The Dropbox integration with the Apple Files app on iPad is the number one reason our customers reach out to us for technical support. Dropbox support forums have many users reporting the same issues across multiple different apps on iPad. The poor Dropbox integration with Apple Files creates a user experience that is frustrating for you and also for us as it has nothing to do with our apps and there is nothing we can do to address the issue. Dropbox has to fix the issue, and until they do we no longer recommend Dropbox as a cloud storage solution to use with our iPad apps.
This support article that explains the issue and offers some solutions:
This support article offers another solution by using drag and drop to import files:
If you use Box, Microsoft OneDrive, or Google Drive, their integrations work well with the Apple Files app and we can recommend using those cloud storage providers to import files into our apps.
If you want to continue using Dropbox as your cloud storage provider, we recommend using a third party iPad app called Total Files that can act as a conduit between Dropbox and our apps. It is a free app and therefore has no cost, but does offer an in app purchase if you want to remove the advertising. We have no affiliation with the app or the developer so we cannot offer technical support, however in our testing it seems very straightforward and works well. Total Files can be downloaded from the iPad App Store here: https://apps.apple.com/app/id557285579
After downloading Total Files, go through the onboarding slides and then tap on the Dropbox icon to log into your Dropbox account. You can find Dropbox and other cloud storage options after onboarding under the Cloud tab in Total Files. The next time you launch TrialPad or one of the other LIT SUITE apps you should see Total in the sidebar (do not tap on it yet). Open an existing Case File or create a new one, then tap on the Plus button under the document list. In the popover, tap on Import Documents which will present you with the file picker. In this popup window tap on the Total icon in the sidebar and you will see your Dropbox cloud storage. Navigate to the files you want to import, tap to select them (or choose Select All) and tap on Open to import them into the Case File.