I have a friend who needs to send me a few files, the largest of which is 2.5 GB which is too large for Signal. We tried Send but despite running the latest versions of iOS (18.1.1) and Safari, the button to add files simply doesn’t do anything. It darkens so we know they’re pressing it, but it doesn’t allow them to pick a file to add. The other PG-recommended file sharing app (OnionShare) is only available on desktop.
Proton Drive isn’t an option because the free plan only supports 2 GB (not to mention how tedious it’d be) and Bitwarden Premium is paid. I thought of maybe using one of the PG-recommended encryption applications only to realize that Cryptomator is paid on mobile and both Picocrypt and VeraCrypt are only on desktop.
Looking through more options on PrivacyGuides, I found a soft recommendation for Canary Mail which could use PGP. However, it is paid, proprietary, and prohibitively tedious to use. Not to mention PGP isn’t exactly ideal security for E2EE.
This does not really answer your question, so feel free to mark it as spam but…
It sounds like enough time and effort has been spent where it might be reasonable to just buy cryptomator for a year at their discounted price and be done with the issue. Added bonus of supporting a good product.
I bring this up because I think a lot of people in general do not value their time nearly enough, in the effort to save money.
Yeah, unfortunately money is tight and we’ve only ever really needed it for this one file transfer. This option would make more sense if we needed to use it more often but after years of being friends, we’ve never been in this particular predicament before and don’t anticipate something similar happening again.
Anyway, your options are to use Picocrypt’s online encryption service and Google Drive if the sender still has a Google account. Turn off the internet prior to encrypting the files if you are paranoid. Not sure if this works for mobile though.
I couldn’t easily find Signal’s documentation on file size limits, but based on the numbers provided by Business Insider, it wouldn’t be feasible. We’d have to try and split it up into many dozens of files. Keep in mind 2.5 GB was just the largest file size, there are a few other files that are probably a few hundred megabytes or maybe a gigabyte.
Yeah we can definitely try it as a last resort.
Update: Apparently it’s only free up to 20MB so not an option unfortunately.
A functionally limited web app is available here which allows you to encrypt and decrypt standard Picocrypt volumes (no advanced features or keyfiles) on any modern browser, including mobile devices. It’s a simple, future-proof way to encrypt files that should work indefinitely due to the web’s stable nature. Note that you can only encrypt single files up to a maximum size of 1 GiB.
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:
If the senders and receivers are together in-person and using Apple devices, AirDrop should be fine.
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.
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.
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.
So I went back to my friend and had them re-try. It turns out they can add images, but when they try to add videos the “add” button doesn’t do anything. It isn’t a file size issue as they tested with videos far smaller than 2.5 GB which is the maximum the official instance supports.
