Given enough money/power likely everything can be compromised. But it seems that Fastmail take enough precaution against the 'can it be compromised' threats.

Regarding the blanket statements: I wouldn't trust an US based company with such a statement because of the Patriot Act and what we learned from the 'Snowden documents' about Google, Facebook, Microsoft, Apple etc. and the lying and selective truth by NSA. But I would trust companies which are based in countries where one (in general) is allowed to reveal when information has been requested.

The Fastmail privacy statements [1] seem fine to me. Additionaly with Fastmail I also appreciate that they have only part of information about me and not a much broader aggregated set of browsing/search history, location, credit card numbers, youtube... as would be the case with e.g. Google.

>>There is no equivalent in Australia to the US fourth amendment. Even illegally gathered evidence can be used in a trial depending on the discretion of the judge.

Until Patriot act has been relaxed/abolished and NSA splitted in smaller units (and relieved of part of their immense budget) the fourth amendment can imho only be a last-rescue instrument. Also afaik it doesn't 'protect' me as a foreign customer (of e.g. Google and Apple).

[1]: https://www.fastmail.com/help/legal/privacy.html

Furthermore, and I think we're going to disagree here, I believe there is a balance to be played between trust, security, and following laws. For instance, a safe deposit box at a bank is generally secure. A bank won't usually open it, but they can if the need arises, and law enforcement can obtain the contents if they go through the proper channels and provide a warrant. In theory, I believe this to be an inherently good thing. The police must be able to pursue criminals, and, by providing evidence, be granted access to things they would otherwise be unable to access. I believe there to be a direct analogy between an email provider that does not routinely give access to its users emails but would respond to warrants as necessary.

Now, I would be naive if I didn't realize that the spy agencies of the world weren't holding up to their government's part of the bargain here. But I believe the answer to be in government accountability, not completely locked down security.

Aside from philosophical views, I also believe that this is a much more pragmatic approach. Do you know why people give up all their personal information, email, etc. to the Googles and Facebooks of the world? Because it's so goddamned convenient. Google provides so many great services for free. And full security is hard and inconvenient. You're going to have a tough pitch to sell fully encrypted email just on the basis of services not being able to provide a good search experience, because I gotta tell ya, Gmail search is really amazing, and it provides many people with tangible benefits. Fully encrypted email provides value that is much more intangible.

On the other hand, if you're not doing client side encryption, preferably offline, then you're not protected against a global threat, period. This is because, even if FastMail refuses to cooperate, well funded security agencies can do MITM attacks in spite of SSL/TLS.

I can really recommend self-hosted email. This is not as hard as it sounds. Of course, you should have the following abilities:

1) find some good documentation (or friend) that explains a clean setup with spam filter, correct DNS/SPF and HELO entries, such that you don't get on the blacklists. Note that this is almost a one-time effort, you'll have to adjust things every 5-10 years, I guess. [1]

2) be able to administrate a Linux/BSD machine, i.e. to keep it simple and up-to-date in the long term.

I really hope that Tuxevara will finish his series about a modern email setup. This is his first part:

http://www.tuxevara.de/2014/11/mailserver-reloaded-step-1/

[1] For example, I had to add SPF entries since my mailserver also had an IPv6 address, otherwise Google and others blocked me - for understandable reasons.

Yes, this is very unfortunate. It means that you'll either have to rent some server or virtual server (which makes sense if you want to run tons of other services there).

Or, you'll need some VPN (possibly in addition to an IPv6 tunnel), which is cheaper.

A third option is to rent an own server/vserver, but to keep the costs low by sharing it with friends.

For me the biggest hurdle is absolutely not the manual setup process or the need to adjust things from time to time. Rather, it’s the fact that there doesn’t seem to be a simple, quick and reliable way to tell if my setup actually works.

How can I be sure that my email actually reaches its destination? That there’s no error in my DNS entries? That an obscure email service used by one of my clients doesn’t whitelist only major email providers? Can I be sure that things fail loudly when they don’t work?

I really hope I’m wrong and it’s possible to implement some kind of monitoring that tests my self-hosted setup and alerts me by SMS if something’s wrong with it.

I've had no problems, but just recently I had two separate emails be ignored by GMail users. Some followup communication suggests to me the mails were never seen, but I am unable to find out if they ended up in the spam folder or not. (At least one other GMail user did receive a recent mail from me.)

That has shaken my confidence in my email setup, which has run without issue for many years now.

And I don't have any end-to-end tests, other than seeing people reply to my emails. I occasionally check my domain on various blacklist checkers.

These are simply symptoms of FUD. Using that line of argument, you'll always end up with the biggest players, even though there is no technical reason to do so.

> to implement some kind of monitoring that tests my self-hosted setup and alerts me by SMS

On the other hand, how would you check that $BIGPLAYER's mail setup works with any other email service? You can't. Could you blame anybody at $BIGPLAYER? In a free service: No.

So why would you want do put so much higher standard on your own setup than on $BIGPLAYER's setup? Just to be able to say: "Oh no, available technology is not good enough, I'm staying with $BIGPLAYER."

This doesn't make any sense to me.