Like AirDrop, but between your Mac and your Windows PC.

No. AirDrop is Apple-only and always has been: it is built on Bluetooth Low Energy for discovery plus a direct peer-to-peer WiFi link, and Apple has never published the protocol, so no Windows app can speak it. Anything advertising itself as “AirDrop for Windows” is a different program doing a similar job under a borrowed name. This page is about one of those, and it is honest about being one.

Both computers run the free Webstarted Toolbox app, both open the “Send to another computer” tab, and each one sees the other by name on your local network; you pick the file, the other machine sees who is sending, the filename and the size, and presses Accept. The file lands in Downloads. There is no account, no server in the middle, and nothing to configure.

No. Finding the other computer is a broadcast on your own network, and the transfer is a direct connection between the two machines on a single port they both open. There is no relay, no storage bucket and nowhere to sign in, which also means the two computers have to genuinely be on the same network rather than merely both being online.

Up to 4 GiB per file. It is a sanity ceiling rather than a technical wall: neither side ever holds the file in memory, because the sender reads from disk in 256 KiB chunks and the receiver writes the same way, so a 4 GB video costs about as much memory as a 4 KB one. Text and pasted images have their own smaller limits, 256 KB and 25 MB.

No, and that is the honest answer rather than the flattering one. The content crosses your local network in the clear. This is fine for your own two machines on your own desk and wrong for airport or café WiFi. There is an optional shared code, but be clear about what it buys: it decides who is allowed to send to you, not who could read the traffic. For anything confidential, use a tool that encrypts in transit. AirDrop does; this does not.

The sender computes a SHA-256 of the file before sending, the receiver hashes what it writes, and the transfer only counts as finished when they match. While it is arriving, what exists on the receiving disk is a “.wtbx-part” file that is not yet your file; it is renamed to the real name only after the check passes, and a failed check deletes it and tells both sides. That is what stops a cut transfer from leaving you a truncated zip that opens and is quietly wrong.

Not today, and this is the limit most likely to matter to you. It is one file per send: there is no multi-select and no folder support, so a folder gets zipped first or sent piece by piece. If you routinely move whole directories between the two machines, a network share is a better fit than this.

You start it again. There is no resume, on purpose: on a local network even 4 GiB is a few minutes, so repairing a broken transfer would be more machinery than the problem deserves. Either side can cancel at any point, and a transfer that has already started survives you hiding the popover and clicking away, so the risk is smaller than it sounds.

No. This is desktop to desktop: macOS and Windows, menu bar and system tray. There is no iOS or Android app, so iPhone-to-PC is not something it does, which is worth saying because most “AirDrop for Windows” results are about exactly that. If you want your phone talking to your PC, Microsoft’s Phone Link is the thing to look at, not this.

Because finding the other computer means broadcasting on your network, and macOS gates that behind a prompt. It appears when you press Enable inside the widget, not when you open the app. If you dismissed it, the list of computers stays empty and nothing else will work; the widget has a button that opens the exact System Settings pane so you can turn it back on.

Yes, and it is the single most common reason the other machine never shows up. Windows blocks incoming connections by default, so the app detects that it is being blocked and offers to create the rule for you, which needs one administrator confirmation. Until that rule exists, a Windows PC can send but not be found.

Almost always one of four things. Both machines need that tab open, because the ports only exist while you are looking at it. On macOS the Local Network permission has to be granted. On Windows the firewall rule has to exist. And the network itself has to pass broadcasts, which a guest network with client isolation, a VPN capturing traffic, two WiFi bands routed apart or two different subnets will all quietly prevent.

No, and it is deliberately built so it cannot. Toolbox ships a local MCP server that widgets can expose actions to, and this one exposes none of its sending commands to it or to deep links, because a command that mails any readable file to any host on the network would be a one-step data leak. The only seam a neighbouring widget gets is one that attaches a file to the panel for you to review; a human still picks the recipient and presses Send, and the other human still accepts.

Yes. Webstarted Toolbox is a free beta, it needs no account, and this comes built into the app rather than being a separate download or an add-on: install it on both computers and it is already there, in the Share tab.