To start off, my threat model is not one of safety at the moment. It’s being pissed off that my data is being sold and that my products I buy are getting worse because of it.
Quick background: I run two different companies, one for construction, and one for software development. Because of this, I have a multitude of devices that are used for different purposes. A Samsung phone that is used for personal things (I had too many Pixels break on me, and I want to be able to text my family from my PC, so no iPhone here). A Samsung for construction things (similar situation, need to be able to screenshot plans from my computer and send them fast to employees and contractors). An iPhone for software development (mostly because I needed a non Android platform for testing, plus the cameras are extremely superior to the Samsungs).
There is a very nice separation of work and personal here for messaging. However, in order to make sure all of my daily activities line up, I do have things on all of them that match. My calendars are across all three. My files are across all three. I try to perform as many activities as I can on the iPhone, as I know their privacy track record is better than Samsung’s, though not perfect. But does this matter if it all ends up syncing to the Samsung phones anyways?
I’m in a similar boat with computers. Windows PC for construction. Mac for software development. Linux for personal. But I have Proton Drive syncing across all three because I never know what device I’ll be using when I need to suddenly access a document. Again, I try to utilize Linux and Mullvad as much as I can, but when I need to get something done, I need it there, and I need it ready.
Does just having apps and files syncing to multiple devices severely compromise privacy? I’ve played around with the idea of just nuking most of the apps from my personal Samsung phone and installing them on the iPhone, but then I realized I don’t carry it on me often enough to do this.
As long as you follow recommended OPSEC for all your devices and activities, there is no reason to think having multiple devices is a problem from privacy POV.
I would however once audit all that you use and how to see you have no weak link anywhere - whether it be for passwords or sync or anything of the sort. This also means removing unused apps, ensuring 2FA wherever possible, etc. Like I said, just check up on and ensure good OPSEC overall.
But you know your work and personal life best so its hard for us to say or recommend anything one way or the other that would fit in your workflow as you want. So, any advice here can’t be too personal but only generic - atleast as I see it.
All this said, I do think using fewer devices means less of an attack surface if that’s at all a concern and less of a likelihood of anything happening.
I don’t know how long ago you’ve used Pixel but they are reliable and well made these days. Even if you don’t install GrapheneOS, stock Android with the right settings makes it a great device with great security and software support. And iPhone 17 onward with the new chipset and MTE, it also makes for a great device for your smartphone needs.
Since you have three use cases - 2 for work and 1 for personal, having compartmentalization does help with keeping things organized.
The two services you specifically mentioned were Calendar & File Sharing
Both have E2EE options listed under PG. You mentioned Proton Drive, that’s a good one. Tuta for Calendar is pretty good. Using these services ensures your data is private & secure in transit
Your ISP won’t be able to see your comms, but they will be able to see that you’re accessing these servers across different devices via DNS. Mitigate this with the VPN - you mention Mulvad, great choice. Barring any functional concerns, just configure it to be always on. I have heard VPNs on iPhone are not as strong as Android, though I can’t speak towards that very much
With this setup, your ISP & the individual providers can only see that your devices all connect with Mulvad servers. They can’t link any data or services to you
The only holes left are the device OSs themselves. I’m sure I don’t have to tell you that Samsung & Microsoft are not private. Apple is marginally better, but still. If the iPhone is only for debugging, perhaps consider removing it as a daily driver & airgapping it. The Samsungs are gonna be difficult to lock up, Google is built into the OS & Samsung itself is pretty notorious. You’ll need to weigh your personal threat model against the convenience & functionality of Windows & Android.
I’ve had the triple phone setup for the last 7 years. Pixel was my personal phone choice from the Pixel 2 to the Pixel 8a. During that time, not only did I have subpar battery life and worse performance than the iPhones, but I had consistent hardware failures as well. Bluetooth antenna just suddenly breaking. Camera suddenly breaking. Screen suddenly developing pink and green lines. Call dropping constantly when they switched to Tensor.
I am not hard on my phones. And I know I’ll probably get the “well MINE have always worked fine” response here. But in those 7 years, I have had two Samsungs and two iPhones, both with zero issues. I have had 9 pixels. 6 of those were RMAs. The other three should have been as well, but due to Google’s extremely anti consumer customer service, I had to purchase them. And their RMA process resulted in multiple weeks without a phone, once or twice a year. And there is a disproportionate amount of reports of hardware issues for pixels, by my family members, individual Redditors, and tech journalists.
So while they may work for others, I believe Google’s garbage software practices have extended to their hardware. And I will not subject myself to that again.