Historical quay walls, constructed in unreinforced masonry, play a crucial role in the infrastructure of many Dutch cities. Designed originally as gravity retaining walls, these structures are increasingly subjected to traffic loads due to vehicles operating on roads built on their backfill. This study conducts a preliminary numerical evaluation of a strengthening technique aimed at prolonging the service life of such quay walls, focusing on a specific case in Amsterdam. The strengthening method involves drilling tubular steel piles through the existing masonry to anchor into a stable soil layer, with the piles bonded to the masonry using low-shrinkage casting concrete. The assessment models the interaction between the strengthening technique and the existing quay structures, including a detailed simulation of the installation process, identified as critical for proper simulation of the structural behaviour. While the technique significantly enhances the quay's force capacity, an improvement in displacement capacity was not evident, highlighting the need for further investigation.