diff --git a/ansible/ci.yml b/ansible/ci.yml
index 85f7ad01..35231984 100644
--- a/ansible/ci.yml
+++ b/ansible/ci.yml
@@ -67,6 +67,7 @@
     - role: buildkite_agent
       priority: 5 # Higher priority agents are assigned work first
       tags: buildkite_agent
+        - gcc-multilib # for 32-bit builds
 
 - hosts: ci.dlang.io
   roles:
diff --git a/buildkite.sh b/buildkite.sh
index 03da473a..c1be0cdd 100755
--- a/buildkite.sh
+++ b/buildkite.sh
@@ -59,6 +59,33 @@ cat << 'EOF'
   - wait
 EOF
 
+################################################################################
+# Test bootstrapping with different compilers
+################################################################################
+
+case "${BUILDKITE_REPO:-x}" in
+    "https://github.com/dlang/dmd.git" | \
+    "https://github.com/dlang/druntime.git" | \
+    "https://github.com/dlang/phobos.git" | \
+    "https://github.com/dlang/ci.git")
+
+for line in dmd-64 ldc-64 ; do
+    # TODO: dmd-32, gdc-64
+    IFS=- read -r compiler model <<< "$line"
+cat << EOF
+  - command: |
+        ${LOAD_CI_FOLDER}
+        DMD=$compiler MODEL=$model ./buildkite/test_bootstrap.sh
+    label: "Bootstrap ($compiler)"
+    ${DEFAULT_COMMAND_PROPS}
+EOF
+
+done
+    ;;
+    *)
+    ;;
+esac
+
 ################################################################################
 # Style & coverage targets
 # Must run after the 'wait' to avoid blocking the build_distribution step
diff --git a/buildkite/test_bootstrap.sh b/buildkite/test_bootstrap.sh
new file mode 100755
index 00000000..dc1f30d3
--- /dev/null
+++ b/buildkite/test_bootstrap.sh
@@ -0,0 +1,37 @@
+#!/bin/bash
+
+PS4="~> " # needed to avoid accidentally generating collapsed output
+set -uexo pipefail
+
+echo "--- Setting build variables"
+
+DIR="$( cd "$( dirname "${BASH_SOURCE[0]}" )" && pwd )"
+
+"$DIR/clone_repositories.sh"
+
+echo "--- Patching DMD and druntime (remove failing tests)"
+
+# patch makefile which requires gdb 8 - see https://github.com/dlang/ci/pull/301
+sed "s/TESTS+=rt_trap_exceptions_drt_gdb//" -i druntime/test/exceptions/Makefile
+
+# remove tests which require gdb 8 for now (see https://github.com/dlang/ci/pull/291)
+rm dmd/test/runnable/gdb{1,10311,14225,14276,14313,14330,4149}.d
+rm dmd/test/runnable/gdb15729.sh
+
+echo "--- Exporting build variables"
+
+export BRANCH="${BUILDKITE_PULL_REQUEST_BASE_BRANCH:-}"
+export N=2
+export OS_NAME=linux
+export FULL_BUILD="${BUILDKITE_PULL_REQUEST+false}"
+
+echo "--- Go to dmd and source ci.sh"
+
+cd dmd
+source ci.sh
+
+echo "--- Installing $DMD"
+install_d "$DMD" # Source a D compiler
+
+echo "--- Running the testsuite"
+testsuite