Patrick Crowley stepped down as CEO of York Teaching Hospital NHS Foundation Trust after announcing his retirement last May and has since been replaced by deputy chief executive Mike Proctor.
The search for a new boss began in July and a two-day selection process took place in September.
However, after months of scouring, the trust is yet to find a suitable candidate and has re-advertised the post.
The job advert says the trust is seeking "an outstanding individual who will bring visible, inspirational leadership as well as resilience and substantial experience at a very senior level of a complex healthcare organisation".
It also goes on to say that the successful candidate "will have the opportunity to shape and transform the delivery of services to our communities, including with the creation of a comprehensive Combined Emergency Assessment Unit at Scarborough Hospital following our successful Â£40 million capital bid".
Applications for the post close on tomorrow (Friday) with interviews being held on 28 and 29 January.
A spokesperson from the trust said: “Our first round of recruitment didn’t find anyone appointable, despite the excellent field of candidates, as we were unable to identify a candidate who fitted exactly with the needs of the Trust and our wider health economy.
“We have continued our search for a new chief executive and the post is currently being advertised. We expect to appoint in the coming weeks.”