diff --git a/.github/workflows/publish-docker.yml b/.github/workflows/publish-docker.yml
index a47af66..d374587 100644
--- a/.github/workflows/publish-docker.yml
+++ b/.github/workflows/publish-docker.yml
@@ -54,21 +54,42 @@ jobs:
             echo "minor=$MINOR"
           } >> "$GITHUB_OUTPUT"
 
+      # JSON API can return 200 before the simple index / CDN edges that pip
+      # hits inside the Docker build. Require JSON + simple-index listing +
+      # a reachable wheel URL before building (see #217).
       - name: Wait for PyPI package
         env:
           VERSION: ${{ steps.version.outputs.version }}
           PACKAGE: create-awesome-python-app
         run: |
           set -euo pipefail
-          attempts=24
+          attempts=36
           delay=15
+          normalized="${PACKAGE//-/_}"
           for attempt in $(seq 1 "$attempts"); do
+            json_ok=0
+            simple_ok=0
+            wheel_ok=0
             if curl -sfL "https://pypi.org/pypi/${PACKAGE}/${VERSION}/json" \
               | jq -e '.urls[] | select(.packagetype=="sdist") | .digests.sha256' >/dev/null; then
-              echo "PyPI has ${PACKAGE}==${VERSION}"
+              json_ok=1
+            fi
+            if curl -sfL "https://pypi.org/simple/${PACKAGE}/" \
+              | grep -Fq "${normalized}-${VERSION}"; then
+              simple_ok=1
+            fi
+            wheel_url="$(curl -sfL "https://pypi.org/pypi/${PACKAGE}/${VERSION}/json" \
+              | jq -r '.urls[] | select(.packagetype=="bdist_wheel") | .url' \
+              | head -n1 || true)"
+            if [ -n "${wheel_url}" ] && curl -sfI "$wheel_url" >/dev/null; then
+              wheel_ok=1
+            fi
+            if [ "$json_ok" -eq 1 ] && [ "$simple_ok" -eq 1 ] && [ "$wheel_ok" -eq 1 ]; then
+              echo "PyPI ready for ${PACKAGE}==${VERSION} (json+simple+wheel)"
               exit 0
             fi
-            echo "::warning::PyPI not ready for ${PACKAGE}==${VERSION} (attempt ${attempt}/${attempts}); retrying in ${delay}s"
+            echo "::warning::PyPI not ready for ${PACKAGE}==${VERSION}"
+            echo "::warning::json=${json_ok} simple=${simple_ok} wheel=${wheel_ok} attempt=${attempt}/${attempts}; sleep ${delay}s"
             sleep "$delay"
           done
           echo "::error::Timed out waiting for ${PACKAGE}==${VERSION} on PyPI"
diff --git a/Dockerfile b/Dockerfile
index f815227..5e3e111 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -6,13 +6,22 @@ FROM python:3.12-slim-bookworm
 # reproducible for its tag).
 ARG VERSION=latest
 
+# Retry pip install: PyPI simple-index / CDN edges can lag the JSON API
+# that CI already observed as ready (see #217).
 # hadolint ignore=DL3013
 RUN useradd --create-home --uid 1000 --shell /bin/bash app \
     && if [ "$VERSION" = "latest" ]; then \
-        pip install --no-cache-dir create-awesome-python-app; \
+        pkg="create-awesome-python-app"; \
     else \
-        pip install --no-cache-dir "create-awesome-python-app==${VERSION}"; \
-    fi
+        pkg="create-awesome-python-app==${VERSION}"; \
+    fi \
+    && attempt=1 \
+    && until pip install --no-cache-dir "$pkg"; do \
+        if [ "$attempt" -ge 12 ]; then exit 1; fi; \
+        echo "pip install failed (attempt ${attempt}/12); retrying in 15s"; \
+        attempt=$((attempt + 1)); \
+        sleep 15; \
+    done
 
 USER app
 WORKDIR /home/app