diff --git a/main.go b/main.go
index 2cd5cfe..d696acf 100644
--- a/main.go
+++ b/main.go
@@ -201,7 +201,7 @@ func put(fileName string, pathName string, fileType int, auxType int, inFileName
 	defer file.Close()
 	fileInfo, err := os.Stat(fileName)
 
-	err = prodos.WriteFileFromFile(file, pathName, fileType, auxType, fileInfo.ModTime(), inFileName)
+	err = prodos.WriteFileFromFile(file, pathName, fileType, auxType, fileInfo.ModTime(), inFileName, false)
 	if err != nil {
 		fmt.Printf("Failed to write file %s", err)
 	}
diff --git a/prodos/directory.go b/prodos/directory.go
index 7c6487b..d06b757 100644
--- a/prodos/directory.go
+++ b/prodos/directory.go
@@ -248,6 +248,7 @@ func getFreeFileEntryInDirectory(readerWriter ReaderWriterAt, directory string)
 		fileEntry := parseFileEntry(buffer[entryOffset:entryOffset+0x28], blockNumber, entryOffset)
 
 		if fileEntry.StorageType == StorageDeleted {
+			fileEntry = FileEntry{}
 			fileEntry.DirectoryBlock = blockNumber
 			fileEntry.DirectoryOffset = entryOffset
 			fileEntry.HeaderPointer = directoryHeader.StartingBlock
diff --git a/prodos/file.go b/prodos/file.go
index 0b84580..e9d3637 100644
--- a/prodos/file.go
+++ b/prodos/file.go
@@ -52,7 +52,7 @@ func WriteFile(readerWriter ReaderWriterAt, path string, fileType int, auxType i
 
 	existingFileEntry, _ := GetFileEntry(readerWriter, path)
 	if existingFileEntry.StorageType != StorageDeleted {
-		DeleteFile(readerWriter, path)
+		return errors.New(("file already exists"))
 	}
 
 	// get list of blocks to write file to
@@ -126,6 +126,10 @@ func incrementFileCount(readerWriter ReaderWriterAt, fileEntry FileEntry) error
 // DeleteFile deletes a file from a ProDOS volume
 func DeleteFile(readerWriter ReaderWriterAt, path string) error {
 	fileEntry, err := GetFileEntry(readerWriter, path)
+	// DumpFileEntry(fileEntry)
+	// oldDirectoryBlock, _ := ReadBlock(readerWriter, fileEntry.DirectoryBlock)
+	// DumpBlock(oldDirectoryBlock)
+
 	if err != nil {
 		return errors.New("file not found")
 	}
@@ -169,6 +173,12 @@ func DeleteFile(readerWriter ReaderWriterAt, path string) error {
 	return nil
 }
 
+// FileExists return true if the file exists
+func FileExists(reader io.ReaderAt, path string) (bool, error) {
+	fileEntry, _ := GetFileEntry(reader, path)
+	return fileEntry.StorageType != StorageDeleted, nil
+}
+
 // GetDirectoryAndFileNameFromPath gets the directory and filename from a path
 func GetDirectoryAndFileNameFromPath(path string) (string, string) {
 	path = strings.ToUpper(path)
diff --git a/prodos/host.go b/prodos/host.go
index 843411d..9276cab 100644
--- a/prodos/host.go
+++ b/prodos/host.go
@@ -22,7 +22,8 @@ func AddFilesFromHostDirectory(
 	readerWriter ReaderWriterAt,
 	directory string,
 	path string,
-	recursive bool) error {
+	recursive bool,
+) error {
 
 	path, err := makeFullPath(path, readerWriter)
 
@@ -42,7 +43,7 @@ func AddFilesFromHostDirectory(
 		}
 
 		if file.Name()[0] != '.' && !file.IsDir() && info.Size() > 0 && info.Size() <= 0x1000000 {
-			err = WriteFileFromFile(readerWriter, path, 0, 0, info.ModTime(), filepath.Join(directory, file.Name()))
+			err = WriteFileFromFile(readerWriter, path, 0, 0, info.ModTime(), filepath.Join(directory, file.Name()), true)
 			if err != nil {
 				return err
 			}
@@ -56,8 +57,14 @@ func AddFilesFromHostDirectory(
 			newFullPath := strings.ToUpper(path + newPath)
 
 			newHostDirectory := filepath.Join(directory, file.Name())
-			CreateDirectory(readerWriter, newFullPath)
-			AddFilesFromHostDirectory(readerWriter, newHostDirectory, newFullPath+"/", recursive)
+			err = CreateDirectory(readerWriter, newFullPath)
+			if err != nil {
+				return err
+			}
+			err = AddFilesFromHostDirectory(readerWriter, newHostDirectory, newFullPath+"/", recursive)
+			if err != nil {
+				return err
+			}
 		}
 	}
 
@@ -71,7 +78,9 @@ func WriteFileFromFile(
 	fileType int,
 	auxType int,
 	modifiedTime time.Time,
-	inFileName string) error {
+	inFileName string,
+	ignoreDuplicates bool,
+) error {
 
 	inFile, err := os.ReadFile(inFileName)
 	if err != nil {
@@ -117,7 +126,17 @@ func WriteFileFromFile(
 		pathName = strings.Join(paths, "")
 	}
 
-	fmt.Printf("Source: %s Destination: %s\n", inFileName, pathName)
+	// skip if file already exists and ignoring duplicates
+	if ignoreDuplicates {
+		exists, err := FileExists(readerWriter, pathName)
+		if err != nil {
+			return err
+		}
+		if exists {
+			return nil
+		}
+	}
+
 	return WriteFile(readerWriter, pathName, fileType, auxType, time.Now(), modifiedTime, inFile)
 }