diff --git a/test/client-entrypoint.sh b/test/client-entrypoint.sh
index de23a13..e4e9234 100755
--- a/test/client-entrypoint.sh
+++ b/test/client-entrypoint.sh
@@ -12,6 +12,123 @@ fi
 
 echo "TUN device ready"
 
+WAIT_TIMEOUT_SIGNAL="${WAIT_TIMEOUT_SIGNAL:-300}"
+WAIT_TIMEOUT_VPN="${WAIT_TIMEOUT_VPN:-120}"
+WAIT_TIMEOUT_GATEWAY="${WAIT_TIMEOUT_GATEWAY:-120}"
+WAIT_TIMEOUT_REVOKE="${WAIT_TIMEOUT_REVOKE:-60}"
+
+wait_until() {
+	local description="$1"
+	local timeout="$2"
+	local interval="$3"
+	shift 3
+
+	local start elapsed
+	start=$(date +%s)
+	until "$@"; do
+		elapsed=$(($(date +%s) - start))
+		if [ "$elapsed" -ge "$timeout" ]; then
+			echo "FAIL: Timed out after ${timeout}s waiting for $description"
+			return 1
+		fi
+		echo "Waiting for $description... (${elapsed}/${timeout}s)"
+		sleep "$interval"
+	done
+}
+
+wait_for_file() {
+	local path="$1"
+	local description="$2"
+	local timeout="${3:-$WAIT_TIMEOUT_SIGNAL}"
+
+	wait_until "$description" "$timeout" 2 test -f "$path"
+}
+
+tun_has_ipv4() {
+	ip addr show tun0 2>/dev/null | grep -q "inet "
+}
+
+wait_for_tun_ipv4() {
+	local description="$1"
+	local log_file="$2"
+	local timeout="${3:-$WAIT_TIMEOUT_VPN}"
+	local elapsed=0
+
+	until tun_has_ipv4; do
+		if [ "$elapsed" -ge "$timeout" ]; then
+			echo "FAIL: Timed out after ${timeout}s waiting for $description"
+			ip addr show 2>&1 || true
+			if [ -f "$log_file" ]; then
+				echo "OpenVPN log tail:"
+				tail -50 "$log_file"
+			fi
+			exit 1
+		fi
+		echo "Waiting for tun0... (${elapsed}/${timeout}s)"
+		if [ -f "$log_file" ]; then
+			tail -3 "$log_file"
+		fi
+		sleep 2
+		elapsed=$((elapsed + 2))
+	done
+}
+
+gateway_ping_ok() {
+	ping -c 3 -W 2 "$VPN_GATEWAY" >/dev/null 2>&1
+}
+
+gateway_unreachable() {
+	! ping -c 1 -W 2 "$VPN_GATEWAY" >/dev/null 2>&1
+}
+
+wait_for_gateway_ping() {
+	local description="$1"
+
+	if ! wait_until "$description" "$WAIT_TIMEOUT_GATEWAY" 3 gateway_ping_ok; then
+		echo "FAIL: Cannot ping $VPN_GATEWAY"
+		ip addr show 2>&1 || true
+		ip route show 2>&1 || true
+		exit 1
+	fi
+	echo "PASS: Can ping $description"
+}
+
+wait_for_revoked_reconnect_rejected() {
+	local log_file="$1"
+	local timeout="${2:-$WAIT_TIMEOUT_VPN}"
+	local elapsed=0
+
+	while [ "$elapsed" -le "$timeout" ]; do
+		if tun_has_ipv4; then
+			echo "FAIL: Connection succeeded with revoked certificate!"
+			cat "$log_file" 2>/dev/null || true
+			exit 1
+		fi
+
+		if [ -f "$log_file" ] && grep -qi "certificate verify failed\|TLS Error\|AUTH_FAILED\|certificate revoked" "$log_file"; then
+			echo "Connection correctly rejected (certificate revoked)"
+			return 0
+		fi
+
+		if [ "$elapsed" -ge "$timeout" ]; then
+			echo "FAIL: Timed out after ${timeout}s waiting for revoked certificate rejection"
+			cat "$log_file" 2>/dev/null || true
+			exit 1
+		fi
+
+		echo "Checking revoked connection status... (${elapsed}/${timeout}s)"
+		if [ -f "$log_file" ]; then
+			tail -3 "$log_file"
+		fi
+		sleep 2
+		elapsed=$((elapsed + 2))
+	done
+
+	echo "FAIL: Timed out after ${timeout}s waiting for revoked certificate rejection"
+	cat "$log_file" 2>/dev/null || true
+	exit 1
+}
+
 test_dns_resolution() {
 	local label="$1"
 	local success=false
@@ -37,10 +154,7 @@ test_dns_resolution() {
 
 # Wait for client config to be available
 echo "Waiting for client config..."
-while [ ! -f /shared/client.ovpn ]; do
-	sleep 2
-	echo "Waiting for client config..."
-done
+wait_for_file /shared/client.ovpn "client config"
 
 echo "Client config found!"
 cat /shared/client.ovpn
@@ -67,14 +181,7 @@ openvpn --config /shared/client.ovpn --daemon --log /var/log/openvpn.log
 
 # Wait for connection
 echo "Waiting for VPN connection..."
-while ! ip addr show tun0 2>/dev/null | grep -q "inet "; do
-	sleep 2
-	echo "Waiting for tun0..."
-	# Show recent log for debugging
-	if [ -f /var/log/openvpn.log ]; then
-		tail -3 /var/log/openvpn.log
-	fi
-done
+wait_for_tun_ipv4 "VPN connection" /var/log/openvpn.log
 
 echo "=== VPN Connected! ==="
 ip addr show tun0
@@ -113,13 +220,9 @@ if [ "${CLIENT_IPV6:-n}" = "y" ]; then
 	fi
 fi
 
-# Test 2: Ping VPN gateway (IPv4) (retries indefinitely, relies on job timeout)
+# Test 2: Ping VPN gateway (IPv4)
 echo "Test 2: Pinging VPN gateway (IPv4) ($VPN_GATEWAY)..."
-while ! ping -c 3 -W 2 "$VPN_GATEWAY" >/dev/null 2>&1; do
-	echo "Ping failed, retrying..."
-	sleep 3
-done
-echo "PASS: Can ping VPN gateway (IPv4)"
+wait_for_gateway_ping "VPN gateway (IPv4)"
 
 # Test 2b: Ping VPN gateway (IPv6, if enabled)
 if [ "${CLIENT_IPV6:-n}" = "y" ]; then
@@ -146,10 +249,7 @@ touch /shared/initial-tests-passed
 # =====================================================
 echo ""
 echo "=== Waiting for post-renewal config ==="
-while [ ! -f /shared/renewal-config-ready ]; do
-	sleep 2
-	echo "Waiting for renewal config..."
-done
+wait_for_file /shared/renewal-config-ready "renewal config"
 
 echo "Renewal config ready, reconnecting..."
 pkill openvpn || true
@@ -158,13 +258,7 @@ sleep 2
 openvpn --config /shared/client.ovpn --daemon --log /var/log/openvpn-renewal.log
 
 echo "Waiting for VPN connection after renewal..."
-while ! ip addr show tun0 2>/dev/null | grep -q "inet "; do
-	sleep 2
-	echo "Waiting for tun0..."
-	if [ -f /var/log/openvpn-renewal.log ]; then
-		tail -3 /var/log/openvpn-renewal.log
-	fi
-done
+wait_for_tun_ipv4 "VPN connection after renewal" /var/log/openvpn-renewal.log
 
 echo "=== VPN Connected after renewal! ==="
 ip addr show tun0
@@ -173,11 +267,7 @@ echo "Waiting for routing to stabilize..."
 sleep 5
 
 echo "Test: Pinging VPN gateway after renewal ($VPN_GATEWAY)..."
-while ! ping -c 3 -W 2 "$VPN_GATEWAY" >/dev/null 2>&1; do
-	echo "Ping failed, retrying..."
-	sleep 3
-done
-echo "PASS: Can ping VPN gateway after renewal"
+wait_for_gateway_ping "VPN gateway after renewal"
 
 test_dns_resolution "Test: Post-renewal DNS"
 
@@ -195,10 +285,7 @@ REVOKE_CLIENT="revoketest"
 
 # Wait for revoke test client config
 echo "Waiting for revoke test client config..."
-while [ ! -f /shared/revoke-client-config-ready ]; do
-	sleep 2
-	echo "Waiting for revoke test config..."
-done
+wait_for_file /shared/revoke-client-config-ready "revoke test config"
 
 if [ ! -f "/shared/$REVOKE_CLIENT.ovpn" ]; then
 	echo "FAIL: Revoke test client config file not found"
@@ -218,23 +305,13 @@ openvpn --config "/shared/$REVOKE_CLIENT.ovpn" --daemon --log /var/log/openvpn-r
 
 # Wait for connection
 echo "Waiting for VPN connection with revoke test client..."
-while ! ip addr show tun0 2>/dev/null | grep -q "inet "; do
-	sleep 2
-	echo "Waiting for tun0..."
-	if [ -f /var/log/openvpn-revoke.log ]; then
-		tail -3 /var/log/openvpn-revoke.log
-	fi
-done
+wait_for_tun_ipv4 "VPN connection with revoke test client" /var/log/openvpn-revoke.log
 
 echo "PASS: Connected with '$REVOKE_CLIENT' certificate"
 ip addr show tun0
 
-# Verify connectivity (retries indefinitely, relies on job timeout)
-while ! ping -c 3 -W 2 "$VPN_GATEWAY" >/dev/null 2>&1; do
-	echo "Ping failed, retrying..."
-	sleep 3
-done
-echo "PASS: Can ping VPN gateway with revoke test client"
+# Verify connectivity
+wait_for_gateway_ping "VPN gateway with revoke test client"
 
 # Signal server that we're connected with revoke test client
 touch /shared/revoke-client-connected
@@ -242,18 +319,8 @@ touch /shared/revoke-client-connected
 # Wait for server to revoke and auto-disconnect us via management interface
 # We detect disconnect by checking if ping to VPN gateway fails
 echo "Waiting for server to revoke certificate and disconnect us..."
-DISCONNECT_DETECTED=false
-for i in $(seq 1 60); do
-	if ! ping -c 1 -W 2 "$VPN_GATEWAY" >/dev/null 2>&1; then
-		echo "Disconnect detected: cannot ping VPN gateway"
-		DISCONNECT_DETECTED=true
-		break
-	fi
-	sleep 1
-	echo "Still connected, waiting for revoke/disconnect ($i/60)..."
-done
-
-if [ "$DISCONNECT_DETECTED" = true ]; then
+if wait_until "server to revoke and disconnect client" "$WAIT_TIMEOUT_REVOKE" 1 gateway_unreachable; then
+	echo "Disconnect detected: cannot ping VPN gateway"
 	echo "PASS: Client was auto-disconnected by revoke"
 	# Kill openvpn process to clean up
 	pkill openvpn 2>/dev/null || true
@@ -268,9 +335,7 @@ touch /shared/revoke-client-disconnected
 
 # Wait for server to signal us to try reconnecting
 echo "Waiting for server to signal reconnect attempt..."
-while [ ! -f /shared/revoke-try-reconnect ]; do
-	sleep 2
-done
+wait_for_file /shared/revoke-try-reconnect "reconnect signal"
 
 # Try to reconnect with the now-revoked certificate (should fail)
 echo "Attempting to reconnect with revoked certificate (should fail)..."
@@ -280,31 +345,7 @@ openvpn --config "/shared/$REVOKE_CLIENT.ovpn" --daemon --log /var/log/openvpn-r
 # Wait and check if connection fails
 # The connection should fail due to certificate being revoked
 echo "Waiting to verify connection is rejected..."
-CONNECT_FAILED=false
-while true; do
-	sleep 2
-
-	# Check if tun0 came up (would mean revocation didn't work)
-	if ip addr show tun0 2>/dev/null | grep -q "inet "; then
-		echo "FAIL: Connection succeeded with revoked certificate!"
-		cat /var/log/openvpn-revoke-fail.log || true
-		exit 1
-	fi
-
-	# Check for certificate verification failure in log
-	if [ -f /var/log/openvpn-revoke-fail.log ]; then
-		if grep -qi "certificate verify failed\|TLS Error\|AUTH_FAILED\|certificate revoked" /var/log/openvpn-revoke-fail.log; then
-			echo "Connection correctly rejected (certificate revoked)"
-			CONNECT_FAILED=true
-			break
-		fi
-	fi
-
-	echo "Checking connection status..."
-	if [ -f /var/log/openvpn-revoke-fail.log ]; then
-		tail -3 /var/log/openvpn-revoke-fail.log
-	fi
-done
+wait_for_revoked_reconnect_rejected /var/log/openvpn-revoke-fail.log
 
 # Kill any remaining openvpn process
 pkill openvpn 2>/dev/null || true
@@ -316,13 +357,7 @@ if ip addr show tun0 2>/dev/null | grep -q "inet "; then
 	exit 1
 fi
 
-if [ "$CONNECT_FAILED" = true ]; then
-	echo "PASS: Connection with revoked certificate was correctly rejected"
-else
-	echo "PASS: Connection with revoked certificate did not succeed (no tun0)"
-	echo "OpenVPN log:"
-	cat /var/log/openvpn-revoke-fail.log || true
-fi
+echo "PASS: Connection with revoked certificate was correctly rejected"
 
 # Signal server that reconnect with revoked cert failed
 touch /shared/revoke-reconnect-failed
@@ -335,10 +370,7 @@ echo "=== Testing connection with recreated certificate ==="
 
 # Wait for server to create new cert and signal us
 echo "Waiting for new client config with same name..."
-while [ ! -f /shared/new-client-config-ready ]; do
-	sleep 2
-	echo "Waiting for new config..."
-done
+wait_for_file /shared/new-client-config-ready "new client config"
 
 if [ ! -f "/shared/$REVOKE_CLIENT-new.ovpn" ]; then
 	echo "FAIL: New client config file not found"
@@ -354,23 +386,13 @@ openvpn --config "/shared/$REVOKE_CLIENT-new.ovpn" --daemon --log /var/log/openv
 
 # Wait for connection
 echo "Waiting for VPN connection with new certificate..."
-while ! ip addr show tun0 2>/dev/null | grep -q "inet "; do
-	sleep 2
-	echo "Waiting for tun0..."
-	if [ -f /var/log/openvpn-new.log ]; then
-		tail -3 /var/log/openvpn-new.log
-	fi
-done
+wait_for_tun_ipv4 "VPN connection with new certificate" /var/log/openvpn-new.log
 
 echo "PASS: Connected with new '$REVOKE_CLIENT' certificate"
 ip addr show tun0
 
-# Verify connectivity (retries indefinitely, relies on job timeout)
-while ! ping -c 3 -W 2 "$VPN_GATEWAY" >/dev/null 2>&1; do
-	echo "Ping failed, retrying..."
-	sleep 3
-done
-echo "PASS: Can ping VPN gateway with new certificate"
+# Verify connectivity
+wait_for_gateway_ping "VPN gateway with new certificate"
 
 # Signal server that we connected with new cert
 touch /shared/new-client-connected
@@ -388,10 +410,7 @@ PASSPHRASE_CLIENT="passphrasetest"
 
 # Wait for passphrase test client config
 echo "Waiting for passphrase test client config..."
-while [ ! -f /shared/passphrase-client-config-ready ]; do
-	sleep 2
-	echo "Waiting for passphrase test config..."
-done
+wait_for_file /shared/passphrase-client-config-ready "passphrase test config"
 
 if [ ! -f "/shared/$PASSPHRASE_CLIENT.ovpn" ]; then
 	echo "FAIL: Passphrase test client config file not found"
@@ -416,23 +435,13 @@ openvpn --config "/shared/$PASSPHRASE_CLIENT.ovpn" --askpass "/shared/$PASSPHRAS
 
 # Wait for connection
 echo "Waiting for VPN connection with passphrase-protected client..."
-while ! ip addr show tun0 2>/dev/null | grep -q "inet "; do
-	sleep 2
-	echo "Waiting for tun0..."
-	if [ -f /var/log/openvpn-passphrase.log ]; then
-		tail -3 /var/log/openvpn-passphrase.log
-	fi
-done
+wait_for_tun_ipv4 "VPN connection with passphrase-protected client" /var/log/openvpn-passphrase.log
 
 echo "PASS: Connected with passphrase-protected '$PASSPHRASE_CLIENT' certificate"
 ip addr show tun0
 
-# Verify connectivity (retries indefinitely, relies on job timeout)
-while ! ping -c 3 -W 2 "$VPN_GATEWAY" >/dev/null 2>&1; do
-	echo "Ping failed, retrying..."
-	sleep 3
-done
-echo "PASS: Can ping VPN gateway with passphrase-protected client"
+# Verify connectivity
+wait_for_gateway_ping "VPN gateway with passphrase-protected client"
 
 # Signal server that we connected with passphrase client
 touch /shared/passphrase-client-connected
diff --git a/test/server-entrypoint.sh b/test/server-entrypoint.sh
index 8136a39..1c3b23c 100755
--- a/test/server-entrypoint.sh
+++ b/test/server-entrypoint.sh
@@ -12,6 +12,37 @@ fi
 
 echo "TUN device ready"
 
+WAIT_TIMEOUT_SIGNAL="${WAIT_TIMEOUT_SIGNAL:-300}"
+WAIT_TIMEOUT_CONNECT="${WAIT_TIMEOUT_CONNECT:-180}"
+WAIT_TIMEOUT_REVOKE="${WAIT_TIMEOUT_REVOKE:-60}"
+
+wait_until() {
+	local description="$1"
+	local timeout="$2"
+	local interval="$3"
+	shift 3
+
+	local start elapsed
+	start=$(date +%s)
+	until "$@"; do
+		elapsed=$(($(date +%s) - start))
+		if [ "$elapsed" -ge "$timeout" ]; then
+			echo "FAIL: Timed out after ${timeout}s waiting for $description"
+			return 1
+		fi
+		echo "Waiting for $description... (${elapsed}/${timeout}s)"
+		sleep "$interval"
+	done
+}
+
+wait_for_file() {
+	local path="$1"
+	local description="$2"
+	local timeout="${3:-$WAIT_TIMEOUT_SIGNAL}"
+
+	wait_until "$description" "$timeout" 2 test -f "$path"
+}
+
 # Configuration for install
 export FORCE_COLOR=1
 VPN_SUBNET_IPV4=10.9.0.0 # Custom subnet to test configurability
@@ -371,10 +402,7 @@ echo "=== TLS 1.3 Configuration Verified ==="
 # =====================================================
 echo ""
 echo "=== Waiting for initial client connectivity tests ==="
-while [ ! -f /shared/initial-tests-passed ]; do
-	sleep 2
-	echo "Waiting for initial tests..."
-done
+wait_for_file /shared/initial-tests-passed "initial client connectivity tests"
 echo "Initial client tests passed, proceeding with renewal tests"
 
 # =====================================================
@@ -564,10 +592,7 @@ echo "Updated client config with renewed certificates"
 # =====================================================
 echo ""
 echo "=== Waiting for post-renewal client connectivity tests ==="
-while [ ! -f /shared/renewal-tests-passed ]; do
-	sleep 2
-	echo "Waiting for renewal tests..."
-done
+wait_for_file /shared/renewal-tests-passed "post-renewal client connectivity tests"
 echo "Post-renewal client tests passed"
 
 # =====================================================
@@ -806,10 +831,7 @@ touch /shared/revoke-client-config-ready
 
 # Wait for client to confirm connection with revoke test client
 echo "Waiting for client to connect with '$REVOKE_CLIENT' certificate..."
-while [ ! -f /shared/revoke-client-connected ]; do
-	sleep 2
-	echo "Waiting for revoke test connection..."
-done
+wait_for_file /shared/revoke-client-connected "revoke test client connection" "$WAIT_TIMEOUT_CONNECT"
 echo "PASS: Client connected with '$REVOKE_CLIENT' certificate"
 
 # =====================================================
@@ -884,14 +906,7 @@ fi
 
 # Wait for client to confirm it was disconnected by the revoke
 echo "Waiting for client to confirm auto-disconnect..."
-DISCONNECT_WAIT=0
-while [ ! -f /shared/revoke-client-disconnected ] && [ $DISCONNECT_WAIT -lt 60 ]; do
-	sleep 2
-	DISCONNECT_WAIT=$((DISCONNECT_WAIT + 2))
-	echo "Waiting for disconnect confirmation... ($DISCONNECT_WAIT/60s)"
-done
-
-if [ -f /shared/revoke-client-disconnected ]; then
+if wait_for_file /shared/revoke-client-disconnected "disconnect confirmation" "$WAIT_TIMEOUT_REVOKE"; then
 	echo "PASS: Client was auto-disconnected by revoke command"
 else
 	echo "FAIL: Client was not disconnected within 60 seconds"
@@ -903,10 +918,7 @@ touch /shared/revoke-try-reconnect
 
 # Wait for client to confirm that connection with revoked cert failed
 echo "Waiting for client to confirm revoked cert connection failure..."
-while [ ! -f /shared/revoke-reconnect-failed ]; do
-	sleep 2
-	echo "Waiting for reconnect failure confirmation..."
-done
+wait_for_file /shared/revoke-reconnect-failed "revoked cert reconnect failure confirmation" "$WAIT_TIMEOUT_CONNECT"
 echo "PASS: Connection with revoked certificate correctly rejected"
 
 echo "=== Certificate Revocation Tests PASSED ==="
@@ -1080,10 +1092,7 @@ touch /shared/new-client-config-ready
 
 # Wait for client to confirm successful connection with new cert
 echo "Waiting for client to connect with new '$REVOKE_CLIENT' certificate..."
-while [ ! -f /shared/new-client-connected ]; do
-	sleep 2
-	echo "Waiting for new cert connection..."
-done
+wait_for_file /shared/new-client-connected "new certificate connection" "$WAIT_TIMEOUT_CONNECT"
 echo "PASS: Client connected with new '$REVOKE_CLIENT' certificate"
 
 echo "=== Reuse of Revoked Client Name Tests PASSED ==="
@@ -1151,10 +1160,7 @@ touch /shared/passphrase-client-config-ready
 
 # Wait for client to confirm connection with passphrase client
 echo "Waiting for client to connect with '$PASSPHRASE_CLIENT' certificate..."
-while [ ! -f /shared/passphrase-client-connected ]; do
-	sleep 2
-	echo "Waiting for passphrase client connection..."
-done
+wait_for_file /shared/passphrase-client-connected "passphrase client connection" "$WAIT_TIMEOUT_CONNECT"
 echo "PASS: Client connected with passphrase-protected certificate"
 
 echo "=== PASSPHRASE Support Tests PASSED ==="