Plant species reintroductions for the restoration of valuable habitats can only be achieved if the success is ensured over the long-term. This can be accomplished with adequate monitoring and understanding of interactions between the species we target for reintroductions and their habitats that have been heavily modified through time due to human activities. We want to increase the proportion of translocations reaching self-sustainability by providing monitoring guidelines completing the IUCN ones by reviewing success criteria used worldwide and assessing their relevance according to the species’ life history traits and timeframe. We aim to fill the lack of defined success criteria reported by previous studies with accurate success criteria embedded in an unifying framework taking into account the population dynamics in order to make monitoring a powerful tool for restoration. We review various translocations not only to create relevant monitoring guidelines but also to create a database to improve collaborations and knowledge sharing. Concerns are additionally rising about habitat quality and previous failures in translocations due to unsuitable sites with no further investigation conducted to improve the current knowledge status. We take advantage of the different biogeographical regions in Switzerland to revisit successful and unsuccessful old translocation sites which were anthropized and restored and compare the target species optimum values for various factors with the current conditions on site to see how it influences the populations’ viability. We investigate the influence of habitat’s quality on plant reintroductions playing a role in their long-term success with growing importance in a changing world.