Tag Archives: email

Review of Reputable, Functional, and Secure Email Service

I last reviewed email services in 2019. That review focused a lot of attention on privacy. At the time, I selected mailbox.org as my provider, and have been using them for these 5 years since. However, both their service and their support have gone significantly downhill since, so it is time for me to look at other options.

Here I am focusing strongly on email. Some of the providers mentioned here provide other services (IM, video calls, groupware, etc.), and to the extent they do, I am ignoring them.

What Matters in 2024

I want to start off by acknowledging that what you need in email probably depends on your circumstances and the country in which you live. For me, I begin by naming that the largest threat most of us face isn’t from state actors but from criminals: hackers, ransomware gangs, etc. It is important to take as many steps as possible to secure one’s account against that. Privacy and security are both part of the mix. I still value privacy but I am acknowledging, as Migadu does, that “Email as we know it and encryption are incompatible.” Although some of these services strongly protect parts of the conversation, the reality is that most people will be emailing people using plain old email services which don’t. For stronger security, something like Signal would be needed. (I wrote about Signal in 2021 also.)

Interestingly, OpenPGP support seems to be something of a standard feature in the providers I reviewed by this point. All or almost all of them provide integration with browser-based encryption as well as server-side encryption if you prefer that.

Although mailbox.org can automatically PGP-encrypt every message that arrives in plaintext, for general use, this is unwieldy; there isn’t good tooling for searching mailboxes where every message is encrypted, etc. So I never enabled that feature at Mailbox. I still value security and privacy, but a pragmatic approach addresses the most pressing threats first.

My criteria

The basic requirements for an email service include:

  1. Ability to use my own domains
  2. Strong privacy policy
  3. Ability for me to use my own IMAP and SMTP clients on both desktop and mobile
  4. It must be extremely reliable
  5. It must not be free
  6. It must have excellent support for those rare occasions when it is needed
  7. Support for basic aliases

Why do I say it must not be free? Because if someone is providing a service with the quality I’m talking about here, and not charging for it, it implies something is fishy: either they are unscrupulous, are financially unstable, or the product is something else like ads. I am not aware of any provider that matches the other criteria with a free account anyhow. These providers range from about $30 to $90 per year, so cheaper than a Netflix subscription.

Immediately, this rules out several options:

  • Proton doesn’t let me use my own clients on mobile (their bridge is desktop-only)
  • Tuta also doesn’t let me use my own clients
  • Posteo doesn’t let me use my own domain
  • mxroute.com lacks a strong privacy policy, and its policy has numerous causes for concern (for instance, “If you repeatedly send email to invalid/unroutable recipients, they may be published on our GitHub”)

I will have a bit more to say about a couple of these providers below.

There are some additional criteria that are strongly desired but not absolutely required:

  1. Ability to set individual access passwords for every device/app
  2. Support for two-factor authentication (2FA/TFA/TOTP) for web-based access
  3. Support for basics in filtering: ability to filter on envelope recipient (so if I get BCC’d, I can still filter), and ability to execute more than one action on filter match (eg, deliver to two folders, or deliver to a folder and forward to someone else)

IMAP and SMTP don’t really support 2FA, so by setting individual passwords for every device, you can at least limit the blast radius and cut off a specific device if something is (or might be) compromised.

The candidates

I considered these providers: Startmail, Mailfence, Runbox, Fastmail, Kolab, Mailbox.org, and Migadu. I’ll review each, and highlight the pricing of the plan I would most likely use. Each provider offers multiple plans; some may be more expensive and some may be cheaper than the one I reviewed. I included a link to each provider’s full pricing information so you can compare for your needs.

I set up trials with each of these (except Mailbox.org, with which I already had a paid account). It so happend that I had actual questions for support for each one, which gave me an opportunity to see how support responded. I did not fabricate questions, and would not have contacted support if I didn’t have real ones. (This means that I asked different questions of each provider, because they were the REAL questions I had.) I’ll jump to the spoiler right now: I eventually chose Migadu, with Fastmail and Mailfence as close seconds.

I looked for providers myself, and also solicited recommendations in a Mastodon thread.

Mailbox.org

I begin with Mailbox, as it was my top choice in 2019 and the incumbent.

Until this year, I had been quite happy with it. I had cause to reach their support less than once a year on average, and each time they replied the same day or next day. Now, however, they are failing on reliability and on support.

Their spam filter has become overly aggressive. It has blocked quite a bit of legitimate mail. When contacting their support about a prior issue earlier this year, they initially took 4 days to reply, and then 6 days to reply after that. Ouch. They had me disable some spam settings.

It didn’t really help. I continue to lose mail. I don’t know how much, because they block a lot of it before it even hits the spam folder. One of my friends texted to say mail was dropping. I raised a new ticket with mailbox, which took them 5 days to reply to. Their reply was unhelpful. “As the Internet is not a static system, unforeseen events can always occur.” Well yes, that’s true, and I get it, false positives exist with email. But this was from an ISP’s mail system with an address that had been established for years, and it was part of a larger pattern of rejecting quite a bit of legit mail. And every interaction with them recently hasn’t resulted in them actually doing anything to resolve anything. It’s just a paragraph or two of reply that does nothing and helps nothing.

When I complained that it took 5 days to reply, they said “We have not been able to reply sooner as we are currently experiencing a high volume of customer enquiries.” Even though their SLA for my account is a not-great “48 business hour” turnaround, they still missed it and their reason is “we’re busy.” I finally asked what RBL had caught the blocked email, since when I checked, the sender wasn’t on any RBL. Mailbox’s reply: they only keep their logs for 7 days, so next time I should contact them within 7 days. Which, of course, I DID; it was them that kept delaying. Ugh! It’s like they’ve become a cable company.

Even worse is how they have been blocking mail from GrapheneOS’s discussion form. See their thread about it. In short, Graphene’s mail server has a clean reputation and Mailbox has no problem with it. But because one of Graphene’s IPv6 webservers has an IPv6 allocation of a size Mailbox doesn’t like, they drop mail. It’s ridiculous, and Mailbox was dismissive of this well-known and well-regarded Open Source project. So if the likes of GrapheneOS can’t get good faith effort to deliver their mail, what chance does an individual like me have?

I’m sorry, but I’m literally paying you to deliver email for me and provide good support. If you can’t do either of those, you don’t get to push that problem down onto me. Hire appropriate staff.

On the technical side, they support aliases, my own clients, and have a reasonable privacy policy. Their 2FA support exists for the web interface (though weirdly not the support site), though it is somewhat weird. They do not support app passwords.

A somewhat unique feature is the @secure.mailbox.org domain. If you try to receive mail at that address, mailbox.org will block it unless it uses TLS. Same for sending. This isn’t E2EE, but it does at least require things not be in plaintext for the last hop to Mailbox.

Verdict: not recommended due to poor reliability and support.

Mailbox.Org summary:

  • Website: https://mailbox.org/en/
  • Reliability: iffy due to over-aggressive spam filtering
  • Support: Poor; takes 4-6 days for a reply and replies are unhelpful
  • Individual access passwords: No
  • 2FA: Yes, but with a PIN instead of a password as the other factor
  • Filtering: Full SIEVE feature set and GUI editor
  • Spam settings: greylisting on/off, reject some/all spam, etc. But they’re insufficient to address Mailbox’s overzealousness, which support says I cannot workaround within the interface.
  • Server storage location: Germany
  • Plan as reviewed: standard [pricing link]
    • Cost per year: EUR 30 (about $33)
    • Mail storage included: 10GB
    • Limits on send/receive volume: none
    • Aliases: 50 on your domain name, 25 on mailbox.org
    • Additional mailboxes: Available; each one at the same fee as the primary mailbox

Startmail

I really wanted to like Startmail. Its “vault” is an interesting idea and should contribute to the security and privacy of an account. They clearly care about privacy.

It falls down in filtering. They have no way to filter on envelope recipient (BCC or similar). Their support confirmed this to me and that’s a showstopper.

Startmail support was also as slow as Mailbox, taking 5 days to respond to me.

Two showstoppers right there.

Verdict: Not recommended due to slow support responsiveness and weak filtering.

Startmail summary:

  • Website: https://www.startmail.com/
  • Reliability: Seems to be fine
  • Support: Mediocre; Took 5 days for a reply, but the reply was helpful
  • Individual app access passwords: Yes
  • 2FA: Yes
  • Filtering: Poor; cannot filter on envelope recipient, and can’t build filters with multiple actions
  • Spam settings: None
  • Server storage location: The Netherlands
  • Plan as reviewed: Custom domain (trial was Personal), [pricing link]
    • Cost per year: $70
    • Mail storage included: 20GB
    • Limits on send/receive volume: none
    • Aliases: unlimited, with lots of features: can set expiration, etc.
    • Additional mailboxes: not available

Kolab

Kolab Now is mainly positioned as a full groupware service, but they do have a email-only option which I investigated. There isn’t much documentation about it compared to other providers, and also not much in the way of settings. You can turn greylisting on or off. And…. that’s it.

It has a full suite of filtering options. They set an X-Envelope-To header which you can use with the arbitrary header match to do the right thing even for BCC situations. Filters can have multiple conditions and multiple actions. It is SIEVE-based and you can download your SIEVE definitions.

If you enable 2FA, you disable IMAP and SMTP; not great.

Verdict: Not an impressive enough email featureset to justify going with it.

Kolab Now summary:

  • Website: https://kolabnow.com/
  • Reliability: Seems to be fine
  • Support: Fine responsiveness (next day)
  • Invidiaul app passwords: no
  • 2FA: Yes, but if you enable it, they disable IMAP and SMTP
  • Filtering: Excellent
  • Spam settings: Only greylisting on/off
  • Server storage location: Switzerland; they have lots of details on their setup
  • Plan as reviewed: “Just email” [pricing link]
    • Cost per year: CHF 60, about $66
    • Mail storage included: 5GB
    • Limitations on send/receive volume: None
    • Aliases: Yes. Not sure if there are limits.
    • Additional mailboxes: Yes if you set up a group account. “Flexible pricing based on user count” is not documented anywhere I could find.

Mailfence

Mailfence is another option, somewhat similar to Startmail but without the unique vault. I had some questions about filters, and support was quite responsive, responding in a couple of hours.

Some of their copy on their website is a bit misleading, but support clarified when I asked them. They do not offer encryption at rest (like most of the entries here).

Mailfence’s filtering system is the kind I’d like to see. It allows multiple conditions and multiple actions for each rule, and has some unique actions as well (notify by SMS or XMPP). Support says that “Recipients” matches envelope recipients. However, one ommission is that I can’t match on arbitrary headers; only the canned list of headers they provide.

They have only two spam settings:

  • spam filter on/off
  • whitelist

Given some recent complaints about their spam filter being overly aggressive, I find this lack of control somewhat concerning. (However, I discount complaints about people begging for more features in free accounts; free won’t provide the kind of service I’m looking for with any provider.) There are generally just very few settings for email as well.

Verdict: Response and helpful support, filtering has the right structure but lacks arbitrary header match. Could be a good option.

Mailfence summary:

  • Website: https://mailfence.com/
  • Reliability: Seems to be fine
  • Support: Excellent responsiveness and helpful replies (after some initial confusion about my question of greylisting)
  • Individual app access passwords: No. You can set a per-service password (eg, an IMAP password), but those will be shared with all devices speaking that protocol.
  • 2FA: Yes
  • Filtering: Good; only misses the ability to filter on arbitrary headers
  • Spam settings: Very few
  • Server storage location: Belgium
  • Plan as reviewed: Entry [pricing link]
    • Cost per year: $42
    • Mail storage included: 10GB, with a maximum of 50,000 messages
    • Limits on send/receive volume: none
    • Aliases: 50. Aliases can’t be deleted once created (there may be an exeption to this for aliases on your own domain rather than mailfence.com)
    • Additional mailboxes: Their page on this is a bit confusing, and the pricing page lacks the information promised. It looks like you can pay the same $42/year for additional mailboxes, with a limit of up to 2 additional paid mailboxes and 2 additional free mailboxes tied to the account.

Runbox

This one came recommended in a Mastodon thread. I had some questions about it, and support response was fantastic – I heard from two people that were co-founders of the company! Even within hours, on a weekend. Incredible! This kind of response was only surpassed by Migadu.

I initially wrote to Runbox with questions about the incoming and outgoing message limits, which I hadn’t seen elsewhere, as well as the bandwidth limit. They said the bandwidth limit is no longer enforced on paid accounts. The incoming and outgoing limits are enforced, and all email (even spam) counts towards the limit. Notably the outgoing limit is per recipient, so if you send 10 messages to your 50-recipient family group, that’s the limit. However, they also indicated a willingness to reset the limit if something happens. Unfortunately, hitting the limit results in a hard bounce (SMTP 5xx) rather than a temporary failure (SMTP 4xx) so it can result in lost mail. This means I’d be worried about some attack or other weirdness causing me to lose mail.

Their filter is a pain point. Here are the challenges:

  • You can’t directly match on a BCC recipient. Support advised to use a “headers” match, which will search for something anywhere in the headers. This works and is probably “good enough” since this data is in the Received: headers, but it is a little more imprecise.
  • They only have a “contains”, not an “equals” operator. So, for instance, a pattern searching for “test@example.com” would also match “newtest@example.com”. Support advised to put the email address in angle brackets to avoid this. That will work… mostly. Angle brackets aren’t always required in headers.
  • There is no way to have multiple actions on the filter (there is just no way to file an incoming message into two folders). This was the ultimate showstopper for me.

Support advised they are planning to upgrade the filter system in the future, but these are the limitations today.

Verdict: A good option if you don’t need much from the filtering system. Lots of privacy emphasis.

Runbox summary:

  • Website: https://runbox.com/
  • Reliability: Seems to be fine, except returning 5xx codes if per-day limits are exceeded
  • Support: Excellent responsiveness and replies from founders
  • Individual app passwords: Yes
  • 2FA: Yes
  • Filtering: Poor
  • Spam settings: Very few
  • Server storage location: Norway
  • Plan as reviewed: Mini [pricing link]
    • Cost per year: $35
    • Mail storage included: 10GB
    • Limited on send/receive volume: Receive 5000 messages/day, Send 500 recipients/day
    • Aliases: 100 on runbox.com; unlimited on your own domain
    • Additional mailboxes: $15/yr each, also with 10GB non-shared storage per mailbox

Fastmail

Fastmail came recommended to me by a friend I’ve known for decades.

Here’s the thing about Fastmail, compared to all the services listed above: It all just works. Everything. Filtering, spam prevention, it is all there, all feature-complete, and all just does the right thing as you’d hope. Their filtering system has a canned dropdown for “To/Cc/Bcc”, it supports multiple conditions and multiple actions, and just does the right thing. (Delivering to multiple folders is a little cumbersome but possible.) It has a particularly strong feature set around administering multiple accounts, including things like whether users can prevent admins from reading their mail.

The not-so-great part of the picture is around privacy. Fastmail is based in Australia, where the government has extensive power around spying on data, even to the point of forcing companies to add wiretap capabilities. Fastmail’s privacy policy states user data may be held in Australia, USA, India, and Netherlands. By default, they share data with unidentified “spam companies”, though you can disable this in settings. On the other hand, they do make a good effort towards privacy.

I contacted support with some questions and got back a helpful response in three hours. However, one of the questions was about in which countries my particular data would be stored, and the support response said they would have to get back to me on that. It’s been several days and no word back.

Verdict: A featureful option that “just works”, with a lot of features for managing family accounts and the like, but lacking in the privacy area.

Fastmail summary:

  • Website: https://www.fastmail.com/
  • Reliability: Seems to be fine
  • Support: Good response time on most questions; dropped the ball on one tha trequired research
  • Individual app access passwords: Yes
  • 2FA: Yes
  • Filtering: Excellent
  • Spam settings: Can set filter aggressiveness, decide whether to share spam data with “spam-fighting companies”, configure how to handle backscatter spam, and evaluate the personal learning filter.
  • Server storage locations: Australia, USA, India, and The Netherlands. Legal jurisdiction is Australia.
  • Plan as reviewed: Individual [pricing link]
    • Cost per year: $60
    • Mail storage included: 50GB
    • Limits on send/receive volume: 300/hour
    • Aliases: Unlimited from what I can see
    • Additional mailboxes: No; requires a different plan for that

Migadu

Migadu was a service I’d never heard of, but came recommended to me on Mastodon.

I listed Migadu last because it is a class of its own compared to all the other options. Every other service is basically a webmail interface with a few extra settings tacked on.

Migadu has a full-featured email admin console in addition. By that I mean you can:

  • View usage graphs (incoming, outgoing, storage) over time
  • Manage DNS (if you want Migadu to run your nameservers)
  • Manage multiple domains, and cross-domain relationships with mailboxes
  • View a limited set of logs
  • Configure accounts, reset their passwords if needed/authorized, etc.
  • Configure email address rewrite rules with wildcards and so forth

Basically, if you were the sort of person that ran your own mail servers back in the day, here is Migadu giving you most of that functionality. Effectively you have a web interface to do all the useful stuff, and they handle the boring and annoying bits. This is a really attractive model.

Migadu support has been fantastic. They are quick to respond, and went above and beyond. I pointed out that their X-Envelope-To header, which is needed for filtering by BCC, wasn’t being added on emails I sent myself. They replied 5 hours later indicating they had added the feature to add X-Envelope-To even for internal mails! Wow! I am impressed.

With Migadu, you buy a pool of resources: storage space and incoming/outgoing traffic. What you do within that pool is up to you. You can set up users (“mailboxes”), aliases, domains, whatever you like. It all just shares the pool. You can restrict users further so that an individual user has access to only a subset of the pool resources.

I was initially concerned about Migadu’s daily send/receive message count limits, but in visiting with support and reading the documentation, what really comes out is that Migadu is a service with a personal touch. Hitting the incoming traffic limit will cause a SMTP temporary fail (4xx) response so you won’t lose legit mail – and support will work with you if it’s a problem for legit uses. In other words, restrictions are “soft” and they are interpreted reasonably.

One interesting thing about Migadu is that they do not offer accounts under their domain. That is, you MUST bring your own domain. That’s pretty easy and cheap, of course. It also puts you in a position of power, because it is easy to migrate email from one provider to another if you own the domain.

Filtering is done via SIEVE. There is a GUI editor which lets you accomplish most things, though it has an odd blind spot where you can’t file a message into multiple folders. However, you can edit a SIEVE ruleset directly and you get the full SIEVE featureset, which is extensive (and does support filing a message into multiple folders). I note that the SIEVE :envelope match doesn’t work, but Migadu adds an X-Envelope-To header which is just as good.

I particularly love a company that tells you all the reasons you might not want to use them. Migadu’s pro/con list is an honest drawbacks list (of course, their homepage highlights all the features!).

Verdict: Fantastically powerful, excellent support, and good privacy. I chose this one.

Migadu summary:

  • Website: https://migadu.com/
  • Reliability: Excellent
  • Support: Fantastic. Good response times and they added a feature (or fixed a bug?) a few hours after I requested it.
  • Individual access passwords: Yes. Create “identities” to support them.
  • 2FA: Yes, on both the admin interface and the webmail interface
  • Filtering: Excellent, based on SIEVE. GUI editor doesn’t support multiple actions when filing into a folder, but full SIEVE functionality is exposed.
  • Spam settings:
    • On the domain level, filter aggressiveness, Greylisting on/off, black and white lists
    • On the mailbox level, filter aggressiveness, black and whitelists, action to take with spam; compatible with filters.
  • Server storage location: France; legal jurisdiction Switzerland
  • Plan as reviewed: mini [pricing link]
    • Cost per year: $90
    • Mail storage included: 30GB (“soft” quota)
    • Limits on send/receive volume: 1000 messgaes in/day, 100 messages out/day (“soft” quotas)
    • Aliases: Unlimited on an unlimited number of domains
    • Additional mailboxes: Unlimited and free; uses pooled quotas, but individual quotas can be set

Others

Here are a few others that I didn’t think worthy of getting a trial:

  • mxroute was recommended by several. Lots of concerning things in their policy, such as:
    • if you repeatedly send mail to unroutable recipients, they may publish the addresses on Github
    • they will terminate your account if they think you are “rude” or want to contest a charge
    • they reserve the right to cancel your service at any time for any (or no) reason.
  • Proton keeps coming up, and I will not consider it so long as I am locked into their client on mobile.
  • Skiff comes up sometimes, but they were acquired by Notion.
  • Disroot comes up; this discussion highlights a number of reasons why I avoid them. Their Terms of Service (ToS) is inconsistent with a general-purpose email account (I guess for targeting nonprofits and activists, that could make sense). Particularly laughable is that they claim to be friends of Open Source, but then would take down your account if you upload “copyrighted” material. News flash: in order for an Open Source license to be meaningful, the underlying work is copyrighted. It is perfectly legal to upload copyrighted material when you wrote it or have the license to do so!

Conclusions

There are a lot of good options for email hosting today, and in particular I appreciate the excellent personal support from companies like Migadu and Runbox. Support small businesses!

Asynchronous Email: Exim over NNCP (or UUCP)

Following up to yesterday’s article about how NNCP rehabilitates asynchronous communication with modern encryption and onion routing, here is the first of my posts showing how to put it into action.

Email is a natural fit for async; in fact, much of early email was carried by UUCP. It is useful for an airgapped machine to be able to send back messages; errors from cron, results of handling incoming data, disk space alerts, etc. (Of course, this would apply to a non-airgapped machine also).

The NNCP documentation already describes how to do this for Postfix. Here I will show how to do it for Exim.

A quick detour to UUCP land

When you encounter a system such as email that has instructions for doing something via UUCP, that should be an alert to you that “here is some very relevant information for doing this same thing via NNCP.” The syntax is different, but broadly, here’s a table of similar NNCP commands:

Purpose UUCP NNCP
Connect to remote system uucico -s, uupoll nncp-call, nncp-caller
Receive connection (pipe, daemon, etc) uucico (-l or similar) nncp-daemon
Request remote execution, stdin piped in uux nncp-exec
Copy file to remote machine uucp nncp-file
Copy file from remote machine uucp nncp-freq
Process received requests uuxqt nncp-toss
Move outbound requests to dir (for USB stick, airgap, etc) N/A nncp-xfer
Create streaming package of outbound requests N/A nncp-bundle

If you used UUCP back in the day, you surely remember bang paths. I will not be using those here. NNCP handles routing itself, rather than making the MTA be aware of the network topology, so this simplifies things considerably.

Sending from Exim to a smarthost

One common use for async email is from a satellite system: one that doesn’t receive mail, or have local mailboxes, but just needs to get email out to the Internet. This is a common situation even for conventionally-connected systems; in Exim speak, this is a “satellite system that routes mail via a smarthost.” That is, every outbound message goes to a specific target, which then is responsible for eventual delivery (over the Internet, LAN, whatever).

This is fairly simple in Exim.

We actually have two choices for how to do this: bsmtp or rmail mode. bsmtp (batch SMTP) is the more modern way, and is essentially a derivative of SMTP that explicitly can be queued asynchronously. Basically it’s a set of SMTP commands that can be saved in a file. The alternative is “rmail” (which is just an alias for sendmail these days), where the data is piped to rmail/sendmail with the recipients given on the command line. Both can work with Exim and NNCP, but because we’re doing shiny new things, we’ll use bsmtp.

These instructions are loosely based on the Using outgoing BSMTP with Exim HOWTO. Some of these may assume Debianness in the configuration, but should be easily enough extrapolated to other configs as well.

First, configure Exim to use satellite mode with minimal DNS lookups (assuming that you may not have working DNS anyhow).

Then, in the Exim primary router section for smarthost (router/200_exim4-config_primary in Debian split configurations), just change transport = remote_smtp_smarthost to transport = nncp.

Now, define the NNCP transport. If you are on Debian, you might name this transports/40_exim4-config_local_nncp:

nncp:
  debug_print = "T: nncp transport for $local_part@$domain"
  driver = pipe
  user = nncp
  batch_max = 100
  use_bsmtp
  command = /usr/local/nncp/bin/nncp-exec -noprogress -quiet hostname_goes_here rsmtp
.ifdef REMOTE_SMTP_HEADERS_REWRITE
  headers_rewrite = REMOTE_SMTP_HEADERS_REWRITE
.endif
.ifdef REMOTE_SMTP_RETURN_PATH
  return_path = REMOTE_SMTP_RETURN_PATH
.endif

This is pretty straightforward. We pipe to nncp-exec, run it as the nncp user. nncp-exec sends it to a target node and runs whatever that node has called rsmtp (the command to receive bsmtp data). When the target node processes the request, it will run the configured command and pipe the data in to it.

More complicated: Routing to various NNCP nodes

Perhaps you would like to be able to send mail directly to various NNCP nodes. There are a lot of ways to do that.

Fundamentally, you will need a setup similar to the UUCP example in Exim’s manualroute manual, which lets you define how to reach various hosts via UUCP/NNCP. Perhaps you have a star topology (every NNCP node exchanges email with a central hub). In the NNCP world, you have two choices of how you do this. You could, at the Exim level, make the central hub the smarthost for all the side nodes, and let it redistribute mail. That would work, but requires decrypting messages at the hub to let Exim process. The other alternative is to configure NNCP to just send to the destinations via the central hub; that takes advantage of onion routing and doesn’t require any Exim processing at the central hub at all.

Receiving mail from NNCP

On the receiving side, first you need to configure NNCP to authorize the execution of a mail program. In the section of your receiving host where you set the permissions for the client, include something like this:

      exec: {
        rsmtp: ["/usr/sbin/sendmail", "-bS"]
      }

The -bS option is what tells Exim to receive BSMTP on stdin.

Now, you need to tell Exim that nncp is a trusted user (able to set From headers arbitrarily). Assuming you are running NNCP as the nncp user, then add MAIN_TRUSTED_USERS = nncp to a file such as /etc/exim4/conf.d/main/01_exim4-config_local-nncp. That’s it!

Some hosts, of course, both send and receive mail via NNCP and will need configurations for both.

Review of Secure, Privacy-Respecting Email Services

I’ve been hosting my own email for several decades now. Even before I had access to a dedicated Internet link, I had email via dialup UUCP (and, before that, a FidoNet gateway).

But self-hosting email is becoming increasingly difficult. The time required to maintain spam and virus filters, SPF/DKIM settings, etc. just grows. The importance of email also is increasing. Although my own email has been extremely reliable, it is still running on a single server somewhere and therefore I could stand to have a lot of trouble if it went down while I was unable to fix it

Email with Pretty Good Privacy & Security

(Yes, this heading is a pun.)

There’s a lot of important stuff linked to emails. Family photos. Password resets for banks, social media sites, chat sites, photo storage sites, etc. Shopping histories. In a lot of cases, if your email was compromised, it wouldn’t be all that hard to next compromise your bank account, buy stuff with your Amazon account, hijack your Netflix, etc. There are lots of good resources about why privacy matters; here’s one informative video even if you think you have “nothing to hide”.

There is often a tradeoff between security and usability. A very secure system would be airgapped; you’d always compose your messages and use your secret keys on a system that has no Internet access and never will. Such a system would be quite secure, but not particularly usable.

On the other end of the spectrum are services such as Gmail, which not only make your email available to you, but also to all sorts of other systems within the service that aim to learn about your habits so they can sell this information to advertisers.

This post is about the services in the middle – ones that are usable, can be easily used on mobile devices, and yet make a serious and credible effort to provide better security and privacy than the “big services” run by Google, Yahoo, and Microsoft. Some elements of trust are inherent here; for instance, that the description of the technical nuances of the provider’s services are accurate. (Elements of trust are present in any system; whether your firmware, binaries, etc. are trustworthy.) I used the list at Privacy Tools as a guide to what providers to investigate, supplemented by searches and NoMoreGoogle.

It so happens that most of these services integrate PGP in some way. PGP has long been one of the better ways to have secure communication via email, but it is not always easy for beginners to use. These services make it transparent to a certain degree. None of them are as good as a dedicated client on an airgapped machine, but then again, such a setup isn’t very practical for everyday use. These services give you something better — pretty good, even — but of course not perfect. All of these pay at least lip service to Open Source, some of them actually publishing source for some of their components, but none are fully open.

I pay particular attention to how they handle exchanges with people that do not have PGP, as this kind of communication constitutes the vast majority of my email.

A final comment – if what you really need is an easy and secure way to communicate with one or two people, email itself may not be the right option. Consider Signal.

Protonmail

Protonmail is, in many ways, the gold standard of privacy-respecting email. Every email is stored encrypted in a way that even they can’t see, being decrypted on the client side (using a Javascript PGP implementation or other clients). They definitely seem to be pushing the envelope for security and privacy; they keep no IP logs, don’t require any personal information to set up an account, and go into quite a lot of detail about how your keys are protected.

A side effect of this is that you can’t just access your email with any mail reader. Since the decryption is done on the client side, you pretty much have to use a Protonmail client. They provide clients for iOS and Android, the Web interface, and a “bridge” that exposes IMAP and SMTP ports to localhost and lets you connect a traditional mail client to the system. The bridge, in this case, handles the decryption for you. The bridge works really well and supports Windows, Mac, and Linux, though it is closed source. (The source for the Linux bridge has been “coming soon” for awhile now.) Protonmail provides very good support for bringing your own domain, and in my testing this worked flawlessly. It supports Sieve-based filters, which can also act on envelope recipients (yes!) The web interface is sleek, very well done, tightly integrated, and just generally exceptionally easy to use and just works.

Unfortunately, the mobile clients get the job done for only light use. My opinion: they’re bad. Really bad. For instance:

  • There’s no way to change the sort order on a mail folder
  • The Android client has an option to automatically download all message bodies. The iOS client lacks this option, but no matter; it doesn’t work on Android anyhow.
  • They’re almost completely unusable offline. You can compose a brand new message but that’s it.

There are some other drawbacks. For one, they don’t actually encrypt mail metadata, headers, or subject lines (though this is common to all of the solutions here, Protonmail’s marketing glosses over this). They also seem to have a lot of problems with overly-aggressive systems blocking people’s accounts: here’s a report from 2017, and I’ve seen more recent ones from people that had paid, but then had the account disabled. Apparently protonmail is used by scammers a fair bit and this is a side-effect of offering free, highly secure accounts – some of their deactivations have been legitimate. Nevertheless, it makes me nervous, especially given the high number of reports of this on reddit.

Unfortunately, Proton seems more focused on new products than on fixing these issues. They’ve been long-simmering in the community but what they talk about is more about their upcoming new products.

Protonmail’s terms of service include both a disclaimer that it’s as-is and an SLA, as well as an indemnification clause. Update 2019-03-04: Protonmail’s privacy policy states they use Matomo analytics, that they don’t record your login IP address by default (but IP logs might be kept if you enable it or if they suspect spamming, etc), collect mobile app analytics, IP addresses on incoming messages, etc. Data is retained “indefinitely” for active accounts and for 14 days after account deletion for closed accounts.

Support: email ticket only

Pricing: $4/mo if paid annually; includes 5GB storage, 5 aliases, and 1 custom domain

Location: Switzerland

MFA: TOTP only

Plus address extensions: yes

Transparency report: yes

Mailfence

Mailfence is often mentioned in the same sentence as ProtonMail. They also aim to be a privacy-respecting, secure email solution.

While it is quite possible they use something like LUKS to encrypt data at rest (safeguarding it from a stolen hard drive), unlike ProtonMail, Mailfence does have access to the full content of any plaintext messages sent or received by your account. Mailfence integrates PGP into the Web interface, claiming end-to-end encryption with a “zero-knowledge environment” using, of all things, the same openpgpjs library that is maintained by ProtonMail. While ProtonMail offers a detailed description of key management, I haven’t been able to find this with Mailfence – other than that the private key is stored encrypted on their servers and is protected by a separate passphrase from the login. If we assume the private key is decrypted on the client side, then for PGP-protected communications, the level of security is similar to ProtonMail. With Mailfence, decrypting these messages is a separate operation, while with ProtonMail it happens automatically once logged in. (Update 2019-03-01: Mailfence emailed me, pointing to their document on key storage – it is AES-256 encrypted by the client and stored on the server. They also passed along a link describing their PGP keystore. They also said they plan to work on a feature th encrypt plain text messages.)

While technical measures are part of the story, business policies are another, and Mailfence does seem to have some pretty good policies in place.

In experimenting with it, I found that Mailfence’s filters don’t support filtering based on the envelope recipient, which limits the utility of its aliases since BCC and the like won’t filter properly. A workaround might be possible via the IMAP connection filtering based on Received: headers, but that is somewhat ugly.

Mailfence also supports “secure” documents (word processor, spreadsheet, etc), WebDAV file storage, contacts, and calendars. There is no detail on what makes it “secure” – is it just that it uses TLS or is there something more? I note that the online document editor goes to a URL under writer.zoho.com, so this implies some sort of leakage to me and a possible violation of their “no third-party access to your data” claim. (Update 2019-03-01: Mailfence emailed me to point out that, while it’s not disclosed on the page I liked to, it is disclosed on their blog, and that since I evaluated it, they added a popup warning in the application before sending the documents to Zoho.)

Mailfence supports POP, IMAP, SMTP, and — interestingly — Exchange ActiveSync access to their services. I tested ActiveSync on my Android device, and it appeared to work exactly as planned. This gives a lot of client flexibility and very nice options for calendar and contact sync (*DAV is also supported).

Mailfence’s terms of use is fairly reasonable, though it also includes an indemnification clause. It makes no particular uptime promises. Update 2019-03-04: Per their privacy policy, Mailfence logs IP addresses and use Matomo analytics on the website but not within the application. Deleted messages and documents are retained for 45 days. The policy does not specify retention for logs.

Support: email ticket or business-hours phone support for paying customers

Pricing: EUR 2.50/mo paid annually, includes 5GB storage, 10 aliases, and 1 custom domain

Location: Belgium

MFA: TOTP only

Plus address extensions: Yes

Transparency report: Yes

Mailbox.org

Mailbox.org has been in the hosting business for a long time, and also has a privacy emphasis. Their security is conceptually similar to that of Mailfence. They offer two web-based ways of dealing with PGP: OX Guard and Mailvelope. Mailvelope is a browser extension that does all encryption and decryption on the client side, similar to Mailfence and ProtonMail. OX Guard is part of the Open-Xchange package which mailbox.org uses. It stores the encryption keys on the server, protected by a separate key passphrase, but all encryption and decryption is done server-side. Mailbox’s KB articles on this makes it quite clear and spell out the tradeoffs. The basic upshot is that messages you receive in plaintext will still be theoretically visible to the service itself.

Mailbox.org offers another interesting feature: automatic PGP-encryption of any incoming email that isn’t already encrypted. This encrypts everything inbound. If accessed using Mailvelope or some other external client, it provides equivalent security to ProtonMail. (OX Guard is a little different since the decryption happens server-side.)

They also offer you an @secure.mailbox.org email address that will reject any incoming mail that isn’t properly secured by TLS. You can also send from that address, which will fail to send unless the outgoing connection is properly secured as well. This is one of the more interesting approaches to dealing with the non-PGP-using public. Even if you don’t use that, if you compose in their web interface, you get immediate feedback about the TLS that will be used. It’s not end-to-end, but it’s better than nothing. Mailfence and Protonmail both offer an “secure email” that basically emails a link to a recipient, that links back to their server and requires the recipient to enter a password that was presumably exchanged out of band. Mailbox Guard will automatically go this route when you attempt to send email to someone for whom the PGP keys weren’t known, but goes a step further and invites them to reply there or set up their PGP keys.

Mailbox.org runs Open-Xchange, a semi-Open Source web-based office suite. As such, it also offers calendar, contacts, documents, task lists, IMAP/SMTP/POP, ActiveSync, and so forth. Their KB specifically spells out that things like the calendar are not encrypted with PGP. The filtering does the right thing with envelope recipients.

Mailbox.org has an amazingly comprehensive set of options, a massive knowledge base, even a user forum. Some of the settings I found to be interesting, besides the ones already mentioned, include:

  • Spam settings: greylisting on or off, RBL use, executable file attachment blocking, etc.
  • Restoring email from a backup
  • Disposable addresses (automatically deleted after 30 days)
  • A “catch-all” alias, that just counts as one of your regular aliases, and applies to all usernames under a domain not otherwise aliased.

I know Protonmail has frequent third-party security audits; I haven’t seen any mention of this on the mailbox.org site. However, it looks probable that less of their code was written in house, and it may have been audited without a mention.

Overall, I’ve been pretty impressed with them. They give details on EVERYTHING. It’s the geeky sort of comprehensive, professional solution I’d like. I wish it would have full end-to-end transparent encryption like ProtonMail, but honestly what they’re doing is more practical and useful to a lot of folks.

Mailbox has a reasonable T&C (though it does include an indemnity clause as many others do) and a thorough data protection and privacy policy. Some providers don’t log IP addresses at all; mailbox.org does, but destroys them after 4 days. (Update 2019-03-04: Discovered that all of the providers reviewed may do this at times; updated the other reviews and removed incorrect text; mailbox.org’s is actually one of the better policies) mailbox.org goes into a lot more detail than others, and also explicitly supports things such as Tor for greater anonymity.

Support: email ticket (phone for business-level customers)

Pricing: EUR 1/mo for 2GB storage and 3 aliases; EUR 2.50/mo for 5GB storage and 25 aliases. Expansions possible (for instance, 25GB storage costs a total of EUR 3.50/mo)

Location: Germany

MFA: Yubikey, OATH, TOTP, HOTP, MOTP (web interface only)

Plus address extensions: Yes

Transparency Report: Yes

Startmail

Startmail is a service from the people behind the privacy-respecting search engine Startpage. There is not a lot of information about the technical implementation of Startmail, with the exception of a technical white paper from 2016. It is unclear if this white paper remains accurate, but this review will assume it is. There are also some articles in the knowledge base.

I was unable to fully review Startmail, because the free trial is quite limited (doesn’t even support IMAP) and anything past that level requires an up-front payment of $60. While I paid a few dollars for a month’s real account elsewhere, this was rather too much for a few paragraphs’ review.

However, from the trial, it appears to have a feature set roughly akin to Mailfence. Its mail filters are actually more limited, and it’s mail only: no documents, calendars, etc.

Startmail a somewhat unique setup, in which a person’s mail, PGP keys, etc. are stored in a “vault” which turns out to be a LUKS-encrypted volume. This vault is opened when a person logs in and closed when they log out, and controlled by a derivative of their password. On the one hand, this provides an even stronger level of security than Protonmail (since headers are also encrypted). On the other hand, when the vault is “open” – when one must presume it is quite frequently for an account being polled by IMAP – it is no better than anything else.

They explicitly state that they have not had a third-party audit.

Support: ticket only

Pricing: $60/yr ($5/mo), must be paid as an entire year up-front

Location: Netherlands

MFA: TOTP only

Plus address extensions: unknown

Transparency report: no

Not Reviewed

Some other frequently-used providers I didn’t review carefully:

  • posteo.de: encrypts your mail using a dovecot extension that decrypts it using a derivation of your password when you connect. Something better than nothing but less than Protonmail. Didn’t evaluate because it didn’t support my own domain.
  • Tutanota: Seems to have a security posture similar to ProtonMail, but has no IMAP support at all. If I can’t use emacs to read my mail, I’m not going to bother.

Conclusions

The level of security represented by Protonmail was quite appealing to me. I wish that the service itself was more usable. It looks like an excellent special-needs service, but just isn’t quite there yet as a main mail account for people that have a lot of mail.

I am likely to pursue mailbox.org some more, as although it isn’t as strong as Protonmail when it comes to privacy, it is still pretty good and is amazing on usability and flexibility.

A Final Word on Trust

Trust is a big part of everything going on here. For instance, if you use ProtonMail, where does trust come into play? Well, you trust that they aren’t serving you malicious JavaScript that captures your password and sends it to them out of band. You trust that your browser provides a secure environment for JavaScript and doesn’t have leakage. Or if you use mailbox.org, you trust that the server is providing a secure environment and that when you supply your password for the PGP key, it’s used only for that. ProtonMail will tell you how great it is to have this code client-side. Startmail will tell you how bad Javascript in a browser is for doing things related to security. Both make good, valid points.

To be absolutely sure, it is not possible or practical for any person to verify every component in their stack on every use. Different approaches have different trust models. The very best is still standalone applications.

The providers reviewed here raise the average level of privacy and security on the Internet, and do it by making it easier for the average user. That alone is a good thing and worthy of support. None of them can solve every problem, but all of them are a step up from the standard, which is almost no security at all.