diff --git a/install.sh b/install.sh
index 7026595..ef1eda9 100755
--- a/install.sh
+++ b/install.sh
@@ -114,6 +114,9 @@ install_packages "${MEDIA[@]}"
 echo "Installing fonts..."
 install_packages "${FONTS[@]}"
 
+echo "Installing pipx applications..."
+install_pipx_apps "${PIPX[@]}"
+
 # Enable all systemd services listed in SERVICES array, then register the SSH
 # Avahi service so the machine is discoverable over mDNS
 echo "Configuring services..."
diff --git a/packages.conf b/packages.conf
index 71cb326..e95495e 100644
--- a/packages.conf
+++ b/packages.conf
@@ -84,6 +84,7 @@ DEV_TOOLS=(
   python-myst-parser
   python-pillow
   python-pip
+  python-pipx
   python-pygments
   rust
   starship
@@ -134,6 +135,11 @@ FONTS=(
   ttf-nerd-fonts-symbols
 )
 
+# Python applications installed with pipx
+PIPX=(
+  terrahour
+)
+
 # Services to enable
 SERVICES=(
   avahi-daemon.service
diff --git a/updates.d/40-ruby.sh b/updates.d/40-ruby.sh
index 4d05984..baaa207 100644
--- a/updates.d/40-ruby.sh
+++ b/updates.d/40-ruby.sh
@@ -9,4 +9,8 @@ mise self-update -y
 echo "Updating Ruby and Rails..."
 mise upgrade --bump ruby
 mise reshim
+# A new Ruby's bundled gems (e.g. minitest) come with executables RubyGems
+# doesn't recognise as its own, so gem update stops to ask whether to overwrite
+# them. Regenerating them first lets the update go through without asking.
+gem pristine --all --only-executables > /dev/null
 gem update
diff --git a/updates.d/60-pipx.sh b/updates.d/60-pipx.sh
index ef5602a..0ba9fe2 100644
--- a/updates.d/60-pipx.sh
+++ b/updates.d/60-pipx.sh
@@ -1,5 +1,15 @@
 #!/bin/bash
 
+COREDESKTOP="$HOME/.local/share/coredesktop"
+
+source "$COREDESKTOP/utils.sh"
+source "$COREDESKTOP/packages.conf"
+
+STATUS=0
+
+echo "Checking for new pipx applications..."
+install_pipx_apps "${PIPX[@]}" || STATUS=1
+
 # pipx venvs are tied to the Python they were built with, so a Python upgrade
 # breaks them in a way `pipx upgrade-all` can't repair. Rebuild them when the
 # Python version changes, or when an upgrade fails.
@@ -15,4 +25,6 @@ else
         echo "pipx upgrade-all failed, reinstalling pipx applications..."
         pipx reinstall-all
     fi
-fi && mkdir -p "$(dirname "$STAMP")" && echo "$CURRENT_PYTHON" > "$STAMP"
+fi && mkdir -p "$(dirname "$STAMP")" && echo "$CURRENT_PYTHON" > "$STAMP" || STATUS=1
+
+exit $STATUS
diff --git a/utils.sh b/utils.sh
index 7444007..fdc85fc 100755
--- a/utils.sh
+++ b/utils.sh
@@ -27,6 +27,20 @@ install_packages() {
   fi
 }
 
+# Function to install pipx applications if not already installed
+install_pipx_apps() {
+  local installed app status=0
+  installed="$(pipx list --short 2> /dev/null | cut -d' ' -f1)"
+
+  for app in "$@"; do
+    if ! grep -qx "$app" <<< "$installed"; then
+      echo "Installing $app with pipx..."
+      pipx install "$app" || status=1
+    fi
+  done
+  return $status
+}
+
 # Function to remove pacman/AUR packages if installed
 remove_packages() {
   local packages=("$@")