On Tuesday (May 1), one of the biggest Cabinet shake-ups in recent years takes effect. The changes announced last week involve all but one ministry.
Insight looks at the four ministries that will see the biggest changes in terms of leadership: Education, Trade and Industry, Communications and Information, and Manpower.
What are the challenges ahead for their fourth-generation leaders when Parliament resumes on May 7?
And what are the main issues observers hope the new team can address?
Education: Preparing students for new jobs, helping needy kids
Preparing for jobs in the new economy and boosting students from poor backgrounds are two challenges ahead for the Ministry of Education (MOE), which will now come under one minister.
Mr Ong Ye Kung, 48, who oversees higher education and skills, will have an expanded role, taking over the schools portfolio from Mr Ng Chee Meng, who joins the National Trades Union Congress full time.
Manpower: Upgrading workers' skills, assisting those in gig economy
Questions about how to better protect workers who may fall through the cracks and help them reskill are among those the Ministry of Manpower's (MOM) new leaders will likely have to wrestle with, says Mr Zainal Sapari, deputy chairman of the Government Parliamentary Committee (GPC) for Manpower.
Take defining a living wage for workers. The Government has long refrained from following in the footsteps of other countries like Britain that have done so.
Trade and Industry: Boosting innovation, enterprise as trade war looms
With concerns mounting that Singapore could suffer collateral damage if an international trade war erupts, coupled with business anxieties over a restructuring economy, Mr Chan Chun Sing will have his plate full in his new role as Trade and Industry Minister.
Mr Chan, who read economics at Cambridge University and graduated with first-class honours, will take over the ministry on Tuesday.
COMMUNICATIONS AND INFORMATION: Leading Smart Nation push while curbing database breaches
Fake news, the Facebook-Cambridge Analytica data scandal, and fears over abuse of surveillance data amid plans by the Government to roll out an interconnected network of smart lamp posts here.
These are concerns that have dominated the headlines in recent months and illustrate the main challenge confronting the Ministry of Communications and Information (MCI) in the next session of Parliament: How to make the information landscape healthier for all amid the proliferation of information and technology in current times.
Issues other ministries face
PRIME MINISTER'S OFFICE
•Smart Nation efforts
•Immigration and integration
•Countering drug abuse
•Relations with the United States and China
•Malaysia's sovereignty claims over the island of Pedra Branca
•Implementing e-commerce tax
•Matching demand for infrastructure with supply of funds
•Potential legislation against deliberate online falsehoods
•Reforms to family justice system and civil law
•Disruptions to taxi and ride-hailing sector
•Long-term planning for land use needs
ENVIRONMENT AND WATER RESOURCES
•Implementing carbon tax
•Tackling climate change
•Integration of senior care services
SOCIAL AND FAMILY DEVELOPMENT
•Better coordination of help services