Applies to: Everyone
This article explains certain behaviors users may notice when uploading files and folders to DealCentre AI. These are largely driven by how Windows and macOS handle files locally, rather than by DealCentre AI itself.
Unexpected file and folder upload behaviors
Sort order of files and folders
Issue: I uploaded files and folders to DealCentre AI, but they did not follow the order I have on my computer.
Applies to: Windows and macOS
Reason: The sort order on Windows and macOS is dynamic and based on the user's view preference: files can be sorted alphanumerically, by type, by created/modified date, among other options. This preference cannot be carried over during upload.
What to do: DealCentre AI sorts bulk-uploaded files and folders alphanumerically by default. Additional content will be automatically placed last in the destination. To change the order in which content is displayed in a Deal, simply drag and drop them to the desired order.
Empty folders
Issue: I uploaded a folder using the Select Folder option, but empty folders were not included.
Applies to: Windows and macOS
Reason: Empty folders can only be uploaded using drag-and-drop.
What to do: To upload empty folders, use drag-and-drop instead of Select Folder.
Maximum path length
Issue: My file upload failed with no clear reason.
Applies to: Windows only
Reason: Windows supports a maximum path length of 260 characters. If a file's full path (folder structure plus file name) exceeds this limit, the upload will fail.
What to do: Shorten folder names or reduce folder nesting so the full path stays under 260 characters.
Duplicate file with a ~$ prefix
Issue: I see a duplicate file with a ~$ prefix. Example: ~$contract.docx and contract.docx. I get an error message when attempting to open files with this prefix in the Deal.
Applies to: Windows only
Reason: If a Microsoft Office file is open at the time of upload, Windows creates a temporary hidden file with a "~$" prefix alongside the original. This hidden file can sometimes be included in the upload.
What to do: Close any open files in your computer before you upload. You can safely delete these files from your Deal.
Shortened file names
Issue: I see a shortened file name in DealCentre AI. Example: MLConsultingReport2026.docx appears as MLCONS~1.docx.
Applies to: Windows only
Reason: Windows may generate shortened file names using the legacy 8.3 naming format during file access or drag-and-drop operations, which can cause the uploaded file name to differ from the original.
What to do: Use shorter file names before you upload. If the file is already uploaded, you can rename it directly in the Deal without the need to reupload.
Deep folder structures
Issue: My upload failed when my folder had many nested subfolders.
Applies to: Windows, macOS could also be affected depending on the depth of the structure.
Reason: Excessively nested folder structures may cause upload failures due to local path and character limitations.
What to do: Keep your folder hierarchy as shallow as possible before uploading. It helps you navigate the content easily and avoids hitting local thresholds.
Hidden system files
Issue: Some files did not upload.
Applies to: Windows and macOS
Reason: System-generated hidden files such as Thumbs.db on Windows and .DS_Store on macOS are excluded from upload as they do not contain usable information.
What to do: No action is required. These files are not needed and ignored during the upload process.
Shortcuts, aliases and symbolic links
Issue: I uploaded a symbolic link, shortcut or alias, but the target file or folder was not included.
Applies to: Windows and macOS
Reason: Shortcuts, aliases and symbolic links that point to a file or folder but do not contain actual content.
What to do: Go to the location that the links point to and upload the content directly from there.
Unsupported filename characters
Issue: My file was rejected, or its name changed unexpectedly.
Applies to: Windows, limited impact on macOS
Reason: These characters are not supported } : | \ / ` ^ ‘ ?
What to do: Rename files and folders removing these characters before you upload.
Reserved file names
Issue: Certain files did not upload.
Applies to: Windows, limited impact on macOS
Reason: Some filenames are reserved by the operating system and cannot be used, including CON, PRN, AUX, NUL, COM1, and LPT1.
What to do: Rename any file using one of these reserved names before you upload.
Package and application bundles
Issue: My macOS package file (such as a .pages or .key document) did not upload as expected.
Applies to: macOS only
Reason: Package-based files such as .app, .pages, .numbers, and .key are technically folders containing multiple internal files, so they may not upload as a single item.
What to do: Where possible, export package-based files to a standard format before uploading. For example, PDF or .docx.
Best practices to avoid issues and improve user navigation
Keep file paths short and avoid deep folder structures. Folders and file names may appear clipped making it hard for users navigating the content to understand topics. Excessively deep folder structures can confuse readers, and content may be unintentionally missed.
Avoid empty folders. Some user roles cannot see a folder until it contains files that they are permissioned to view.
Use standard file names. Unsupported characters and reserved file names may cause uploads to fail.
Always verify uploaded content. This ensures that all expected content is present in your deal and that all files open correctly.
Additional information