diff --git a/roles/upload-pypi/README.rst b/roles/upload-pypi/README.rst
index cbcc0dab1..aba4b56f4 100644
--- a/roles/upload-pypi/README.rst
+++ b/roles/upload-pypi/README.rst
@@ -35,3 +35,9 @@ Upload python packages to PyPI
    :default: twine
 
    Path to twine executable.
+
+.. zuul:rolevar:: pypi_register_first
+  :default: false
+
+  Whether the role should register the package before uploading it. This may
+  be required when uploading for the first time to a devPI instance.
diff --git a/roles/upload-pypi/defaults/main.yaml b/roles/upload-pypi/defaults/main.yaml
index c0cb93b96..1d4b7501f 100644
--- a/roles/upload-pypi/defaults/main.yaml
+++ b/roles/upload-pypi/defaults/main.yaml
@@ -3,3 +3,4 @@ pypi_path: "src/{{ zuul.project.canonical_name }}/dist"
 pypi_repository: "{{ pypi_info.repository|default('pypi') }}"
 pypi_repository_url: "{{ pypi_info.repository_url|default(None) }}"
 pypi_twine_executable: twine
+pypi_register_first: false
diff --git a/roles/upload-pypi/tasks/main.yaml b/roles/upload-pypi/tasks/main.yaml
index 864fe4def..fb5c10cc8 100644
--- a/roles/upload-pypi/tasks/main.yaml
+++ b/roles/upload-pypi/tasks/main.yaml
@@ -20,6 +20,11 @@
     msg: "Found no wheels to upload: {{found_wheels.msg}}"
   when: found_wheels.files == []
 
+- name: Register packages on the PyPI server (via wheels)
+  command: "{{ pypi_twine_executable }} register --config-file {{ _pypirc_tmp.path }} --repository {{ pypi_repository }} {{ item.path }}"
+  with_items: "{{ found_wheels.files }}"
+  when: pypi_register_first
+
 - name: Upload wheel with twine before tarballs
   command: "{{ pypi_twine_executable }} upload --config-file {{ _pypirc_tmp.path }} -r {{ pypi_repository }} {{ item.path }}"
   with_items: "{{ found_wheels.files }}"
@@ -35,6 +40,13 @@
     msg: "Found no tarballs to upload: {{found_tarballs.msg}}"
   when: found_tarballs.files == []
 
+- name: Register packages on the PyPI server (via tarballs)
+  command: "{{ pypi_twine_executable }} register --config-file {{ _pypirc_tmp.path }} --repository {{ pypi_repository }} {{ item.path }}"
+  with_items: "{{ found_tarballs.files }}"
+  when:
+    - pypi_register_first
+    - found_wheels.files == []
+
 - name: Upload tarballs with twine
   command: "{{ pypi_twine_executable }} upload --config-file {{ _pypirc_tmp.path }} -r {{ pypi_repository }} {{ item.path }}"
   with_items: "{{ found_tarballs.files }}"