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Flavio Poletti

Irreducible Perler.

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Do you use Taskwarrior and want to setup a private remote server for backing stuff up and sync across multiple devices? Here’s a few notes you might find interesting.

Table of Contents

What will we talk about?

First of all, the Taskwarrior site has comprehensive instructions on how to setup your own sync server. Take it as a good starting point, it will actually work quite well if you are doing all on your own.

In the following sections, we will begin with a brief introduction to the concepts related to setting up the security part of the Taskserver. This is by far the most tricky part of the setup, and the one more likely to make you angry.

If you’re in a hurry, you can skip the following section about securing the communications, and jump directly to the configuration parts. Enjoy!

Securing The Communications

Taskwarrior allows you to setup encrypted communications between client and server, and rightly so. This is done using a protocol called Transport Layer Security (or TLS), which requires you to use keys, certificates, certification authorities and certificate revocation lists.

Sounds complicated? It is! We will not get into the details but just look at the core concepts that matter in configuring Taskwarrior (see Information security for additional resources).

When you care about security in syncing your local changes to a remote server, the immediate issue you are probably worried with is confidentiality, i.e.: how do I make sure that nobody else is able to understand what me and the server are saying?

Another aspect you should care about is whether the system you’re syncing with is actually what it claims to be, and not something set up to appear so. If you have confidentiality, but you’re telling your secrets to the wrong system… that’s not very secure, is it? This works also the other way around, of course: they system accepting sync requests has to be sure that you are who you claim to be, otherwise others might impersonate you and mess with your data.

For both aspects (there are more, of course) maths come to the rescue. In particular, encryption can give you confidentiality, while digital signatures can give you reasonable proof of someone’s identity.


At the core of both are techniques that go under the umbrella of asymmetric cryptography. Asymmetric means that for security reasons each subject has two keys, one called private that has to be kept secret at all times, and one public that can be distributed freely. They act as keys where one can open whatever the other is capable of closing, so they always come as a key pair.

For example, if you want to send a message (think of it like “closing the message in a box”) you use the recipient’s public key to do that, and be sure that only the recipient will be able to read it using the private key. This is encryption.

On the other hand, if you want proof that the peer has the private key corresponding to the public key you already have, you tell them to lock a message you invent on the spot inside a box, and use their public key to open the box: it will work only if the two keys form a pair. This is signing, or putting a signature.


At this point you might be thinking that this whole construction works only as long as you actually trust that the public key you have actually comes from the right source. The best way to ensure this is to get this public key in some way that you trust, like e.g. meet the person and get the key from a USB pen, or ask them to spell it on the phone. Whatever makes you feel good for your level of secrecy.

While theoretically correct, this method has the non-trivial flaw of being completely impractical for today’s Internet size. This would mean going to your bank and taking the key, going to Google’s and take their key, then Facebook, Twitter, and whatever service you use that leverages TLS. This is where certificates come into play.

A certificate is basically a public key with some information attached, in particular with the identity of the owner of that public key, in the form of a Common Name (abbreviated CN), which is basically a domain name owned by the organization (like www.example.com). It’s like you had a key and put a label on it saying that this key is owned by the same people that run www.example.com.

Certification Authorities

Of course everybody would be able to put a label about www.example.com on their own public key, so we’re the catch? In addition to containing a public key and a CN, a certificate also contains a signature by a third party called the Certification Authority (abbreviated CA). So the certificate says: this public key is owned by the people that also own this CN, and this is guaranteed by the CA. At this point, of course, you must have the CA certificate to verify that their signature is valid (because the CA certificate will contain their public key and their identity!).

This shifts your trust from the people that run the CN to the people that run the CA. While it may seem that this didn’t improve things too much (you still have to figure out how to trust the CA people!), this actually makes things easier for you, because the same CA can emit certificates for a lot of CNs. Hence, instead of going to everyone’s and get their public key, you just go to the CA and get theirs: this will make sure that all the certificate they signed actually come from the CNs written in the certificates.

A chain of CAs

This same process might apply to CAs too. A little CA might ask a bigger one to sign its certificate to declare that they are entitled to sign certificates, and so on. Hence, when some web site sends you their certificate, they might also send you a chain of intermediate CA certificates where each certificate is about the CA that signed the certificate immediately before, up to the last that is signed by some well-known CA.

At this point you might ask: “Hey! I didn’t ever go to any well known CA to get this rule-them-all CA certificate!”. Right, you didn’t. But most browsers come with a bunch of pre-recorded certificates of well known CAs, so here’s how you got them behind the scenes. Now you should ask yourself if you really trust your browser, shouldn’t you?

There are quite some CAs out there, from the most famous like Comodo, Symantec and GoDaddy, to minor ones. The most famous are those whose certificates get installed in browsers and TLS libraries by default. They have a non-trivial work to do, because they have to keep their private keys very private (if someone stole them, they could be used to issue false certificates!) and they also have to make sure that people asking a certificate for a CN actually own that CN (i.e. they have to go there instead of you). This is why certificates usually come with a cost, which varies depending on the level of trust that they provide (bank’s certificates undergo a much deeper scrutiny with respect to some casual user’s home page), and this is also why browsers can show a simple lock for lesser certificates up to a full green indication for the most trusted ones.

Which CA for Taskwarrior?

Back to Taskwarrior, if you don’t want to shell out money for setting up your own sync server, you have a couple of alternatives:

  • you can set up your fake CA and sign your own certificates. In a private context this makes absolutely sense, because you are sure to trust everyone involved… unless you suffer from multiple personalities and you are not sure about a couple of them!
  • if you have a real domain hosted somewhere, you can get certificates for free in a few places, one of which is Let’s Encrypt. They will issue you real certificates, although they are an intermediate CA so they will also provide their own certificate that is signed by a bigger well-known company.

Which way should you go? In a private or very controlled environment, you can definitely go with the first option. The instructions you find in Taskwarrior’s instructions page actually assume that this is they way you are going to take. This will require a bit more complicated procedure on the client side, because you will have to take care that the client actually trusts the fake CA you set up (but you have the certificate for this fake CA, so you’re going to be fine).

On the other hand, if you plan to give access to a wider audience, your best chance is probably to go for a certificate issued by a real CA, like Let’s Encrypt. Which one you choose depends on which guarantees you want to have about the CA: the higher you need, the more you will have to spend on it.

What about clients?

Up to now, we discussed how can your client be sure about the server (which might be a web server, or a taskd installed somewhere). For the web, this is most of the times all that you need.

In the case of Taskwarrior this is not all, though. Put yourself into taskd’s shoes: should it blindly accept all updates that claim to come from you as valid? What if someone else tries to sync updated pretenting to be you, and mess up with your precious activities?

The same story we saw above with key pairs and certificates applies to clients as well. So, you can generate a pair of key, set the private one in the client and keep the public one in the server, inside a certificate that tells who you are.

Expiration and Certificate Revocation List

One last thing to keep in mind is that certificates are usually issued with an expiration date. The more time passes, the more the public key can be subject to an attack to try to figure out the associated private key, for example; or the more you might have leaked your private key. So, although it’s a hassle to take care of renewing your keys and certificates, this is actually a safety measure.

In addition to expiration, you might want to invalidate certificates ahead of time. This might e.g. happen if you discover that the private key was leaked somehow. For this reason. so-called Certificate Revocation Lists (abbreviated CRL) can help you track certificates that aren’t trusted anymore, even if they have a valid signature and have not expired yet.

The CRL is usually kept by the CA, because it’s the entity that guarantees about the validity of the certificates it signs.


After this long digression, we come to the following summary conclusions:

  • there are three types of entities involved in this whole TLS story:
    • users
    • servers
    • CAs
  • there are three basic kind of artifacts that we have to take care of:
    • private keys, which we will simply call keys in the following;
    • (public) certificates
    • (public) certificate revocation lists

Each entity involved (users, servers, CAs) will have the first two kind of artifact (a key and a certificate), while CAs will also have a CRL. So, you will have to deal with the following artifacts:

  • user key and user certificate
  • server key and server certificate
  • CA key, CA certificate and CA CRL.

It helps to remember that they are all data that is saved into files, although there might be a many-to-one relation (e.g. a file containing certificates might contain a server certificate, followed by a chain of CA certificates up to one signed by a well-known CA).

Setup Remote Sync

Before starting, we will assume that:

  • you have some degree of control over a domain. It must not necessarily be a real one, i.e. visible from the outside or registered in official DNSs; it suffices that you can somehow control the resolution process in clients so that that particular domain points to the IP Address of the Taskserver you set up. In this example, we will call this domain taskd.example.com, although we will also assume that it is stored in environment variable DOMAIN;
  • you will use the port stored in the environment variable PORT, which you already ensured that will be available elsewhere (e.g. you opened the right ports in the firewall, etc.). Just for you to know, it’s customary to set the port to 53589;
  • your Taskserver software is already installed and ready to be started, only missing the right configuration for security. We will assume it is stored in a directory whose path is stored in environment variable TWSERVER;
  • your Taskwarrior software in the client is already installed and working. We will assume that its base directory’s path is stored in environment variable TWCLIENT.

User accounts

Whatever the way you choose to configure keys, certificates etc. you will need to enable your user(s) for syncing their tasks, ensuring that they will not trump onto each other.

Users can be grouped in organizations. To create an organization you can issue the following command on the server:

taskd add org name-of-your-org

where name-of-your-org can be whatever you choose to call your organization. Suggestion: use letters, numbers, underscores and hyphens only. If you plan to keep things simple (all users inside the same organization) this is the only time you will need to issue this command.

After this, for each user you want to create you have to run the following command, still on the server:

taskd add user name-of-your-org 'Name O. User'

You will get back something like this:

New user key: cf31f287-ee9e-43a8-843e-e8bbd5de4294
Created user 'Name O. User' for organization 'name-of-your-org'

where the key will be different (each user will get its own unique key).

In the following, we will assume that environment variables ORGANIZATION, USER_NAME and USER_KEY contain… what you think that they should contain. In our example, they contain respectively the strings name-of-your-org, Name O. User and cf31f287-ee9e-43a8-843e-e8bbd5de4294.

Alternative 1: DIY

If your setup is sufficiently restricted and you have good control over your clients, you can go the do it yourself way and be the CA of yourself. This is also the easiest thing to do with what ships with Taskwarrior by default, because there are scripts that allow you to do exactly this.

All the heavy lifting is done within a directory named pki. Depending on the distribution/system you use, it might be located in a different location; we will let you find it and wait patiently here. Just for a hint, this is what you should find in that directory (this example was run in Alpine Linux):

/ $ cd /usr/share/taskd/pki/
/usr/share/taskd/pki $ ls -l
total 28
-rw-r--r--    1 root     root          1272 May 10  2015 README
-rwxr-xr-x    1 root     root           664 May 10  2015 generate
-rwxr-xr-x    1 root     root           633 May 10  2015 generate.ca
-rwxr-xr-x    1 root     root           778 May 10  2015 generate.client
-rwxr-xr-x    1 root     root           889 May 10  2015 generate.crl
-rwxr-xr-x    1 root     root           866 May 10  2015 generate.server
-rw-r--r--    1 root     root           138 May 10  2015 vars

Before running anything, you MUST edit the file vars, that initially appears like this:

ORGANIZATION="Göteborg Bit Factory"
STATE="Västra Götaland"

The only, single important thing that you MUST change is the CN setting (remember the Common Name? Well, this is it!). As we are assuming to operate taskd.example.com, this is what we have to setup here. It does not hurt to change a few of the other parameters of course, but it’s not strictly necessary. This is how we will change it in this example:

ORGANIZATION="Yadda Yadda Yadda"

It does not hurt to repeat: change CN to your domain.

Now, you just run the shell script generate inside the directory, and let the magic happen. It boils down to the following four commands (at least as of release 2.5.1):

./generate.client client

It should be pretty clear at this point:

  • first of all, a fake CA is generated. This is us acting as a CA, that is not widely recognised but that we can totally trust! This step generates files ca.key.pem (the CA’s private key) and ca.cert.pem (the public certificate). This certificate is somehow special, because it tells two things:
    • first, that it’s from a Certification Authority, so it should be trusted when used for signing other certificates;
    • second, that it’s signed… by the certificate owner itself. This is why it’s also called a self-signed certificate.
  • Now that we have a CA, we can sign certificates for other entities, i.e. servers and clients. The second step takes care to generate the server’s key pair, saving the private key in server.key.pem and generating a certificate that includes the public key in server.cert.pem. This is where the details in file vars are used.
  • The third step generates a Certificate Revocation List. This is probably overkill for a small setup, but it does not hurt to have one anyway. The step generates the file server.crl.pem.
  • The fourth step generates a (private) key and a certificate for a client, so that it will be able to demonstrate its identity back to the server. This step generates client.key.pem and client.cert.pem.

One interesting thing is that the CA we created in the first step has a double role here, because it signs the certificates for both the server and the clients. This is not the most generic setup that you can have, as we will see below; for the moment, we will stick with it.

This is a summary of the generated files and where you should put them:

SERVER                          CLIENT
---------------------------     ---------------------------
"$TWSERVER"/server.key.pem      "$TWCLIENT"/client.key.pem
"$TWSERVER"/server.cert.pem     "$TWCLIENT"/client.cert.pem
"$TWSERVER"/server.crl.pem      "$TWCLIENT"/ca.cert.pem

To be completely right, you should also ensure to keep ca.key.pem somewhere, because it will be needed to regenerate the server.crl.pem file in case of need.

Server configuration

Now you only have to do the configurations. On the server you have to setup the files we generated and moved into the right location, plus where the daemon should be listening (we will copy also a couple of additional configurations while we are at it):

taskd config --force -- server      "$DOMAIN:$PORT"
taskd config --force -- log         "$TWSERVER"/taskd.log
taskd config --force -- pid.file    "$TWSERVER"/taskd.pid
taskd config --force -- server.key  "$TWSERVER"/server.key.pem
taskd config --force -- server.cert "$TWSERVER"/server.cert.pem
taskd config --force -- server.crl  "$TWSERVER"/server.crl.pem
taskd config --force -- ca.cert     "$TWSERVER"/ca.cert.pem

Client configuration

Configuration on the client involves the following items:

  • tell the client where the server for synchronization is;
  • make sure we will accept the server’s certificate. As this is signed by our fake CA, we have to make sure that the TLS library will accept it by loading the fake CA certificate at the right time;
  • set the trust model to the strictest mode, because we care about security (otherwise, you wouldn’t be reading this!)
  • tell the client about our own user identifier and the organization we will save our data within;
  • set the client key and certificate so that it will be able to provide them when requested by the server.

This is what we can do then:

task config --force -- taskd.server      "$DOMAIN:$PORT"
task config --force -- taskd.ca          "$TWCLIENT"/ca.cert.pem
task config --force -- taskd.trust       strict
task config --force -- taskd.credentials "$ORGANIZATION/$USER_NAME/$USER_KEY"
task config --force -- taskd.key         "$TWCLIENT"/client.key.pem
task config --force -- taskd.certificate "$TWCLIENT"/client.cert.pem


Alternative 2: Real certificate

First thing to do: just do Alternative 1 and start from there. It’s really not much different and you don’t really want to read it again.

Done? OK, now let’s move on.

One thing to keep in mind is that with real certificates there are two CAs that come into play:

  • the CA that signs your server certificate, and
  • the CA that signs your clients’ certificates.

In the previous example, we used the same CA for both, but in this case the first one is outside of our control (unless you are the people behind some well-known CA, of course!) while the second one most probably will remain ours. Why? Well, those certificates are needed to ensure that the people that ask to connect actually were allowed by us, so it’s quite reasonable that we do still provide them without asking those people to pay for a certificate.

To start with, just repeat whatever was described in Alternative 1 above. We will be using probably a different key and surely a different certificate for the server, but all the rest remains exactly as described so it’s worth to just repeat the steps.

In this example, we will assume that you get your certificate with Let’s Encrypt. It’s a bit of work to set it up, but after that you can automate the renewal of the certificate (as a matter of fact, this automation is encouraged) and forget about it in some crontab line.

Now go get your certificate for your domain. We will wait here until you’re done.


At the end you will end up with the same files as in the previous section, with the addition of a domain.key and a domain.crt file that come from the setup for Let’s Encrypt. It’s worth to remember that you MUST NEVER send your domain.key to anyone, including Let’s Encrypt!

Server configuration

On the server side, all you have to do is copy domain.key over server.key.pem and domain.crt over server.cert.pem, then restart taskd if it was running using the previous certificates.

This is really all that you need to do on the server side. The CA certificate in the server does not change, because this is the certificate for the CA that generates the clients’ certificates, not the server’s.

Client configuration

Theoretically, on the client side you should not need to do anything. This is because the certificate file you get from Let’s Encrypt should already contain two certificates inside, one for your server followed by one for the CA of Let’s Encrypt (this latter signed by a well-known CA, of course). Clients are able to follow the chain of certificates in a file they receive, automatically.

Anyway, as of version 2.5.1 you will discover that this does not really work out of the box. Why is this? Well, it’s because the code does not load the well-known certificates, so the client follows the chain of certificates (correct) but it eventually lands on a CA that it does not know of, despite it’s a well-known one. This will be probably corrected in some future release (although most probably it will work only for clients compiled against a version of the library GnuTLS that is at least 3.0.20).

So are we out of luck? Not really. After completing the configuration like in the Alternative 1 above, all we have to do is to get the last (CA) certificate from the new server certificate, and save it inside file $TWCLIENT/ca.cert.pem in the client.

It’s easy to extract the certificate, just look for the last section in the file that is included between clear BEGIN CERTIFICATE and END CERTIFICATE markers:

.................................... | THIS IS THE SERVER CERTIFICATE
pOlsXXuFidxtdN6ey7iA+SgLE+ZEZWfC9... /
.................................... | THIS IS THE CA CERTIFICATE
+X+Q7UNKEkROb3N6KOqkqm57TH2H3eDJA... /

Now, from the next invocation of task sync, the server will send the new shiny real certificate, and the client will not reject it because it’s configured to trust the Let’s Encrypt CA. YAY!

Quick consideration on clients authentication

You might have noticed at this point that there’s something going on with client authentication. This actually happens at two levels:

  • at the TLS level, the server asks the client for its client certificate;
  • at the Taskwarrior level, the server asks the client for the organization, the username and the user key (the one generated by taskd, not the TLS private key!) that acts both as a unique identifier for the account AND as a password.

These two authentications are not actually connected together, although they probably should. In particular, it would be great if the client’s certificate CN included the string we are setting for taskd.credentials in the client.

Anyway, this is not how it works today. So, for any practical reason, you don’t strictly need to generate a new TLS key and certificate for each new user you want to manage… because everyone will just be fine with the client.key.pem and client.cert.pem files you generated in the first place. Which also means: if some of your users figures out the username and the taskd user key of someone else, they will be able to sync against them. There’s always space for improvement!

Summing Up

Taskwarrior is really a great and useful piece of code. Being able to setup your own Taskserver for syncing up all your devices is a very useful addition too; doing it properly requires some attention but it’s really not difficult as long as you follow the instructions carefully.

Using it with real certificates is definitely doable, although the process can be enhanced to make it even simpler (with less configurations needed on the client side). Even now it’s not really difficult and just requires one step more than what would be ideal.

The clients authentication process should probably relate user accounts managed by Taskwarrior to the certificates generated for clients. This would allow better restriction of access (like “you can access a specific resource if and only if you know the resources details and you also have the certificate attached to that resource”) and also an effective usage of the Certificate Revocation List. Anyway, Taskwarrior is under active development… and you might be the one to implement those enhancements!

Until then… happy tasking!