There’s a great step by step guide for setting up letsencrypt certs on dreamhost here! This post will parrot most of the stuff that it says with a few highlighted points that tripped me up.

I’m going to avoid all the letsencrypt setup and jump straight into running the thing.

$ ./letsencrypt-auto certonly --manual -d

Now that might pop up a thing about logging your IP address. If you aren’t cool with that then you can’t have a certificate, so make sure you say yes.

Next the command will pause waiting for you to press enter. DO NOT PRESS ENTER YET! I made that mistake and had to run the command again. Before you can proceed, you need to create some folders and a file under the domain you are creating the certificate for. The folders are /.well-known/acme-challenge and the file is named some random hash of characters. The file content is some other hash of characters.

An example path is /.well-known/acme-challenge/RcapSBi_ZOlYnrByap1cRRrHln1lzKOIXwg2NowrZt5

SSH into your dreamhost server and run

$ mkdir -p
$ echo "RcapSBi_ZOlYnrByap1cRRrHln1lzKOIXwg2NowrZt5.lvgVdH1KypqK217AlBi9qE6ZYiusmdqZrzYNqOMGp3o" > .well-known/acme-challenge/RcapSBi_ZOlYnrByap1cRRrHln1lzKOIXwg2NowrZt5

Finally make sure that the file is reachable in your browser by visiting

Now, after all that, you can hit enter.

Once the command finishes you should see a congratulations under the “IMPORTANT NOTES” output.

The next step is to visit the dreamhost panel and go to Domains > Secure Hosting. Then click the “Add Secure Hosting” button and select your desired domain, in our case (You don’t need to add a unique IP)

Dreamhost should give you a success message saying that it’s using a self-signed certificate. Instead, we want it to use the certificate letsencrypt generated so click the edit button next to the domain and choose “Manual configuration”.

Now you should see 4 text boxes labeled “Certificate Signing Request”, “Certificate”, “Private Key”, and “Intermediate Certificate” respectively.

  • Certificate Signing Request: Delete everything from this box.
  • Certificate: Copy the text from cat /etc/letsencrypt/live/ | pbcopy into this box.
  • Private Key: Run the following command openssl rsa -in /etc/letsencrypt/live/ and copy the outputted result into this box.
  • Intermediate Certificate: Copy the text from cat /etc/letsencrypt/live/ | pbcopy into this box.

After that, click “Save changes now!” and you’re all set.