diff --git a/lib/mrsk/cli/accessory.rb b/lib/mrsk/cli/accessory.rb
index 90a4be2a..cf3775ec 100644
--- a/lib/mrsk/cli/accessory.rb
+++ b/lib/mrsk/cli/accessory.rb
@@ -18,7 +18,8 @@ class Mrsk::Cli::Accessory < Mrsk::Cli::Base
     accessory = MRSK.accessory(name)
     on(accessory.host) do
       accessory.files.each do |(local, remote)|
-        execute *accessory.make_directory_for(local, remote)
+        accessory.ensure_local_file_present(local)
+        execute *accessory.make_directory_for(remote)
         upload! local, remote
         execute :chmod, "755", remote
       end
diff --git a/lib/mrsk/commands/accessory.rb b/lib/mrsk/commands/accessory.rb
index d9542967..894d2530 100644
--- a/lib/mrsk/commands/accessory.rb
+++ b/lib/mrsk/commands/accessory.rb
@@ -46,10 +46,6 @@ class Mrsk::Commands::Accessory < Mrsk::Commands::Base
     ).join(" "), host: host
   end
 
-  def make_directory_for(local, remote)
-    if Pathname.new(local).exist?
-      [ :mkdir, "-p", Pathname.new(remote).dirname.to_s ]
-    else
   def exec(*command, interactive: false)
     docker :exec,
       ("-it" if interactive),
@@ -73,10 +69,16 @@ class Mrsk::Commands::Accessory < Mrsk::Commands::Base
     exec_over_ssh "bash", host: host
   end
 
+  def ensure_local_file_present(local)
+    if !local.is_a?(StringIO) && !Pathname.new(local).exist?
       raise "Missing file: #{local}"
     end
   end
 
+  def make_directory_for(remote)
+    [ :mkdir, "-p", Pathname.new(remote).dirname.to_s ]
+  end
+
   def remove_files
     [ :rm, "-rf", service_name ]
   end
diff --git a/lib/mrsk/configuration/accessory.rb b/lib/mrsk/configuration/accessory.rb
index 163742cd..5d36063c 100644
--- a/lib/mrsk/configuration/accessory.rb
+++ b/lib/mrsk/configuration/accessory.rb
@@ -46,7 +46,7 @@ class Mrsk::Configuration::Assessory
   def files
     specifics["files"]&.to_h do |local_to_remote_mapping|
       local_file, remote_file = local_to_remote_mapping.split(":")
-      [ expand_local_file_path(local_file), expand_remote_file_path(remote_file) ]
+      [ expand_local_file(local_file), expand_remote_file(remote_file) ]
     end || {}
   end
 
@@ -65,18 +65,26 @@ class Mrsk::Configuration::Assessory
       { "service" => service_name }
     end
 
-    def expand_local_file_path(local_file)
-      Pathname.new(File.expand_path(local_file)).to_s
+    def expand_local_file(local_file)
+      if local_file.end_with?("erb")
+        read_dynamic_file(local_file)
+      else
+        Pathname.new(File.expand_path(local_file)).to_s
+      end
     end
 
-    def expand_remote_file_path(remote_file)
+    def expand_remote_file(remote_file)
       service_name + remote_file
     end
 
     def remote_files_as_volumes
       specifics["files"]&.collect do |local_to_remote_mapping|
         _, remote_file = local_to_remote_mapping.split(":")
-        "$PWD/#{expand_remote_file_path(remote_file)}:#{remote_file}"
+        "$PWD/#{expand_remote_file(remote_file)}:#{remote_file}"
       end || []
     end
+
+    def read_dynamic_file(local_file)
+      StringIO.new(ERB.new(IO.read(local_file)).result)
+    end
 end
diff --git a/test/configuration/accessory_test.rb b/test/configuration/accessory_test.rb
index 1bc42a0a..54c39bfa 100644
--- a/test/configuration/accessory_test.rb
+++ b/test/configuration/accessory_test.rb
@@ -90,4 +90,11 @@ class ConfigurationAccessoryTest < ActiveSupport::TestCase
     assert_equal ["--volume", "$PWD/app-mysql/etc/mysql/my.cnf:/etc/mysql/my.cnf", "--volume", "$PWD/app-mysql/docker-entrypoint-initdb.d/structure.sql:/docker-entrypoint-initdb.d/structure.sql"], @config.accessory(:mysql).volume_args
     assert_equal ["--volume", "/var/lib/redis:/data"], @config.accessory(:redis).volume_args
   end
+
+  test "dynamic file expansion" do
+    @deploy[:accessories]["mysql"]["files"] << "test/fixtures/files/structure.sql.erb:/docker-entrypoint-initdb.d/structure.sql"
+    @config = Mrsk::Configuration.new(@deploy)
+
+    assert_equal "This was dynamically expanded", @config.accessory(:mysql).files.keys[2].read
+  end
 end
diff --git a/test/fixtures/files/structure.sql.erb b/test/fixtures/files/structure.sql.erb
new file mode 100644
index 00000000..102f8132
--- /dev/null
+++ b/test/fixtures/files/structure.sql.erb
@@ -0,0 +1 @@
+<%= "This was dynamically expanded" %>
\ No newline at end of file