Sultan Mahmud is associated with the Malay legend of Puteri Gunung Ledang which is about his failed courtship of a princess.
The death of Tun Perak changed Sultan Mahmud into a more responsible ruler, although his rule was turbulent in his twilight years.
It was turbulent since his administration was ineffective and weak, and that Tun Mutahir took bribes and anointed ministers on a whim.
[2] During the Portuguese admiral Diogo Lopes de Sequeira's visit to Malacca from 1509 to 1510, the sultan planned to assassinate him.
However, Sequeira learned of this plot and fled Malacca after losing a few followers to the sultan's guards.
When the famous Portuguese naval officer Afonso de Albuquerque received word, he decided to utilize this to embark upon his expeditions of conquest in Asia.
Mahmud Shah then moved south and with his capital on the island of Bintan (now part of Indonesia), southeast of Singapore, he continued to receive the tribute and allegiance from surrounding states that had rendered him as ruler of Malacca.