New revelations on Monday from the "Paradise Papers" shed light on Apple's tax avoidance strategy which shifted profits from one fiscal haven to another.
They are the latest disclosures from a trove of documents released by the US-based International Consortium of Investigative Journalists (ICIJ) concerning secretive offshore deals that have proved deeply embarrassing.
According to documents cited by the New York Times and BBC, the offshore legal services firm Appleby helped the iPhone maker shift tens of billions of dollars from Ireland to the Channel Islands when it appeared to face a tougher stand on taxes by Dublin.
The report said Apple transferred funds to the small island of Jersey, which typically does not tax corporate income and is largely exempt from European Union tax regulations.
Apple told the New York Times it follows the law in each country where it operates.
At a 2013 congressional hearing, Apple chief Tim Cook denied the use of "gimmicks" to avoid taxes. The company is now facing an EU demand for about $14.5 billion in taxes based on a ruling that its tax structure in Ireland amounted to illegal state aid.
Apple's questionnaire
After the EU announced in 2013 that it was investigating Apple's Irish arrangement, the Irish government decided that firms incorporated there could no longer be stateless for tax purposes.
In order to keep its tax rates low, Apple needed to find an offshore financial centre that would serve as the tax residency for its Irish subsidiaries.
In March 2014, Apple's legal advisers sent a questionnaire to Appleby, a leading offshore finance law firm and source of much of the Paradise Papers leak.
It asked what benefits different offshore jurisdictions - the British Virgin Islands, Bermuda, the Cayman Islands, Mauritius, the Isle of Man, Jersey and Guernsey - could offer Apple.
They also asked whether a change of government was likely, what information would be visible to the public and how easy it would be to exit the jurisdiction. Leaked emails also make it clear that Apple wanted to keep the move secret.Apple, Ireland versus the EU
In August 2016, after a three-year investigation, the European Commission finds that Ireland gave an illegal tax benefit to Apple.
The EC says Apple must repay Ireland taxes for the period within its remit of investigation, 2003-2013, a total of €13bn plus interest of €1bn. Ireland and Apple launch an appeal.
Apple's Tim Cook calls the EC ruling "total political crap", with "no reason for it in fact or in law". Ireland says the EU is encroaching on sovereign taxation. It fears multinationals will go elsewhere.
Ireland agrees to collect the €13bn, to be held in a managed escrow account pending the appeal verdict.
In October 2017, the EU says it will take Ireland to court as it has not yet collected the money. Ireland says it is complicated and it needs time.
