rules say commissioners have to respect a "cooling-off" period, then 18 months, during which new jobs require the approval of the commission.
As a commissioner, Ms Kroes oversaw digital and competition policy, and was a high-profile scourge of big tech, playing a leading role in hitting Microsoft and
Intel with massive fines.
But of all the companies she could have worked for after leaving, Uber was a particularly controversial choice.
In her home country, the Netherlands, the UberPop ridesharing service had also brought legal and political trouble.
Uber drivers were arrested in October 2014, and that December a judge in the Hague banned UberPop, threatening fines up to 100,000 euros. In March 2015, Uber's Amsterdam office was raided by Dutch police.
Emails say that Ms Kroes called ministers and other members of the government to persuade them to back down during the raid.During another raid a week later, Ms Kroes again contacted a Dutch minister the Uber Files show, and, in the words of an email, "harassed" the head of the Dutch civil service.