This paper endeavors to determine the accuracy of Google Translate in newspaper headlines from Kiswahili to English and vice versa, while using the human translator as the yardstick. Newspaper headlines in both Kiswahili and English were identified and randomly selected. Three human translators were used to so that the Google Translate translations could be measured against the human translators. The Relevance Theory was applied during the research. This study made use of both Qualitative and Quantitative Research Methodology and a Descriptive Research Design. Simple Random Sampling was used to select the data to be used while Purposive Sampling was used when choosing the human translators. Fifty data sets were tested, twenty-five of which were in Kiswahili while the rest were in English. Content analysis was thereafter applied to interpret the translation output. The study found that the human translator is more accurate than Google Translate. In addition, some human translations were found to slightly differ from Google translations in the wording but still had the same meaning. The study focused on the communicativeness of the translated data and found that some items translated exhibited meaning losses. It was found that Google Translate was able to accurately render the meaning of 28/50 (56%) of the instructions examined, implying that it is 56% accurate in translating Kiswahili to English and vice versa. Mistranslations were found to be more prevalent in the Kiswahili source data. This therefore means that sometimes miscommunication occurs as some items are not accurately rendered. This study thus offers useful insight on areas of intervention in Machine Translation, particularly Google Translate.