This would check for the existance of the directory as well.

File file = new File("c:\\cygwin\\cygwin.bat");
if (!file.isDirectory())
   file = file.getParentFile();
if (file.exists()){
    ...
}

It seems like file.canWrite() does not give you a clear indication if you have permissions to write to the directory.

File.getCanonicalPath() is quite useful for this purpose. IO exceptions are thrown for certain types of invalid filenames (e.g. CON, PRN, *?* in Windows) when resolving against the OS or file system. However, this only serves as a preliminary check; you will still need to handle other failures when actually creating the file (e.g. insufficient permissions, lack of drive space, security restrictions).

A number of things can go wrong when you try and create a file:

• Your lack the requisite permissions;
• There is not enough space on the device;
• The device experiences an error;
• Some policy of custom security prohibits you from creating a file of a particular type;
• etc.

More to the point, those can change between when you try and query to see if you can and when you actually can. In a multithreaded environment this is one of the primary causes of race conditions and can be a real vulnerability of some programs.

Basically you just have to try and create it and see if it works. And that's the correct way to do it. It's why things like ConcurrentHashMap has a putIfAbsent() so the check and insert is an atomic operation and doesn't suffer from race conditions. Exactly the same principle is in play here.

If this is just part of some diagnostic or install process, just do it and see if it works. Again there's no guarantee that it'll work later however.

Basically your program has to be robust enough to die gracefully if it can't write a relevant file.

Here's something you can do that works across operating systems

Using regex match to check for existing known invalid characters.

if (newName.matches(".*[/\n\r\t\0\f`?*\\<>|\":].*")) {
    System.out.println("Invalid!");
} else {
    System.out.println("Valid!");
}

Pros

• This works across operating systems
• You can customize it whatever way you want by editing that regex.

Cons

• This might not be a complete list and need more research to fill in more invalid patterns or characters.

Just do it (and clean up after yourself)

A possible approach may be attempting to create the file and eventually deleting it if the creation succeeded, but I hope there is a more elegant way of achieving the same result.

Maybe that's the most robust way.

Below is canCreateOrIsWritable that determines whether your program is able to create a file and its parent directories at a given path, or, if there's already a file there, write to it.

It does so by actually creating the necessary parent directories as well as an empty file at the path. Afterwards, it deletes them (if there existed a file at the path, it's left alone).

Here's how you might use it:

var myFile = new File("/home/me/maybe/write/here.log")

if (canCreateOrIsWritable(myFile)) {
    // We're good. Create the file or append to it
    createParents(myFile);
    appendOrCreate(myFile, "new content");
} else {
    // Let's pick another destination. Maybe the OS's temporary directory:
    var tempDir = System.getProperty("java.io.tmpdir");
    var alternative = Paths.get(tempDir, "second_choice.log");
    appendOrCreate(alternative, "new content in temporary directory");
}

The essential method with a few helper methods:

static boolean canCreateOrIsWritable(File file) {
    boolean canCreateOrIsWritable;

    // The non-existent ancestor directories of the file.
    // The file's parent directory is first
    List<File> parentDirsToCreate = getParentDirsToCreate(file);

    // Create the parent directories that don't exist, starting with the one
    // highest up in the file system hierarchy (closest to root, farthest
    // away from the file)
    reverse(parentDirsToCreate).forEach(File::mkdir);

    try {
        boolean wasCreated = file.createNewFile();
        if (wasCreated) {
            canCreateOrIsWritable = true;
            // Remove the file and its parent dirs that didn't exist before
            file.delete();
            parentDirsToCreate.forEach(File::delete);
        } else {
            // There was already a file at the path → Let's see if we can
            // write to it
            canCreateOrIsWritable = java.nio.file.Files.isWritable(file.toPath());
        }
    } catch (IOException e) {
        // File creation failed
        canCreateOrIsWritable = false;
    }
    return canCreateOrIsWritable;
}

static List<File> getParentDirsToCreate(File file) {
    var parentsToCreate = new ArrayList<File>();
    File parent = file.getParentFile();
    while (parent != null && !parent.exists()) {
        parentsToCreate.add(parent);

        parent = parent.getParentFile();
    }
    return parentsToCreate;
}

static <T> List<T> reverse(List<T> input) {
    var reversed = new ArrayList<T>();
    for (int i = input.size() - 1; i >= 0; i--) {
        reversed.add(input.get(i));
    }
    return reversed;
}

static void createParents(File file) {
    File parent = file.getParentFile();
    if (parent != null) {
        parent.mkdirs();
    }
}

Keep in mind that between calling canCreateOrIsWritable and creating the actual file, the contents and permissions of your file system might have changed.