James Smith pushed the woman 'multiple times' when she tried to stop him leaving without paying for £98 of goods, on April 4, said prosecutor Daniel Pietryka.
The 34-year-old kicked the woman, leaving her with 'pain and discomfort', when other members of staff tried to detain him, and he ran off.
Later on the same day he was challenged by staff after walking out of Asda without paying for a £200 trampoline, and he abandoned his trolley.
But then he walked back into the Wharf Road store and stole two bottles of whisky, Mr Pietryka added.
The court heard Smith was last in trouble in 2019, when he was jailed for theft in Cumbria.
Abbey Edwards, mitigating, said his addiction to heroin is ‘the only way he nows how to deal with the harsh reality of sleeping rough.’
“He was evicted from his supported accommodation when he turned up under the influence of drugs,” she added. “He is particularly remorseful about the assault.”
Probation officer Greg Rowe said that Smith’s substance misuse started when he left home aged 15.
He said Smith’s probation worker ‘spoke very positively of him, and said ‘he had been proactive in trying to tackle his issues.’
Smith, of Water Lane, Retford, admitted theft and common assault when he appeared at Mansfield Magistrates Court, on Tuesday.
He received a 12-month community order with a six-month drug programme. He must pay £100 compensation, with £85 costs and a £95 surcharge.