diff --git a/.docker-images b/.docker-images
index 984a3183..4ceaf139 100644
--- a/.docker-images
+++ b/.docker-images
@@ -2,8 +2,7 @@ images:
   - name: cloudflared
     dockerfile: Dockerfile.$ARCH
     context: .
-    versions: 
-      - latest
+    version_file: versions
     registries:
     - name: docker.io/cloudflare
       user: env:DOCKER_USER
diff --git a/Makefile b/Makefile
index 691da9bb..7652ff21 100644
--- a/Makefile
+++ b/Makefile
@@ -131,6 +131,10 @@ endif
 container:
 	docker build --build-arg=TARGET_ARCH=$(TARGET_ARCH) --build-arg=TARGET_OS=$(TARGET_OS) -t cloudflare/cloudflared-$(TARGET_OS)-$(TARGET_ARCH):"$(VERSION)" .
 
+.PHONY: generate-docker-version
+generate-docker-version:
+	echo latest $(VERSION) > versions
+
 .PHONY: test
 test: vet
 ifndef CI
diff --git a/cfsetup.yaml b/cfsetup.yaml
index 9b8981de..7b7b9cd4 100644
--- a/cfsetup.yaml
+++ b/cfsetup.yaml
@@ -78,6 +78,12 @@ stretch: &stretch
       # same logic as above, but for FIPS packages only
       - ./build-packages-fips.sh
       - make github-release-built-pkgs
+  generate-versions-file:
+    build_dir: *build_dir
+    builddeps: 
+      - build-essential
+    post-cache:
+      - make generate-docker-version
   build-deb:
     build_dir: *build_dir
     builddeps: &build_deb_deps