Yes, you can use both. While rare, there actually are some use cases when using both a VPN and a proxy server is the best approach. Two common stacks exist:
- Proxy over VPN: you first connect to the VPN (encrypted tunnel, new IP), then set an app to use a proxy server. This way, the sites see the proxy’s IP while your hop to it stays encrypted.
- VPN over proxy: your VPN client connects through a proxy (HTTP/SOCKS) to reach the VPN server. This can be useful when direct VPN traffic is blocked or rate-limited.
Keep in mind that both of these methods come with risks, which is why it's important to weigh them beforehand. As you add latency, more moving parts, and a larger trust surface, misconfigurations can leak DNS or break logins, and troubleshooting gets more complicated.
These chains are niche but sometimes justified. Use cases include: multi-layer IP masking, navigating extreme network restrictions (strict firewalls, captive environments), or specialized, high-anonymity research where splitting metadata across layers helps.