#
# Copyright 2015, Noah Kantrowitz
#
# Licensed under the Apache License, Version 2.0 (the "License");
# you may not use this file except in compliance with the License.
# You may obtain a copy of the License at
#
# http://www.apache.org/licenses/LICENSE-2.0
#
# Unless required by applicable law or agreed to in writing, software
# distributed under the License is distributed on an "AS IS" BASIS,
# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
# See the License for the specific language governing permissions and
# limitations under the License.
#

require 'net/http'

require 'serverspec'
set :backend, :exec

describe 'rackup' do
  context '/opt/rack1' do
    describe port(8000) do
      it { is_expected.to be_listening }
    end

    describe process('rackup') do
      it { is_expected.to be_running }
    end

    describe 'HTTP response' do
      subject { Net::HTTP.new('localhost', 8000).get('/').body }
      it { is_expected.to eq 'Hello world' }
    end
  end # /context /opt/rack1

  context '/opt/rack2' do
    describe port(8001) do
      it { is_expected.to be_listening }
    end

    describe 'HTTP response' do
      subject { Net::HTTP.new('localhost', 8001).get('/').body }
      it { is_expected.to start_with '/opt/rack2' }
    end
  end # /context /opt/rack2
end

#
# Copyright 2015, Noah Kantrowitz
#
# Licensed under the Apache License, Version 2.0 (the "License");
# you may not use this file except in compliance with the License.
# You may obtain a copy of the License at
#
# http://www.apache.org/licenses/LICENSE-2.0
#
# Unless required by applicable law or agreed to in writing, software
# distributed under the License is distributed on an "AS IS" BASIS,
# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
# See the License for the specific language governing permissions and
# limitations under the License.
#

require 'net/http'

require 'serverspec'
set :backend, :exec

describe 'rackup' do
  context '/opt/rack1' do
    describe port(8000) do
      it { is_expected.to be_listening }
    end

    describe 'HTTP response' do
      subject { Net::HTTP.new('localhost', 8000).get('/').body }
      it { is_expected.to eq 'Hello world' }
    end
  end # /context /opt/rack1

  context '/opt/rack2' do
    describe port(8001) do
      it { is_expected.to be_listening }
    end

    describe 'HTTP response' do
      subject { Net::HTTP.new('localhost', 8001).get('/').body }
      it { is_expected.to start_with '/opt/rack2' }
    end
  end # /context /opt/rack2
end

Remove the process check because rackup isn't run directly anymore.
Remove the process check because rackup isn't run directly anymore.

The important thing is that the app works anyway :)