diff --git a/scripts/entrypoint.sh b/scripts/entrypoint.sh
index c9803ae..fcc219b 100755
--- a/scripts/entrypoint.sh
+++ b/scripts/entrypoint.sh
@@ -171,9 +171,26 @@ log "Setting up OpenSMTPD service..."
 # Start OpenSMTPD if configuration exists
 OPENSMTPD_CONFIG="/workspace/src/backend/app/opensmtpd/install/etc/smtpd.conf"
 OPENSMTPD_PID_FILE="/workspace/src/backend/app/opensmtpd/install/var/run/smtpd.pid"
-OPENSMTPD_BINARY="/workspace/src/backend/app/opensmtpd/install/sbin/smtpd"
+OPENSMTPD_CUSTOM_BINARY="/workspace/src/backend/app/opensmtpd/install/sbin/smtpd"
+OPENSMTPD_SYSTEM_BINARY="/usr/sbin/smtpd"
 
-if [ -f "$OPENSMTPD_CONFIG" ] && [ -x "$OPENSMTPD_BINARY" ]; then
+# Determine which binary to use (prefer custom, fallback to system)
+OPENSMTPD_BINARY=""
+if [ -x "$OPENSMTPD_CUSTOM_BINARY" ]; then
+    OPENSMTPD_BINARY="$OPENSMTPD_CUSTOM_BINARY"
+    log "Using custom OpenSMTPD binary: $OPENSMTPD_BINARY"
+elif [ -x "$OPENSMTPD_SYSTEM_BINARY" ]; then
+    OPENSMTPD_BINARY="$OPENSMTPD_SYSTEM_BINARY"
+    log "Using system OpenSMTPD binary: $OPENSMTPD_BINARY"
+else
+    # Try to find in PATH
+    if command -v smtpd &>/dev/null; then
+        OPENSMTPD_BINARY="$(command -v smtpd)"
+        log "Using OpenSMTPD from PATH: $OPENSMTPD_BINARY"
+    fi
+fi
+
+if [ -n "$OPENSMTPD_BINARY" ] && [ -f "$OPENSMTPD_CONFIG" ]; then
     log "OpenSMTPD configuration found at $OPENSMTPD_CONFIG"
     
     # Ensure required directories exist with proper permissions
@@ -204,8 +221,8 @@ else
     if [ ! -f "$OPENSMTPD_CONFIG" ]; then
         log "  Config file missing: $OPENSMTPD_CONFIG"
     fi
-    if [ ! -x "$OPENSMTPD_BINARY" ]; then
-        log "  Binary not executable: $OPENSMTPD_BINARY"
+    if [ -z "$OPENSMTPD_BINARY" ]; then
+        log "  Binary not found at: $OPENSMTPD_CUSTOM_BINARY or $OPENSMTPD_SYSTEM_BINARY"
     fi
 fi
 
diff --git a/scripts/healthcheck.sh b/scripts/healthcheck.sh
index c2f1a92..fdcf142 100644
--- a/scripts/healthcheck.sh
+++ b/scripts/healthcheck.sh
@@ -174,8 +174,20 @@ main() {
 
     # Check OpenSMTPD service (ports 25, 587, 465)
     health_log "INFO" "=== OpenSMTPD Service ==="
-    OPENSMTPD_BINARY="/workspace/src/backend/app/opensmtpd/install/sbin/smtpd"
-    if [ -x "$OPENSMTPD_BINARY" ]; then
+    OPENSMTPD_CUSTOM_BINARY="/workspace/src/backend/app/opensmtpd/install/sbin/smtpd"
+    OPENSMTPD_SYSTEM_BINARY="/usr/sbin/smtpd"
+    
+    # Determine which binary to use (prefer custom, fallback to system)
+    OPENSMTPD_BINARY=""
+    if [ -x "$OPENSMTPD_CUSTOM_BINARY" ]; then
+        OPENSMTPD_BINARY="$OPENSMTPD_CUSTOM_BINARY"
+    elif [ -x "$OPENSMTPD_SYSTEM_BINARY" ]; then
+        OPENSMTPD_BINARY="$OPENSMTPD_SYSTEM_BINARY"
+    elif command -v smtpd &>/dev/null; then
+        OPENSMTPD_BINARY="$(command -v smtpd)"
+    fi
+    
+    if [ -n "$OPENSMTPD_BINARY" ]; then
         # Check SMTP port 25
         if check_port 25 "SMTP"; then
             health_log "INFO" "✓ SMTP port 25 is listening"
@@ -205,7 +217,7 @@ main() {
             health_log "WARN" "⚠ OpenSMTPD process not found (may be disabled)"
         fi
     else
-        health_log "INFO" "OpenSMTPD not installed at expected location, skipping SMTP checks"
+        health_log "INFO" "OpenSMTPD not installed (checked: $OPENSMTPD_CUSTOM_BINARY, $OPENSMTPD_SYSTEM_BINARY, PATH), skipping SMTP checks"
     fi
 
     # ttyd service has been removed, no longer checking port 4501