diff --git a/README.md b/README.md
index aa17e74..fd4034f 100644
--- a/README.md
+++ b/README.md
@@ -22,6 +22,9 @@ This GitHub Action provides the following features:
   with `.templateignore` in the root directory in the same format as
   `.gitignore`. Follow the [glob pattern][glob-pattern] in defining the files
   and folders that the action should excluded.
+- Add support for updates and removal of files inside the downstream repository
+  as configured inside the `cookiecutter.json` file, allowing easier migration
+  of existing files and removal of old files as part of standard updates.
 
 [glob-pattern]: https://en.wikipedia.org/wiki/Glob_(programming)
 
diff --git a/bin/prepare b/bin/prepare
index b4e1652..8f13143 100755
--- a/bin/prepare
+++ b/bin/prepare
@@ -51,9 +51,7 @@ rm -f "${TMP}.tar.gz"
 # with preference to the local copy as so to ensure any new configuration
 # settings are set with the defaults and local overrides are kept
 show_step "Merging the upstream and downstream cookiecutter.json files"
-jq -s '.[0] * .[1]' \
-  "${TEMPLATES}/cookiecutter.json" \
-  "cookiecutter.json" \
+merge_cookiecutters "${TEMPLATES}/cookiecutter.json" "cookiecutter.json" \
   > "${TMP}/cookiecutter.json"
 # Once merged, move the configuration into the template directory so it can be
 # used to re-render the upstream templates based on the local settings (it will
diff --git a/lib/prepare.sh b/lib/prepare.sh
index 8c3381f..520741a 100644
--- a/lib/prepare.sh
+++ b/lib/prepare.sh
@@ -2,8 +2,26 @@
 
 set -euo pipefail
 
+# Call GitHub and get the commit SHA value of the source branch we're going to
+# use for the templates to render and apply over the top
 function get_template_commit {
   gh api "/repos/${REPOSITORY}/branches/${BRANCH}" \
     --jq .commit.sha 2> /dev/null
   exit ${?}
 }
+
+# Merge all downstream values over the top of upstream as the base
+# configuration, except for .changes.updates and .changes.removes which should
+# be then taken from upstream override downstream (in effect a two-way merge)
+function merge_cookiecutters {
+  local upstream="${1}"
+  local downstream="${2}"
+
+  jq -s '.[0] * .[1] +
+    { "changes":
+      { "updates":.[0].changes.updates,
+        "removes":.[0].changes.removes } }' \
+    "${upstream}" \
+    "${downstream}"
+  return ${?}
+}
diff --git a/tests/assets/prepare/downstream.json b/tests/assets/prepare/downstream.json
new file mode 100644
index 0000000..ed3dcdc
--- /dev/null
+++ b/tests/assets/prepare/downstream.json
@@ -0,0 +1,41 @@
+{
+  "repository": {
+    "owner": "n3tuk",
+    "name": "downstream"
+  },
+  "provider": "null",
+  "name": "module",
+  "components": {
+    "terraform": {
+      "version": "1.4.6"
+    },
+    "examples": [
+      "default",
+      "complete"
+    ],
+    "submodules": [],
+    "terratest": {
+      "options": {}
+    }
+  },
+  "changes": {
+    "updates": [
+      {
+        "source": "a.txt",
+        "destination": "b.txt"
+      },
+      {
+        "source": "b.txt",
+        "destination": "c.txt"
+      }
+    ],
+    "removes": [
+      {
+        "source": "y.txt"
+      },
+      {
+        "source": "z.txt"
+      }
+    ]
+  }
+}
diff --git a/tests/assets/prepare/upstream.json b/tests/assets/prepare/upstream.json
new file mode 100644
index 0000000..e0eff71
--- /dev/null
+++ b/tests/assets/prepare/upstream.json
@@ -0,0 +1,40 @@
+{
+  "repository": {
+    "owner": "n3tuk",
+    "name": "upstream"
+  },
+  "provider": "null",
+  "name": "module",
+  "components": {
+    "terraform": {
+      "version": "1.4.6"
+    },
+    "examples": [
+      "default",
+      "complete"
+    ],
+    "submodules": [],
+    "terratest": {
+      "options": {}
+    }
+  },
+  "changes": {
+    "updates": [
+      {
+        "source": "c.txt",
+        "destination": "d.txt"
+      }
+    ],
+    "removes": [
+      {
+        "source": "x.txt"
+      },
+      {
+        "source": "y.txt"
+      },
+      {
+        "source": "z.txt"
+      }
+    ]
+  }
+}
diff --git a/tests/prepare.bats b/tests/prepare.bats
index 8934aa5..a034bd8 100644
--- a/tests/prepare.bats
+++ b/tests/prepare.bats
@@ -2,12 +2,13 @@
 
 bats_load_library "bats-support"
 bats_load_library "bats-assert"
+bats_load_library "bats-file"
 
 load "helpers/common"
 load "helpers/gh"
 
 setup() {
-  set_environment_variables
+  set_environment_variables prepare
 }
 
 teardown() {
@@ -21,3 +22,31 @@ teardown() {
   assert_output "${COMMIT}"
   assert_success
 }
+
+@test "merge_cookiecutters() correctly two-way merges cookiecutter files" {
+  source lib/common.sh
+  source lib/prepare.sh
+  run merge_cookiecutters \
+    "${TEMPLATES}/upstream.json" \
+    "${TEMPLATES}/downstream.json"
+
+  assert_output --partial '"owner": "n3tuk"'
+  # Prove this has not been overridden in the merge of downstream over upstream
+  assert_output --partial '"name": "downstream"'
+  # Prove these have been overridden in the merge of upstream over downstream
+  assert_output --partial '"source": "c.txt"'
+  assert_output --partial '"destination": "d.txt"'
+  assert_output --partial '"source": "x.txt"'
+  assert_output --partial '"source": "y.txt"'
+  assert_output --partial '"source": "z.txt"'
+
+  # Prove this has been overridden in the merge of downstream over upstream
+  refute_output --partial '"name": "upstream"'
+  # Prove these have been overridden in the merge of upstream over downstream
+  refute_output --partial '"source": "a.txt"'
+  refute_output --partial '"destination": "b.txt"'
+  refute_output --partial '"source": "b.txt"'
+  refute_output --partial '"destination": "c.txt"'
+
+  assert_success
+}