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The man and his partner, who are parents to an eight-year-old, are taking business classes at Te Wānanga O Aotearoa in Ōtara, South Auckland.
While his partner is eligible for a student allowance, he is not, because he used up his quota years ago.
He has depression and anxiety, so is not seeking work. He is too old for a student loan and he has been told that going on a sickness benefit will affect his partner's benefit, which will leave them struggling.
The man, who asked to remain anonymous, thought that enrolling in a night course would give him confidence and set him up for work or even starting a business.
"It's something that I've always wanted to do, to get more business-minded and to be able to run a business that I'm happy with and my partner's happy with and also maybe grow a legacy with our daughter, but just at the moment it's going nowhere fast."
He has been told by StudyLink that if he and his partner both want to access full benefits, one of them will have to give up their studies.
Work and Income told his Auckland Action Against Poverty advocate that he was not entitled to the student allowance because, at 55, he was too old and had studied in the past.
His other option is to withdraw from study and become a 'dependent partner' - which will boost their income up to just under $500.
He said the system had tunnel vision.
"They're saying, you know 'people should get off the benefit and go and do a job or do a course'.
"So what I am doing? We're doing things the honest way and that's to go out and do a course that is free."
He said stopping study could seriously affect his mental health and the family was already struggling.
"There is nothing positive for us to focus on because our money's just gone. We don't even see our money basically ... and it shouldn't be that way."
He has chosen to stay on the course but isn't getting any support from the government, meaning his family is surviving off his partner's student allowance and the families tax credit - around $340 a week.
If they were allowed to retain their benefits while studying they would have an extra couple of hundred dollars a week.
The couple's beneficiary advocate Alastair Russell, from Auckland Action Against Poverty, said Work and Income was not putting people first.
"What they are looking at is a rigid interpretation of a set of legislation and ignoring other legislation, which allows them to use discretion to meet this couple's needs.
"The culture within Work and Income remains toxic and we have a government that will not change any of the legislation, which allows Work and Income to act in brutal ways towards people.
"If we don't change the legislation ... we change nothing."
In recent weeks, Prime Minister Jacinda Ardern has called upon welfare providers to act with kindness and flexibility towards people seeking support.
In a statement, the lead ministry for StudyLink and Work and Income, the Ministry of Social Development, said it would look into the case fully today and make sure the couple get all the support they are entitled to.
A government overhaul of the welfare system has been promised as part of the coalition agreement with the Green Party.