To fuel her gambling addiction, an accounts executive forged 21 company cheques totalling more than $300,000 over five months.
This is Tay Hui Ling's third brush with the law for similar offences - having been jailed twice before, in 2001 and 2008.
The 42-year-old was yesterday sentenced to seven years of corrective training, a prison regime for repeat offenders with no remission for good behaviour.
She was employed by real estate firm Murray. Its director, Mr Satinder Singh Garcha, 44, is a high-net-worth, India-born Singapore citizen who has invested $250 million in recent years buying heritage properties and converting them into upmarket hotels here and in Santiago, Chile.
Tay had admitted to eight of 21 charges of forging OCBC Bank cheques purportedly issued by Murray. The total amount involved in all the charges is $366,242.
The court heard that Tay, who joined the company in October 2015, was entrusted with a blank OCBC chequebook so that she could issue cheques to its clients and creditors. Between Dec 1, 2015, and April 28 last year, she executed a scheme involving the blank cheques.
She would insert her name as payee, fill in the amount to be paid to her and fraudulently sign off as Mr Singh, who is the authorised signatory.
She then either deposited these cheques into her own bank account or encashed them and obtained cash directly from the bank.
Mr Singh, who is also known for captaining the Singapore polo team to a SEA Games silver medal, reported her to the police on May 5 last year after Tay had come clean.
No restitution has been made.
The court heard that Tay had gambled away the money obtained.
The maximum penalty for forgery is 15 years' jail and a fine.