In Express, middleware can run conditionally by checking request details like path. When a request comes in, middleware checks if the condition is true. If yes, it runs its code; if no, it calls next() to skip itself and let other middleware or route handlers run. This lets you run middleware only for certain routes or situations. For example, middleware can check if req.path equals '/special' and run only then. If the condition is false, it calls next() to continue. This prevents blocking the request. Always remember to call next() when skipping middleware, or the request will hang. This trace shows requests with different paths and how middleware runs or skips based on the condition.