Days after the Islamic State in Iraq and Syria (ISIS) declared its caliphate in June 2014, Singaporean Imran Kassim took an oath of allegiance to the group's leader Abu Bakr al-Baghdadi.
Imran, now 34, tried to make his way to Syria at least twice and was so deeply radicalised that he was prepared to attack Singapore Armed Forces troops deployed in the global coalition against ISIS, or hold them as hostages to demand ransom from the Government.
The Ministry of Home Affairs (MHA) released details of his radicalisation in a statement on his arrest and detention under the Internal Security Act (ISA) yesterday.
Since May, the managing director of a logistics company had also harboured intentions of joining pro-ISIS militants in Marawi, who are battling Philippine forces.
He was one of two Singaporeans arrested in July for terror-related activities. The other person is female administrative assistant Shakirah Begam Abdul Wahab, 23, who was issued a Restriction Order (RO) that limits her activities for having made and maintained contact with foreign fighters.
The ministry said Imran's radical, pro-militant views attracted the attention of those close to him, who reported him to the authorities.
Investigations by the Internal Security Department found he had travelled to Syria in February 2014 to oversee the delivery of humanitarian aid to a refugee camp which his company was handling.
"At the refugee camp, he had intended to slip away from his hosts and make his way to join ISIS, but was unsuccessful," said MHA.
In March 2015, he contacted a pro-ISIS foreign contact in a bid to enter Syria to join the terror group, but did not get a reply.
Imran also tried to galvanise support for ISIS on social media, using different accounts and personas to post pro-ISIS material. He also tried - unsuccessfully - to influence some of his friends with his views.
His intention to take up arms in conflict zones abroad was not confined to Syria, and he had previously wanted to join the Bangsamoro Islamic Freedom Fighters in the southern Philippines, MHA added.
S. Rajaratnam School of International Studies senior analyst Jasminder Singh said Imran probably had an interest in joining the conflict in Syria and used the humanitarian mission as an "excuse" to travel there.
"There will be more scrutiny of humanitarian groups now. They have to... be on the lookout for indivi- duals who might be radicalised and use this opportunity to join armed groups," he said.
"We cannot let Singapore's image in humanitarian circles be tainted."
Company records and information on Imran's career history paint a picture of an educated man who was well-heeled and well-travelled.
A political science graduate, he lived in a terraced house and ran a family firm involved in air and sea freight forwarding.
For ISEAS - Yusof Ishak Institute research fellow Norshahril Saat, the arrest drove home the point that "anyone can be radicalised".
"We need to go deeper and see what triggered this; it could be personal problems. This is why it is important for families and communities to be vigilant," he said.
Minister-in-charge of Muslim Affairs Yaacob Ibrahim said in a Facebook post that the incident underscores the importance of friends and loved ones staying vigilant, and seeking help for those with signs of radicalisation. "Those close to Imran had come forward to seek help and guidance when he tried to influence them. This is the right thing to do."
As for Shakirah, MHA said she first contacted ISIS fighters in 2013 after reading about the Syrian conflict in media reports and online.
She came across social media details of a foreign fighter, contacted him, and over time formed a network of several foreign fighters.
"The investigation showed that Shakirah maintained contact with the foreign fighters mainly because she enjoyed their attention, and not because she had been deeply radicalised by the violent propaganda of ISIS," said MHA. She stopped contacting them early last year, but continued to keep herself informed of developments in Syria.
"Shakirah has demonstrated a propensity to engage in risky behaviour, which renders her vulnerable to adverse influence and recruitment by terrorists who belong to a group that poses a security threat to Singapore," MHA added.
The arrests come as the terror threat here is at its highest in years, and as the authorities ramp up public education and security exercises.
Yesterday, MHA also said ISA detainees Amiruddin Sawir, 54, and Muhammad Harith Jailani, 20, were released last month and placed on ROs as they "have been cooperative and shown good progress in their rehabilitation".
And the RO of former Jemaah Islamiah member Samad Subari, 60, was allowed to lapse in July, as he was responsive to rehabilitation efforts and "no longer requires further supervision under the RO regime".