diff --git a/TODO.md b/TODO.md
index 8552100..79abbe2 100644
--- a/TODO.md
+++ b/TODO.md
@@ -2,13 +2,17 @@
 
 ## DeploymentConfig
 
+- Content is not rendering correctly (need to read file instead of passing filename)
+- Directory is there twice
 - Don't upload configs if they already exist
 - Use `service` instead of `deployment` for config generation
 - Make `config` part of a `deployment`
+- Tests should go through the whole flow and actually upload something
 
 ## Bugs
 
 - If the container count changes, it is mixing up stopping with replacing
+- Changing order of role/service definitions should not change the version
 
 ## Naming
 
diff --git a/lib/cove/configuration/service.rb b/lib/cove/configuration/service.rb
index eed89c4..e775792 100644
--- a/lib/cove/configuration/service.rb
+++ b/lib/cove/configuration/service.rb
@@ -26,6 +26,7 @@ def roles
             ports: role_config["ingress"],
             mounts: role_config["mounts"],
             environment_variables: role_environment,
+            configs: role_config["configs"],
             hosts: role_config["hosts"].map { |host_id| @host_registry[host_id] }
           )
         end
diff --git a/lib/cove/deployment.rb b/lib/cove/deployment.rb
index 287bd67..8692ace 100644
--- a/lib/cove/deployment.rb
+++ b/lib/cove/deployment.rb
@@ -55,7 +55,7 @@ def labels
     private
 
     def build_version
-      Digest::SHA2.hexdigest([role.id, role.image, role.command, role.environment_variables, role.ports].to_json)[0..12]
+      Digest::SHA2.hexdigest([role.id, role.image, role.command, role.environment_variables, role.ports, role.configs].to_json)[0..12]
     end
   end
 end
diff --git a/lib/cove/deployment_config.rb b/lib/cove/deployment_config.rb
index 3ce2380..bbec9dd 100644
--- a/lib/cove/deployment_config.rb
+++ b/lib/cove/deployment_config.rb
@@ -2,6 +2,8 @@ module Cove
   class DeploymentConfig
     def self.prepare(registry, deployment)
       entries = deployment.configs.map do |name, definition|
+        # TODO: Make sure we always symbolize keys when parsing the config
+        definition = definition.with_indifferent_access
         Entry.new(
           registry: registry, deployment: deployment,
           name: name, source: definition[:source],
diff --git a/lib/cove/deployment_config/config_file.rb b/lib/cove/deployment_config/config_file.rb
index 70099a0..20f37f3 100644
--- a/lib/cove/deployment_config/config_file.rb
+++ b/lib/cove/deployment_config/config_file.rb
@@ -7,6 +7,11 @@ def initialize(path:, content:)
         @path = path
         @content = content
       end
+
+      def directory
+        dir = File.dirname(path)
+        dir unless dir == "."
+      end
     end
   end
 end
diff --git a/lib/cove/deployment_config/entry.rb b/lib/cove/deployment_config/entry.rb
index e4a9259..74a6d3c 100644
--- a/lib/cove/deployment_config/entry.rb
+++ b/lib/cove/deployment_config/entry.rb
@@ -18,7 +18,7 @@ def digestables
       end
 
       def directories
-        files.map(&:directory).uniq
+        files.map(&:directory).compact.uniq
       end
 
       def files
diff --git a/lib/cove/invocation/service_up.rb b/lib/cove/invocation/service_up.rb
index 86e943c..ac6a733 100644
--- a/lib/cove/invocation/service_up.rb
+++ b/lib/cove/invocation/service_up.rb
@@ -48,8 +48,10 @@ def initialize(connection, registry, service, roles)
         def run
           roles.each do |role|
             deployment = Deployment.new(role)
+            config = DeploymentConfig.prepare(registry, deployment)
 
             Steps::EnsureEnvironmentFileExists.call(connection, deployment)
+            Steps::EnsureConfigsExist.call(connection, config)
             Steps::PullImage.call(connection, deployment)
             Steps::CreateMissingContainers.call(connection, deployment)
             Steps::RollContainers.call(connection, deployment)
diff --git a/lib/cove/role.rb b/lib/cove/role.rb
index dbc555c..251249d 100644
--- a/lib/cove/role.rb
+++ b/lib/cove/role.rb
@@ -23,7 +23,7 @@ class Role
     # @return [String] The name of the service this role belongs to
     delegate :name, to: :service, prefix: true
 
-    def initialize(name:, service:, hosts:, container_count: 1, command: [], environment_variables: {}, ports: [], mounts: [], configs: [])
+    def initialize(name:, service:, hosts:, container_count: 1, command: [], environment_variables: {}, ports: [], mounts: [], configs: {})
       @name = name
       @service = service
       @hosts = hosts
diff --git a/lib/cove/steps/ensure_configs_exist.rb b/lib/cove/steps/ensure_configs_exist.rb
index 869fe48..887e661 100644
--- a/lib/cove/steps/ensure_configs_exist.rb
+++ b/lib/cove/steps/ensure_configs_exist.rb
@@ -1,6 +1,8 @@
 module Cove
   module Steps
     class EnsureConfigsExist
+      include Callable
+
       attr_reader :connection, :deployment_config
 
       def initialize(connection, deployment_config)