How to Send Files to Multiple Devices at Once
Sharing the same set of files across several devices, conference slides with a small group, or your own files across your phone, tablet, and laptop, is a common real scenario that most one-to-one transfer tools don't have an obvious answer for.
Why one-to-one is the default
A direct, peer-to-peer connection is inherently a link between two specific devices, so "send to five people" doesn't map onto a single connection the way uploading once to a shared cloud link does.
The straightforward approach: pair and send in sequence
The most reliable method with a peer-to-peer tool is exactly what it sounds like: pair with each device in turn and send. It's slower than a single broadcast, but every transfer gets its own direct, encrypted connection and its own confirmation that the file actually arrived.
When a shared link makes more sense instead
It's worth being honest about the trade-off here: if the real goal is "many people, not all known in advance, grabbing the same file over time," a cloud-hosted shareable link is genuinely the better-suited tool for that job, that's the client-server model's actual strength.
For your own devices specifically
Sending the same folder to your own phone, tablet, and laptop is the most common real case for "multiple devices." Pairing with each in turn, while slower than a single click, keeps every copy coming directly from the source instead of through a store-and-forward link.
A practical middle ground
For a small, known group, sequential direct transfers often finish faster overall than the wait-for-everyone-to-download pattern of a shared link, since there's no upload step to sit through first before anyone can start receiving.
Roughly how much slower sequential transfers actually are
It's worth setting realistic expectations rather than leaving "slower" vague: pairing typically takes only a few seconds per device, so sending the same modest folder to three devices in sequence generally adds a small, fixed amount of overhead, a handful of seconds of pairing per additional device, on top of however long each individual transfer itself takes. For a small group, that overhead is usually a minor, predictable cost, not a serious practical obstacle to actually doing it this way.
A reasonable order to send in
When sending to several of your own devices, it's worth starting with whichever one you'll need the files on soonest, rather than working through them in whatever order they happen to be sitting in front of you. That way the most time-sensitive copy finishes first, and any remaining transfers can run afterward without anyone waiting on the specific device they actually need right now.
What changes if one recipient is on a much slower connection
Sequential transfers have a real advantage worth naming here: one recipient's slow or unstable connection only affects their own transfer, not everyone else's. A shared link doesn't have this problem either, since each person downloads independently, but a broadcast-style transfer to multiple devices simultaneously, if a tool offered one, would risk the whole batch moving at the pace of the slowest participant. Pairing and sending one at a time sidesteps that entirely, at the cost of the sender's own time managing each step in turn.
Related reading
Send Folders Peer-to-Peer vs Client-Server: How File Sharing Actually Moves Your Data Cloud Storage vs Direct Transfer: Where Does Your Data Actually Go File Sharing for Remote Teams Without a Shared Cloud Account Phone to PC Local File Sharing Without Cloud Uploads