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There is no one-size-fits-all solution and there likely isn’t a solution that works for everyone even in specific situations due to different threat models. Purchasing and using a custom domain is often listed as a good practice for maintaining a person’s privacy. However, it can be even more detrimental to a person’s privacy than just using a trusted email masking/forwarding service and trusted email provider. For example:
- The domain is purchased without WHOIS protection (or without using non-personal information) or the WHOIS protection is not renewed
- The email server is hosted on hardware that can be linked to other services that identify the individual (eg: the email is self hosted using a home IP address)
- A self hosted email server is configured in a way that leaks information or is configured insecurely
- The email domain is used by only one person, which enables agencies to link each individual, unique email address back to that individual and create an aggregated profile across various accounts/services
- If the domain/DNS is not configured properly (or if the domain is not renewed), then the domain (and thus the email accounts) can be hijacked, which could lead to any additional accounts/services that are still using the domain vulnerable to a take over attack
- The email server is hosted by a privacy invasive company/service
- The person assumes that all emails are private since they use a custom domain on a trusted email provider (or self hosted email server), but continue to send emails containing sensitive information to email accounts running privacy invasive email services (eg: Gmail)
Please note that I am not saying that this is not a good option, but I just wanted to note some of the things that should be considered if a person decides to use a custom email domain to improve their digital privacy.
If you know your VPN’s DNS server, you can change your local DNS so that it redirects your specified domains/subdomains to the appropriate, local IP address and all other requests would then use your VPN’s DNS.
If you don’t know your VPN provider’s DNS server information, you may be able to still do something similar to the above depending on your setup. Otherwise, you could run your own DNS resolver or use a different DNS provider. I guess doing so could potentially be used to further fingerprint you, but the concern about “DNS fingerprinting” is moreso DNS leaks where your DNS queries are accessible to unintended parties due to improper configuration.
I believe the only other option would be to change your hosts file on each device you want to use to connect to your services, which is probably not the best approach and may be challenging/impossible for certain devices.
Also, unless you setup the self signed certs to be trusted on a network/domain level (or again on each individual device), you will likely get a warning/error about the self signed certs when accessing your services. You may need to work through this process each time the certs renew.
I recommend buying a domain if you do not already have one and finding a service that provides wildcard certification challenges. This would allow you to setup a valid, trusted certificate that you could reuse for all of your services. The only thing that you would need to provide is an email address (can be any email address) and your domain name (in addition to other information that may be required to setup an account at the cert provider, but you may already have an account there as it could be the domain name registrar or other services like VPS providers, Cloudflare, etc.). Since it is a wildcard cert, each subdomain does not need to be set publicly and if you only use the domain within your network, the domain does not need to be publicly associated with any IP address.
If you do go forward with that approach, you could use the wildcard cert directly within NginxProxyManager or other reverse proxies. They will also automatically update/maintain the cert for you.