diff --git a/utils/build.ps1 b/utils/build.ps1
index 47f28a021463f..f160b16703cff 100644
--- a/utils/build.ps1
+++ b/utils/build.ps1
@@ -188,14 +188,6 @@ $WiXVersion = "4.0.5"
 # Avoid $env:ProgramFiles in case this script is running as x86
 $UnixToolsBinDir = "$env:SystemDrive\Program Files\Git\usr\bin"
 
-$python = "${env:ProgramFiles(x86)}\Microsoft Visual Studio\Shared\Python39_64\python.exe"
-if (-not (Test-Path $python)) {
-  $python = (where.exe python) | Select-Object -First 1
-  if (-not (Test-Path $python)) {
-    throw "Python.exe not found"
-  }
-}
-
 if ($Android -and ($AndroidSDKs.Length -eq 0)) {
   # Enable all android SDKs by default.
   $AndroidSDKs = @("aarch64","armv7","i686","x86_64")
@@ -352,6 +344,10 @@ function Get-BisonExecutable {
   return Join-Path -Path $BinaryCache -ChildPath "win_flex_bison\win_bison.exe"
 }
 
+function Get-PythonExecutable {
+  return Join-Path -Path $BinaryCache -ChildPath "Python$($HostArch.CMakeName)-$PythonVersion\tools\python.exe"
+}
+
 function Get-InstallDir($Arch) {
   if ($Arch -eq $HostArch) {
     $ProgramFilesName = "Program Files"
@@ -740,10 +736,43 @@ function Fetch-Dependencies {
     }
   }
 
+  function Ensure-PythonModules($Python) {
+    # First ensure pip is installed, else bootstrap it
+    try {
+      Invoke-Program -OutNull $Python -m pip *> $null
+    } catch {
+      Write-Output "Installing pip ..."
+      Invoke-Program -OutNull $Python '-I' -m ensurepip -U --default-pip
+    }
+    # 'packaging' is required for building LLVM 18+
+    try {
+      Invoke-Program -OutNull $Python -c 'import packaging' *> $null
+    } catch {
+      $WheelURL = "https://files.pythonhosted.org/packages/08/aa/cc0199a5f0ad350994d660967a8efb233fe0416e4639146c089643407ce6/packaging-24.1-py3-none-any.whl"
+      $WheelHash = "5b8f2217dbdbd2f7f384c41c628544e6d52f2d0f53c6d0c3ea61aa5d1d7ff124"
+      DownloadAndVerify $WheelURL "$BinaryCache\python\packaging-24.1-py3-none-any.whl" $WheelHash
+      Write-Output "Installing 'packaging-24.1-py3-none-any.whl' ..."
+      Invoke-Program -OutNull $Python '-I' -m pip install "$BinaryCache\python\packaging-24.1-py3-none-any.whl" --disable-pip-version-check
+    }
+    # 'setuptools' provides 'distutils' module for Python 3.12+, required for SWIG support
+    # https://github.com/swiftlang/llvm-project/issues/9289
+    try {
+      Invoke-Program -OutNull $Python -c 'import distutils' *> $null
+    } catch {
+      $WheelURL = "https://files.pythonhosted.org/packages/ff/ae/f19306b5a221f6a436d8f2238d5b80925004093fa3edea59835b514d9057/setuptools-75.1.0-py3-none-any.whl"
+      $WheelHash = "35ab7fd3bcd95e6b7fd704e4a1539513edad446c097797f2985e0e4b960772f2"
+      DownloadAndVerify $WheelURL "$BinaryCache\python\setuptools-75.1.0-py3-none-any.whl" $WheelHash
+      Write-Output "Installing 'setuptools-75.1.0-py3-none-any.whl' ..."
+      Invoke-Program -OutNull $Python '-I' -m pip install "$BinaryCache\python\setuptools-75.1.0-py3-none-any.whl" --disable-pip-version-check
+    }
+  }
+
   Download-Python $HostArchName
   if ($IsCrossCompiling) {
     Download-Python $BuildArchName
   }
+  # Ensure Python modules that are required as host build tools
+  Ensure-PythonModules "$(Get-PythonExecutable)"
 
   if ($Android) {
     # Only a specific NDK version is supported right now.
@@ -1411,6 +1440,9 @@ function Build-Compilers() {
       }
     }
 
+    $PythonRoot = "$BinaryCache\Python$($Arch.CMakeName)-$PythonVersion\tools"
+    $PythonLibName = "python{0}{1}" -f ([System.Version]$PythonVersion).Major, ([System.Version]$PythonVersion).Minor
+
     # The STL in VS 17.10 requires Clang 17 or higher, but Swift toolchains prior to version 6 include older versions
     # of Clang. If bootstrapping with an older toolchain, we need to relax to relax this requirement with
     # ALLOW_COMPILER_AND_STL_VERSION_MISMATCH.
@@ -1442,10 +1474,10 @@ function Build-Compilers() {
         LLVM_NATIVE_TOOL_DIR = $BuildTools;
         LLVM_TABLEGEN = (Join-Path $BuildTools -ChildPath "llvm-tblgen.exe");
         LLVM_USE_HOST_TOOLS = "NO";
-        Python3_EXECUTABLE = "$python";
-        Python3_INCLUDE_DIR = "$BinaryCache\Python$($Arch.CMakeName)-$PythonVersion\tools\include";
-        Python3_LIBRARY = "$BinaryCache\Python$($Arch.CMakeName)-$PythonVersion\tools\libs\python39.lib";
-        Python3_ROOT_DIR = "$BinaryCache\Python$($Arch.CMakeName)-$PythonVersion\tools";
+        Python3_EXECUTABLE = (Get-PythonExecutable);
+        Python3_INCLUDE_DIR = "$PythonRoot\include";
+        Python3_LIBRARY = "$PythonRoot\libs\$PythonLibName.lib";
+        Python3_ROOT_DIR = $PythonRoot;
         SWIFT_BUILD_SWIFT_SYNTAX = "YES";
         SWIFT_CLANG_LOCATION = (Get-PinnedToolchainTool);
         SWIFT_ENABLE_EXPERIMENTAL_CONCURRENCY = "YES";
@@ -1715,7 +1747,7 @@ function Build-Runtime([Platform]$Platform, $Arch) {
       })
   }
 
-  Invoke-Program $python -c "import plistlib; print(str(plistlib.dumps({ 'DefaultProperties': { 'DEFAULT_USE_RUNTIME': 'MD' } }), encoding='utf-8'))" `
+  Invoke-Program "$(Get-PythonExecutable)" -c "import plistlib; print(str(plistlib.dumps({ 'DefaultProperties': { 'DEFAULT_USE_RUNTIME': 'MD' } }), encoding='utf-8'))" `
     -OutFile "$($Arch.SDKInstallRoot)\SDKSettings.plist"
 }
 
@@ -1942,7 +1974,7 @@ function Build-Testing([Platform]$Platform, $Arch, [switch]$Test = $false) {
 
 function Write-PlatformInfoPlist($Arch) {
     $PList = Join-Path -Path $Arch.PlatformInstallRoot -ChildPath "Info.plist"
-    Invoke-Program $python -c "import plistlib; print(str(plistlib.dumps({ 'DefaultProperties': { 'XCTEST_VERSION': 'development', 'SWIFT_TESTING_VERSION': 'development', 'SWIFTC_FLAGS': ['-use-ld=lld'] } }), encoding='utf-8'))" `
+    Invoke-Program "$(Get-PythonExecutable)" -c "import plistlib; print(str(plistlib.dumps({ 'DefaultProperties': { 'XCTEST_VERSION': 'development', 'SWIFT_TESTING_VERSION': 'development', 'SWIFTC_FLAGS': ['-use-ld=lld'] } }), encoding='utf-8'))" `
       -OutFile "$PList"
 }