diff --git a/eng/pipelines/templates/steps/use-python-version.yml b/eng/pipelines/templates/steps/use-python-version.yml
index 4b8abd59c000..94446e4201c8 100644
--- a/eng/pipelines/templates/steps/use-python-version.yml
+++ b/eng/pipelines/templates/steps/use-python-version.yml
@@ -12,6 +12,60 @@ steps:
       }
     displayName: 'Use Public Feed'
 
+  # Optional override for the hosted toolcache PyPy build. Activated when the
+  # matrix entry sets:
+  #   OverridePyPyVersion: "true"
+  #   PyPyBuildVersion: "v7.3.22"   (or any release from downloads.python.org/pypy)
+  #   PyPyLangVersion:  "3.11.15"   (the Python language version directory in the toolcache)
+  # Rationale: PyPy 7.3.21 (currently in the hosted toolcache for Python 3.11.15)
+  # crashes with `Fatal RPython error: AssertionError` from
+  # `PythonCodeMaker_duplicate_exits_without_lineno` while compiling
+  # `azure.ai.ml`. PyPy 7.3.22+ does not exhibit this bug.
+  - bash: |
+      set -euo pipefail
+      PYPY_BUILD="${PYPY_BUILD_VERSION:?PyPyBuildVersion must be set in the matrix when OverridePyPyVersion=true}"
+      PY_LANG="${PYPY_LANG_VERSION:?PyPyLangVersion must be set in the matrix when OverridePyPyVersion=true}"
+      TARGET="/opt/hostedtoolcache/PyPy/${PY_LANG}/x64"
+      WANT_MICRO="${PYPY_BUILD#v}"
+      if [ -x "${TARGET}/bin/python3" ]; then
+        CURRENT=$("${TARGET}/bin/python3" -c 'import sys; v=sys.pypy_version_info; print(f"{v.major}.{v.minor}.{v.micro}")') || CURRENT="unknown"
+        echo "Existing toolcache PyPy: ${CURRENT}"
+        if [ "$CURRENT" = "$WANT_MICRO" ]; then
+          echo "PyPy ${WANT_MICRO} already installed; nothing to do."
+          exit 0
+        fi
+      fi
+      echo "Installing PyPy ${PYPY_BUILD} for Python ${PY_LANG} into ${TARGET}..."
+      TARBALL="pypy3.11-${PYPY_BUILD}-linux64.tar.bz2"
+      cd /tmp
+      curl -sSLO "https://downloads.python.org/pypy/${TARBALL}"
+      tar xjf "${TARBALL}"
+      sudo rm -rf "${TARGET}"
+      sudo mkdir -p "$(dirname "${TARGET}")"
+      sudo mv "pypy3.11-${PYPY_BUILD}-linux64" "${TARGET}"
+      # Recreate the python3/python symlinks that the upstream toolcache layout provides.
+      if [ ! -e "${TARGET}/bin/python3" ]; then
+        sudo ln -sf "${TARGET}/bin/pypy3.11" "${TARGET}/bin/python3"
+      fi
+      if [ ! -e "${TARGET}/bin/python" ]; then
+        sudo ln -sf "${TARGET}/bin/pypy3.11" "${TARGET}/bin/python"
+      fi
+      sudo touch "${TARGET}.complete"
+      "${TARGET}/bin/python3" --version
+      # The plain pypy tarball does not include pip; the Azure hosted
+      # toolcache build does. Bootstrap pip via ensurepip so downstream
+      # steps (e.g. `python -m pip install uv`) keep working.
+      if ! "${TARGET}/bin/python3" -c "import pip" >/dev/null 2>&1; then
+        echo "Bootstrapping pip via ensurepip..."
+        sudo "${TARGET}/bin/python3" -m ensurepip --upgrade
+      fi
+      "${TARGET}/bin/python3" -m pip --version
+    env:
+      PYPY_BUILD_VERSION: $(PyPyBuildVersion)
+      PYPY_LANG_VERSION: $(PyPyLangVersion)
+    displayName: 'Override hosted toolcache PyPy build'
+    condition: and(succeeded(), eq(variables['Agent.OS'], 'Linux'), eq(variables['OverridePyPyVersion'], 'true'))
+
   - task: UsePythonVersion@0
     displayName: "Use Python ${{ parameters.versionSpec }}"
     inputs:
diff --git a/sdk/ml/ci.yml b/sdk/ml/ci.yml
index 82c4f5a25c82..2569853d82ef 100644
--- a/sdk/ml/ci.yml
+++ b/sdk/ml/ci.yml
@@ -32,6 +32,11 @@ extends:
     ServiceDirectory: ml
     TestTimeoutInMinutes: 75
     TestProxy: true
+    MatrixConfigs:
+      - Name: Python_ml_ci_matrix
+        Path: sdk/ml/platform-matrix.json
+        Selection: sparse
+        GenerateVMJobs: true
     # This is a short term solution to create API review for python azure-ml package only when running pipeline manually
     # Long term solution should be to have different versions on main branch and release branch for python package so APIView can have different revisions for each version.
     # Tracking issue: https://github.com/Azure/azure-sdk-for-python/issues/29196
diff --git a/sdk/ml/platform-matrix.json b/sdk/ml/platform-matrix.json
new file mode 100644
index 000000000000..290055b0ed6a
--- /dev/null
+++ b/sdk/ml/platform-matrix.json
@@ -0,0 +1,76 @@
+{
+  "displayNames": {
+    "--disablecov": "",
+    "false": "",
+    "true": ""
+  },
+  "matrix": {
+    "Agent": {
+      "ubuntu-24.04": { "OSVmImage": "env:LINUXVMIMAGE", "Pool": "env:LINUXPOOL" },
+      "windows-2022": { "OSVmImage": "env:WINDOWSVMIMAGE", "Pool": "env:WINDOWSPOOL" }
+    },
+    "PythonVersion": [ "3.10", "3.12" ],
+    "CoverageArg": "--disablecov",
+    "TestSamples": "false"
+  },
+  "include": [
+    {
+      "MacTestConfig": {
+        "macos311": {
+          "OSVmImage": "env:MACVMIMAGE",
+          "Pool": "env:MACPOOL",
+          "PythonVersion": "3.11",
+          "CoverageArg": "--disablecov",
+          "TestSamples": "false"
+        }
+      }
+    },
+    {
+      "PyPyConfig": {
+        "ubuntu2404_pypy311": {
+          "OSVmImage": "env:LINUXVMIMAGE",
+          "Pool": "env:LINUXPOOL",
+          "PythonVersion": "pypy3.11",
+          "CoverageArg": "--disablecov",
+          "TestSamples": "false",
+          "OverridePyPyVersion": "true",
+          "PyPyBuildVersion": "v7.3.22",
+          "PyPyLangVersion": "3.11.15"
+        }
+      }
+    },
+    {
+      "CoverageConfig": {
+        "ubuntu2404_310_coverage": {
+          "OSVmImage": "env:LINUXVMIMAGE",
+          "Pool": "env:LINUXPOOL",
+          "PythonVersion": "3.10",
+          "CoverageArg": "",
+          "TestSamples": "false"
+        }
+      }
+    },
+    {
+      "Config": {
+        "Ubuntu2404_313": {
+          "OSVmImage": "env:LINUXVMIMAGE",
+          "Pool": "env:LINUXPOOL",
+          "PythonVersion": "3.13",
+          "CoverageArg": "--disablecov",
+          "TestSamples": "false"
+        }
+      }
+    },
+    {
+      "Config": {
+        "Ubuntu2404_314": {
+          "OSVmImage": "env:LINUXVMIMAGE",
+          "Pool": "env:LINUXPOOL",
+          "PythonVersion": "3.14",
+          "CoverageArg": "--disablecov",
+          "TestSamples": "false"
+        }
+      }
+    }
+  ]
+}