Sharing files with family in 2018

My wife and I often go hiking, and one of these evenings we decided to hike up a mountain, and set up a tent on top so we can stay overnight and see the sunrise from up there.

I took lots of photos which I would like to send her. I have an iPhone and she's using an Android phone. The question is - how to make that happen?

Let's just send them over WhatsApp.

Unless you've been living under a rock, you're probably aware of the huge privacy screw-up that is called Facebook. WhatsApp is owned by Facebook, so it's safe to assume that whatever stuff you write or whatever files you share via WhatsApp will at some point end up on Facebook servers and will be sold to third parties.

I don't want that to happen. So we're not pursuing this option any further.

Alright, how about Signal?

Signal is better. They have a photo of Edward Snowden on their homepage saying "Use anything by Open Whisper Systems". For me that's a good enough sign that I can use this app.

Convinced, both of us install Signal on our respective phones. Next, I open the Photos app on my iPhone, select the 68 photos and try to share them via Signal. Strangely, it only shows me 1 photo that it'll send.

Did I just find a bug?

Interestingly, no. This is a feature request since 2014. Looks like the devs haven't had the time to merge this feature in. My sense of self-entitlement (which comes from installing and using an app that didn't cost me a cent but costed some other people a lot of their time and effort) is screaming but I shut it up and start thinking about other alternatives.

(Btw, huge shout out to the people at Signal for making this messenger happen!)

Wait, isn't iCloud built right in?

Right. iPhones have iCloud. I could just sync those photos up to iCloud and have my wife use iCloud on her phone so she has the photos as well. This should work, right?

Not really. She's on an Android phone, and the top 10 results for "icloud android" on DuckDuckGo are blog posts. And when the top few search results for something that you're searching for are blog posts or "howto" articles, that's a sign that the solution is not straight forward.

This is a file-sharing problem, not photo-sharing. Google Drive?

Finally my developer mind starts generalizing the problem. Why am I thinking of these files in terms of photos? These are all just files. Any solution that lets me sync files between different phones should work.

I don't want to use Google Drive for this purpose. Granted, it's a pretty attractive offering and the free storagae space they're giving out is pretty generous and Picasa probably auto-categorizes all your photos and lets you apply fancy filters and what not.

But I think Google is getting too big, and not that them not having my useless files would make a difference to their growth, but I would still like to avoid using Drive to store my personal data. To some extent I do believe that "if you're not paying, you are the product", and it seems to apply here.


Dropbox should work. I use it on a daily basis at work and it works good enough. Also, I pay them 10 euros a month so I have reasons to believe that I'm not the product.

Seems promising so far. Why didn't I start with Dropbox in the first place?

Mobile App

Since the photos are on my phone, I download and install the Dropbox iOS app. Now, I have a weird way of thinking in that I don't allow apps full access to all my photos. If an app supports doing something with photos (Instagram for example), I disable the app's access to my photos, and instead open the photo in the Photos app and then share using iOS sharing.

You can call me crazy, and you probably would be right, but I just don't feel comfortable doing it any other way. Some day when iOS lets me give out permissions on select folders to select apps - maybe. Until then, that's not happening.

So then I open the Photos app again, select one photo, and share it with the Dropbox app to test things out. It works! I can see the photo appear on my wife's phone automagically.

Next, I select the remaining 67 photos and click on the share icon. Strangely, I don't see the Dropbox icon anymore. Does sharing multiple files not work? I have no idea. At this point, I'm starting to lose my patience, so I decide not to investigate this option any further and look at another alternative.

Connect iPhone to laptop

Maybe if I connect my phone to my laptop, I could copy the files directly to the Dropbox folder.

I use Linux (GNOME) on my personal laptop. Initially I thought this might be a problem, but (surprisingly) there weren't really any issues here.

I plugged in my iPhone to the laptop. The phone asked me whether or not to trust this computer (I clicked "yes"). GNOME immediately identified the phone as an external storage device, and I could look inside the DCIM folder which contains all the media on the phone. The folder structure does look a bit funky; there are folders called 100APPLE and 101APPLE and things like that, but I'm OK with that. All good as long as I can see the stupid photos.

The "Files" application on GNOME, for some reason, decides not to show me the thumbnails. Which means I had to do a binary-search-kind-of-a-thing on the filenames to figure out where the photoset starts and where it ends.

Minor annoyance, and it took a few minutes extra to find the first/last photos by their names, but I guess that's the price you pay for being a bit crazy.

So what is all this supposed to mean?

Even though the services mentioned in this blog post do a fine job at serving 99% of the use cases they're targeting, the entire process can be quite frustrating if what you're trying to do falls under the remaining 1%.