Jamaica
I roamed onto the Digicel network during the 6 days I recently spent in Jamaica. I was in the Montego Bay and Negril areas.
My Nexus 5 automatically found the network and I had phone, SMS, and data service while still in the MBJ airport via Digicel. My Nexus 7 tablet would only work for SMS but no data service on Digicel. By the time I reached Negril my phone had dropped data service as well.
I have an app installed that I used to look at my connection, and saw that the data connection was not registering. After toggling airplane mode on and off to re-register, checking APN settings, and rebooting the phone, I finally got it to connect by trying to register on the other provider (Lime) and then selecting Digicel again. I fixed my tablet's connection the same way.
This was perplexing to me since my roaming in many other countries had just worked before. Once working, service was OK on 3G (HSPA, HSPA+) connections and painfully slow on Edge. Wiki updated with Jamaica Digicel added to the Americas section.