diff --git a/lib/properties.go b/lib/properties.go
index 9e620b9..50f3899 100644
--- a/lib/properties.go
+++ b/lib/properties.go
@@ -26,11 +26,41 @@ func (c *Converter) parseJavaProperties(input []byte) (*TunnelConfig, error) {
 	return config, nil
 }
 
+// parsePropertyKey parses a single Java I2P property key-value pair and updates the TunnelConfig.
+// Supports multiple Java I2P property patterns:
+//
+// Flat properties:
+//   - name, type, interface, listenPort, targetDestination, targetHost, description
+//   - proxyList, sharedClient, startOnLoad, accessList, targetPort, spoofedHost (stored in Tunnel map)
+//   - i2cpHost, i2cpPort (stored in I2CP map)
+//
+// Numbered tunnel patterns:
+//   - tunnel.N.property (e.g., tunnel.0.name, tunnel.1.type, tunnel.2.interface)
+//
+// Option prefixes:
+//   - option.i2cp.* -> stored in I2CP map
+//   - option.i2ptunnel.* -> stored in Tunnel map
+//   - option.inbound.* -> stored in Inbound map
+//   - option.outbound.* -> stored in Outbound map
+//   - option.persistentClientKey -> sets PersistentKey field
+//
+// Comments (#) and configFile properties are ignored.
 func (c *Converter) parsePropertyKey(k, s string, config *TunnelConfig) {
 	if strings.HasPrefix(k, "#") || strings.HasPrefix(k, "configFile") {
 		return // Skip comments and config file path
 	}
 
+	// Handle tunnel.N.property patterns for numbered tunnels
+	if strings.HasPrefix(k, "tunnel.") && strings.Contains(k, ".") {
+		parts := strings.SplitN(k, ".", 3)
+		if len(parts) == 3 {
+			// Format: tunnel.N.property (e.g., tunnel.0.name, tunnel.1.type)
+			property := parts[2]
+			c.parseNumberedTunnelProperty(property, s, config)
+			return
+		}
+	}
+
 	// Handle flat keys
 	switch k {
 	case "name":
@@ -47,8 +77,40 @@ func (c *Converter) parsePropertyKey(k, s string, config *TunnelConfig) {
 		config.Target = s
 	case "targetHost":
 		config.Target = s // Alternative naming
+	case "targetPort":
+		if port, err := strconv.Atoi(s); err == nil {
+			if config.Tunnel == nil {
+				config.Tunnel = make(map[string]interface{})
+			}
+			config.Tunnel["targetPort"] = port
+		}
 	case "description":
 		config.Description = s
+	case "proxyList":
+		if config.Tunnel == nil {
+			config.Tunnel = make(map[string]interface{})
+		}
+		config.Tunnel["proxyList"] = parseValue(s)
+	case "sharedClient":
+		if config.Tunnel == nil {
+			config.Tunnel = make(map[string]interface{})
+		}
+		config.Tunnel["sharedClient"] = parseValue(s)
+	case "startOnLoad":
+		if config.Tunnel == nil {
+			config.Tunnel = make(map[string]interface{})
+		}
+		config.Tunnel["startOnLoad"] = parseValue(s)
+	case "accessList":
+		if config.Tunnel == nil {
+			config.Tunnel = make(map[string]interface{})
+		}
+		config.Tunnel["accessList"] = parseValue(s)
+	case "spoofedHost":
+		if config.Tunnel == nil {
+			config.Tunnel = make(map[string]interface{})
+		}
+		config.Tunnel["spoofedHost"] = parseValue(s)
 	case "i2cpHost":
 		if config.I2CP == nil {
 			config.I2CP = make(map[string]interface{})
@@ -70,6 +132,84 @@ func (c *Converter) parsePropertyKey(k, s string, config *TunnelConfig) {
 		}
 		key := strings.TrimPrefix(k, "option.i2cp.")
 		config.I2CP[key] = parseValue(s)
+	} else if strings.HasPrefix(k, "option.i2ptunnel.") {
+		if config.Tunnel == nil {
+			config.Tunnel = make(map[string]interface{})
+		}
+		key := strings.TrimPrefix(k, "option.i2ptunnel.")
+		config.Tunnel[key] = parseValue(s)
+	} else if strings.HasPrefix(k, "option.inbound.") {
+		if config.Inbound == nil {
+			config.Inbound = make(map[string]interface{})
+		}
+		key := strings.TrimPrefix(k, "option.inbound.")
+		config.Inbound[key] = parseValue(s)
+	} else if strings.HasPrefix(k, "option.outbound.") {
+		if config.Outbound == nil {
+			config.Outbound = make(map[string]interface{})
+		}
+		key := strings.TrimPrefix(k, "option.outbound.")
+		config.Outbound[key] = parseValue(s)
+	} else if k == "option.persistentClientKey" {
+		config.PersistentKey = parseValue(s).(bool)
+	}
+}
+
+// parseNumberedTunnelProperty handles properties from tunnel.N.property patterns
+// For numbered tunnel configurations, we treat each as a separate tunnel instance
+// but for this converter we only support single tunnel configs, so we merge all numbered properties
+func (c *Converter) parseNumberedTunnelProperty(property, value string, config *TunnelConfig) {
+	switch property {
+	case "name":
+		// If config.Name is empty, use this as the primary name
+		// If config.Name exists, treat as additional tunnel option
+		if config.Name == "" {
+			config.Name = value
+		} else {
+			if config.Tunnel == nil {
+				config.Tunnel = make(map[string]interface{})
+			}
+			config.Tunnel["alternateName"] = value
+		}
+	case "type":
+		if config.Type == "" {
+			config.Type = value
+		}
+	case "interface":
+		if config.Interface == "" {
+			config.Interface = value
+		}
+	case "listenPort":
+		if config.Port == 0 {
+			if port, err := strconv.Atoi(value); err == nil {
+				config.Port = port
+			}
+		}
+	case "targetDestination":
+		if config.Target == "" {
+			config.Target = value
+		}
+	case "targetHost":
+		if config.Target == "" {
+			config.Target = value
+		}
+	case "targetPort":
+		if port, err := strconv.Atoi(value); err == nil {
+			if config.Tunnel == nil {
+				config.Tunnel = make(map[string]interface{})
+			}
+			config.Tunnel["targetPort"] = port
+		}
+	case "description":
+		if config.Description == "" {
+			config.Description = value
+		}
+	default:
+		// Store other numbered tunnel properties in the Tunnel map
+		if config.Tunnel == nil {
+			config.Tunnel = make(map[string]interface{})
+		}
+		config.Tunnel[property] = parseValue(value)
 	}
 }
 
@@ -135,20 +275,36 @@ func (c *Converter) generateJavaProperties(config *TunnelConfig) ([]byte, error)
 	}
 
 	for k, v := range config.I2CP {
-		sb.WriteString(fmt.Sprintf("option.i2cp.%s=%v\n", k, v))
+		sb.WriteString(fmt.Sprintf("option.i2cp.%s=%s\n", k, formatPropertyValue(v)))
 	}
 
 	for k, v := range config.Tunnel {
-		sb.WriteString(fmt.Sprintf("option.i2ptunnel.%s=%v\n", k, v))
+		// Handle special flat properties that should not have option.i2ptunnel prefix
+		switch k {
+		case "proxyList", "sharedClient", "startOnLoad", "accessList", "spoofedHost", "targetPort":
+			sb.WriteString(fmt.Sprintf("%s=%s\n", k, formatPropertyValue(v)))
+		default:
+			// Other tunnel options use the option.i2ptunnel prefix
+			sb.WriteString(fmt.Sprintf("option.i2ptunnel.%s=%s\n", k, formatPropertyValue(v)))
+		}
 	}
 
 	for k, v := range config.Inbound {
-		sb.WriteString(fmt.Sprintf("option.inbound.%s=%v\n", k, v))
+		sb.WriteString(fmt.Sprintf("option.inbound.%s=%s\n", k, formatPropertyValue(v)))
 	}
 
 	for k, v := range config.Outbound {
-		sb.WriteString(fmt.Sprintf("option.outbound.%s=%v\n", k, v))
+		sb.WriteString(fmt.Sprintf("option.outbound.%s=%s\n", k, formatPropertyValue(v)))
 	}
 
 	return []byte(sb.String()), nil
 }
+
+// formatPropertyValue formats a property value for output
+// Arrays/slices are formatted as comma-separated values
+func formatPropertyValue(v interface{}) string {
+	if slice, ok := v.([]string); ok {
+		return strings.Join(slice, ",")
+	}
+	return fmt.Sprint(v)
+}
diff --git a/lib/properties_test.go b/lib/properties_test.go
index c559e5a..b1292ae 100644
--- a/lib/properties_test.go
+++ b/lib/properties_test.go
@@ -1,6 +1,10 @@
 package i2pconv
 
-import "testing"
+import (
+	"fmt"
+	"reflect"
+	"testing"
+)
 
 func TestPropertyConversion(t *testing.T) {
 	input := `
@@ -26,7 +30,7 @@ sharedClient=true
 		t.Fatalf("Failed to generate YAML: %v", err)
 	}
 
-	// Expected YAML structure matching actual format:
+	// Expected YAML structure matching enhanced parsing:
 	expected := `tunnels:
   I2P HTTP Proxy:
     name: I2P HTTP Proxy
@@ -39,6 +43,11 @@ sharedClient=true
       - "4"
       - "0"
       reduceIdleTime: 900000
+    options:
+      proxyList: exit.stormycloud.i2p
+      sharedClient: true
+    inbound:
+      length: 3
 `
 	// Compare YAML output
 	if string(yaml) != expected {
@@ -47,3 +56,312 @@ sharedClient=true
 		t.Logf("YAML output:\n%s", yaml)
 	}
 }
+
+func TestEnhancedPropertiesParser(t *testing.T) {
+	tests := []struct {
+		name     string
+		input    string
+		expected *TunnelConfig
+	}{
+		{
+			name: "numbered tunnel properties",
+			input: `
+tunnel.0.name=HTTPProxy
+tunnel.0.type=httpclient
+tunnel.0.interface=127.0.0.1
+tunnel.0.listenPort=4444
+tunnel.0.description=HTTP proxy tunnel
+`,
+			expected: &TunnelConfig{
+				Name:        "HTTPProxy",
+				Type:        "httpclient",
+				Interface:   "127.0.0.1",
+				Port:        4444,
+				Description: "HTTP proxy tunnel",
+				I2CP:        make(map[string]interface{}),
+				Tunnel:      make(map[string]interface{}),
+				Inbound:     make(map[string]interface{}),
+				Outbound:    make(map[string]interface{}),
+			},
+		},
+		{
+			name: "option prefixes",
+			input: `
+name=TestTunnel
+type=server
+option.i2ptunnel.useCompression=true
+option.inbound.length=3
+option.outbound.length=2
+option.persistentClientKey=true
+`,
+			expected: &TunnelConfig{
+				Name:          "TestTunnel",
+				Type:          "server",
+				PersistentKey: true,
+				I2CP:          make(map[string]interface{}),
+				Tunnel: map[string]interface{}{
+					"useCompression": true,
+				},
+				Inbound: map[string]interface{}{
+					"length": 3,
+				},
+				Outbound: map[string]interface{}{
+					"length": 2,
+				},
+			},
+		},
+		{
+			name: "additional flat properties",
+			input: `
+name=WebServer
+type=httpserver
+proxyList=example.i2p,another.i2p
+sharedClient=false
+startOnLoad=true
+accessList=allow
+targetPort=8080
+spoofedHost=example.com
+`,
+			expected: &TunnelConfig{
+				Name: "WebServer",
+				Type: "httpserver",
+				I2CP: make(map[string]interface{}),
+				Tunnel: map[string]interface{}{
+					"proxyList":    []string{"example.i2p", "another.i2p"},
+					"sharedClient": false,
+					"startOnLoad":  true,
+					"accessList":   "allow",
+					"targetPort":   8080,
+					"spoofedHost":  "example.com",
+				},
+				Inbound:  make(map[string]interface{}),
+				Outbound: make(map[string]interface{}),
+			},
+		},
+		{
+			name: "mixed numbered and flat properties",
+			input: `
+tunnel.0.name=MixedTunnel
+tunnel.1.type=client
+interface=192.168.1.1
+listenPort=7070
+proxyList=proxy.i2p
+option.i2cp.reduceIdleTime=600000
+`,
+			expected: &TunnelConfig{
+				Name:      "MixedTunnel",
+				Type:      "client",
+				Interface: "192.168.1.1",
+				Port:      7070,
+				I2CP: map[string]interface{}{
+					"reduceIdleTime": 600000,
+				},
+				Tunnel: map[string]interface{}{
+					"proxyList": "proxy.i2p",
+				},
+				Inbound:  make(map[string]interface{}),
+				Outbound: make(map[string]interface{}),
+			},
+		},
+	}
+
+	conv := &Converter{}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			config, err := conv.parseJavaProperties([]byte(tt.input))
+			if err != nil {
+				t.Fatalf("Failed to parse properties: %v", err)
+			}
+
+			// Check basic fields
+			if config.Name != tt.expected.Name {
+				t.Errorf("Name: expected %q, got %q", tt.expected.Name, config.Name)
+			}
+			if config.Type != tt.expected.Type {
+				t.Errorf("Type: expected %q, got %q", tt.expected.Type, config.Type)
+			}
+			if config.Interface != tt.expected.Interface {
+				t.Errorf("Interface: expected %q, got %q", tt.expected.Interface, config.Interface)
+			}
+			if config.Port != tt.expected.Port {
+				t.Errorf("Port: expected %d, got %d", tt.expected.Port, config.Port)
+			}
+			if config.Description != tt.expected.Description {
+				t.Errorf("Description: expected %q, got %q", tt.expected.Description, config.Description)
+			}
+			if config.PersistentKey != tt.expected.PersistentKey {
+				t.Errorf("PersistentKey: expected %t, got %t", tt.expected.PersistentKey, config.PersistentKey)
+			}
+
+			// Check map fields using proper comparison
+			for k, v := range tt.expected.I2CP {
+				if actualV, ok := config.I2CP[k]; !ok {
+					t.Errorf("I2CP[%q]: missing key", k)
+				} else if !valuesEqual(v, actualV) {
+					t.Errorf("I2CP[%q]: expected %v, got %v", k, v, actualV)
+				}
+			}
+			for k, v := range tt.expected.Tunnel {
+				if actualV, ok := config.Tunnel[k]; !ok {
+					t.Errorf("Tunnel[%q]: missing key", k)
+				} else if !valuesEqual(v, actualV) {
+					t.Errorf("Tunnel[%q]: expected %v, got %v", k, v, actualV)
+				}
+			}
+			for k, v := range tt.expected.Inbound {
+				if actualV, ok := config.Inbound[k]; !ok {
+					t.Errorf("Inbound[%q]: missing key", k)
+				} else if !valuesEqual(v, actualV) {
+					t.Errorf("Inbound[%q]: expected %v, got %v", k, v, actualV)
+				}
+			}
+			for k, v := range tt.expected.Outbound {
+				if actualV, ok := config.Outbound[k]; !ok {
+					t.Errorf("Outbound[%q]: missing key", k)
+				} else if !valuesEqual(v, actualV) {
+					t.Errorf("Outbound[%q]: expected %v, got %v", k, v, actualV)
+				}
+			}
+		})
+	}
+}
+
+func TestPropertiesRoundTrip(t *testing.T) {
+	// Test that parsing and then generating produces consistent results
+	input := `name=RoundTripTest
+type=httpclient
+interface=127.0.0.1
+listenPort=8888
+targetDestination=example.i2p
+description=Test tunnel for round-trip conversion
+proxyList=proxy1.i2p,proxy2.i2p
+sharedClient=true
+startOnLoad=false
+option.i2cp.leaseSetEncType=4,0
+option.i2cp.reduceIdleTime=900000
+option.i2ptunnel.useCompression=true
+option.inbound.length=3
+option.outbound.length=2
+option.persistentClientKey=true`
+
+	conv := &Converter{}
+
+	// Parse properties
+	config, err := conv.parseJavaProperties([]byte(input))
+	if err != nil {
+		t.Fatalf("Failed to parse properties: %v", err)
+	}
+
+	// Generate properties back
+	output, err := conv.generateJavaProperties(config)
+	if err != nil {
+		t.Fatalf("Failed to generate properties: %v", err)
+	}
+
+	// Parse the generated output again
+	config2, err := conv.parseJavaProperties(output)
+	if err != nil {
+		t.Fatalf("Failed to re-parse generated properties: %v", err)
+	}
+
+	// Compare the two configs
+	if config.Name != config2.Name {
+		t.Errorf("Round-trip Name: expected %q, got %q", config.Name, config2.Name)
+	}
+	if config.Type != config2.Type {
+		t.Errorf("Round-trip Type: expected %q, got %q", config.Type, config2.Type)
+	}
+	if config.Interface != config2.Interface {
+		t.Errorf("Round-trip Interface: expected %q, got %q", config.Interface, config2.Interface)
+	}
+	if config.Port != config2.Port {
+		t.Errorf("Round-trip Port: expected %d, got %d", config.Port, config2.Port)
+	}
+	if config.Target != config2.Target {
+		t.Errorf("Round-trip Target: expected %q, got %q", config.Target, config2.Target)
+	}
+	if config.Description != config2.Description {
+		t.Errorf("Round-trip Description: expected %q, got %q", config.Description, config2.Description)
+	}
+	if config.PersistentKey != config2.PersistentKey {
+		t.Errorf("Round-trip PersistentKey: expected %t, got %t", config.PersistentKey, config2.PersistentKey)
+	}
+
+	// Check that all options were preserved
+	for k, v := range config.I2CP {
+		if v2, ok := config2.I2CP[k]; !ok || fmt.Sprint(v) != fmt.Sprint(v2) {
+			t.Errorf("Round-trip I2CP[%q]: expected %v, got %v", k, v, v2)
+		}
+	}
+
+	t.Logf("Round-trip successful. Generated properties:\n%s", string(output))
+}
+
+func TestPropertiesEdgeCases(t *testing.T) {
+	conv := &Converter{}
+
+	// Test comments and config file paths are ignored
+	input := `# This is a comment
+configFile=/path/to/file
+name=TestTunnel
+# Another comment
+type=client`
+
+	config, err := conv.ParseInput([]byte(input), "properties")
+	if err != nil {
+		t.Fatalf("Failed to parse properties: %v", err)
+	}
+
+	if config.Name != "TestTunnel" {
+		t.Errorf("Expected name 'TestTunnel', got %q", config.Name)
+	}
+	if config.Type != "client" {
+		t.Errorf("Expected type 'client', got %q", config.Type)
+	}
+
+	// Test alternate tunnel destination naming
+	input2 := `name=AltTunnel
+type=server
+targetHost=alt.example.i2p
+i2cpHost=127.0.0.1
+i2cpPort=7654`
+
+	config2, err := conv.ParseInput([]byte(input2), "properties")
+	if err != nil {
+		t.Fatalf("Failed to parse properties: %v", err)
+	}
+
+	if config2.Target != "alt.example.i2p" {
+		t.Errorf("Expected target 'alt.example.i2p', got %q", config2.Target)
+	}
+	if config2.I2CP["host"] != "127.0.0.1" {
+		t.Errorf("Expected I2CP host '127.0.0.1', got %v", config2.I2CP["host"])
+	}
+	if config2.I2CP["port"] != 7654 {
+		t.Errorf("Expected I2CP port 7654, got %v", config2.I2CP["port"])
+	}
+
+	// Test numbered tunnel conflicts (second values should be ignored when flat values exist)
+	input3 := `name=FirstName
+tunnel.0.name=SecondName
+type=client
+tunnel.1.type=server`
+
+	config3, err := conv.ParseInput([]byte(input3), "properties")
+	if err != nil {
+		t.Fatalf("Failed to parse properties: %v", err)
+	}
+
+	// Should keep the first flat value
+	if config3.Name != "FirstName" {
+		t.Errorf("Expected name 'FirstName', got %q", config3.Name)
+	}
+	if config3.Type != "client" {
+		t.Errorf("Expected type 'client', got %q", config3.Type)
+	}
+}
+
+// valuesEqual compares two values, handling slices properly
+func valuesEqual(expected, actual interface{}) bool {
+	return reflect.DeepEqual(expected, actual)
+}