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The send flow stacked two .fileImporter modifiers on the same view (one for files, one for folders). On iOS/macOS before 27, SwiftUI can't have two presentation modifiers of the same kind on one view — the second shadows the first, so toggling the files importer presented nothing and "Choose files" appeared to do nothing. macOS/iOS 27 changed presentation handling, which is why it worked there. Collapse the two importers into a single .fileImporter that switches its allowedContentTypes and allowsMultipleSelection based on whether a file or folder pick is pending. Behavior is unchanged on 27 and now works on 26 and earlier.