diff --git a/plugins/git/git-from-directory b/plugins/git/git-from-directory
index b204c3526..3958f4566 100755
--- a/plugins/git/git-from-directory
+++ b/plugins/git/git-from-directory
@@ -18,9 +18,14 @@ trigger-git-git-from-directory() {
   # shellcheck disable=SC2086
   trap "rm -rf '$TMP_WORK_DIR' '$TMP_WORK_DIR_2' >/dev/null" RETURN INT TERM EXIT
 
-  dokku_log_info1 "Updating git repository with specified build context"
+  local has_code=true
   local git_objects="$(fn-git-cmd "$APP_ROOT" count-objects 2>/dev/null || true)"
   if [[ -z "$git_objects" ]] || [[ "$git_objects" == "0 objects, 0 kilobytes" ]]; then
+    local has_code=false
+  fi
+
+  dokku_log_info1 "Updating git repository with specified build context"
+  if [[ "$has_code" == "false" ]]; then
     # setup new repo
     cp -rT "$SOURCECODE_WORK_DIR" "$TMP_WORK_DIR"
     suppress_output fn-git-cmd "$TMP_WORK_DIR" init
@@ -44,7 +49,7 @@ trigger-git-git-from-directory() {
     if suppress_output fn-git-cmd "$TMP_WORK_DIR" diff-index --quiet HEAD --; then
       dokku_log_warn "No changes detected, skipping git commit"
       dokku_log_warn "Call 'ps:rebuild' on app to rebuild the app from existing source"
-      return
+      return 1
     fi
 
     suppress_output fn-git-cmd "$TMP_WORK_DIR" commit -m "Automated commit @ $(date +%s)"
@@ -54,7 +59,18 @@ trigger-git-git-from-directory() {
   fi
 
   rm -rf "$TMP_WORK_DIR" "$TMP_WORK_DIR_2" >/dev/null
-  git_receive_app "$APP" "$REV"
+  if git_receive_app "$APP" "$REV"; then
+    return
+  else
+    local exit_code=$?
+    local DOKKU_DEPLOY_BRANCH="$(fn-git-deploy-branch "$APP")"
+    if [[ "$has_code" == "false" ]]; then
+      fn-git-cmd "$APP_ROOT" update-ref -d HEAD
+    else
+      fn-git-cmd "$APP_ROOT" update-ref "refs/heads/$DOKKU_DEPLOY_BRANCH" "$DOKKU_DEPLOY_BRANCH^"
+    fi
+    return "$exit_code"
+  fi
 }
 
 trigger-git-git-from-directory "$@"
diff --git a/tests/apps/python/alt.Dockerfile b/tests/apps/python/alt.Dockerfile
index 289b02f6a..0c600e36b 100644
--- a/tests/apps/python/alt.Dockerfile
+++ b/tests/apps/python/alt.Dockerfile
@@ -1,5 +1,9 @@
 FROM python:3.11.0-buster
 
+ARG BUILD_ARG=key
+
 WORKDIR /app
 
 COPY . /app
+
+RUN echo $BUILD_ARG > BUILD_ARG.contents
diff --git a/tests/apps/python/web.py b/tests/apps/python/web.py
index c7c3d36a3..e14bb903c 100644
--- a/tests/apps/python/web.py
+++ b/tests/apps/python/web.py
@@ -1,6 +1,7 @@
 import http.server
 import json
 import os
+import sys
 
 
 class GetHandler(http.server.BaseHTTPRequestHandler):
@@ -17,6 +18,10 @@ class GetHandler(http.server.BaseHTTPRequestHandler):
 
 
 if __name__ == "__main__":
+    if os.getenv("FAIL_ON_STARTUP") == "true":
+        print("Failing on startup due to FAIL_ON_STARTUP=true")
+        sys.exit(1)
+
     port = int(os.getenv("PORT", 5000))
     server = http.server.HTTPServer(("0.0.0.0", port), GetHandler)
     print("Listening on port {0}".format(port))
diff --git a/tests/unit/git_4.bats b/tests/unit/git_4.bats
index 6d26de148..8f78a701f 100644
--- a/tests/unit/git_4.bats
+++ b/tests/unit/git_4.bats
@@ -58,6 +58,80 @@ teardown() {
   assert_success
 }
 
+@test "(git) git:from-image [failing deploy]" {
+  local CUSTOM_TMP=$(mktemp -d "/tmp/dokku.me.XXXXX")
+  trap 'popd &>/dev/null || true; rm -rf "$CUSTOM_TMP"' INT TERM
+  rmdir "$CUSTOM_TMP" && cp -r "${BATS_TEST_DIRNAME}/../../tests/apps/python" "$CUSTOM_TMP"
+
+  run /bin/bash -c "docker image build -t dokku-test/$TEST_APP:latest -f $CUSTOM_TMP/alt.Dockerfile $CUSTOM_TMP"
+  echo "output: $output"
+  echo "status: $status"
+  assert_success
+
+  run /bin/bash -c "docker image build -t dokku-test/$TEST_APP:v2 --build-arg BUILD_ARG=value -f $CUSTOM_TMP/alt.Dockerfile $CUSTOM_TMP"
+  echo "output: $output"
+  echo "status: $status"
+  assert_success
+
+  run /bin/bash -c "dokku config:set --no-restart $TEST_APP FAIL_ON_STARTUP=true"
+  echo "output: $output"
+  echo "status: $status"
+  assert_success
+
+  run /bin/bash -c "dokku git:from-image $TEST_APP dokku-test/$TEST_APP:latest"
+  echo "output: $output"
+  echo "status: $status"
+  assert_failure
+
+  run /bin/bash -c "dokku config:get $TEST_APP FAIL_ON_STARTUP"
+  echo "output: $output"
+  echo "status: $status"
+  assert_success
+  assert_output "true"
+
+  run /bin/bash -c "dokku git:status $TEST_APP"
+  echo "output: $output"
+  echo "status: $status"
+  assert_failure
+  assert_output "fatal: this operation must be run in a work tree"
+
+  run /bin/bash -c "dokku config:set --no-restart $TEST_APP FAIL_ON_STARTUP=false"
+  echo "output: $output"
+  echo "status: $status"
+  assert_success
+
+  run /bin/bash -c "dokku git:from-image $TEST_APP dokku-test/$TEST_APP:latest"
+  echo "output: $output"
+  echo "status: $status"
+  assert_success
+
+  run /bin/bash -c "dokku config:set --no-restart $TEST_APP FAIL_ON_STARTUP=true"
+  echo "output: $output"
+  echo "status: $status"
+  assert_success
+
+  run /bin/bash -c "dokku git:from-image $TEST_APP dokku-test/$TEST_APP:v2"
+  echo "output: $output"
+  echo "status: $status"
+  assert_failure
+
+  run /bin/bash -c "dokku config:set --no-restart $TEST_APP FAIL_ON_STARTUP=false"
+  echo "output: $output"
+  echo "status: $status"
+  assert_success
+
+  run /bin/bash -c "dokku git:from-image $TEST_APP dokku-test/$TEST_APP:v2"
+  echo "output: $output"
+  echo "status: $status"
+  assert_success
+  assert_output_contains "No changes detected, skipping git commit" 0
+
+  run /bin/bash -c "docker image rm dokku-test/$TEST_APP:latest dokku-test/$TEST_APP:v2"
+  echo "output: $output"
+  echo "status: $status"
+  assert_success
+}
+
 @test "(git) git:from-image [onbuild]" {
   local TMP=$(mktemp -d "/tmp/dokku.me.XXXXX")
   trap 'popd &>/dev/null || true; rm -rf "$TMP"' INT TERM