TLDR: The setup I finally implemented consists of 2 custom domains, 1 email aliasing service combined with a password manager( simple login + proton pass) and 1 email server (tutanota).
Ever since I decided to give importance to my digital privacy and get out of Google's ecosystem , "putting all my eggs in one basket" was never an option. So naturally being the newbie I was I went deep into the rabbit hole and came up with an overly complicated solution.
I started with having multiple emails with privacy respecting email providers for compartmentalization. Instead of going breath first and see what all setups could have been viable and compare that to my threat model, I went depth first into the first system that I researched about. This setup was not convenient at all and though it did solve a lot of problems compared to my single gmail to rule them all setup, it also introduced a lot of new issues.
The main problem that I was facing with this system was missing out on emails, I had around 10+ email ids which had their own mailboxes. There was no specific rule as to which type of service should be registered under which email so with every new registration I had to spend a couple of minutes just trying to recollect all my emails and their use cases. One particular email out of these become my temporary registration mailbox which eventually became the go to email for new registrations. It had become a mess to say the least and because of it's sheer complexity of creating newer emails it was not scalable enough for me to fix and hence I got back to the drawing board to figure out a new system. A system which accounts for all the problems that I faced till now and one which would be a nice balance between privacy, security and convenience.
The research gave me a lot of insights, however it also induced a lot of confusion and contradictions as well. This time before going head first into resetting everything, I decided to filter each potential setup that resonated with me through my threat model and only take the approach that ranked the highest. Below are the key areas under which I rated these systems:
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Security : The setup had to be secure. Data breaches are happening everyday, I wanted a robust system where if one particular service leaked my email, other emails of mine should potentially be safe and I should be able to quickly stop the spam and issue a new email address to this particular service. This for me was the most important aspect and probably the easiest to implement as well. A password manager along with email aliasing does the trick.
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Privacy : I wanted my email providers to not go through my email content to generate data on me in order to sell it or serve ads. Sure I have nothing to hide but I have nothing to share either. I also get that email is not ideal for sensitive communication because even if my email provider is privacy respecting, its not of much use considering 90% of emails going in and out of my inbox would likely be hosted with Google, Microsoft and the likes, still it was an important factor for me. The choices were very limited and I trusted the community's feedback to choose a provider.
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Convenience : After living with such a painful email setup where I was constantly missing out on emails because there were just too many accounts and I had no idea which service is registered to which account. Not to mention the barrage of spams and no real filtering option for me to block those either. Having a unified email inbox with multiple filtering levels was an ideal candidate for me. A email firewall is what I was looking for.
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Anonymity : This was the factor that kept me from deciding on a system for the longest time and I eventually had to take a step back to look and revise my threat model and take decisions based on that instead. I had gotten too much into the rabbit hole of staying anonymous that I was looking at purchasing and maintaining multiple custom domains with multiple email aliasing service and multiple email accounts. Now when I look at it, if my insurance already has all the details about me down to my address, I think it's okay if the registered email also has my name. For me anonymity was inversely proportional to convenience and after filtering through my threat model, its importance decreased.
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Freedom and Scalability: : I needed my setup to allow me the freedom of switching between providers with ease. The setup is an ever-growing beast. I want exit strategies as well. Sure I am registering with the best of the best providers as of now, but in the privacy world, services are very volatile for multiple reasons. I needed to make sure that I am never caught up in an ecosystem and If I want to change, simply because of the sheer amount of emails and registrations I don't end up spending days worth of time in switching providers.
After going through these factors and assessing all my options I finalized on a system where I am using 1 email provider/server and hence 1 mail box so that I do not miss out on emails (Sure I could have gone for an app that combines multiple email inboxes into one but setting it up on every platform/device will always be a hassle). I am using 2 custom domains, 1 with my name which is used in places where my personal information is already part of the registration and the second custom domain is for registering anonymously.
For either of the cases I create a new email alias on these domains so that my system is also secure during data breaches. If any of my email is compromised, the damage is limited to that service only, it does not trickle down to other services. For anonymous registrations, if the service is an important one such as my photos backup solution or my cloud storage I use an email aliased on my custom domain, if the service is not important and I only need it temporarily I end up with an email aliased form the common domains provided by simple login which are then forwarded to an alias on my custom domain. This also adds a layer of protection and also helps me in stopping email spams by simply turning off the forwarding in the simple login dashboard.This setup does require a lot of time and effort to setup initially but in the long run it's stability will be very beneficial. It is still a work in progress but so far I feel that this system is robust, easy to setup during new emails/registrations, highly scalable and future proof since I own these custom domains and I wont be locked out of these emails even if I have to leave tuta or simple login at some point.
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