diff --git a/ansible/roles/dev-desktop/tasks/cleanup.yml b/ansible/roles/dev-desktop/tasks/cleanup.yml
new file mode 100644
index 000000000..5d77eff5f
--- /dev/null
+++ b/ansible/roles/dev-desktop/tasks/cleanup.yml
@@ -0,0 +1,18 @@
+---
+- name: Copy cleanup script
+  template:
+    src: clean-unused-checkouts.sh
+    dest: /etc/cron.cleanup_disk_space
+    owner: root
+    group: root
+    mode: 0744
+
+- name: Set up the cleanup cron job
+  template:
+    src: cron_cleanup_disk_space.j2
+    dest: /etc/cron.d/cleanup_disk_space
+  # if the cron job is running right now, keep retrying until it finishes
+  register: cleanup_cron_result
+  until: cleanup_cron_result is not failed
+  retries: 10
+  delay: 5
diff --git a/ansible/roles/dev-desktop/tasks/main.yml b/ansible/roles/dev-desktop/tasks/main.yml
index 8e0d6d372..08fd2ac71 100644
--- a/ansible/roles/dev-desktop/tasks/main.yml
+++ b/ansible/roles/dev-desktop/tasks/main.yml
@@ -7,6 +7,7 @@
 - include_tasks: usermod.yml
   with_items: "{{ vars_user_config }}"
   when: vars_user_config is not none and vars_user_config | length > 0
+- include_tasks: cleanup.yml
 - include_tasks: team_login.yml
 - include_tasks: github.yml
 - include_tasks: motd.yml
diff --git a/ansible/roles/dev-desktop/tasks/team_login.yml b/ansible/roles/dev-desktop/tasks/team_login.yml
index 72d1e9b75..a6f3e3ea8 100644
--- a/ansible/roles/dev-desktop/tasks/team_login.yml
+++ b/ansible/roles/dev-desktop/tasks/team_login.yml
@@ -13,7 +13,7 @@
 
 - name: Set up the team login cron job
   template:
-    src: crontab_append
+    src: cron_team_login.j2
     dest: /etc/cron.d/team_login
   # if the cron job is running right now, keep retrying until it finishes
   register: task_result
diff --git a/ansible/roles/dev-desktop/templates/clean-unused-checkouts.sh b/ansible/roles/dev-desktop/templates/clean-unused-checkouts.sh
new file mode 100644
index 000000000..4e7927ca6
--- /dev/null
+++ b/ansible/roles/dev-desktop/templates/clean-unused-checkouts.sh
@@ -0,0 +1,74 @@
+#!/usr/bin/env bash
+
+#
+# {{ ansible_managed }}
+#
+
+# Clean up unused checkouts
+#
+# This script is used to find old checkouts that are no longer in use. Given the
+# size of the build directory, regularly cleaning them up can save significant
+# amounts of disk space.
+
+# Enable strict mode for Bash
+# http://redsymbol.net/articles/unofficial-bash-strict-mode/
+set -euo pipefail
+IFS=$'\n\t'
+
+# Print directories and their size instead of deleting them
+dry_run=false
+
+# Default to search for checkouts older than 60 days
+time="60"
+
+while [[ $# -gt 0 ]]; do
+  case $1 in
+    --dry-run)
+      dry_run=true
+      shift # past argument
+      ;;
+    -t|--time)
+      time="${2}"
+      shift # past argument
+      shift # past value
+      ;;
+    -*)
+      echo "Unknown option $1"
+      exit 1
+      ;;
+  esac
+done
+
+# Find all build or target directories created by users
+#
+# This command combines (`-o`) two different conditions to find all build and
+# target directories that users have created. Within each home directory, we
+# recursively look for directories that either have a file named `x.py` and a
+# directory named `build`, or a file named `Cargo.toml` and a directory named
+# `target`.
+all_cache_directories=$(find /home -type d \( -name build -execdir test -f "x.py" \; -o -name target -execdir test -f "Cargo.toml" \; \) -print | sort | uniq)
+
+# For each checkout, we want to determine if the user has been working on it
+# within the `$time` number of days.
+unused_cache_directories=$(for directory in $all_cache_directories; do
+  project=$(dirname "${directory}")
+
+  # Find all directories with files that have been modified less than $time days ago
+  modified=$(find "${project}" -type f -mtime -"${time}" -printf '%h\n' | xargs -r dirname | sort | uniq)
+
+  # If no files have been modified in the last 90 days, then the project is
+  # considered old.
+  if [[ -z "${modified}" ]]; then
+    echo "${directory}"
+  fi
+done)
+
+# Delete the build directories in the unused checkouts
+for directory in $unused_cache_directories; do
+  if [[ "${dry_run}" == true ]]; then
+    du -sh "${directory}"
+  else
+    echo "Deleting ${directory}"
+    rm -rf "${directory}"
+  fi
+done
diff --git a/ansible/roles/dev-desktop/templates/cron_cleanup_disk_space.j2 b/ansible/roles/dev-desktop/templates/cron_cleanup_disk_space.j2
new file mode 100644
index 000000000..e17b44264
--- /dev/null
+++ b/ansible/roles/dev-desktop/templates/cron_cleanup_disk_space.j2
@@ -0,0 +1,2 @@
+PATH=/usr/local/sbin:/usr/local/bin:/sbin:/bin:/usr/sbin:/usr/bin
+0 0 * * * root /etc/cron.cleanup_disk_space
diff --git a/ansible/roles/dev-desktop/templates/crontab_append b/ansible/roles/dev-desktop/templates/cron_team_login.j2
similarity index 100%
rename from ansible/roles/dev-desktop/templates/crontab_append
rename to ansible/roles/dev-desktop/templates/cron_team_login.j2