The number of online continuous education and training initiatives continues to increase in Caribbean Small Island Developing States (SIDS) and by extension, the number of adult learners who are unfamiliar with the peculiarities of the online teaching and learning environment. The extent to which these learners can derive maximum benefit from these initiatives depends on the rate at which they can adapt to the new circumstances and, as a result, function effectively in this type of teaching and learning environment. To this end, while supporting learners is recognized as a critical success factor little has been explored or documented specific to the Caribbean-SIDS context. The purpose of this study therefore was to describe the support services provided first time online learners in the context of Caribbean-SIDS and examine what if any benefit learners derived from them through their perceptions of these services. The findings reveal that participants’ overall perception of the support services was high. They also reveal that although participants’ awareness of ongoing support services was variable, their rating of the need for and importance of this type of support was also high. The findings suggest that providing support for first time online learners in the context of Caribbean SIDS positively impacts their performance in the online teaching and learning environment.