It’s 2023. You Should Be Using an Ed25519 SSH Key (And Other Current Best Practices)

I often have to ask other IT professionals for the Public SSH key for access to a server or for other tasks. I really cringe when they ask me what that is or how to create one. I kindof cringe when they give me one from PuttyGen in its native format. I feel a little better when they provide a 4096-bit RSA key without needing an explanation. When somebody provides an Ed25519 key, I feel like I’m working with somebody who knows what they are doing.

A 4096-bit RSA Keys look like this:

ssh-rsa AAAAB3NzaC1yc2EAAAADAQABAAABgQDowuIZFbN2EWbVwK9TG+O0S85yqr7EYc8Odv76H8+K6I7prrdS23c3rIYsKl2mU0PjOKGyyRET0g/BpnU8WZtDGH0lKuRaNUT5tpKvZ1iKgshdYlS5dy25RxpiVC3LrspjmKDY/NkkflKQba2WAF3a5M4AaHxmnOMydk+edBboZhklIUPqUginLglw7CRg/ck99M9kFWPn5PiITIrpSy2y2+dt9xh6eNKI6Ax8GQ4GPHTziGrxFrPWRkyLKtYlYZr6G259E0EsDPtccO5nXR431zLSR7se0svamjhskwWhfhCEAjqEjNUyIXpT76pBX/c7zsVTBc7aY4B1onrtFIfURdJ9jduYwn/qEJem9pETli+Vwu8xOiHv0ekXWiKO9FcON6U7aYPeiTUEkSDjNTQPUEHVxpa7ilwLZa+2hLiTIFYHkgALcrWv/clNszmgifdfJ06c7pOGeEN69S08RKZR+EkiLuV+dH4chU5LWbrAj/1eiRWzHc2HGv92hvS9s/c= someuser@brandonsLaptop

And for comparison, an Ed25519 Key looks like this:

ssh-ed25519 AAAAC3NzaC1lZDI1NTE5AAAAIBLEURucCueNvq4hPRklEMHdt5tj/bSbirlC0BkXrPDI someuser@ip-172-31-74-201

The Ed25519 key is much shorter, so initially you might think it is less secure. But these keys use a totally different algorithm, so although the key has fewer characters, it is, for all practical purposes, as secure as the RSA key above. You can ask your favorite search engine or AI for more details about the differences.

The Ed25519 algorithm has been around for ~10 years now. It is widely supported by any modern software, and as such is the current standard for most professional users. Creating a key is simple with the ssh-keygen command. But before jumping to the actual command, I wanted to also explain a couple other tips that I use, and think others should pick up as well.

Keys should be issued to individuals, not groups

You should never, ever share your private key with anybody. Ever. If a key is ever shared, you have to assume that the other party can impersonate you on any system in which it is used.

I’ve seen some organizations who create a new machine and use a new SSH Key on it. Then share the key with all of the individuals who need to access the machine. Perhaps this practice comes from AWS or other hosting providers who create an SSH key for you, along with a new machine, and the user not knowing any better.

Although it kindof works, that’s the backwards way of doing it. Individuals should own their own keys. They should be private. And you can add multiple public keys to resources where multiple people need access. You then revoke access by removing the public key, instead of having to re-issue a new key whenever the group changes. (Or worse, not changing the key at all!)

Rotating your keys

You should rotate your SSH keys on some kind of schedule. The main risk you are trying to avoid here is that if you have used the same key for 20 years, and then your laptop with your private key gets lost, or your key compromised, every machine that you’ve been granted access to over that time is potentially at risk, because administrators are notoriously bad about revoking access. By changing out your key regularly, you limit the potential access in the case of a compromised key. Generating a new SSH key also ensures that you are using more modern algorithms and key sizes.

I like to start a new key about every year. To remind my self to do this, I embed the year I created the key within its name. So I last created a key in March 2023, which I have named brandon+2022-03@roundsphere. When it gets to be 2024, I’ll be subtly reminded each time I use it that it’s time to create a new key. I keep all of my older keys if I need them. But they aren’t in memory or in my SSH-Agent. If I do need to use one, it is enough of a process to find the old one, that the first thing I’ll do is update my key as soon as I get in a system where an old key was needed.

Don’t use the default comment

Make the comment meaningful. If you don’t provide a comment, it defaults to your_username@you_machine name which just might be silly or meaningless. In a professional setting, it should clearly identify you. For example BrandonChecketts as a comment is better than me00101@billys2017_macbook_air. It should be meaningful both to you, and to whomever you are sharing it.

I mentioned including the creation month above, which I like because when sharing it, it subtly demonstrates that I am at least somewhat security conscious and I know what I’m doing. The comment at the end of the key isn’t necessary for the key to work correctly, so you can change it when sharing it. I often change the comment to be more meaningful if someone provides me with a key that doesn’t clearly indicate its owner.

Always use a passphrase

Your SSH key is just a tiny file on disk. If your machine is ever lost, stolen, or compromised in any way by an attacker, the file is pretty easy for them to copy. Without it being encrypted with a pass phrase, it is directly usable. And if someone has access to your SSH private key, they probably have access to your history and would know where to use it.

As such, it is important to protect your SSH private key with a decent pass phrase. Note that you can use SSH-Agent so you don’t need to type the passphrase every time you need to use the key.

The Command

This is the command you should use to create your ED25519 Key:

ssh-keygen -t ed25519 -f ~/.ssh/your-key-filename -C "your-key-comment"

That will ask you for a pass phrase and then show you a cool randomart image that represents your public key when it is created

 $ ssh-keygen -t ed25519 -f ./deleteme -C "brandon+2023-09@roundsphere"
Generating public/private ed25519 key pair.
Enter passphrase (empty for no passphrase):
Enter same passphrase again:
Your identification has been saved in ./deleteme
Your public key has been saved in ./
The key fingerprint is:
SHA256:HiCF8gbV6DpBTC2rq2IMudwAc5+QuB9NqeGtc3pmqEY brandon+2023-09@roundsphere
The key's randomart image is:
+--[ED25519 256]--+
| o.o.+.          |
|  * +..          |
| o O...          |
|+ B *. .         |
|.B % .  S        |
|=E* =  . .       |
|=+o=    .        |
|+==.=            |
|B..B             |

Obsessive/Compulsive Tip

I maybe have spent 10 minutes creating a key over an over until I found a key that ended in a few character that I like. One of my keys ends in 7srus, so I think of it as my “7’s ‘R’ Us” key. You can do that over and over again until you find a key that you like with this one-liner:

rm newkey; rm; ssh-keygen -t ed25519 -f ./newkey -C "" -N ''; cat;

That creates a key without a passphrase, so you can do it over and over quickly until you find a public key that you “like”. Then protect it with a passphrase with the command

ssh-keygen -p -f newkey

And obviously, then you rename it from newkey to something more meaningful.

What else? Any other tips for creating an SSH key and looking like a professional in 20223?

How Do Clients Securely Connect to SSL & HTTPS Servers?

This question arose from Steven Chu on my previous post about MySQL SSL Connections without Client Certificates. How is the client able to securely connect to a server using SSL if it doesn’t already know or trust the Server Certificate?

It is important to understand that there are a few different, interrelated topics here. All of these involve SSL and certificates, but in differing ways, so they are often conflated. Secure communication over SSH shares the same concepts, but has different mechanisms.

  1. Encryption of the traffic between client and server.
  2. Verification that the server is who the client believes it to be.
  3. Authentication of the client to the server.

For SSL and HTTPS communication, the first two concepts are accomplished together because there is no point in communicating securely with a remote party if you can’t verify that the remote party is who they claim to be and that there isn’t a “Man in the Middle” able to intercept the secure traffic.

You actually communicate securely with unknown servers all of the time. When you loaded this web page, your browser didn’t know anything about beforehand. Same thing when you load your bank’s website. You never configured your browser specifically to trust their website. So how is it able to verify that it is actually your bank, and not an attacker who is impersonating your bank?

Certificate Authorities

Anybody can create an SSL Certificate with any name on it. In my SSL Certificate Notes post, you can find instructions for creating an SSL certificate. Note that you simply type in the name for the certificate. So you could attempt to create a certificate for any host you care to try. However, an essential part of the process is the Signing of the Certificate. You can self-sign a certificate with any name on it. But if you want your certificate to be recognized and trusted by anybody else, you need to have a recognized Certificate Authority (CA) sign it. If you were to try to create a certificate for, no Certificate Authority is going to sign that since you can’t validate that you are authorized to create certificatesnobody else in the world is going to trust it.

When a Certificate Authority signs a certificate, it is their job to verify that the certificate owner is who they claim to be in some way. On the public internet, that is largely done through DNS or Email validation. For example, on this site, I use a certificate issued by Amazon Web Services. In order obtain that certificate, I had to verify that I own the domain. Since the domain is also hosted at AWS, it is quite easy for me to create the DNS records for verification, and AWS can validate it within seconds. I couldn’t, for example, validate a certificate that was for ‘’. I’d be unable to validate it with any certificate authority since I can’t make the required DNS entries or receive emails to the required email addresses for

Extended Validation certificates, offered by some Certificate Authorities, and recognized by some web browsers with a different color banner, often have additional verification steps other than just DNS or Email.

Intermediate Certificates and Multiple layers of Certificate Authoritiees

When a certificate is signed by a recognized Certificate Authority, your client can trust it, because it trusts the Certificate Authority. On the public Internet, most of the time there are multiple layers of Certificate Authorities.

On OSX, you can find the list of root certificates it trusts in the “Keychain Access” system app, in the “System Roots” section. On an Ubuntu or Debian Linux system, the trusted certificates are files that exist or are symlinked in `/etc/ssl/certs`. These systems have dozens to hundreds of certificates that they trust. Look closely and you’ll see that most of them expire 10+ years into the future. These “Root” certificates are highly protected and usually don’t directly sign certificates. The Certificate Authority will often delegate access to intermediate authorities with their own keys that can further sign certificates.

In Chrome, you can click the lock icon next to the URL, and find details about the certificate, including the intermediate certificates. As of the writing of this post, you can see that the SSL Certificate issued to is issued by “Amazon”, which is trusted by the root certificate named “Amazon Root CA 1”. I can find that root certificate in the list of certificates trusted by my OSX system.

Client Authentication

I mentioned the third step above about the client authenticating to the server. In many cases, like this website, there is no need for the client to authenticate to the server since the content is public and intended to be viewed anonymously. If authentication is required, for instance to create a new post, then I simply log in with a username and password entered of the HTTPS connection. Same as you do every day.

Many well-meaning articles about generating SSL Certificates for services other than HTTPS often mention creating an SSL client certificate. The Client Certificate is then provided to the server so that the server can validate the client is who they claim to be. The Client Certificate is simply an alternate (often thought of as “more secure”) method of authenticating than a username and password, or sometimes even in addition to a username and password. In practice, I’ve seen that usernames and passwords transmitted over an encrypted connection are very common, well understood, and just as secure as using an SSL Client Certificate.

Using LastPass to Save Passwords and Log In to Multiple AWS Accounts With Two-Factor Authentication

I have multiple businesses, so I log into AWS multiple times per day.

That is a little tricky to do using LastPass since AWS has some hidden form fields that must be filled in
when using two-factor authentication through Google Authenticator.

In order to make it work correctly, I’ve had to modify the extra details in LastPass to add some extra hidden fields. If you set these up in your LastPass credentials for AWS, you should be able to log in with just a couple clicks, like usual, instead of having to type in some of those fields every time or having them overwritten.

Also, make sure to check the “Disable Autofill” checkbox an all of your AWS LastPass entries. Otherwise, one of them will overwrite the hidden form fields on the Two-Factor authentication page

Ubuntu 20.04 Cloud-Init Example to Create a User That Can Use sudo

Use the steps below and example config to create a cloud-init file that creates a user, sets their password, and enables SSH access. The Cloud Config documentation has some examples, but they don’t actually work for being able to ssh into a server and run commands via sudo

First, create a password hash with mkpasswd command:

$ mkpasswd -m sha-512

Make note of the output string. You need to enter it exactly in the passwd line of your cloud-init config.

This is the minimal configuration to create a user using cloud-init:

  - name: brandon
    groups: [ sudo ]
    shell: /bin/bash
    lock_passwd: false
    passwd: "$6$nq4v1BtHB8bg$Oc2TouXN1KZu7F406ELRUATiwXwyhC4YhkeSRD2z/I.a8tTnOokDeXt3K4mY8tHgW6n0l/S8EU0O7wIzo.7iw1"
    - ssh-ed25519 AAAAC3NzaC1lZDI1zzzBBBGGGg3BZFFzTexMPpOdq34a6OlzycjkPhsh4Qg2tSWZyXZ my-key-name

A few things that are noteworthy:

  • The string in the passwd field is enclosed in quotes
  • lock_passwd: false is required to use sudo. Otherwise, the system user account created will have a disabled password and will be unable to use sudo. You’ll just continually be asked for a password, even if you enter it correctly.
  • I prefer the method of adding the user to the sudo group to grant access to sudo. There are other ways to make that work as well, but I feel like this is the cleanest.
  • Adding any users, will prevent the default ubuntu user from being created.
  • LastPass Challenges with Multiple Organizations

    As a parallel entrepreneur, I’m a participating member of multiple companies. That brings with it some unique challenges, as many software tools don’t gracefully handle a user belonging to multiple organizations. I’ve learned to deal with that in many situations. Typically I’ll often having to log out and back in as the desired user or have multiple browsers or browser profiles open – one for each organization.

    One area that has been particularly challenging has been group password management. There are not a lot of software options, although there are getting to be some new players. LastPass is the most mature option, and is the product that I have used for a long time. I investigated some alternatives including 1Password and DashLane. Both of those looked a little more modern and polished, but neither seemed to have mature support for multiple organizations.

    Lastpass does claim to have robust support for organizations, but there is minimal, if any, mention on their website or elsewhere that mentions belonging to multiple organizations. It has taken me a lot of experimenting, but I’ve finally come up with a solution that works well.

    You might think, as the diagram above indicates, that each organization to which you belong should invite your personal account to become a member of the organization. You would be wrong. Although this seems like the intuitive relationship, it does not work since LastPass only allows a personal account to attach to exactly one LastPass Enterprise account. Not more.

    The correct way to belong to multiple Enterprise Accounts in LastPass is to choose one of the organizations to be your “Main” account to which you log in on a daily basis. You connect your Personal account to this enterprise account so that your personal sites appear alongside your work passwords.

    Then, to add additional organizations, you don’t purchase a user license in those other organizations. Instead you create one or more shared folders, and share the folders with the email address for your “Main” organization account. There is a limitation that you can’t be an admin of the shared folders in these other organizations since you are not part of the Enterprise, but sharing and day-to-day password usage works generally as expected.

    This method seems less intuitive, but works well now that I’ve figured it out. As I’ve learned more about how LastPass works internally, I understand why this unorthodox configuration is required

    A few other quirks I’ve found, which just take some getting used-to:

    • Shared folders from my personal account DO NOT SHOW UP when logged into my enterprise account. You have to share to your main organization email address instead.
    • Folder structure in my Personal Account is not confusing in the User-Interface when browsing passwords in my enterprise account. The folder-within-folder structure doesn’t render well, and it is confusing as to which “level” I’m at.

    I hope that the folks at LastPass are able to simplify this or make it more obvious how it is to be configured.

    Do you have a better solution for password sharing with multiple organizations? Please let me and others know in the comments.

    Setting Up Virtualmin on an OpenVZ Guest

    I’m experimenting with a hosting control panel and am interested in Virtualmin. I generally avoid web-based control panels, because they generally make direct configuration via the command line and manually editing config files very difficult. However one of Virtualmin’s goals is to not interfere with such manual configurations. I’ve had plenty of clients who use Webmin, and they seem to do a good job, so Virtualmin seems like a good choice.

    These are the steps that I went through to get a new OpenVZ guest set up with the GPL version of Virtualmin.

    Download a CentOS 5 OS template and create the guest

    # wget
    # vzctl create <VEID> --ostemplate centos-5-x86_64

    I replaced all of these limits in /etc/vz/<VEID>.conf. This is based off of a different running machine with some fairly generous limits. Most importantly, it includes 1GB of RAM.

    # UBC parameters (in form of barrier:limit)

    Then set up some host-specific parameters and start it up.

    # vzctl set <VEID> --ipadd --hostname --nameserver --diskspace 4G --save
    # vzctl start <VEID>
    # vzctl enter <VEID>

    You are now logged in to the guest, where you can download and install virtualmin

    # yum update
    # cd /root
    # wget
    # sh
     Continue? (y/n) y

    That should install without significant errors. Finally, set a password for root, and then log in to Virtualmin to go through the post-installation configuration

    passwd root

    Login at https://<your-ip>:10000/ and go through the post-installation configuration

    ProFTPd allows multipled DefaultRoot lines for flexible chrooting

    The ProFTPd documentation gives good examples of how to use the DefaultRoot directive to chroot users to a specific directory.

    A customer today wanted to have different chroot directories for different groups of users. The documentation didn’t mention if it was okay to include multiple DefaultRoot lines. After some experimenting, I can verify that it is allowed and works well.

    I used something like this in /etc/proftpd/proftpd.conf

    DefaultRoot                     ~ jailed
    DefaultRoot                     ~/../.. othergroup

    Users in the group ‘jailed’ are chrooted to their own home directory immediately upon logging in. Users in the ‘othergroup’ are chrooted two levels up from their home directory. If you want to get really specific, each user generally has a group of their own, so you can effectively do this a the user-level as well.

    MySQLDump To a Remote Server

    I was running out of disk space on a server today. The server had a large database table that was no longer used, so I wanted to archive it and then drop the table. But the server didn’t have enough disk space to dump it out to disk before copying it off to a remote server for archiving.

    The first thought was to run mysqldump dump on the destination machine, and to access the database over the network. That however, doesn’t compress or encrypt the data. Plus I would have had to create a mysql user with permission to access the database remotely.

    The solution I came up with worked out well: mysqldump directly to the remote host with this command:

    mysqldump <DATABASE_NAME> [mysqldump options] | gzip -c | ssh user@remotehost "cat > /path/to/some-file.sql.gz"

    That pipes the mysqldump command through gzip, then to through and SSH connection. SSH on the remote side runs the ‘cat’ command to read the stdin, then redirects that to the actual file where I want it saved.

    Testing for Vulnerable Caching Name Servers

    Most of the technical community has probably heard of the recently found DNS weakness.  The basic premise is that if a recursive nameserver doesn’t use sufficently random source ports when making recursive queries, it can be vulnerable to an attacker who is trying to poisen the cache, or fill it with incorrect data.

    I’ve now heard reports about it from various news sources who make it sound much more drastic than it actually is.   Granted, it is a serious flaw, but fortunately most companies with any desire for security use SSL, which provides an additional layer for identity verification.  Also, for most any company with an IT staff, patching the DNS server with the required fixes should be a fairly trivial task.   The most important servers to be fixed are those run by ISPs and Datacenters, both of which should have their servers fixed by now.

    Tools for testing your DNS servers are fairly easy to come by. has a web-based test, although I don’t know how it discovers your DNS Servers.  For windows users, you can run ‘nslookup’ like this:

    C:\Documents and Settings\Brandon>nslookup
    Default Server:
    > set type=TXT
    Non-authoritative answer:   canonical name = porttest.y.x.w.v.u.t.s.r.q.p.o.n.m.l.k.
    text =
            " is GREAT: 26 queries in 2.3 seconds from 25 ports with std
     dev 16592"

    To test from a linux machine, you can use dns-oarc’s test with dig like this:

    root@server:~# dig in txt +short
    " is GREAT: 26 queries in 1.2 seconds from 26 ports with std dev 20533"

    Your are looking for a response that contains GOOD or GREAT. If your results contain something else, you should notify your ISP or Data Center to have them fix their servers.

    Random Password Generator

    There are times when I’ve been focusing on programming all day, and it is easier to write a program to do something trivial, then it is to just do it the simple way. Today was such a day. Instead of typing some random character to make up new user’s password, I wrote a script to do it for me:

    ## Quick Random Password Generator
    ## Author: Brandon Checketts
    my $length = $ARGV[0] || 10;
    my $charset = "abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ1234567890";
    my $pw = "";
    for (my $i=0; $i < $length; $i++) {
        my $pos = rand(length($charset));
        $pw .= substr($charset, $pos, 1);
    print "\\nRandom Password: $pw\\n\\n";

    Of course you can modify the default length and/or characters to make something more suitable for your use.

    Sample Usage:

    [root@dev ~]# ~/bin/pwgen
    Random Password: mYTZrSpE8B
    [root@dev ~]# ~/bin/pwgen 20
    Random Password: EoSQpypmeK3SZCVPodaM