On 22 June 2019, Kiprop had a breakthrough to win the Kenyan African Games trials 5000 m in a time of 13:37.1.[4] Despite winning the trials, Kiprop was initially excluded from the Kenyan African Games squad for not meeting the 13:30.00 national standard, but an exception was later made to include him.[5][6] He would go on to win the championships in a time of 13:30.96, leading a Kenyan sweep of the medals in the event.[2] Kiprop went on to finish second at the 2019 Kenyan World Championship trials, but he was not selected for the Kenyan team.[7]
After a lull from 2020 to 2022, in late 2022 Kiprop had a resurgence in winning the 2022 Bangsaen10 road race. In 2023, he secured his second national podium placing, finishing runner-up in the 5000 m at the Kenyan champs.[1] In late 2023 he said his target was to make the 2024 Olympic Games team for Kenya.[3]