[5] Iswaran attended Saint Andrew's School and National Junior College[6] before graduating from the University of Adelaide with first class honours, where he read economics, which was provided for by a Colombo Plan scholarship.

[8][9] Throughout his political career, Iswaran concurrently held directorships in several organisations, including Quintiles Transnational, Sunningdale Tech,[10] Shin Corporation,[11] SciGen, PSA International, Sembcorp Industries,[12][13] and Hyflux.

[9] Iswaran made his political debut in the 1997 general election when he contested as part of a four-member People's Action Party (PAP) team in West Coast GRC and won with 70.14% of the vote, becoming a Member of Parliament.

[16] After the 2006 general election, on 1 April 2008, Iswaran was promoted to Senior Minister of State at the Ministry of Trade and Industry.

Writing in a reply to non-constituency Member of Parliament Hazel Poa, Public Service Minister-in-Charge and Education Minister Chan Chun Sing said that the CPIB had completed a “robust and thorough” investigation and assured that the case "will be put through the due legal process".

[37] Within almost 50 years, Iswaran is also the first minister to serve a jail term following Wee Toon Boon back in 1975 for corruption charges.

On 7 February 2025, after serving four months in prison, Iswaran was transferred to the home detention scheme to continue the rest of his sentence in the community.

As Iswaran served with good behaviour and therefore eligible for parole after two-thirds of his stipulated jail term (equivalent to eight months), he was allowed to transition to the home detention scheme halfway through his reduced sentence.

The decision was made after the prison authorities took into consideration Iswaran's low propensity to re-offend, his strong familial support and that he did not commit any institutional offence during his incarceration.