diff --git a/core/core.go b/core/core.go
index 7203f96..14cda1d 100644
--- a/core/core.go
+++ b/core/core.go
@@ -171,26 +171,27 @@ func CleanAndCheckPaths(paths []string, outputDir string) ([]string, string, err
 		return nil, "", errors.New("empty path sequence")
 	}
 
-	// Clean all paths and outputDir
+	// Clean paths
 	for i := 0; i < len(paths); i++ {
 		paths[i] = filepath.Clean(paths[i])
 	}
-	outputDir = filepath.Clean(outputDir)
-
-	// Check if outputDir is actually a directory
-	fileInfo, err := os.Stat(outputDir)
-	if err != nil {
-		return nil, "", err
-	}
-	if !fileInfo.IsDir() {
-		return nil, "", fmt.Errorf("'%v' is not a directory", filepath.Base(outputDir))
-	}
 
 	if hasDuplicates(paths) {
 		return nil, "", errors.New("duplicate paths are not allowed")
 	}
 
-	if len(outputDir) > 0 && outputDir != "." {
+	if outputDir != "" {
+		outputDir = filepath.Clean(outputDir)
+
+		// Check if outputDir is actually a directory
+		fileInfo, err := os.Stat(outputDir)
+		if err != nil {
+			return nil, "", err
+		}
+		if !fileInfo.IsDir() {
+			return nil, "", fmt.Errorf("'%s' is not a directory", filepath.Base(outputDir))
+		}
+
 		if hasDuplicateFilenames(paths) {
 			return nil, "", errors.New("duplicate filenames are not allowed with output (-o) flag")
 		}
diff --git a/core/core_test.go b/core/core_test.go
index 4d2ea89..5f46e5a 100644
--- a/core/core_test.go
+++ b/core/core_test.go
@@ -274,13 +274,13 @@ func TestCleanAndCheckPaths(t *testing.T) {
 			[]string{"C:/t./11est/something.txt", "D:/path/something.txt", "C:////\\/"},
 			[]string{filepath.Clean("C:/t./11est/something.txt"), filepath.Clean("D:/path/something.txt"), filepath.Clean("C:////\\/")},
 			"",
-			".",
+			"",
 		},
 		{
 			[]string{"C:\\something.txt", "H:/qq", "a", "/home/\\//user//test/some"},
 			[]string{filepath.Clean("C:\\something.txt"), filepath.Clean("H:/qq"), filepath.Clean("a"), filepath.Clean("/home/\\//user//test/some")},
 			"",
-			".",
+			"",
 		},
 		{
 			[]string{"file1", "./file2", "/////somewhere\\file3"},
@@ -291,7 +291,7 @@ func TestCleanAndCheckPaths(t *testing.T) {
 		{
 			[]string{"file1"},
 			[]string{filepath.Clean("file1")},
-			"",
+			".",
 			".",
 		},
 		{
@@ -341,7 +341,7 @@ func TestCleanAndCheckPathsError(t *testing.T) {
 			"", // Expecting OS specific err
 		},
 		{
-			[]string{"path/to/something", "path\\////to//\\/something/", "file1"},
+			[]string{"path/to/something", "path\\////to//\\/something2/", "file1"},
 			nil,
 			filepath.Join(dir, "small.txt"),
 			"",
diff --git a/core/decrypt.go b/core/decrypt.go
index 5a50ef4..13d1bd0 100644
--- a/core/decrypt.go
+++ b/core/decrypt.go
@@ -100,7 +100,7 @@ func DecryptFiles(paths []string, outputDir, password string, overwrite bool) er
 		go func() {
 			defer wg.Done()
 			fileOut := strings.TrimSuffix(fileIn, ".eddy")
-			if len(outputDir) > 0 {
+			if outputDir != "" {
 				fileOut = filepath.Join(outputDir, filepath.Base(fileOut))
 			}
 			if _, err := os.Stat(fileOut); !errors.Is(err, os.ErrNotExist) && !overwrite {
diff --git a/core/encrypt.go b/core/encrypt.go
index ce9c678..d20b08d 100644
--- a/core/encrypt.go
+++ b/core/encrypt.go
@@ -107,7 +107,7 @@ func EncryptFiles(paths []string, outputDir, password string, overwrite bool) (i
 		go func() {
 			defer wg.Done()
 			fileOut := fileIn + ".eddy"
-			if len(outputDir) > 0 {
+			if outputDir != "" {
 				fileOut = filepath.Join(outputDir, filepath.Base(fileOut))
 			}
 			if _, err := os.Stat(fileOut); !errors.Is(err, os.ErrNotExist) && !overwrite {