diff --git a/plugins/python-build/bin/python-build b/plugins/python-build/bin/python-build
index 783848dc..95d56af2 100755
--- a/plugins/python-build/bin/python-build
+++ b/plugins/python-build/bin/python-build
@@ -2037,14 +2037,23 @@ build_package_get_pip() {
   build_package_symlink_version_suffix
 }
 
+# Pip <21 (in 2.7 and derivatives like PyPy-2.7) doesn't support -I
+build_package_ensurepip_lt21() {
+  build_package_ensurepip lt21
+}
+
 build_package_ensurepip() {
+  local mode="$1"
   local ensurepip_opts
   # Install as `--altinstall` if the Python is installed as `altinstall` (#255)
   if [[ "$PYTHON_MAKE_INSTALL_TARGET" == *"altinstall"* ]]; then
     ensurepip_opts="--altinstall"
   fi
+  local python_opts="-I"
+  if [[ $mode == "lt21" ]]; then python_opts="-s"; fi
+  
   # FIXME: `--altinstall` with `get-pip.py`
-  "$PYTHON_BIN" -I -m ensurepip ${ensurepip_opts} 1>/dev/null 2>&1 || build_package_get_pip "$@" || return 1
+  "$PYTHON_BIN" $python_opts -m ensurepip ${ensurepip_opts} 1>/dev/null 2>&1 || build_package_get_pip "$@" || return 1
   build_package_symlink_version_suffix
 }
 
diff --git a/plugins/python-build/share/python-build/2.7.18 b/plugins/python-build/share/python-build/2.7.18
index 5725575d..6576ca67 100644
--- a/plugins/python-build/share/python-build/2.7.18
+++ b/plugins/python-build/share/python-build/2.7.18
@@ -2,7 +2,7 @@ export PYTHON_BUILD_HOMEBREW_OPENSSL_FORMULA="openssl@1.1 openssl@1.0 openssl"
 install_package "openssl-1.1.1v" "https://www.openssl.org/source/openssl-1.1.1v.tar.gz" mac_openssl --if has_broken_mac_openssl
 install_package "readline-8.0" "https://ftpmirror.gnu.org/readline/readline-8.0.tar.gz#e339f51971478d369f8a053a330a190781acb9864cf4c541060f12078948e461" mac_readline --if has_broken_mac_readline
 if has_tar_xz_support; then
-  install_package "Python-2.7.18" "https://www.python.org/ftp/python/2.7.18/Python-2.7.18.tar.xz#b62c0e7937551d0cc02b8fd5cb0f544f9405bafc9a54d3808ed4594812edef43" standard verify_py27 copy_python_gdb ensurepip
+  install_package "Python-2.7.18" "https://www.python.org/ftp/python/2.7.18/Python-2.7.18.tar.xz#b62c0e7937551d0cc02b8fd5cb0f544f9405bafc9a54d3808ed4594812edef43" standard verify_py27 copy_python_gdb ensurepip_lt21
 else
-  install_package "Python-2.7.18" "https://www.python.org/ftp/python/2.7.18/Python-2.7.18.tgz#da3080e3b488f648a3d7a4560ddee895284c3380b11d6de75edb986526b9a814" standard verify_py27 copy_python_gdb ensurepip
+  install_package "Python-2.7.18" "https://www.python.org/ftp/python/2.7.18/Python-2.7.18.tgz#da3080e3b488f648a3d7a4560ddee895284c3380b11d6de75edb986526b9a814" standard verify_py27 copy_python_gdb ensurepip_lt21
 fi
diff --git a/plugins/python-build/share/python-build/pypy2.7-7.3.13 b/plugins/python-build/share/python-build/pypy2.7-7.3.13
new file mode 100644
index 00000000..0239066b
--- /dev/null
+++ b/plugins/python-build/share/python-build/pypy2.7-7.3.13
@@ -0,0 +1,81 @@
+VERSION='7.3.13'
+PYVER='2.7'
+
+# https://www.pypy.org/checksums.html
+aarch64_hash=f1e20f833cc86a097c1f1318069fc17d01c3988678c1438fe27ed567fcb5cfd0
+linux32_hash=b727d2e759a740f45bab1e333029d001c4384b52949bcbb4bd2ad7912eae8dad
+linux64_hash=e41ceb5dc6c4d3a9311ed5f88edfeedbf3e8abbd1ed3c4f2e151a90a5cf4e1d7
+osarm64_hash=5b86cf0750abc188a0355380d10c7bab1dec51b610cde23ce78f30a9ef296618
+osx64_hash=50769df0091e8fa51c9e4356e0cb204e6f6aa54f502ec5a6e55aef03d0ac5675
+s390x_hash=fbb2f3d92831c02b094f17e9609b95a6202d4bdcddae437e380ab14388d4556e
+
+### end of manual settings - following lines same for every download
+
+function err_no_binary {
+    local archmsg="${1}"
+    local ver="pypy${PYVER}-v${VERSION}-src"
+    local url="https://downloads.python.org/pypy/${ver}.tar.bz2"
+    { echo
+      colorize 1 "ERROR"
+      echo ": The binary distribution of PyPy is not available for ${archmsg}."
+      echo "try '${url}' to build from source."
+      echo
+    } >&2
+    exit 1
+}
+
+function pypy_pkg_data {
+    # pypy architecture tag
+    local ARCH="${1}"
+
+    # defaults
+    local cmd='install_package'  # use bz2
+    local pkg="${ARCH}" # assume matches
+    local ext='tar.bz2'
+    local hash='' # undefined
+
+    # select the hash, fix pkg if not match ARCH
+    case "${ARCH}" in
+    'linux-aarch64' )
+      hash="${aarch64_hash}"
+      pkg='aarch64'
+      ;;
+    'linux' )
+      hash="${linux32_hash}"
+      pkg='linux32'
+      ;;
+    'linux64' )
+      hash="${linux64_hash}"
+      ;;
+    'osarm64' )
+      hash="${osarm64_hash}"
+      pkg='macos_arm64'
+      ;;
+    'osx64' )
+      if require_osx_version "10.13"; then
+        hash="${osx64_hash}"
+        pkg='macos_x86_64'
+      else
+        err_no_binary "${ARCH}, OS X < 10.13"
+      fi
+      ;;
+    's390x' )
+      hash="${s390x_hash}"
+      ;;
+    * )
+      err_no_binary "${ARCH}"
+      ;;
+    esac
+
+    local basever="pypy${PYVER}-v${VERSION}"
+    local baseurl="https://downloads.python.org/pypy/${basever}"
+
+    # result - command, package dir, url+hash
+    echo "${cmd}" "${basever}-${pkg}" "${baseurl}-${pkg}.${ext}#${hash}"
+}
+
+# determine command, package directory, url+hash
+declare -a pd="$(pypy_pkg_data "$(pypy_architecture 2>/dev/null || true)")"
+
+# install
+${pd[0]} "${pd[1]}" "${pd[2]}" 'pypy' "verify_py${PYVER//./}" 'ensurepip_lt21'
diff --git a/plugins/python-build/share/python-build/pypy2.7-7.3.13-src b/plugins/python-build/share/python-build/pypy2.7-7.3.13-src
new file mode 100644
index 00000000..4704161e
--- /dev/null
+++ b/plugins/python-build/share/python-build/pypy2.7-7.3.13-src
@@ -0,0 +1,14 @@
+VERSION='7.3.13'
+PYVER='2.7'
+
+# https://www.pypy.org/checksums.html
+hash=976984bc6ca5ec9d37ae4e219b020cbed2751d1a02267033f59ed700ba8cec40
+
+### end of manual settings - following lines same for every download
+
+ver="pypy${PYVER}-v${VERSION}-src"
+url="https://downloads.python.org/pypy/${ver}.tar.bz2"
+
+prefer_openssl11
+install_package "openssl-1.1.1f" "https://www.openssl.org/source/openssl-1.1.1f.tar.gz#186c6bfe6ecfba7a5b48c47f8a1673d0f3b0e5ba2e25602dd23b629975da3f35" mac_openssl --if has_broken_mac_openssl
+install_package "${ver}" "${url}#${hash}" 'pypy_builder' "verify_py${PYVER//./}" 'ensurepip_lt21'
diff --git a/plugins/python-build/share/python-build/pypy3.10-7.3.13 b/plugins/python-build/share/python-build/pypy3.10-7.3.13
new file mode 100644
index 00000000..1690b6ee
--- /dev/null
+++ b/plugins/python-build/share/python-build/pypy3.10-7.3.13
@@ -0,0 +1,81 @@
+VERSION='7.3.13'
+PYVER='3.10'
+
+# https://www.pypy.org/checksums.html
+aarch64_hash=ac476f01c9653358404f2e4b52f62307b2f64ccdb8c96dadcbfe355824d81a63
+linux32_hash=bfba57eb1f859dd0ad0d6fe841bb12e1256f1f023c7fbca083b536cccbc1233b
+linux64_hash=54936eeafd9350a5ea0375b036272a260871b9bca82e1b0bb3201deea9f5a442
+osarm64_hash=efb3007b7aace0af6e3b30d381088a5bbc175973a6627b6b0d624a2ca2dc63ce
+osx64_hash=2c6238b9ece7b94ffdfd1d9b50619edef4b169a5c78adcdb691fce6709cd6610
+s390x_hash=3c813c7efa6a026b281313b299c186c585155fc164c7538e65d41efdabff87c9
+
+### end of manual settings - following lines same for every download
+
+function err_no_binary {
+    local archmsg="${1}"
+    local ver="pypy${PYVER}-v${VERSION}-src"
+    local url="https://downloads.python.org/pypy/${ver}.tar.bz2"
+    { echo
+      colorize 1 "ERROR"
+      echo ": The binary distribution of PyPy is not available for ${archmsg}."
+      echo "try '${url}' to build from source."
+      echo
+    } >&2
+    exit 1
+}
+
+function pypy_pkg_data {
+    # pypy architecture tag
+    local ARCH="${1}"
+
+    # defaults
+    local cmd='install_package'  # use bz2
+    local pkg="${ARCH}" # assume matches
+    local ext='tar.bz2'
+    local hash='' # undefined
+
+    # select the hash, fix pkg if not match ARCH
+    case "${ARCH}" in
+    'linux-aarch64' )
+      hash="${aarch64_hash}"
+      pkg='aarch64'
+      ;;
+    'linux' )
+      hash="${linux32_hash}"
+      pkg='linux32'
+      ;;
+    'linux64' )
+      hash="${linux64_hash}"
+      ;;
+    'osarm64' )
+      hash="${osarm64_hash}"
+      pkg='macos_arm64'
+      ;;
+    'osx64' )
+      if require_osx_version "10.13"; then
+        hash="${osx64_hash}"
+        pkg='macos_x86_64'
+      else
+        err_no_binary "${ARCH}, OS X < 10.13"
+      fi
+      ;;
+    's390x' )
+      hash="${s390x_hash}"
+      ;;
+    * )
+      err_no_binary "${ARCH}"
+      ;;
+    esac
+
+    local basever="pypy${PYVER}-v${VERSION}"
+    local baseurl="https://downloads.python.org/pypy/${basever}"
+
+    # result - command, package dir, url+hash
+    echo "${cmd}" "${basever}-${pkg}" "${baseurl}-${pkg}.${ext}#${hash}"
+}
+
+# determine command, package directory, url+hash
+declare -a pd="$(pypy_pkg_data "$(pypy_architecture 2>/dev/null || true)")"
+
+# install
+${pd[0]} "${pd[1]}" "${pd[2]}" 'pypy' "verify_py${PYVER//./}" 'ensurepip'
diff --git a/plugins/python-build/share/python-build/pypy3.10-7.3.13-src b/plugins/python-build/share/python-build/pypy3.10-7.3.13-src
new file mode 100644
index 00000000..4ebe5f2f
--- /dev/null
+++ b/plugins/python-build/share/python-build/pypy3.10-7.3.13-src
@@ -0,0 +1,14 @@
+VERSION='7.3.13'
+PYVER='3.10'
+
+# https://www.pypy.org/checksums.html
+hash=4ac1733c19d014d3193c804e7f40ffccbf6924bcaaee1b6089b82b9bf9353a6d
+
+### end of manual settings - following lines same for every download
+
+ver="pypy${PYVER}-v${VERSION}-src"
+url="https://downloads.python.org/pypy/${ver}.tar.bz2"
+
+prefer_openssl11
+install_package "openssl-1.1.1f" "https://www.openssl.org/source/openssl-1.1.1f.tar.gz#186c6bfe6ecfba7a5b48c47f8a1673d0f3b0e5ba2e25602dd23b629975da3f35" mac_openssl --if has_broken_mac_openssl
+install_package "${ver}" "${url}#${hash}" 'pypy_builder' "verify_py${PYVER//./}" 'ensurepip'
diff --git a/plugins/python-build/share/python-build/pypy3.9-7.3.13 b/plugins/python-build/share/python-build/pypy3.9-7.3.13
new file mode 100644
index 00000000..2161b5ce
--- /dev/null
+++ b/plugins/python-build/share/python-build/pypy3.9-7.3.13
@@ -0,0 +1,81 @@
+VERSION='7.3.13'
+PYVER='3.9'
+
+# https://www.pypy.org/checksums.html
+aarch64_hash=317d7876c5825a086f854253648b967a432b993ce87695d2895d3ad6ed0d2716
+linux32_hash=ac695238b4a3635ac6b482e74e04e2ea78b31acca0decd5de601dfd2f4ebf35a
+linux64_hash=323b05a9f607e932cda1995cbe77a96e4ea35994631aa6d734c8035e8479b74e
+osarm64_hash=333131d62c502aa5d5fb58a58cdf01de4bfb2c1db5a9bb4c04515258abe6bced
+osx64_hash=fb1ff67340353e837498102fec2b0b45744bb189dced57ee2e00045785e69662
+s390x_hash=213c88f652a99c4dc4e8e00b4b5b58f381c7f7e9ea1a9b65801fc0eb1e50df0a
+
+### end of manual settings - following lines same for every download
+
+function err_no_binary {
+    local archmsg="${1}"
+    local ver="pypy${PYVER}-v${VERSION}-src"
+    local url="https://downloads.python.org/pypy/${ver}.tar.bz2"
+    { echo
+      colorize 1 "ERROR"
+      echo ": The binary distribution of PyPy is not available for ${archmsg}."
+      echo "try '${url}' to build from source."
+      echo
+    } >&2
+    exit 1
+}
+
+function pypy_pkg_data {
+    # pypy architecture tag
+    local ARCH="${1}"
+
+    # defaults
+    local cmd='install_package'  # use bz2
+    local pkg="${ARCH}" # assume matches
+    local ext='tar.bz2'
+    local hash='' # undefined
+
+    # select the hash, fix pkg if not match ARCH
+    case "${ARCH}" in
+    'linux-aarch64' )
+      hash="${aarch64_hash}"
+      pkg='aarch64'
+      ;;
+    'linux' )
+      hash="${linux32_hash}"
+      pkg='linux32'
+      ;;
+    'linux64' )
+      hash="${linux64_hash}"
+      ;;
+    'osarm64' )
+      hash="${osarm64_hash}"
+      pkg='macos_arm64'
+      ;;
+    'osx64' )
+      if require_osx_version "10.13"; then
+        hash="${osx64_hash}"
+        pkg='macos_x86_64'
+      else
+        err_no_binary "${ARCH}, OS X < 10.13"
+      fi
+      ;;
+    's390x' )
+      hash="${s390x_hash}"
+      ;;
+    * )
+      err_no_binary "${ARCH}"
+      ;;
+    esac
+
+    local basever="pypy${PYVER}-v${VERSION}"
+    local baseurl="https://downloads.python.org/pypy/${basever}"
+
+    # result - command, package dir, url+hash
+    echo "${cmd}" "${basever}-${pkg}" "${baseurl}-${pkg}.${ext}#${hash}"
+}
+
+# determine command, package directory, url+hash
+declare -a pd="$(pypy_pkg_data "$(pypy_architecture 2>/dev/null || true)")"
+
+# install
+${pd[0]} "${pd[1]}" "${pd[2]}" 'pypy' "verify_py${PYVER//./}" 'ensurepip'
diff --git a/plugins/python-build/share/python-build/pypy3.9-7.3.13-src b/plugins/python-build/share/python-build/pypy3.9-7.3.13-src
new file mode 100644
index 00000000..07ff9893
--- /dev/null
+++ b/plugins/python-build/share/python-build/pypy3.9-7.3.13-src
@@ -0,0 +1,14 @@
+VERSION='7.3.13'
+PYVER='3.9'
+
+# https://www.pypy.org/checksums.html
+hash=bc6147268105e7cb3bd57b401e6d97f66aa4ede269104b2712a7cdd9f02f68cd
+
+### end of manual settings - following lines same for every download
+
+ver="pypy${PYVER}-v${VERSION}-src"
+url="https://downloads.python.org/pypy/${ver}.tar.bz2"
+
+prefer_openssl11
+install_package "openssl-1.1.1f" "https://www.openssl.org/source/openssl-1.1.1f.tar.gz#186c6bfe6ecfba7a5b48c47f8a1673d0f3b0e5ba2e25602dd23b629975da3f35" mac_openssl --if has_broken_mac_openssl
+install_package "${ver}" "${url}#${hash}" 'pypy_builder' "verify_py${PYVER//./}" 'ensurepip'