Numerous landslips have affected the road in recent history, particularly around Undercliff Drive between Ventnor and Niton, which has resulted in sections being closed for repair on several occasions.

The road has had to be in part relocated and repaired due to coastal erosion at various times since it was built in the late nineteenth century, and this continues today.

In 1930 or thereabouts, the landowner Sir Charles Seely donated what was then a narrow track to the Isle of Wight Council for public use.

Some vestiges of the original track are still visible along the coast from Shippards Chine to the north west of the slumped area.

By February 2010, another land slip on the section between Brook and Hanover car park, brought the top of the cliff to about 5 metres from the edge of the road.

Due to the unusual geology of the area, with significant clay layers, it has long been vulnerable to weathering and underground watercourses causing erosion in the unstable landscape,[9] with various plans for a long-term stabilisation of the land (including the road) drawn up in the first decade of the 21st century, not without controversy.

[10] Allegations of irregularities regarding the contract to rebuild the road following a landslip in 2001,[11] which could have amounted to "criminal activity or public sector corruption" were investigated by Hampshire Police in November 2007,[12] several senior officers at Isle of Wight Council were suspended,[13] and John Lawson, the Deputy Chief Executive of the council was sacked after his resignation was refused.

[16] However, a significant landslip occurred on 8 February 2014[17] after an "unusually heavy and prolonged rain" while these works were in progress,[18] leading to the indefinite closure of the road to traffic, effectively cutting the numbered route into two separate sections.

Initial works were quickly halted when it became clear they had been carried out on land of unclear ownership in a Site of Special Scientific Interest without permission or consultation with statutory body Natural England.

[35] However, in February 2016, two years after the landslide, Island Roads confirmed that there was no evidence of bat habitation in the majority of the trees which would be affected by the planned works.