diff --git a/docker/base/install_pythons.sh b/docker/base/install_pythons.sh
index 62f6a4ef5..128fcc6d1 100755
--- a/docker/base/install_pythons.sh
+++ b/docker/base/install_pythons.sh
@@ -18,13 +18,13 @@ PYENV_VERSIONS=(
   3.10.14
   3.12.3
   3.13.0a6
-  pypy2.7-7.3.15
+  pypy2.7-7.3.16
   pypy3.5-7.0.0
   pypy3.6-7.3.3
   pypy3.7-7.3.9
   pypy3.8-7.3.11
-  pypy3.9-7.3.15
-  pypy3.10-7.3.15
+  pypy3.9-7.3.16
+  pypy3.10-7.3.16
 )
 git clone "${PYENV_REPO:-https://github.com/pyenv/pyenv.git}" "${PYENV_ROOT}" && (
   cd "${PYENV_ROOT}" && git checkout "${PYENV_SHA:-HEAD}" && src/configure && make -C src
diff --git a/docker/user/Dockerfile b/docker/user/Dockerfile
index a42a3a013..25768a50a 100644
--- a/docker/user/Dockerfile
+++ b/docker/user/Dockerfile
@@ -25,17 +25,6 @@ ENV _PEX_TEST_DEV_ROOT=/development/pex_dev
 # ~/.pex cache.
 VOLUME "/home/${USER}/.pex"
 
-RUN mkdir -p  \
-    /development/pex \
-    /development/pex/.tox \
-    /development/pex_dev \
-    "/home/${USER}/.pex" && \
-  chown -R "${UID}:${GID}" \
-    /development/pex \
-    /development/pex/.tox \
-    /development/pex_dev \
-    "/home/${USER}/.pex"
-
 # This will be a named volume used to persist the pytest tmp tree (/tmp/pytest-of-$USER/) for use \
 # in `./dtox inspect` sessions.
 VOLUME /tmp
diff --git a/dtox.sh b/dtox.sh
index 2982af89a..8e258634c 100755
--- a/dtox.sh
+++ b/dtox.sh
@@ -27,6 +27,7 @@ elif [[ "${BASE_MODE}" == "pull" ]]; then
   docker pull "ghcr.io/pex-tool/pex/base:${base_hash}"
 fi
 
+CONTAINER_HOME="/home/$(id -un)"
 USER_INPUT=(
   "${BASE_INPUT[@]}"
   "${ROOT}/docker/user/Dockerfile"
@@ -48,6 +49,23 @@ if [[ -z "$(user_image_id)" ]]; then
     --tag pex-tool/pex/user:latest \
     --tag "pex-tool/pex/user:${user_hash}" \
     "${ROOT}/docker/user"
+
+  docker run \
+    --rm \
+    --volume pex-caches:/development/pex_dev \
+    --volume "pex-root:${CONTAINER_HOME}/.pex" \
+    --volume pex-tmp:/tmp \
+    --volume pex-tox:/development/pex/.tox \
+    --entrypoint bash \
+    --user root \
+    "pex-tool/pex/user:${user_hash}" \
+    -c "
+      chown -R $(id -un):$(id -gn) \
+      /development/pex_dev \
+      ${CONTAINER_HOME}/.pex \
+      /tmp \
+      /development/pex/.tox
+    "
 fi
 
 if [[ "${CACHE_MODE}" == "pull" ]]; then
@@ -99,11 +117,6 @@ if [[ -n "${TERM:-}" ]]; then
   )
 fi
 
-# This ensures the current user owns the host .tox/ dir before launching the container, which
-# otherwise sets the ownership as root for undetermined reasons
-mkdir -p "${ROOT}/.tox"
-
-CONTAINER_HOME="/home/$(id -un)"
 exec docker run \
   --rm \
   --volume pex-tmp:/tmp \