The vertical expansion of existing landfills can hold significant amounts of domestic waste and solve practical difficulties such as local government site selection. This research topic has become increasingly popular in the field of environmental geotechnical engineering. This study examined vertical expansion stability of landfills considering high leachate water level. The results showed the following. (1) Four slope instability modes for landfill vertical expansion are categorized according to the following slip surface positions: shallow slippage of the existing landfill, shallow slippage of the expanding landfill, interface slip between the existing landfill and expanding landfill, and deep slippage passes through the foundation soil. (2) The factor of safety decreases as the height of leachate level increases. When the height of leachate level rises from 2 m to 20 m, the factor of safety of the landfill is reduced by 13.2–15.4%. (3) As the vertical expansion height increases, the factor of safety of the existing landfill decreases, and when the expansion height increases to 30 m, the stability factor of safety of the old waste landfill is reduced by 4.83%. A landfill in Xi’an is considered as an example for the analysis, which shows that a leachate drainage layer can discharge leachate from the landfill body efficiently, reduce the leachate level height of the landfill body, and improve the stability of vertical expansion of the landfill. This study and its findings can be used as a reference for similar expansion projects.