I ended up having them transfer the files over to their Mac using a USB-C cable, but I’ll summarize the options iOS users have in case someone else needs this in the future. So long as Send doesn’t work for certain files, here are your other options should you need to share things such as videos:
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If the senders and receivers are together in-person and using Apple devices, AirDrop should be fine.
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If your file is under 1 GiB, you can use Picocrypt Web for encryption and send the encrypted file over an unsafe platform like Google Drive.
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Look at secure cloud storage options. If your file is under 2 GiB, you can use Proton Drive for free. If you need larger file sizes you can try to look for alternatives that aren’t endorsed by Privacy Guides which might not be as secure.
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If nothing else works and you cannot safely transfer it to another non-iOS device, you’ll need to fork up money. To my knowledge Bitwarden Send is the cheapest, at least in the short term. A lifetime Cryptomator license might be cheaper long-term but it wasn’t made for file sharing so it’d be more tedious to use. There’s also paid cloud storage which brings back options like Proton Drive if the 2 GB limit was your only issue.