Thanks for working on this, @joshkel! Experiencing the same exception accessing request.info.remoteAddress which brought me here.

Not a core maintainer so take my suggestions with a pinch of salt :)

FWIW, I'm not entirely convinced that there is a need to go through the whole rigmarole of creating a connection and destroying it for this case.

We could just simplify things down to something along the lines of:

it('handles when client address is undefined', async () => {

    const server = Hapi.server();
    server.route({
        method: 'get',
        path: '/',
        handler(request) {

            delete request.raw.req.socket.remoteAddress;
            return request.info.remoteAddress === undefined;
        }
    });
    const { result } = await server.inject('/');
    expect(result).to.equal(true);
});

I believe delete should be safe to use in this scenario.