diff --git a/make/autoconf/basic_tools.m4 b/make/autoconf/basic_tools.m4
index 8e42f9205a454..beb58bd4c736d 100644
--- a/make/autoconf/basic_tools.m4
+++ b/make/autoconf/basic_tools.m4
@@ -56,8 +56,10 @@ AC_DEFUN_ONCE([BASIC_SETUP_FUNDAMENTAL_TOOLS],
   # Tools only needed on some platforms
   UTIL_LOOKUP_PROGS(LOCALE, locale)
   UTIL_LOOKUP_PROGS(PATHTOOL, cygpath wslpath)
-  UTIL_LOOKUP_PROGS(CMD, cmd.exe, $PATH:/cygdrive/c/windows/system32:/mnt/c/windows/system32:/c/windows/system32)
   UTIL_LOOKUP_PROGS(LSB_RELEASE, lsb_release)
+
+  SYSTEM32_PATH=$($PATHTOOL -u "$SYSTEMROOT/system32" 2>/dev/null)
+  UTIL_LOOKUP_PROGS(CMD, cmd.exe, $PATH:$SYSTEM32_PATH)
 ])
 
 ################################################################################
diff --git a/make/autoconf/toolchain_microsoft.m4 b/make/autoconf/toolchain_microsoft.m4
index f577cf1a2a1d6..6af344a48f61a 100644
--- a/make/autoconf/toolchain_microsoft.m4
+++ b/make/autoconf/toolchain_microsoft.m4
@@ -338,7 +338,7 @@ AC_DEFUN([TOOLCHAIN_EXTRACT_VISUAL_STUDIO_ENV],
   OLDPATH="$PATH"
   # Make sure we only capture additions to PATH needed by VS.
   # Clear out path, but need system dir present for vsvars cmd file to be able to run
-  export PATH=$WINENV_PREFIX/c/windows/system32
+  export PATH=$($PATHTOOL -u "$SYSTEMROOT")/system32
   # The "| cat" is to stop SetEnv.Cmd to mess with system colors on some systems
   # We can't pass -vcvars_ver=$VCVARS_VER here because cmd.exe eats all '='
   # in bat file arguments. :-(
diff --git a/make/scripts/fixpath.sh b/make/scripts/fixpath.sh
index 6a524df4c680b..dcf67ce7115d0 100644
--- a/make/scripts/fixpath.sh
+++ b/make/scripts/fixpath.sh
@@ -88,7 +88,9 @@ function setup() {
   fi
 
   if [[ -z ${CMD+x} ]]; then
-    CMD="$DRIVEPREFIX/c/windows/system32/cmd.exe"
+    # Use SYSTEMROOT to find Windows directory regardless of drive letter
+    systemroot_unix="$($PATHTOOL -u "$SYSTEMROOT")"
+    CMD="$systemroot_unix/system32/cmd.exe"
   fi
 
   if [[ -z ${WINTEMP+x} ]]; then
diff --git a/test/jdk/com/sun/jdi/JdbReadTwiceTest.sh b/test/jdk/com/sun/jdi/JdbReadTwiceTest.sh
index 5902abe50ad69..f6894da7bcbd1 100644
--- a/test/jdk/com/sun/jdi/JdbReadTwiceTest.sh
+++ b/test/jdk/com/sun/jdi/JdbReadTwiceTest.sh
@@ -43,6 +43,10 @@ if [ -z "$TESTCLASSES" ] ; then
      exit 1
 fi
 
+# Detect if running on Windows
+IS_WINDOWS=false
+case `uname -s` in CYGWIN*|MINGW*|MSYS*) IS_WINDOWS=true ;; esac
+
 case `uname -s` in
     Linux)
       # Need this to convert to the /.automount/... form which
@@ -84,7 +88,7 @@ failIfNot()
     # $1 is the expected number of occurances of $2 in the jdb output.
     count=$1
     shift
-    if [ -r c:/ ] ; then
+    if [ "$IS_WINDOWS" = "true" ] ; then
        sed -e 's@\\@/@g' $tmpResult > $tmpResult.1
        mv $tmpResult.1 $tmpResult
     fi
@@ -177,7 +181,7 @@ mkFiles $HOME/.jdbrc $here/jdb.ini
     clean
 
 
-if [ ! -r c:/ ] ; then
+if [ "$IS_WINDOWS" != "true" ] ; then
     # No symlinks on windows.
     echo
     echo "+++++++++++++++++++++++++++++++++++"
@@ -191,7 +195,7 @@ if [ ! -r c:/ ] ; then
 fi
 
 
-if [ ! -r c:/ ] ; then
+if [ "$IS_WINDOWS" != "true" ] ; then
     # No symlinks on windows.
     echo
     echo "+++++++++++++++++++++++++++++++++++"
diff --git a/test/jdk/java/awt/Dialog/FileDialogUIUpdate.java b/test/jdk/java/awt/Dialog/FileDialogUIUpdate.java
index f97d947991b43..b479b748d8502 100644
--- a/test/jdk/java/awt/Dialog/FileDialogUIUpdate.java
+++ b/test/jdk/java/awt/Dialog/FileDialogUIUpdate.java
@@ -70,7 +70,7 @@ public FileDialogUIUpdate() {
         Button showButton = new Button("Show FileDialog");
         setLayout(new BorderLayout());
 
-        fd.setDirectory("c:/");
+        fd.setDirectory(System.getenv("SYSTEMROOT"));
         showButton.addActionListener(new ActionListener() {
             public void actionPerformed(ActionEvent e) {
                 fd.setVisible(true);