As defence lawyer Rajan Nair read out Chan's mitigation to the court, what emerged was a picture of a man who had his life derailed after his fiancee died.
After graduating with a degree in civil engineering from Nanyang Technological University in 2006, Chan, the oldest of three sons, joined the Singapore Armed Forces (SAF) on a four-year contract under the SAF Local Study Award.
Promoted to the rank of captain in June 2009, he stayed in the SAF till 2013, when he left to be an insurance agent.
Some time in 2009, Chan's Taiwanese fiancee was diagnosed with womb cancer. She died in late 2010.
That also marked the start of Chan's depressive spiral, his lawyer said.
During his depression, Chan started exchanging obscene material on the Internet with like-minded individuals, Mr Nair said.
While he knew there was something wrong, he did not know where he could seek help.
"He was also apprehensive as to the effect the disclosure of his affliction would have on his career in the SAF, family and friends," his lawyer said.
By late 2012, he had stopped using the e-mail account that he previously used to exchange child pornography.
But some time in November 2013, he "foolishly acceded to requests from an 'Internet friend'" to help arrange a commercial sex trip.
This "friend" turned out to be an undercover policeman, his lawyer said.
After his arrest on March 1, 2014, Chan quit his job in the insurance industry in mid-2014 and worked as a civil engineer until August 2014, when he quit because he did not want his employer's reputation to be "tainted by their connection to him".
When the hearing was postponed in September 2014, he worked part-time in a fruit juice shop.
"The odium of being labelled a paedophile... will stay with him and his family members for the rest of their lives," Mr Nair said.
He added that Chan hoped for a lighter sentence so he may marry his fiancee and start a family.