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The Fastmail article linked my Mr Duggan [0] is also worth a read, they provide a sober and reasonable overview of why they don't offer PGP. Of course, Australi

by roenxi 3y ago

The Fastmail article linked my Mr Duggan [0] is also worth a read, they provide a sober and reasonable overview of why they don't offer PGP. Of course, Australia has a quietly privacy-phobic regulatory regime so we can guarantee [1] that Five Eyes countries and possibly others are reading emails sent through Fastmail. Cost of doing business really, I use Fastmail. Fact is that there isn't a way to use a convenient 3rd party email provider if you want secure emails. Only local clients can provide that feature - which means both sides of the message have to be using trusted local clients, and at some point one side of the conversation will forget their secret and lose access to their email history. It is a tough problem. [0] https://www.fastmail.com/blog/why-we-dont-offer-pgp/ https://www.fastmail.com/blog/why-we-dont-offer-pgp/ [1] https://www.bbc.com/news/world-australia-46463029 https://www.bbc.com/news/world-australia-46463029

mulmen 3y ago
I also use Fastmail and I am a happy customer. My eyes are open. I make no assumption that my mail is private. I think the email analogy is actually very accurate. It’s as secure as postal mail. Maybe slightly more secure than a post card. I’m happy to be supporting a slightly smaller provider. I don’t have to admin anything and I still feel like I’m contributing to an open ecosystem. Plus I own my domain so I can always change providers. I have made peace with the compromise.
- greyface- 3y ago
  I'm in essentially the same place. I do wish their marketing pages didn't make such strong claims of privacy - it's an impossible promise. https://www.fastmail.com/fast-private-email/ https://www.fastmail.com/fast-private-email/
  - mulmen 3y ago
    “We’re more private than Gmail” doesn’t have the same ring even if it’s true.
    - Andrex 3y ago
      That's honestly kinda table stakes for anyone attempting to spin up a new email provider. Being slightly better than the incumbent doesn't make it attractive enough to switch for most people.
- prussia 3y ago
  Well, it's a lot easier to automatically scan and store emails than postcards (eg, flagging all emails with certain keywords or in certain languages)... I guess nowadays they can use OCR to scan postcards, but that would be of doubtful value to any of the 3 letter agencies.
  - mulmen 3y ago
    The USPS literally scans and stores all mail sent through the USPS.
    - kayodelycaon 3y ago
      And it's a feature, their Informed Delivery service will send those scans to you in an email.
    - tristan957 3y ago
      All they get are equivalent to email headers. They don't know what's in the box or envelope unless you've had to declare it with them for some reason.
gerdesj 3y ago
I've been running several small email systems for roughly 25 years in the UK. I generally don't have issues with the big boys and girls. Yes, they send me shit loads of spam and I drop it on the floor. I generally only go as far as SPF and getting A and PTR to match HELO and don't send any spam. I use Exim and rspamd and a few other things. Google and MS email fettlers are not complete wankers and they seem to be quite reasonable. I could quite easily add your Mom's mail domain to my non work post office and probably deliver her mail. I already do it for several others. However, sadly, I don't know you, nor you know me, so a trust relationship is out of the question. Just in case anyone is going to get whizzed up about US vs UK: my company email domain is within .net, which is nominally US based. When we incorporated and eventually sorted out a name, it turned out that the .co.uk domain was "taken", hence why we went for second best.
andai 3y ago
This article confuses me. What would it even mean for Fastmail to offer PGP? The whole point of PGP is that you don't (need) to trust the people who transmit the message. Relying on them to do the encryption for you defeats the entire purpose.
- paulryanrogers 3y ago
  Some may only want encryption between their key custodian and the recipient or their custodian. Email without encryption cannot guarantee it won't be snooped on by any of the other parties involved in transporting it. In practice big providers may be able to ensure that, but email is federated so it's impractical to do that with every provider unless there's a standard.
  - marcus_holmes 3y ago
    The point that Fastmail made in the article, though, is that if Fastmail is handling the encryption, then they know your key. So Fastmail cannot protect you against Fastmail's servers being compromised[0]. And the article linked from their article (hilarious itself) pointed out that this basically comes down to State Actors (Mossad as the example) or Everyone Else. If it's Mossad then there's nothing anyone else can do to protect you (because they can do secret-squirrel things through special security courts and stuff like installing black boxes on undersea cable routers). If Everyone Else, then the normal run-of-the-mill transport encryption is probably good enough, just don't click on any herbal boner-pill adverts. tldr; If you want to be protected, you have to do PGP at the local machine level yourself. [0] Given that Fastmail are Aussies, and that our idiotic government have given the spooks full, secret, access to anything they want, then this is a very real prospect for anyone that five-eyes might be interested in.
    - ComodoHacker 3y ago
      >this basically comes down to State Actors ... or Everyone Else This is oversimplification if not misleading. There are also Bad Guys (who aren't state actors), who usually can't reach for your data. But occasionally they can, when rare Planet Parades like Heartbleed or Meltdown make the news. And they are happy to use this one-in-a-lifetime chance to sell access to your data to everyone else.
chrismorgan 3y ago
> Of course, Australia has a quietly privacy-phobic regulatory regime so we can guarantee [1] that Five Eyes countries and possibly others are reading emails sent through Fastmail. That’s a wildly unfair characterisation, and not in the slightest bit supported by your citation. The Assistance and Access Act which that article is talking about (though it doesn’t even name it!), although a dodgy piece of legislation in the opinion of most technologists, is completely irrelevant to Fastmail, because Fastmail doesn’t offer end-to-end encryption. Fastmail was always subject to the Telecommunications Act, which allows Australian police access with warrants, and Fastmail has always made no bones about the fact that it complies with legal warrants. But that’s nothing like what you’re describing. (Disclosure: I was a Fastmail employee from 2017–2020.)
- abofh 3y ago
  Email encryption _is_ end-to-end encryption. You just explained why the law doesn't apply to what they did, and the parent explained why they didn't do it because of the law. These two are not in conflict.
  - chrismorgan 3y ago
    I’m not sure what you’re saying. The sentence I quoted is written in the present tense, saying that Fastmail is compromised, not as a hypothetical “if they did PGP, it’d be broken for this reason”.
WithinReason 3y ago
These are their objections: 1. Search isn’t possible - It's possible on the client. The total text in an email account is not prohibitively large and can be cached on the client. 2. Previews can’t be calculated - It can be on the client, then reuploaded encrypted. 3. If you lose your private key, we can’t recover your email - Of course, this is equivalent to losing your email account password. 4. Spam checking on content isn’t possible - It is on the client, and on the server based on headers. 5. To access mail on multiple devices, the private key needs to be shared securely between them - Protonmail solved this, what's the problem?
- akdev1l 3y ago
  > It is on the client, and on the server based on headers. The idea of spam filters is that you don’t get the spam so the client never sees it. Also running highly specialized spam filters that actually work reliably might be prohibitive for a lot of people.
  - WithinReason 3y ago
    ProtonMail solved this using email aliases so you never have to give out your real address. If you get spam on one you just redirect it to your spam folder.
LinuxBender 3y ago
Technically all email providers support PGP assuming they support IMAPs. The mobile client is adding it soon if they have not already. I've been using it with Fastmail for some time. Thunderbird makes PGP very easy and happy-clicky. [1] I also just give people my public key out of band and avoid the key servers. Thunderbird also has it's own built in search. I think most peoples non technical relatives could follow the pictured steps easily but if for some reason they can not then a desktop sharing session should get around helping someones mom set it up. I've had no issue with my non technical friends. I should add that if Fastmail added PGP in their interface I would not use it. Nobody could convince me that when a mail provider or anyone else adds E2EE in their application that it's anything other than PP Pinky Promise. They can tamper with it to intercept my communications and no app provider could possibly convince me otherwise. There should probably be an RFC for PP. [1] - https://support.startmail.com/hc/en-us/articles/360014775437-Thunderbird-PGP-Encryption https://support.startmail.com/hc/en-us/articles/360014775437...

by roenxi 3y ago

mulmen 3y ago

I also use Fastmail and I am a happy customer. My eyes are open. I make no assumption that my mail is private. I think the email analogy is actually very accurate. It’s as secure as postal mail. Maybe slightly more secure than a post card. I’m happy to be supporting a slightly smaller provider. I don’t have to admin anything and I still feel like I’m contributing to an open ecosystem. Plus I own my domain so I can always change providers. I have made peace with the compromise.

greyface- 3y ago
I'm in essentially the same place. I do wish their marketing pages didn't make such strong claims of privacy - it's an impossible promise. https://www.fastmail.com/fast-private-email/ https://www.fastmail.com/fast-private-email/
- mulmen 3y ago
  “We’re more private than Gmail” doesn’t have the same ring even if it’s true.
  - Andrex 3y ago
    That's honestly kinda table stakes for anyone attempting to spin up a new email provider. Being slightly better than the incumbent doesn't make it attractive enough to switch for most people.
prussia 3y ago
Well, it's a lot easier to automatically scan and store emails than postcards (eg, flagging all emails with certain keywords or in certain languages)... I guess nowadays they can use OCR to scan postcards, but that would be of doubtful value to any of the 3 letter agencies.
- mulmen 3y ago
  The USPS literally scans and stores all mail sent through the USPS.
  - kayodelycaon 3y ago
    And it's a feature, their Informed Delivery service will send those scans to you in an email.
  - tristan957 3y ago
    All they get are equivalent to email headers. They don't know what's in the box or envelope unless you've had to declare it with them for some reason.

gerdesj 3y ago

I've been running several small email systems for roughly 25 years in the UK. I generally don't have issues with the big boys and girls. Yes, they send me shit loads of spam and I drop it on the floor. I generally only go as far as SPF and getting A and PTR to match HELO and don't send any spam. I use Exim and rspamd and a few other things. Google and MS email fettlers are not complete wankers and they seem to be quite reasonable. I could quite easily add your Mom's mail domain to my non work post office and probably deliver her mail. I already do it for several others. However, sadly, I don't know you, nor you know me, so a trust relationship is out of the question. Just in case anyone is going to get whizzed up about US vs UK: my company email domain is within .net, which is nominally US based. When we incorporated and eventually sorted out a name, it turned out that the .co.uk domain was "taken", hence why we went for second best.

andai 3y ago

This article confuses me. What would it even mean for Fastmail to offer PGP? The whole point of PGP is that you don't (need) to trust the people who transmit the message. Relying on them to do the encryption for you defeats the entire purpose.

paulryanrogers 3y ago
Some may only want encryption between their key custodian and the recipient or their custodian. Email without encryption cannot guarantee it won't be snooped on by any of the other parties involved in transporting it. In practice big providers may be able to ensure that, but email is federated so it's impractical to do that with every provider unless there's a standard.
- marcus_holmes 3y ago
  The point that Fastmail made in the article, though, is that if Fastmail is handling the encryption, then they know your key. So Fastmail cannot protect you against Fastmail's servers being compromised[0]. And the article linked from their article (hilarious itself) pointed out that this basically comes down to State Actors (Mossad as the example) or Everyone Else. If it's Mossad then there's nothing anyone else can do to protect you (because they can do secret-squirrel things through special security courts and stuff like installing black boxes on undersea cable routers). If Everyone Else, then the normal run-of-the-mill transport encryption is probably good enough, just don't click on any herbal boner-pill adverts. tldr; If you want to be protected, you have to do PGP at the local machine level yourself. [0] Given that Fastmail are Aussies, and that our idiotic government have given the spooks full, secret, access to anything they want, then this is a very real prospect for anyone that five-eyes might be interested in.
  - ComodoHacker 3y ago
    >this basically comes down to State Actors ... or Everyone Else This is oversimplification if not misleading. There are also Bad Guys (who aren't state actors), who usually can't reach for your data. But occasionally they can, when rare Planet Parades like Heartbleed or Meltdown make the news. And they are happy to use this one-in-a-lifetime chance to sell access to your data to everyone else.

chrismorgan 3y ago

> Of course, Australia has a quietly privacy-phobic regulatory regime so we can guarantee [1] that Five Eyes countries and possibly others are reading emails sent through Fastmail. That’s a wildly unfair characterisation, and not in the slightest bit supported by your citation. The Assistance and Access Act which that article is talking about (though it doesn’t even name it!), although a dodgy piece of legislation in the opinion of most technologists, is completely irrelevant to Fastmail, because Fastmail doesn’t offer end-to-end encryption. Fastmail was always subject to the Telecommunications Act, which allows Australian police access with warrants, and Fastmail has always made no bones about the fact that it complies with legal warrants. But that’s nothing like what you’re describing. (Disclosure: I was a Fastmail employee from 2017–2020.)

abofh 3y ago
Email encryption _is_ end-to-end encryption. You just explained why the law doesn't apply to what they did, and the parent explained why they didn't do it because of the law. These two are not in conflict.
- chrismorgan 3y ago
  I’m not sure what you’re saying. The sentence I quoted is written in the present tense, saying that Fastmail is compromised, not as a hypothetical “if they did PGP, it’d be broken for this reason”.

WithinReason 3y ago

These are their objections: 1. Search isn’t possible - It's possible on the client. The total text in an email account is not prohibitively large and can be cached on the client. 2. Previews can’t be calculated - It can be on the client, then reuploaded encrypted. 3. If you lose your private key, we can’t recover your email - Of course, this is equivalent to losing your email account password. 4. Spam checking on content isn’t possible - It is on the client, and on the server based on headers. 5. To access mail on multiple devices, the private key needs to be shared securely between them - Protonmail solved this, what's the problem?

akdev1l 3y ago
> It is on the client, and on the server based on headers. The idea of spam filters is that you don’t get the spam so the client never sees it. Also running highly specialized spam filters that actually work reliably might be prohibitive for a lot of people.
- WithinReason 3y ago
  ProtonMail solved this using email aliases so you never have to give out your real address. If you get spam on one you just redirect it to your spam folder.

LinuxBender 3y ago

Technically all email providers support PGP assuming they support IMAPs. The mobile client is adding it soon if they have not already. I've been using it with Fastmail for some time. Thunderbird makes PGP very easy and happy-clicky. [1] I also just give people my public key out of band and avoid the key servers. Thunderbird also has it's own built in search. I think most peoples non technical relatives could follow the pictured steps easily but if for some reason they can not then a desktop sharing session should get around helping someones mom set it up. I've had no issue with my non technical friends. I should add that if Fastmail added PGP in their interface I would not use it. Nobody could convince me that when a mail provider or anyone else adds E2EE in their application that it's anything other than PP Pinky Promise. They can tamper with it to intercept my communications and no app provider could possibly convince me otherwise. There should probably be an RFC for PP. [1] - https://support.startmail.com/hc/en-us/articles/360014775437-Thunderbird-PGP-Encryption https://support.startmail.com/hc/en-us/articles/360014775437...