Sorting Bug in Finder Upload Window

It sounds like you are Grouping, not Sorting. A direct click of the button in toolbar gives Grouping options. Option-click gives Sorting options. Set the Group by to None, then option-click the button to choose the sort.

Firstly, it's essential to ensure that your macOS Ventura 13.5 is up to date with the latest software updates. Apple frequently releases updates to address bugs and improve system stability, so installing any available updates may potentially resolve the sorting issue you're experiencing.

To check for updates on macOS Ventura, you can follow these steps:

1. Click on the Apple menu in the top-left corner of your screen.

2. Select "System Preferences."

3. Click on "Software Update."

4. If any updates are available, click on the "Update Now" button to download and install them.

Once your macOS Ventura is up to date, try sorting files in the Finder upload window again to see if the issue persists.

If the problem persists even after updating your macOS, you may need to explore alternative methods or workarounds to achieve the desired sorting in the Finder upload window. Here are a few suggestions:

1. Use a third-party file management tool: Consider using a third-party file management tool or FTP client that offers more robust sorting and filtering options. These tools may provide better support for sorting files by date modified, added, or created, thereby improving your workflow efficiency.

2. Pre-sort files before uploading: If possible, pre-sort your files in the Finder before initiating the upload process. You can organize files into folders based on their modification dates or other criteria, making it easier to locate and select the files you need during the upload process.

3. Contact Apple Support: If the issue persists and significantly impacts your workflow, consider reaching out to Official Apple Support for further assistance. They may be able to provide additional troubleshooting steps or escalate the issue to Apple's engineering team for investigation and resolution.

Overall, while it's frustrating to encounter sorting issues in the Finder upload window, exploring alternative methods and staying updated with software updates can help mitigate the impact on your workflow. Additionally, providing feedback to Apple about the issue through official channels may contribute to future improvements in macOS.

No problem at all, happy to help clarify things for you. When you click the "Update Now" button in System Preferences under "Software Update," it will indeed check for and install any available updates for your current macOS version, which in your case is Ventura 13.5. However, it won't automatically upgrade your macOS to a newer version like Sonoma unless there is a newer version available and you explicitly choose to install it.

So, if you prefer to stay on Ventura 13.5 and avoid upgrading to Sonoma, you can safely click "Update Now" to install any available updates for Ventura without worrying about being automatically upgraded to Sonoma. The update process only applies patches, security updates, and improvements to your existing Ventura installation.

If you ever decide to upgrade to Sonoma in the future, you would need to explicitly initiate that upgrade process through the App Store or by downloading the Sonoma installer from Apple

I don’t know how that works since they’ve added the upvote/downvote thing.