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Background Singapore’s national digital contact-tracing (DCT) tool—TraceTogether—attained an above 70% uptake by December 2020 after a slew of measures. Sentiment analysis can help policymakers to assess public sentiments on the implementation of new policy measures in a short time, but there is a paucity of sentiment analysis studies on the usage of DCT tools. Objective We sought to understand the public’s knowledge of, concerns with, and sentiments on the use of TraceTogether over time and their preferences for the type of TraceTogether tool. Methods We conducted a cross-sectional survey at a large public hospital in Singapore after the COVID-19 lockdown, from July 2020 through February 2021. In total, 4097 respondents aged 21-80 years were sampled proportionately by sex and 4 age groups. The open-ended responses were processed and analyzed using natural language processing tools. We manually corrected the language and logic errors and replaced phrases with words available in the syuzhet sentiment library without altering the original meaning of the phrases. The sentiment scores were computed by summing the scores of all the tokens (phrases split into smaller units) in the phrase. Stopwords (prepositions and connectors) were removed, followed by implementing the bag-of-words model to calculate the bigram and trigram occurrence in the data set. Demographic and time filters were applied to segment the responses. Results Respondents’ knowledge of and concerns with TraceTogether changed from a focus on contact tracing and Bluetooth activation in July-August 2020 to QR code scanning and location check-ins in January-February 2021. Younger males had the highest TraceTogether uptake (24/40, 60%), while older females had the lowest uptake (8/34, 24%) in the first half of July 2020. This trend was reversed in mid-October after the announcement on mandatory TraceTogether check-ins at public venues. Although their TraceTogether uptake increased over time, older females continued to have lower sentiment scores. The mean sentiment scores were the lowest in January 2021 when the media reported that data collected by TraceTogether were used for criminal investigations. Smartphone apps were initially preferred over tokens, but the preference for the type of TraceTogether tool equalized over time as tokens became accessible to the whole population. The sentiments on token-related comments became more positive as the preference for tokens increased. Conclusions The public’s knowledge of and concerns with the use of a mandatory DCT tool varied with the national regulations and public communications over time with the evolution of the COVID-19 pandemic. Effective communications tailored to subpopulations and greater transparency in data handling will help allay public concerns with data misuse and improve trust in the authorities. Having alternative forms of the DCT tool can increase the uptake of and positive sentiments on DCT.