Joon Ian Wong and Christopher Groskopf of Quartz explain why Apple files so many of its trademarks for new products in Jamaica first:
It did this for Siri, the Apple Watch, macOS, and dozens of its major products months before the equivalent paperwork was lodged in the United States. Likewise, Google, Amazon, and Microsoft routinely file trademarks for their most important products in locales far flung from Silicon Valley and Seattle. These include Jamaica, Tonga, Iceland, South Africa, and Trinidad and Tobago—places where trademark authorities don’t maintain easily searchable databases.
In some ways it’s gotten harder and harder for Apple to maintain secrecy around many of its product launches—especially the ones that entail hardware, since the supply chain often makes sieves look watertight. Three people may be able to keep a secret if two of them are dead, but what about the hundreds if not thousands of people involved in the production of a new device?
Legal and regulatory hurdles make this more challenging as well: between the patent office and the FCC, there are a lot of government agencies who often need to be apprised of a new product in some fashion.
I doubt any tech news organization is quite at the point of bringing on a dedicated correspondent in Jamaica to check the trademark filings on a regular basis, but hey, there’s a nice little job niche.