Drag and drop files — or a whole folder — into an open data room. Peony preserves folder structure. On the Business plan and above, it processes each document on upload — extracting text and building the AI index that makes the room searchable and powers AI document Q&A; processing finishes in under three minutes for most rooms. On the Data Room plan and above, it can also add numbered prefixes automatically (the Index documents setting) so long rooms stay easy to scan.

Supported File Types

Documents — PDF, Word (DOCX), Excel (XLSX), PowerPoint (PPTX), plain text, Markdown
Web & AI artifacts — HTML and HTM, rendered live in the viewer — JavaScript runs, so interactive AI-generated artifacts work as intended (Business plan and up)
Images — PNG, JPG, GIF, WebP
Video and audio — MP4 (H.264) and common codecs (Business plan and up)
Archives — ZIP (contents shown as a folder)

PDFs and Excel render in a secure in-browser viewer, HTML renders live (JavaScript executes), PowerPoint converts for browsing, and videos stream in place. See Supported File Formats for the full list and how each one renders.

HTML, video, and audio uploads require the Business plan or higher. On the Free plan, uploading one of these types is rejected with a message that a Business plan is required — every other type above works on Free.

How to Upload

Drag and drop files or folders into the main upload area
Open the + menu and choose File upload to pick from a file picker, or Folder upload to add a whole folder
Paste from clipboard (for images)

Dropping a folder preserves structure. Financials/2024/ and Financials/2025/ land in the room exactly like that.

Uploading several loose files at the top level of a data room groups them into a new folder (named for the file count, like 5 items). Uploading loose files inside an existing folder places them directly in that folder, with no extra wrapper. Dropping an actual folder always keeps its own structure and name.

Uploading more than one file at once — and Folder upload — require the Business plan or higher. On the Free plan you upload one file at a time.

If a nested folder won't upload from a cloud-synced source (Dropbox, and especially on Macs), it is usually because the files live in the cloud, not on your disk. Make the folder available offline / download it locally first, then drag it in — the nested structure comes through. macOS also adds hidden entries (like .DS_Store) that Peony skips by design; if a count looks short, re-upload the same folder and choose to merge only the missing items.

Organizing Folders

Open the + menu and choose New folder — the Create folder dialog opens for you to name it. Folders and subfolders require the Business plan or higher. A typical deal structure:

01_Company_Overview/
02_Financials/
03_Legal/
04_Commercial/
05_Team/
06_Appendices/

Numbered prefixes keep the order stable. For M&A, borrow the folder tree your counsel uses. Folder rename and moving items both work. Peony blocks moves that would create folder cycles.

Moving Files Between Folders

Hover the top-right corner of a file or folder, open the three-dot menu, and choose Move, then pick a destination. Destinations can be nested — drill into a parent by opening it inside the Move dialog. Drag-to-move also works when you drag from the index (left-most) column. Bulk multi-select move is not yet available; if you need many items moved at once, contact support and we can move them for you.

Sections and Text Blocks

Inside a data room, the + menu also offers Section and Text items. Sections act as dividers to group parts of a room, and Text adds rich-text blocks — useful for a short intro, instructions, or context between folders. Creating or editing Sections and Text blocks requires the Data Room plan ($52 per admin/mo) or higher; below that tier the menu items show an upgrade badge.

AI Auto-Indexing

On the Business plan ($30 per admin/mo) and above, Peony's AI processes each document on upload — extracting text and generating embeddings so you can search across the room and run AI Q&A over every file. For 50–200 documents this finishes in a few minutes. On the Free plan, document AI is unavailable, so rooms are searchable by file name only. AI Q&A usage scales by tier (Business base allotment, Data Room 5x, Deal Team 10x). The separate Index documents setting — a Data Room plan ($52 per admin/mo) and above display option that adds numbered prefixes across documents — is a labeling layer only; it does not extract text or classify files.

Once indexed:

Search across the entire room
AI Q&A with page-number citations — the AI document chat is available on Business and above (see AI Q&A); indexing on Data Room and above adds room-wide context so answers span every document

See AI Auto-Indexing for details.

Upload Failures

Most are transient network issues — retry and it usually works. If it still fails:

Large files (multi-GB video) can time out on slow connections. A message like "1 file could not be uploaded" on a very large file usually means the connection dropped mid-transfer — retry on a stable network.
Don't switch browser tabs mid-upload. Switching tabs can drop the connection and stall the progress circle.
HTML, video, or audio on the Free plan is rejected with a message that a Business plan is required. Upgrade to Business to enable these types. (See Supported File Types.)
Exotic formats may not be supported — convert to PDF.
Try Chrome or Safari — best-tested.
Contact support with the file name if retries fail.

See Upload Issues for more on failed and stalled uploads.

Viewer Uploads

If a link has upload permission enabled, counterparties can upload files back. Their uploads land inside the folder they were granted upload access to — attributed to that link and viewer, and visible to admins. There is no separate system "Uploads" folder; grant upload access on the folder where you want returned files to arrive, then move them from there if needed. Multiple files or a directory dropped at once are placed in a container folder named for the upload (or after the directory's own name).

Counterparties can upload more than one file at a time. Useful for M&A redlines, signed subscription documents, or consulting source materials. Off by default — enable in link settings.

Common Mistakes

Uploading one giant ZIP. AI cannot index nested ZIP contents as richly. Drop folders directly.
Wrong room. Double-check which room tab is open before dropping files.
Expecting viewer uploads to be hidden. They appear inside the folder you gave the viewer upload access to the moment the upload finishes, visible to admins.
Uploading mid-presentation. Indexing takes up to three minutes. Upload ahead of time.

Common Questions

How do I move a file into another folder? Hover the top-right corner of the file, open the three-dot menu, and choose Move, then pick a destination — you can drill into nested folders inside the dialog. Dragging from the index (left-most) column also moves items. Bulk multi-select move is not yet available; support can move a batch for you if you ask.

Why does uploading a nested folder from Dropbox fail? Cloud-synced folders (Dropbox especially, and often on Macs) may live in the cloud rather than on your disk. Make the folder available offline or download it locally first, then drag it in — the nested structure uploads correctly.

Some files seemed to go missing when I uploaded a folder — did they fail? Usually not. macOS adds hidden entries like .DS_Store that Peony skips by design, which can make a count look short. Re-upload the same folder and choose to merge only the missing items to confirm nothing real was dropped.

My video upload keeps failing. First confirm you're on the Business plan or higher — video and audio are Business-gated. Then check for a dropped connection: multi-GB files can time out on slow networks, and switching browser tabs mid-upload can stall the transfer. Retry on a stable connection without switching tabs.

Can counterparties upload more than one file at a time? Yes. Viewers with upload permission can send back multiple files.

Is there a storage or file-count limit? No storage cap and no viewer limits — upload what the deal needs.

On the Roadmap

These are frequently requested and planned, but not available today:

Drag-and-drop directly into a folder (rather than the Move flow)
Bulk multi-select move
Undo-delete / an archive or recycle bin
ZIP upload with automatic folder-structure extraction
Reliable folder drag-and-drop on iPad (the app works best on a laptop or desktop)

Upload and Organize Files