Singapore's outgoing High Commissioner to Malaysia, K. Kesavapany said Malaysia's leadership transition, the regional security situation and negotiations over bilateral issues would continue to be challenges for the two nations.
Ties between the two neighbours have not always been smooth sailing, and so Mr Kesavapany did not want to comment on any specifics of negotiations between Singapore and Malaysia.
He did say that because relations are always in the spotlight, there is a need to always look at the big picture.
Mr Kesavapany said: "Whatever the differences at the political level, I've always had access to the government leaders in Malaysia at all levels. This also was the same with officials at the foreign ministry, Wisma Putra...It is just that issues are complex and take time and one has to be patient that at the end of the day some resolution would be found."
One area he says has seen tremendous progress is people-to-people relations - in all sectors.
Youth leaders of political parties have exchanged visits and two out of three tourists who visit Malaysia are Singaporeans.
He is sure his successor will face challenging times.
Mr Kesavapany said: "Ashok Mirpuri is going to Malaysia at an exciting time. There is the transition of rule from Dr Mahathir to his successor and at a time when Malaysia and Singapore are grappling with regional and international issues."
The veteran diplomat will continue to share his insights as he takes up his post as Director of the Institute of Southeast Asian Studies (ISEAS) next month.