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When you on wifi. Share a drive on the sending pc and from the other pc copy normally from the sending pc from the shared drive in your file explorer.
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I assume you have a wireless network. On the computer that needs to share files, install python 3.
Open a command line promp in the folder with the files, and run this:
python -m http.server 8000
Your computer is now a file server, sharing all files in that folder.
Easiest way IMO and you can download everything with decent speed.
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I use remote desktop and tick the filesharing option.
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I'm using syncthing - syncthing.net.
Works with Android, Linux, macOS, Windows, FreeBSD ...
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Have you tried AirDroid? AirDroid Personal's Nearby feature lets you effortlessly share files with friends and families even without the internet.
Dan
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Lap Link (that takes me back)
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How about setting up a FTP-Server either on the Windows or Mac machine in your local network, i.e FileZilla 
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File transfer using Skype has always worked for me. Just don't make the mistake of centralizing your PCs under a Microsoft account. They will push you in that direction at every opportunity. Create an email account for each of your PCs and use that email to sign in to each of your PCs. No need for an A to B wire. My 12 PCs are mostly ethernet-connected desktops but some are Wifi-connected. Skype used to be P2P, but after Microsoft took over your files will still have to go through their server farm. They didn't used to. But consider this: Skype to Skype transfer of files, any size, anywhere, is still free. And that's probably why they are trying to extinguish Skype with their Teams product. But for now, Skype is certainly a proven technology and is to be preferred over some obscure A B connector technology. Finally, Microsoft PC file sharing ACL is a nightmare. Always has been. Always will be.
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Just use a network cable between them. Works for me just fine, at Gigabit speeds (well, almost, depending on the machine)...
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What I usually do is write something in Python for both machines that transfers via a socket. That's how I transfer files between my Windows PC and a Raspberry Pi.
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In all the discussion, nobody mentioned that you can do this, found on YouTube, by BarTech TV:
How to share a Mac Drive with a Windows 10 PC
Seems like a good solution if you need to do it repeatedly, and files stay local.
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Wire-based transfers between Windows and Mac doesn't seem like a thing happening.
However, I would like to suggest some internet based suggestions as follows:
>>1 Web server (advanced - you will need to configure your firewall for exposing ports)
You can do something like Smb or NFS by using this:
1. Setup a self hosted server and exposing the 80 port to the network.
2. Access the web directory from the other machine
3. Get the files over your wifi
I'd recommend Xampp, works both in Mac and Windows, also comes with a FTP server, that also may be a option.
>>2 Sharefest (also advanced but classy)
Some time ago I used to use sharefest to transfer files via p2p, but seems that the self hosted tool is not up anymore.
If you have basic knowledge of Node, you may want to try set it up in your own machien using their repo.
>>3 Wetransfer (easiest)
Like google drive, but just to send files from one person to another, unidirectional.
>>4 Mega (easiest 2)
Pretty much the same as Google drive and dropbox, but with higher rates, I like it a lot for backup, filesync, and airgap between machines.
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Wordle 367 6/6
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Just managed.
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Wordle 367 5/6
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Software rusts. Simon Stephenson, ca 1994. So does this signature. me, 2012
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Phew! Close one ...
Wordle 367 6/6
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"I have no idea what I did, but I'm taking full credit for it." - ThisOldTony
"Common sense is so rare these days, it should be classified as a super power" - Random T-shirt
AntiTwitter: @DalekDave is now a follower!
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Wordle 367 4/6
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Wordle 367 3/6
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Life should not be a journey to the grave with the intention of arriving safely in a pretty and well-preserved body, but rather to skid in broadside in a cloud of smoke, thoroughly used up, totally worn out, and loudly proclaiming βWow! What a Ride!" - Hunter S Thompson - RIP
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Wordle 367 4/6*
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Happiness will never come to those who fail to appreciate what they already have. -Anon
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Nah, I wouldn't.
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I think you just did. 
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Get me coffee and no one gets hurt!
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Wordle 367 4/6
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