diff --git a/.ci/boot_race/a.toml b/.ci/boot_race/a.toml
new file mode 100644
index 00000000..d8e69fc1
--- /dev/null
+++ b/.ci/boot_race/a.toml
@@ -0,0 +1,14 @@
+public_key = "rp-a-public-key"
+secret_key = "rp-a-secret-key"
+listen = ["127.0.0.1:9999"]
+verbosity = "Verbose"
+
+[api]
+listen_path = []
+listen_fd = []
+stream_fd = []
+
+[[peers]]
+public_key = "rp-b-public-key"
+endpoint = "127.0.0.1:9998"
+key_out = "rp-b-key-out.txt"
diff --git a/.ci/boot_race/b.toml b/.ci/boot_race/b.toml
new file mode 100644
index 00000000..b7609759
--- /dev/null
+++ b/.ci/boot_race/b.toml
@@ -0,0 +1,14 @@
+public_key = "rp-b-public-key"
+secret_key = "rp-b-secret-key"
+listen = ["127.0.0.1:9998"]
+verbosity = "Verbose"
+
+[api]
+listen_path = []
+listen_fd = []
+stream_fd = []
+
+[[peers]]
+public_key = "rp-a-public-key"
+endpoint = "127.0.0.1:9999"
+key_out = "rp-a-key-out.txt"
diff --git a/.ci/boot_race/run.sh b/.ci/boot_race/run.sh
new file mode 100644
index 00000000..4df21f0c
--- /dev/null
+++ b/.ci/boot_race/run.sh
@@ -0,0 +1,48 @@
+#!/bin/bash
+
+iterations="$1"
+sleep_time="$2"
+config_a="$3"
+config_b="$4"
+
+PWD="$(pwd)"
+EXEC="$PWD/target/release/rosenpass"
+
+i=0
+while [ "$i" -ne "$iterations" ]; do
+	echo "=> Iteration $i"
+
+	# flush the PSK files
+	echo "A" >rp-a-key-out.txt
+	echo "B" >rp-b-key-out.txt
+
+	# start the two instances
+	echo "Starting instance A"
+	"$EXEC" exchange-config "$config_a" &
+	PID_A=$!
+	sleep "$sleep_time"
+	echo "Starting instance B"
+	"$EXEC" exchange-config "$config_b" &
+	PID_B=$!
+
+	# give the key exchange some time to complete
+	sleep 3
+
+	# kill the instances
+	kill $PID_A
+	kill $PID_B
+
+	# compare the keys
+	if cmp -s rp-a-key-out.txt rp-b-key-out.txt; then
+		echo "Keys match"
+	else
+		echo "::warning title=Key Exchange Race Condition::The key exchange resulted in different keys. Delay was ${sleep_time}s."
+		# TODO: set this to 1 when the race condition is fixed
+		exit 0
+	fi
+
+	# give the instances some time to shut down
+	sleep 2
+
+	i=$((i + 1))
+done
diff --git a/.github/workflows/regressions.yml b/.github/workflows/regressions.yml
index 3da867e9..1c3cb84d 100644
--- a/.github/workflows/regressions.yml
+++ b/.github/workflows/regressions.yml
@@ -23,3 +23,15 @@ jobs:
       - run: .ci/run-regression.sh 100 20
       - run: |
           [ $(ls -1 output/ate/out | wc -l) -eq 100 ]
+
+  boot-race:
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/checkout@v3
+      - run: cargo build --bin rosenpass --release
+      - run: chmod +x .ci/boot_race/run.sh
+      - run: cargo run --release --bin rosenpass gen-keys .ci/boot_race/a.toml
+      - run: cargo run --release --bin rosenpass gen-keys .ci/boot_race/b.toml
+      - run: .ci/boot_race/run.sh 5 2 .ci/boot_race/a.toml .ci/boot_race/b.toml
+      - run: .ci/boot_race/run.sh 5 1 .ci/boot_race/a.toml .ci/boot_race/b.toml
+      - run: .ci/boot_race/run.sh 5 0 .ci/boot_race/a.toml .ci/boot_race/b.toml