diff --git a/CHANGELOG.md b/CHANGELOG.md
index cbb526477..76755ec9b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -14,6 +14,7 @@ permalink: /docs/en-US/changelog/
 * Provisioner/Hook timings now show milliseconds ( #2735 )
 * Added a `skip_site_provisioner_update` option to prevent site provisioners being overwritten by updates ( #2733 )
 * Only start services that aren't running in post-up scripts ( #2732 )
+* Upgraded Ubuntu from 20.04 to 24.04 for docker provider ( #2739 )
 
 ### Bug Fixes
 
diff --git a/Vagrantfile b/Vagrantfile
index 977eddee1..770d23436 100644
--- a/Vagrantfile
+++ b/Vagrantfile
@@ -480,7 +480,7 @@ Vagrant.configure(VAGRANTFILE_API_VERSION) do |config|
 
   # Docker use image.
   config.vm.provider :docker do |d, override|
-    d.image = 'pentatonicfunk/vagrant-ubuntu-base-images:20.04'
+    d.image = 'pentatonicfunk/vagrant-ubuntu-base-images:24.04'
     d.has_ssh = true
     d.ports =  [ "80:80" ] # HTTP
     d.ports += [ "443:443" ] # HTTPS
diff --git a/config/homebin/vagrant_up b/config/homebin/vagrant_up
index 3056d9d23..606291dee 100755
--- a/config/homebin/vagrant_up
+++ b/config/homebin/vagrant_up
@@ -29,7 +29,7 @@ if [[ -f /srv/config/homebin/vagrant_up_custom ]]; then
 fi
 
 # /etc/host doesn't survive restart on docker
-vvv_info " * Updatin Guest VM /etc/hosts"
+vvv_info " * Updating Guest VM /etc/hosts"
 vvv_update_guest_hosts
 
 if ! sudo service nginx status > /dev/null; then
diff --git a/provision/core/vvv/provision.sh b/provision/core/vvv/provision.sh
index b362a41b9..9d3022344 100644
--- a/provision/core/vvv/provision.sh
+++ b/provision/core/vvv/provision.sh
@@ -96,8 +96,22 @@ function shyaml_setup() {
   # Used for passing custom parameters to the bash provisioning scripts
   if [ ! -f /usr/local/bin/shyaml ]; then
     vvv_info " * Installing Shyaml for bash provisioning.."
-    sudo pip3 install wheel
-    sudo pip3 install shyaml
+
+    local OSVERSION_NUMBER
+    OSVERSION_NUMBER=$(lsb_release -sr)
+
+    # Ubuntu 24 making it hard to install pip packages, throwing externally-managed-environment error
+    # https://stackoverflow.com/a/75722775
+    if dpkg --compare-versions "${OSVERSION_NUMBER[@]}" ge "24.04"
+    then
+      # to make it available globally this is the last workaround, hopefully it doesn't break the system
+      # TODO: try to find a better alternative way to install
+      sudo pip3 install wheel --break-system-packages
+      sudo pip3 install shyaml --break-system-packages
+    else
+      sudo pip3 install wheel
+      sudo pip3 install shyaml
+    fi
   fi
 }
 export -f shyaml_setup