Category Archives: encryption

Re-signing Openssh Certificates

Seldom do I get to write a post where I am offering information which might not actually be out there in a lot of places. I could not find this information on the web, and had to figure it out myself, by reading the code, and doing experiments.

I talked in the last post about the need to re-issue all the openssh certificates, in order to update the hash algorithm used for the signatures. My way of maintaining the certificates, in my repository, would make it easy for the signing box to get all the existing certificates, but not (directly) the public keys that are inside those certificates.

Continue reading Re-signing Openssh Certificates

SSH Certificate signing

I’ve encountered a problem migrating from Fedora to Arch which ends up being about ssh and openssh certificates. I look back and discover that I never posted anything about my movement toward openssh certificates. Curious because I wrote a lengthy document about it (because of my leaky brain – not because I am any kind of authority on it).

I will probably go back and write a post about it, and back date it. But now a problem has arisen. Rather than explain, let the boys at openssh speak for themselves, in the release notes for openssh 8.2:

Continue reading SSH Certificate signing

Apache certificate chains

When I switched my main server to CentOS, described in an earlier post, one of the big pains was that I had to use CentOS 7, and there was a lot of software which had come a long way since CentOS 7, and I had to upgrade a log of things from upstream to get functionality that I had grown reliant upon.

I didn’t realize that Apache itself was one of those things that was sufficiently backwards in CentOS 7 that I would have trouble.

Ever since I move the server to CentOSdid that “upgrade”, I’ve been struggling with problems with the certificates not being honored. For the last few days I have been working pretty diligently to try to figure out this nagging problem, and today I finally figured it out. It is owing to an old Apache.

Continue reading Apache certificate chains

Adding a VPN Router to the network

The topology for the handling of downloads of stuff via a vpn previously involved a vpn client directly on rosemary. The problem with this was that sometimes the vpn would fail – it would get disconnected from the remote end. If I didn’t realize this, and started a download, it would be in the clear.

I thought a better solution was to have a separate router (herein the “vpn” router) between rosemary and the external router, and to have that router establish a constant vpn through it’s wan interface, through the external router. Everything that connected to a lan port on the vpn router would be protected. Rosemary would then use the vpn router as its path to the internet. Everything that rosemary sends or receives from the internet would come exclusively through the vpn router.

Continue reading Adding a VPN Router to the network

Setting Up Openvpn Server

The objective of this project was to install a vpn server on one of the boxes in the cloud (initially asafoetida, then moved to tarragon), in order to provide a VPN server service for a friend who was traveling. My friend uses the name Darrell for his client, so in what follows the vpn is called by this name.

Create a Certificate Authority

A lot of the instructions, even from openvpn site, say to use the “easyrsa” package to generate the certificates for openvpn. This package seems to be put out by the openvpn boys, or at least with their cooperation. But I didn’t do that. I created a ca with raw openssl.

Continue reading Setting Up Openvpn Server

Using openssh certificates

I’m writing this in February 2020, but I should have posted it last April. This is about using openssh certificates for authentication.

For many years I have used exclusively public-key authentication for ssh connections. None of the boxes I support ever allows password authentication for ssh. But as the number of boxes in the constellation has grown, the problem of keeping the public keys up to date has become nightmarish. If I really truly needed NxN capability it would be unmanageable. The truth is though that there are only 3 or 4 boxes from which I typically establish ssh connections to all the others.

Still it is – if not a full-blown nightmare, at least a bad dream. The folks at openssh implemented a mechanism to make it easier: certificates. These are not full blow x509 certificates, they are simpler, but the idea is the same. The problem: how do we arrange to get a public key on to some box with confidence that the public key belongs to the party it purports to represent? The certificate answer is to have the public-key signed by a party that the recipient trusts.

So how does it work. I designate a box as my “signer”. All the other boxes in my world trust the signer. Instead of putting public keys on every box, instead every box has its own public key signed by the “signer”. When it wishes to connect to another box (in my own constellation of boxes) it presents its certificate – i.e. its signed public key. Since the recipient trusts the signer, it will accept the signed public key as being the genuine public key, and it can then proceed to authenticate.

How it works mechanically is that when I initialize a new box, and create a new key pair for it, I have to send the new public key to the signer. Then, on the signer system I sign the key, and send it back to the new box. I’m actually using my repository for the moving of this stuff back and forth. I think this is ok, since the only thing that ever appears in the repository are public keys and public certificates. The public keys exist in the repo for mere moments. The certificates stay there. But the private keys of course never leave the box on which they originate.

Certificates Redux

An earlier post talked about switching my server tarragon (where this blog sits) to a wildcard certificate from letsencrypt. There were two reasons why I was using a wildcard certificate. One had to do with test versions of websites that run on this server, and the need that some of those sites have for wildcards, of the form:,, etc. The other reason was that I have a lot of hosts (oregano, cinnamon, paprika, lemongrass) in addition to tarragon that “need” to have a certificate, for https, for imap, and for smtp, and when I was having to pay for them, it was cheaper to get one wildcard for Continue reading Certificates Redux

Apache Quiet Failure on Certificate/Key mismatch

In an earlier post I related how I had moved to letsencrypt for tarragon. In the process of doing some cleanup of the /etc/letsencypt directory, and my repository, I managed to stupidly get one wrong private key file into the batch of all the https vhosts, such that the http config file for specified an SSLCertificateFile and SSLCertificateKeyFile which did not match.

It took me hours and hours to figure this out, because Apache simply fails to start and gives no indication whatever what has pissed him off. I wasn’t too stupid to figure out that I had been messing with the certs yesterday, and the problem might lie there somehow. But I have about 15 vhosts, so it was tedious. In the end I resorted to strace, and saw the problem.


LetsEncrypt Wildcard Certificates

Comodo is after me to renew, offering a free year. The last time I attempted to install a wildcard certificate from Lets Encrypt, shortly after they introduced the feature, I wasn’t able to figure it out. Now, 9 months later, there is a lot more information about how to do it. Before spending the money for a commercial cert, I thought I would give it a try.

I used the following on tarragon:

certbot certonly \
--server \
-d -d * \
--preferred-challenges dns

It is important that the server url by v02, because v01 servers can’t issue wildcard certs. I had to put TXT records in the DNS for them to verify, and they created the cert into the /etc/letsencrypt/live directory where all the others are.

This was trivially easy. Goodbye Comodo.

Updating certificates to “Let’s Encrypt” with ACME

I’ve used a variety of certificate providers over the years, Thawte, CA-Cert, Verisign, Comodo, Startcom. Until about six months ago I was using Startcom, and had spent a fair amount of energy setting that up for my own site (this one) as well as all the other sites I manage.

Then Wo-Sign acquired Startcom, and browsers starting distrusting Startcom. I ended up buying a cert from Comodo for this site.

But then I found out about Let’s Encrypt. Not only are they free, but they have this whole ACME auto update thing worked out, using various ACME clients. I’ve been using Certbot from EFF. Continue reading Updating certificates to “Let’s Encrypt” with ACME