How to send a whole folder, with the structure intact

Sending one file is easy. Sending a folder — with subfolders, a naming scheme, and four hundred items inside — is where most methods start behaving badly, usually by flattening everything into one pile.

Structure is information. A photographer's folders separate selects from rejects; a developer's project is meaningless with the directories collapsed; an accountant's year is organised by month for a reason. Here is how to keep it.

Why folders are awkward

Email cannot attach a folder at all — the format has no concept of one, only a flat list of attachments. Most upload widgets accept files rather than directories, so dragging a folder in gives you its contents with the hierarchy discarded.

That leaves two honest options: an archive that preserves the tree, or a service that understands folders natively.

Option one: zip it

A zip file is a folder with its structure intact, and it is the most universally understood answer. Every operating system can make one and open one without extra software.

• macOS: right-click the folder, Compress.
• Windows: right-click, Send to, Compressed (zipped) folder.
• Linux: right-click, Compress, or zip -r name.zip folder/.

Zip the folder, not its contents, so the recipient gets one tidy directory rather than four hundred loose items dumped into their Downloads.

Be clear about what compression will and will not do here. If the folder is documents, spreadsheets, text or code, it may shrink substantially. If it is photos, video, audio or PDFs, the archive will be roughly the same size as the folder, because those formats are already compressed. You are zipping for structure, not size — which is a perfectly good reason. More in when zipping actually helps.

Things that trip people up

• Do not split archives into parts unless the recipient has explicitly asked. Multi-part archives are a reliable way to generate a support conversation.
• Avoid RAR and 7z for external recipients. Both are fine formats and neither opens natively on a stock Mac or Windows machine.
• Corporate filters quarantine archives. Plenty of company mail systems strip .zip outright. Another reason to send a link rather than an attachment.
• macOS adds noise. Zipping on a Mac includes __MACOSX and .DS_Store entries, which look like clutter to a Windows recipient. Harmless, but worth a word of warning in your message.

Option two: send the folder as-is

The better experience, when the tool supports it, is to drop the folder straight in and let the service keep the structure. Nothing to compress, nothing to extract, and the recipient can take one file out of it without unpacking the lot.

Here you can drop a folder onto the page and the files go up together as one transfer with one link. The practical limits are per-transfer size — 100 MB without an account, 1 GB on a free one, 10 GB on Pro — and a file count: up to 10 files anonymously, 200 on a free account, 1,000 on Pro.

That file count matters more than people expect with folders. A shoot with 800 RAW files needs a plan that allows 800 files, not just enough gigabytes.

Before you send

• Take out what should not go. Folders accumulate: old versions, working files, a spreadsheet of prices from another client. Look before you send the whole directory.
• Check for hidden system files if a clean delivery matters.
• Name the top folder properly. oakwood-brochure-final-assets tells the recipient what they have. Untitled folder 2 does not.
• Say what is inside. One line about the structure — "selects in /01, full set in /02, RAWs in /03" — saves a round trip.
• Send a small transfer first when the full set is enormous. Getting "these are the wrong shots" after three hours of uploading is avoidable.

A note on very large folders

Once you are past a few hundred gigabytes, the arithmetic stops favouring any network. A physical disk sent by courier still beats an upload measured in days, and for a full archive migration that is the honest recommendation. For anything a person could download in an afternoon, a link is faster door to door.

Related: how to send large files, sharing photos without losing quality for shoots specifically, and why large uploads fail if a big batch keeps stalling.