On a computer: the three selection shortcuts
When the file picker opens, you don't have to choose files one by one. The same shortcuts work in the upload dialog as in File Explorer or Finder:
| To select… | Windows | Mac |
|---|---|---|
| Individual files | Hold Ctrl and click each file | Hold ⌘ Command and click each file |
| A range of files | Click the first, hold Shift, click the last | Click the first, hold Shift, click the last |
| Everything in the folder | Ctrl + A | ⌘ Command + A |
Then click Open. Dragging works too: select the files in File Explorer or Finder, then drag the whole selection onto the upload area of the page.
On iPhone and Android
On iPhone, tap the upload button and choose Photo Library to tick several photos or videos, or Choose Files to pick documents — in the Files app, tap Select, then tap each file. On Android, the picker usually lets you long-press the first file and then tap the others; in Google Photos, long-press one photo and tap the rest.
If the picker only lets you choose one file at a time, the site's upload field wasn't built for multiple files — the dialog, not your phone, is the limit.
Send them all behind one link
- Open the multiple-file upload page and select or drop up to 50 files (2 GB in total, 1 GB per file).
- Choose how long the folder lives — 1, 12 or 24 hours — and, if you like, add a folder password.
- Share the single folder link. Recipients see every file, preview photos, and can save them one by one or with Download all as ZIP.
Should you zip the files first?
Zipping bundles everything into one file, but it rarely makes photos or videos smaller — they're already compressed. It also moves work to the recipient: on a phone, opening a ZIP is fiddly and nothing can be previewed until it's extracted. A folder link keeps each file visible and still offers a ZIP download for whoever wants one.
Zip first only when the files must stay together as a set (a code project, a set of design files), or when a site only accepts a single upload.
If it still won't work
- Check the per-file limit: one oversized video can block the whole batch.
- Rename files with unusual characters or very long names — some systems reject them.
- Hundreds of files? Split them into two folders by date or event; it's easier for recipients to browse too.