diff --git a/Configurations/unix-checker.pm b/Configurations/unix-checker.pm
new file mode 100644
index 0000000000..b39b0eb7cb
--- /dev/null
+++ b/Configurations/unix-checker.pm
@@ -0,0 +1,22 @@
+#! /usr/bin/perl
+
+use Config;
+
+# Check that the perl implementation file modules generate paths that
+# we expect for the platform
+use File::Spec::Functions qw(:DEFAULT rel2abs);
+
+if (rel2abs('.') !~ m|/|) {
+    die <<EOF;
+
+******************************************************************************
+This perl implementation doesn't produce Unix like paths (with forward slash
+directory separators).  Please use an implementation that matches your
+building platform.
+
+This Perl version: $Config{version} for $Config{archname}
+******************************************************************************
+EOF
+}
+
+1;
diff --git a/Configurations/windows-checker.pm b/Configurations/windows-checker.pm
new file mode 100644
index 0000000000..de46fbc1df
--- /dev/null
+++ b/Configurations/windows-checker.pm
@@ -0,0 +1,22 @@
+#! /usr/bin/perl
+
+use Config;
+
+# Check that the perl implementation file modules generate paths that
+# we expect for the platform
+use File::Spec::Functions qw(:DEFAULT rel2abs);
+
+if (rel2abs('.') !~ m|\\|) {
+    die <<EOF;
+
+******************************************************************************
+This perl implementation doesn't produce Windows like paths (with backward
+slash directory separators).  Please use an implementation that matches your
+building platform.
+
+This Perl version: $Config{version} for $Config{archname}
+******************************************************************************
+EOF
+}
+
+1;
diff --git a/Configure b/Configure
index 86f68c7ca0..b7d669c118 100755
--- a/Configure
+++ b/Configure
@@ -993,6 +993,25 @@ $target{build_scheme} = [ $target{build_scheme} ]
 my ($builder, $builder_platform, @builder_opts) =
     @{$target{build_scheme}};
 
+foreach my $checker (($builder_platform."-".$target{build_file}."-checker.pm",
+                      $builder_platform."-checker.pm")) {
+    my $checker_path = catfile($srcdir, "Configurations", $checker);
+    if (-f $checker_path) {
+        my $fn = $ENV{CONFIGURE_CHECKER_WARN}
+            ? sub { warn $@; } : sub { die $@; };
+        if (! do $checker_path) {
+            if ($@) {
+                $fn->($@);
+            } elsif ($!) {
+                $fn->($!);
+            } else {
+                $fn->("The detected tools didn't match the platform\n");
+            }
+        }
+        last;
+    }
+}
+
 push @{$config{defines}}, "NDEBUG"    if $config{build_type} eq "release";
 
 if ($target =~ /^mingw/ && `$target{cc} --target-help 2>&1` =~ m/-mno-cygwin/m)