Sometimes it does work, but what you may get is a never-ending spinner in the file picker window that represents this back and forth between Dropbox and the Files app. If you try to import any of the files that have the cloud icon and a down arrow, the Files app will try to access them from the Dropbox app, but the Dropbox app may not allow them to be imported because they are not downloaded from the Dropbox cloud, i.e. (It is the exact same dialog you see when you choose Attach File when drafting an email in the Mail app.) Once you navigate to the Dropbox location, if any of the files you want to import have a cloud icon with a down arrow, that indicates the files are not stored locally, but are in the Dropbox cloud, and they need to be downloaded. TrialPad is passing the request to iPadOS which in turn is what prompts you to select the files. Our apps use Apple’s file picker to access your files in Dropbox, this is a security feature of iPadOS and not part of our app.

Using TrialPad for this example, when you open a Case File and choose Plus > Import Documents, the popup window that appears is Apple's file picker which is part of the built in Files app. You can make your files available offline by following these directions: When you tap on a file in the Dropbox app it starts to download the file from the Dropbox cloud, and you may see a progress bar, or spinner, as the file downloads. If you open the Dropbox app on your iPad it will display a list of your files, but this does not mean that the files are downloaded and stored locally. In order to import files from Dropbox, the files have to be downloaded and stored locally in the Dropbox app on the iPad.

Dropbox sign in issues iphone