Pro/Con of “Private” Email

Protonmail

Pro: Allows Tor, Many use it so network effect of proton to proton encryption

Con: Huge increases in data handoffs to governments makes you question how much data they can get, some question if it’s a honeypot. Even if not, you’re potentially targeted for even being there, and they have a bad track record.

Tutanota

Pros: Better track record than Protonmail

Cons: Bans Tor and many VPNs. Severe Browser fingerprinting annoyance when signing up. They auto-delete your account if you don’t login for 6 months, but you can get around this by adding 2-factor authentication TOTP with KeePass XC

Skiff

Pro: Fast sign-ups, very easy to get a burner account

Con: They use Cloudflare. Cloudflare intercepts all traffic, so 0% private. This company is essentially propaganda.

Mail in a Box (software)

This is self-hosting using open source software on a VPS

Pro: More private than any provider. It does most of the setup work for you

Con: Requires $5 to 15 a month on a VPS (but can be split among friends). VPS provider can still access emails by snapshots of memory. Unless you put it in a docker container, you can’t do anything else on the VPS

Luke Smith Scripts (software)

Pro: Fast way to get an email VPS setup

Con: Requires it to be put directly on the server, which can mess up OTHER things you got going on there, like using aaPanel

aaPanel (software)

Pro: Easy to manage a lot of services going on, including WordPress or databases with your email

Con: Not worth setting up this whole thing up for JUST email.

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Amazing write up. Do you see any issues regarding mailbox warmup with the VPS routes? I know for businesses it’s critical that they send tons of test emails to ensure they’re not marked as spam as well as setting up DKIM DMARC etc

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Discussion

I am a little confused by your question.

You have to setup dkim and dmarc and SPF records to avoid spam filters. Services like mail-tester.com can help you test it. Then send tests to proton or corrupt gmail, ect

I’m wondering if the warm up process is more challenging for a VPS since it would be a new mail services vs some of the other providers like Skiff and proton

Warm up process meaning how long it takes to turn on? You're running software on a vps that has setup time

Warming up meaning sending sufficient email traffic that is recognized as not spam by other service providers so that it can be used for any purpose including business.

It is very common for new domains to be marked as spam if they don’t do it properly