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Been there with my USB printer; however, Microsoft (I suppose) made magic and Windows 10 supports it again.
"In testa che avete, Signor di Ceprano?"
-- Rigoletto
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I think I used SCART(?) cables for that back in the day.
Had to move my complete desktop for that to happen, but I could transfer files that didn't fit on a 1.44 MB floppy 
Later I'd burn the files on a (re)writable CD, such luxury!
Why would you even want to return to such brutal methods in the age of fast internet? 
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I am sure that your memory must be wrong.
SCART is not at all usable for any sort of file transfer.
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Yeah, it wasn't SCART, can't remember what it was called...
Or maybe it wasn't the cable, but the program or protocol?
I can't stand not knowing this 
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I think you meant a SCSI cable (it was the USB of its day on desktops and high end workstations)
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I was a SCSI fan for several years, trusting it to become The standard for disks, printers, scanners, ... SCSI had professional qualities that deserved a better fate. But when I had to buy an adapter cable for my eight SCSI plug 'standard', and the salesman nodded, 'But there are fourteen different ones in use, I called it quit.
SCSI did have one big disadvantage, though: It was parallel standard, with lots of wires. So cables were thick and stiff, most plug alternatives were large.
I have been fearing that USB would suffer the same fate with a bewilderment of plugs - A, B, Mini, Micro, A 3.x, Micro 3.x, B 3.x, and then C ... There are even Mini A and Micro A that I've never seen in real life. That makes 10 different ones ... After my experiences with SCSIO, I was about to ditch USB completely, and when the first alternative to or variation of USB C comes, I will.
For now, it looks as if USB C may be turn out as a real Standard plug that will live for at least a few more years without 'improvements'. I am in the process of mentally accepting it; it is not quite there yet. (I am using it, but still with some reluctance and distrust.)
There is a good programming (and debugging!) rule, saying that 'Constants ain't! Variables won't!' I am tempted to add: 'Standards ain't!'
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Yes, I find that uploading to Google Drive from one machine and downloading onto the other from there to be the simplest option, and fast one too. Only drawback is that my ISP has a data limit of 1000 GB per month, after which things become really slow.
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1000 GB? That's not a lot...
My parents had the same, but they could request another batch (at no extra cost) when they ran out.
They were on satellite (which isn't a thing in the Netherlands, unless you live in an outside area, like them).
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A terabyte of uploading per month "should be enough for everybody", as the saying goes ...
For "ordinary people", I can think of a single thing that would break even a terabyte of permanent storage space: That is if you do a lot of digital home videos. But nowadays, few people ever sit down to watch daddy's amateur movie from the 2018 Greece vacation - there are much better videos from Greece to be found on YouTube.
A file transfer of a few GB, files that are removed after transfer, is like peanuts on a terabyte budget.
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Quick! Do it at the end of the month.
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What's the dropbox limit?
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Sander Rossel wrote: a 1.44 MB floppy
You must be a lot older than you appear! 
The difficult we do right away...
...the impossible takes slightly longer.
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I don't know how old I appear, but I'm currently 34.
I've been using computers since I was seven or eight years old, which is quite early for someone my age
I think I was the only one at my school who had his own computer.
All the other kids had a shared family computer if they had a computer at all.
Good old days when my uncle got me Warez(?) CDs, illegally downloaded games with movies taken out so more games would fit on a single CD
I remember playing one of those games later and finding out it had cutscenes
That's how I discovered Age of Empires!
Also had lots of demo CDs back then, they came with my monthly PC Zone Benelux subscription (they went bankrupt some 15 years ago, I think).
People download their own illegal stuff now, and companies don't do demos anymore.
Those were the days
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You're a baby, built my first computer (actually wire wrapped most of the boards) back in 78.
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Sander Rossel wrote: I've been using computers since I was seven or eight years old, which is quite early for someone my age
Correction: You were knowingly using computers from you were seven or eight year old. At that time, even two year olds were using computers regularly, but they didn't think of them as such. Embedded computers were all over the place, even in those days.
At the time when you were seven or eight, I was regularly in contact with (and made a few tools for) visually handicapped kids. When their classmates learned to write A, B, C with a pencil, they learned to write A, B, C on their keyboard, using WordPerfect. The first graders never related to it as 'using a computer', but as a writing tool.
They also used 'bulletin boards' (using modems, at 300 bps) to communicate in writing with their friends, not thinking of it as using the internet - which it technically wasn't, but when internet gradually took over, they hardly noticed the technology change. They had known the functionality for years.
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I remember the double density upgrade on an Osborne "luggable" -- 180K. And Turbo Pascal rev 1.0; fitting editor, compiler, debugger all on one disk was a big improvement over previous compiler (name forgotten) on one floppy, Wordstar on the other....
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Sander Rossel wrote: Why would you even want to return to such brutal methods in the age of fast internet?
I have files that I do not want on the internet, so using it as an intermediary is not acceptable.
OTOH, I pay for the MS 365 subscription and have the files that don't matter in OneDrive, so they are accessible on my desktop, laptop, and phone.
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To me, that argument makes perfect sense.
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Maybe LapLink, using a serial cable or special cable to link two printer ports?
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When I was teaching at a Tech. College in the early 1990s, one of the student exercises were implementing a simplified Kermit over a serial line between two PCs. The first part of the exercise was soldering a null modem cable. This was commonly known among the lecturers as The exercise that the students would remember, and come back to the lecturers to thank them for providing, many years later. The students learned a lot about communication, synchronization, debugging of distributed systems, ... Even though the setup was very simple, all the elements were there.
At that time, I also learned that the oil company of the Norwegian state (it has been renamed a few times; I think it was named Statoil back then) actually used Kermit for transferring data from their 'technical', VAX based systems, to their 'administrative', IBM mainframe based systems holding their huge databases. They had made several unsuccessful attempts at finding some protocol implementation for direct VAX to IBM communication, but both companies were famous for their 'Protocol xyz with a twist' policy, using that 'twist' as a wrench to force their customers into obedience. But both were willing to pass files to/from PCs (of their own DOS variants, of course), and both PCs were capable of running Kermit over a null modem cable. When I visited them with a group of students, they proudly showed us the two PCs, side by side on a small desk, running as "modems" between this huge IBM mainframe and this powerful top-range VAX, transferring data at 19.2 kbps 24/7.
Bottom line: Kermit may be an alternative. It has been used for such purposes by billion-dollar companies.
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I used a product called LapLink long ago, with special blue or yellow cables, depending on serial or parallel.
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Share a folder and use a network cable
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Not an RJ45 connector on the MacBook Air. Not sure where to find its network cable.
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