Wellington city is characterised by steep hilly terrain, and as such several tunnels have been constructed since the beginning of the last century to provide critical transport access in the city. These tunnels are still used today as part of the city’s transport routes, while also being an integral part of the city’s history and heritage. Wellington is among the most seismically active areas in New Zealand. Three major active faults located within the Wellington Region and the proximity to the subduction zone are the main contributors to the high seismicity. The aging tunnels were designed and constructed prior to the advent of earthquake design standards and are subject to deterioration. Hence, they require maintenance and strengthening to ensure operational integrity and resilience to earthquake and other hazard events. Authorities have been supported by the authors in managing the risk through identifying key vulnerabilities, and prioritisation and implementation of strengthening measures. Best practice investigation and strengthening techniques have been applied through the process to ensure resilience and cost effectiveness. The paper presents case histories that highlight the value of investigations and assessment in understanding the risks, and novel strengthening measures developed to enhance resilience while preserving the heritage of the tunnels. Case histories include the seismic strengthening of the Hataitai Bus Tunnel, the Northland and Seatoun road tunnels and the investigation and assessment of the iconic Wellington Cable Car tunnels.