The story behind how we got to this situation dates back to the 1950's, when the area codes defined in the North American Numbering Plan (NANP) were introduced to the public as part of direct distance dialing (DDD). Until this time, all long distance calls had required operator assistance. The advent of DDD reduced the cost of long distance calls, increased ease of use, and increased the amount of traffic that could be handled. International direct distance dialing (IDDD) could only be dreamed of at the time; naturally, being part of the NANP would be a boon for the economies of other countries that might be included.
In addition to area codes for the U.S. and Canada, area code 809 was assigned to Puerto Rico and countries in the Caribbean. However, the rate structure for calls to Caribbean countries, remains largely dictated by charges imposed by the regulatory bodies of these countries, and can be as high as several dollars per minute.
Meanwhile, three relevant events occurred:
The purveyors of these premium services started looking for ways to circumvent these restrictions. They turned to "700" numbers, carrier access codes, and international calls using the "011" prefix. With international calls, they could advertise that there were no premium charges that applied, and customers who refused to pay the charges could actually have their local service canceled, unlike with 900 numbers. However, the "011" prefix helped to alert customers that they were calling an unusual number that might have extraordinary charges.
Area code 809 offered all the advantages of other international calls, without the disadvantage of the 011 prefix. While some consumers might recognize 809 as the area code for the Caribbean, many more might not realize that there could be high international long distance rates associated with such calls.
What happened next, though, created the untenable situation we have now. Puerto Rico was "kicked out" of the 809 area code, and all the other countries in area code 809 except for one got their own area codes assigned. Now there are about two dozen area codes for Caribbean countries, which are not obviously distinguishable from the dozens of area codes being introduced in the U.S. and Canada.
There are various technical solutions that could resolve this problem, that would not require the agreement of these other countries: