So, let’s say you created a ProtonMail account entirely on your Tor Browser through the Tor mirror the entire time and then also signed up to SimpleLogin/AnonAddy to have an e-mail alias/cloak for each account that you have (for example, say you have make an Reddit account and you go and create an alias for the Reddit account and that alias will be used ONLY for that account and nothing else)
Would it be a bad idea to make aliases and use them for stuff tied to your personal identity (such as banks or stuff you’ve previously used payment options tied to your name etc) or it wouldn’t matter?
One thing to note is that SimpleLgoin (haven’t used AnonDady) is that it can generate different kinds of aliases.
One option allows you to specify the part of the email before the @. These will all use a common randomly generated sub domain. As these subdomains are assigned to individual users, you can correlate two aliases to the same user. It’s probably not picked us as easily as an exact match, but far from impossible.
Simple login does have the option to generate completely random emails which don’t use a common subdomain. This mixes your usage with every other user of the service.