diff --git a/pkg/snclient/check_files.go b/pkg/snclient/check_files.go
index 2c791b7a..9cf05948 100644
--- a/pkg/snclient/check_files.go
+++ b/pkg/snclient/check_files.go
@@ -592,6 +592,18 @@ func (l *CheckFiles) normalizePath(path string) string {
 	// Special handling for Windows drive letters,
 	// Files directly under the drive do not have separators, e.g: C:pagefile.sys
 	// This confuses the depth calculation
+	if runtime.GOOS == "windows" {
+		// Convert forward slashes to backward slashes
+		fromSlash := filepath.FromSlash(path)
+		path = fromSlash
+	}
+
+	// Remove groups of seperators next to each other , and replace them with a single separator
+	sep := string(os.PathSeparator)
+	for strings.Contains(path, sep+sep) {
+		path = strings.ReplaceAll(path, sep+sep, sep)
+	}
+
 	if runtime.GOOS == "windows" {
 		// C: -> C:\
 		if len(path) == 2 && unicode.IsUpper(rune(path[0])) && path[1] == ':' {
diff --git a/pkg/snclient/check_files_windows_test.go b/pkg/snclient/check_files_windows_test.go
index 5a0c0c4a..775c4904 100644
--- a/pkg/snclient/check_files_windows_test.go
+++ b/pkg/snclient/check_files_windows_test.go
@@ -88,3 +88,31 @@ func TestCheckDriveLetterPaths(t *testing.T) {
 
 	StopTestAgent(t, snc)
 }
+
+func TestCheckPathSpecifications(t *testing.T) {
+	snc := StartTestAgent(t, "")
+	var res *CheckResult
+
+	// ===============  C:\Windows\Fonts\arial.ttf
+	// Intended separator is backward slashes like this
+	res = snc.RunCheck("check_files", []string{"path=C:\\Windows\\fonts", "max-depth=1", "filter= type == 'file' and name == 'arial.ttf' "})
+	assert.Containsf(t, string(res.BuildPluginOutput()), "OK - All 1 files are ok", "output matches")
+
+	// Forward slashes should be converted to backward slashes
+	res = snc.RunCheck("check_files", []string{"path=C:/Windows/fonts", "max-depth=1", "filter= type == 'file' and name == 'arial.ttf' "})
+	assert.Containsf(t, string(res.BuildPluginOutput()), "OK - All 1 files are ok", "output matches")
+
+	// Multiple backward slashes that do not actually go into subfolders and add depth should be ignored
+	res = snc.RunCheck("check_files", []string{"path=C:\\\\\\Windows\\\\fonts", "max-depth=1", "filter= type == 'file' and name == 'arial.ttf' "})
+	assert.Containsf(t, string(res.BuildPluginOutput()), "OK - All 1 files are ok", "output matches")
+
+	// Multiple backward slashes that do not actually go into subfolders and add depth should be ignored
+	res = snc.RunCheck("check_files", []string{"path=C:\\\\Windows\\\\fonts", "max-depth=1", "filter= type == 'file' and name == 'arial.ttf' "})
+	assert.Containsf(t, string(res.BuildPluginOutput()), "OK - All 1 files are ok", "output matches")
+
+	// Multiple forward slashes that do not actually go into subfolders and add depth should be ignored
+	res = snc.RunCheck("check_files", []string{"path=C://Windows////fonts", "max-depth=1", "filter= type == 'file' and name == 'arial.ttf' "})
+	assert.Containsf(t, string(res.BuildPluginOutput()), "OK - All 1 files are ok", "output matches")
+
+	StopTestAgent(t, snc)
+}