diff --git a/README.md b/README.md
index 1bdea635..54420a1f 100644
--- a/README.md
+++ b/README.md
@@ -68,6 +68,9 @@ Command Options:
     --no-display         Do not start the VNC client app
     --shared-dir <dir>   Share directory with VM (format: path[:ro|rw])
     --mount <path>       For Linux VMs only, attach a read-only disk image
+    --registry <url>     Container registry URL (default: ghcr.io)
+    --organization <org> Organization to pull from (default: trycua)
+    --vnc-port <port>    Port to use for the VNC server (default: 0 for auto-assign)
 
   set:
     --cpu <cores>        New number of CPU cores (e.g., 4)
diff --git a/src/Commands/Run.swift b/src/Commands/Run.swift
index f8faaf4a..a8c9f3ae 100644
--- a/src/Commands/Run.swift
+++ b/src/Commands/Run.swift
@@ -25,6 +25,9 @@ struct Run: AsyncParsableCommand {
     @Option(help: "Organization to pull the images from. Defaults to trycua")
     var organization: String = "trycua"
     
+    @Option(name: [.customLong("vnc-port")], help: "Port to use for the VNC server. Defaults to 0 (auto-assign)")
+    var vncPort: Int = 0
+    
     private var parsedSharedDirectories: [SharedDirectory] {
         get throws {
             try sharedDirectories.map { dirString -> SharedDirectory in
@@ -75,7 +78,8 @@ struct Run: AsyncParsableCommand {
             sharedDirectories: dirs,
             mount: mount,
             registry: registry,
-            organization: organization
+            organization: organization,
+            vncPort: vncPort
         )
     }
 }
\ No newline at end of file
diff --git a/src/Errors/Errors.swift b/src/Errors/Errors.swift
index 15f77954..d52a8e47 100644
--- a/src/Errors/Errors.swift
+++ b/src/Errors/Errors.swift
@@ -125,6 +125,7 @@ enum VMError: Error, LocalizedError {
     case stopTimeout(String)
     case resizeTooSmall(current: UInt64, requested: UInt64)
     case vncNotConfigured
+    case vncPortBindingFailed(requested: Int, actual: Int)
     case internalError(String)
     case unsupportedOS(String)
     case invalidDisplayResolution(String)
@@ -148,6 +149,11 @@ enum VMError: Error, LocalizedError {
             return "Cannot resize disk to \(requested) bytes, current size is \(current) bytes"
         case .vncNotConfigured:
             return "VNC is not configured for this virtual machine"
+        case .vncPortBindingFailed(let requested, let actual):
+            if actual == -1 {
+                return "Could not bind to VNC port \(requested) (port already in use). Try a different port or use port 0 for auto-assign."
+            }
+            return "Could not bind to VNC port \(requested) (port already in use). System assigned port \(actual) instead. Try a different port or use port 0 for auto-assign."
         case .internalError(let message):
             return "Internal error: \(message)"
         case .unsupportedOS(let os):
diff --git a/src/FileSystem/VMConfig.swift b/src/FileSystem/VMConfig.swift
index 98d03a33..7a7144d0 100644
--- a/src/FileSystem/VMConfig.swift
+++ b/src/FileSystem/VMConfig.swift
@@ -25,7 +25,6 @@ struct VMConfig: Codable {
     private var _display: VMDisplayResolution
     private var _hardwareModel: Data?
     private var _machineIdentifier: Data?
-    private var _vncPort: Int?
     
     // MARK: - Initialization
     init(
@@ -36,8 +35,7 @@ struct VMConfig: Codable {
         macAddress: String? = nil,
         display: String,
         hardwareModel: Data? = nil,
-        machineIdentifier: Data? = nil,
-        vncPort: Int? = nil
+        machineIdentifier: Data? = nil
     ) throws {
         self.os = os
         self._cpuCount = cpuCount
@@ -47,7 +45,6 @@ struct VMConfig: Codable {
         self._display = VMDisplayResolution(string: display) ?? VMDisplayResolution(string: "1024x768")!
         self._hardwareModel = hardwareModel
         self._machineIdentifier = machineIdentifier
-        self._vncPort = vncPort
     }
     
     var display: VMDisplayResolution {
@@ -84,11 +81,6 @@ struct VMConfig: Codable {
         get { _macAddress }
         set { _macAddress = newValue }
     }
-
-    var vncPort: Int? {
-        get { _vncPort }
-        set { _vncPort = newValue }
-    }
     
     mutating func setCpuCount(_ count: Int) {
         _cpuCount = count
@@ -118,10 +110,6 @@ struct VMConfig: Codable {
         self._display = newDisplay
     }
 
-    mutating func setVNCPort(_ port: Int) {
-        _vncPort = port
-    }
-
     // MARK: - Codable
     enum CodingKeys: String, CodingKey {
         case _cpuCount = "cpuCount"
@@ -132,7 +120,6 @@ struct VMConfig: Codable {
         case _hardwareModel = "hardwareModel"
         case _machineIdentifier = "machineIdentifier"
         case os
-        case _vncPort = "vncPort"
     }
     
     init(from decoder: Decoder) throws {
@@ -146,7 +133,6 @@ struct VMConfig: Codable {
         _display = VMDisplayResolution(string: try container.decode(String.self, forKey: .display))!
         _hardwareModel = try container.decodeIfPresent(Data.self, forKey: ._hardwareModel)
         _machineIdentifier = try container.decodeIfPresent(Data.self, forKey: ._machineIdentifier)
-        _vncPort = try container.decodeIfPresent(Int.self, forKey: ._vncPort)
     }
     
     func encode(to encoder: Encoder) throws {
@@ -160,6 +146,5 @@ struct VMConfig: Codable {
         try container.encode(display.string, forKey: .display)
         try container.encodeIfPresent(_hardwareModel, forKey: ._hardwareModel)
         try container.encodeIfPresent(_machineIdentifier, forKey: ._machineIdentifier)
-        try container.encodeIfPresent(_vncPort, forKey: ._vncPort)
     }
 }
diff --git a/src/LumeController.swift b/src/LumeController.swift
index 74d22859..b4b04106 100644
--- a/src/LumeController.swift
+++ b/src/LumeController.swift
@@ -255,7 +255,8 @@ final class LumeController {
         sharedDirectories: [SharedDirectory] = [],
         mount: Path? = nil,
         registry: String = "ghcr.io",
-        organization: String = "trycua"
+        organization: String = "trycua",
+        vncPort: Int = 0
     ) async throws {
         let normalizedName = normalizeVMName(name: name)
         Logger.info(
@@ -265,6 +266,7 @@ final class LumeController {
                 "no_display": "\(noDisplay)",
                 "shared_directories": "\(sharedDirectories.map( { $0.string } ).joined(separator: ", "))",
                 "mount": mount?.path ?? "none",
+                "vnc_port": "\(vncPort)",
             ])
 
         do {
@@ -284,7 +286,7 @@ final class LumeController {
 
             let vm = try get(name: normalizedName)
             SharedVM.shared.setVM(name: normalizedName, vm: vm)
-            try await vm.run(noDisplay: noDisplay, sharedDirectories: sharedDirectories, mount: mount)
+            try await vm.run(noDisplay: noDisplay, sharedDirectories: sharedDirectories, mount: mount, vncPort: vncPort)
             Logger.info("VM started successfully", metadata: ["name": normalizedName])
         } catch {
             SharedVM.shared.removeVM(name: normalizedName)
diff --git a/src/VM/VM.swift b/src/VM/VM.swift
index 8e73ed3c..8f79cead 100644
--- a/src/VM/VM.swift
+++ b/src/VM/VM.swift
@@ -88,7 +88,7 @@ class VM {
 
     // MARK: - VM Lifecycle Management
     
-    func run(noDisplay: Bool, sharedDirectories: [SharedDirectory], mount: Path?) async throws {
+    func run(noDisplay: Bool, sharedDirectories: [SharedDirectory], mount: Path?, vncPort: Int = 0) async throws {
         guard vmDirContext.initialized else {
             throw VMError.notInitialized(vmDirContext.name)
         }
@@ -111,7 +111,8 @@ class VM {
             "diskSize": "\(vmDirContext.config.diskSize ?? 0)",
             "sharedDirectories": sharedDirectories.map(
                 { $0.string }
-            ).joined(separator: ", ")
+            ).joined(separator: ", "),
+            "vncPort": "\(vncPort)"
         ])
 
         // Create and configure the VM
@@ -125,7 +126,7 @@ class VM {
             )
             virtualizationService = try virtualizationServiceFactory(config)
             
-            let vncInfo = try await setupVNC(noDisplay: noDisplay)
+            let vncInfo = try await setupVNC(noDisplay: noDisplay, port: vncPort)
             Logger.info("VNC info", metadata: ["vncInfo": vncInfo])
             
             // Start the VM
@@ -337,13 +338,11 @@ class VM {
         return vncService.url
     }
     
-    private func setupVNC(noDisplay: Bool) async throws -> String {
+    private func setupVNC(noDisplay: Bool, port: Int = 0) async throws -> String {
         guard let service = virtualizationService else {
             throw VMError.internalError("Virtualization service not initialized")
         }
         
-        // Use configured port or default to 0 (auto-assign)
-        let port = vmDirContext.config.vncPort ?? 0
         try await vncService.start(port: port, virtualMachine: service.getVirtualMachine())
         
         guard let url = vncService.url else {
@@ -401,13 +400,4 @@ class VM {
     func finalize(to name: String, home: Home) throws {
         try vmDirContext.finalize(to: name)
     }
-
-    // Add method to set VNC port
-    func setVNCPort(_ port: Int) throws {
-        guard !isRunning else {
-            throw VMError.alreadyRunning(vmDirContext.name)
-        }
-        vmDirContext.config.setVNCPort(port)
-        try vmDirContext.saveConfig()
-    }
 } 
\ No newline at end of file
diff --git a/src/VNC/PassphraseGenerator.swift b/src/VNC/PassphraseGenerator.swift
index 9f54ad36..089e97d3 100644
--- a/src/VNC/PassphraseGenerator.swift
+++ b/src/VNC/PassphraseGenerator.swift
@@ -1,4 +1,5 @@
 import Foundation
+import CryptoKit
 
 final class PassphraseGenerator {
     private let words: [String]
@@ -9,11 +10,39 @@ final class PassphraseGenerator {
     
     func prefix(_ count: Int) -> [String] {
         guard count > 0 else { return [] }
-        return (0..<count).map { _ in words.randomElement() ?? words[0] }
+        
+        // Use secure random number generation
+        var result: [String] = []
+        for _ in 0..<count {
+            let randomBytes = (0..<4).map { _ in UInt8.random(in: 0...255) }
+            let randomNumber = Data(randomBytes).withUnsafeBytes { bytes in
+                bytes.load(as: UInt32.self)
+            }
+            let index = Int(randomNumber % UInt32(words.count))
+            result.append(words[index])
+        }
+        return result
     }
     
+    // A much larger set of common, easy-to-type words
     private static let defaultWords = [
-        "apple", "banana", "cherry", "date",
-        "elder", "fig", "grape", "honey"
+        "alpha", "bravo", "charlie", "delta", "echo", "foxtrot", "golf", "hotel",
+        "india", "juliet", "kilo", "lima", "mike", "november", "oscar", "papa",
+        "quebec", "romeo", "sierra", "tango", "uniform", "victor", "whiskey", "xray",
+        "yankee", "zulu", "zero", "one", "two", "three", "four", "five",
+        "six", "seven", "eight", "nine", "apple", "banana", "cherry", "date",
+        "elder", "fig", "grape", "honey", "iris", "jade", "kiwi", "lemon",
+        "mango", "nectarine", "orange", "peach", "quince", "raspberry", "strawberry", "tangerine",
+        "red", "blue", "green", "yellow", "purple", "orange", "pink", "brown",
+        "black", "white", "gray", "silver", "gold", "copper", "bronze", "steel",
+        "north", "south", "east", "west", "spring", "summer", "autumn", "winter",
+        "river", "ocean", "mountain", "valley", "forest", "desert", "island", "beach",
+        "sun", "moon", "star", "cloud", "rain", "snow", "wind", "storm",
+        "happy", "brave", "calm", "swift", "wise", "kind", "bold", "free",
+        "safe", "strong", "bright", "clear", "light", "soft", "warm", "cool",
+        "eagle", "falcon", "hawk", "owl", "robin", "sparrow", "swan", "dove",
+        "tiger", "lion", "bear", "wolf", "deer", "horse", "dolphin", "whale",
+        "maple", "oak", "pine", "birch", "cedar", "fir", "palm", "willow",
+        "rose", "lily", "daisy", "tulip", "lotus", "orchid", "violet", "jasmine"
     ]
 }
\ No newline at end of file
diff --git a/src/VNC/VNCService.swift b/src/VNC/VNCService.swift
index 8ec3b2b8..971ab011 100644
--- a/src/VNC/VNCService.swift
+++ b/src/VNC/VNCService.swift
@@ -42,25 +42,45 @@ final class DefaultVNCService: VNCService {
         
         vncServer = server
         
-        // Wait for port to be assigned if using port 0 (auto-assign)
-        while port == 0 {
-            if let assignedPort: UInt16 = server.port.asUInt16, assignedPort != 0 {
-                // Get the local IP address for the URL - prefer IPv4
-                let hostIP = try getLocalIPAddress() ?? "127.0.0.1"
-                let url = "vnc://:\(password)@127.0.0.1:\(assignedPort)"  // Use localhost for local connections
-                let externalUrl = "vnc://:\(password)@\(hostIP):\(assignedPort)"  // External URL for remote connections
-                
-                Logger.info("VNC server started", metadata: [
-                    "local": url,
-                    "external": externalUrl
-                ])
-                
-                // Save session information with local URL for the client
-                let session = VNCSession(url: url)
-                try vmDirectory.saveSession(session)
-                break
+        // Wait for port to be assigned (both for auto-assign and specific port)
+        var attempts = 0
+        let maxAttempts = 20  // 1 second total wait time
+        while true {
+            if let assignedPort: UInt16 = server.port.asUInt16 {
+                // If we got a non-zero port, check if it matches our request
+                if assignedPort != 0 {
+                    // For specific port requests, verify we got the requested port
+                    if port != 0 && Int(assignedPort) != port {
+                        throw VMError.vncPortBindingFailed(requested: port, actual: Int(assignedPort))
+                    }
+                    
+                    // Get the local IP address for the URL - prefer IPv4
+                    let hostIP = try getLocalIPAddress() ?? "127.0.0.1"
+                    let url = "vnc://:\(password)@127.0.0.1:\(assignedPort)"  // Use localhost for local connections
+                    let externalUrl = "vnc://:\(password)@\(hostIP):\(assignedPort)"  // External URL for remote connections
+                    
+                    Logger.info("VNC server started", metadata: [
+                        "local": url,
+                        "external": externalUrl
+                    ])
+                    
+                    // Save session information with local URL for the client
+                    let session = VNCSession(url: url)
+                    try vmDirectory.saveSession(session)
+                    break
+                }
             }
-            try await Task.sleep(nanoseconds: 50_000_000)
+            
+            attempts += 1
+            if attempts >= maxAttempts {
+                // If we've timed out and we requested a specific port, it likely means binding failed
+                vncServer = nil
+                if port != 0 {
+                    throw VMError.vncPortBindingFailed(requested: port, actual: -1)
+                }
+                throw VMError.internalError("Timeout waiting for VNC server to start")
+            }
+            try await Task.sleep(nanoseconds: 50_000_000)  // 50ms delay between checks
         }
     }
     
diff --git a/tests/Mocks/MockVM.swift b/tests/Mocks/MockVM.swift
index cad394d2..3ff2d0e7 100644
--- a/tests/Mocks/MockVM.swift
+++ b/tests/Mocks/MockVM.swift
@@ -18,9 +18,9 @@ class MockVM: VM {
         try vmDirContext.saveConfig()
     }
     
-    override func run(noDisplay: Bool, sharedDirectories: [SharedDirectory], mount: Path?) async throws {
+    override func run(noDisplay: Bool, sharedDirectories: [SharedDirectory], mount: Path?, vncPort: Int = 0) async throws {
         mockIsRunning = true
-        try await super.run(noDisplay: noDisplay, sharedDirectories: sharedDirectories, mount: mount)
+        try await super.run(noDisplay: noDisplay, sharedDirectories: sharedDirectories, mount: mount, vncPort: vncPort)
     }
     
     override func stop() async throws {
diff --git a/tests/VMTests.swift b/tests/VMTests.swift
index d197806e..50961a9a 100644
--- a/tests/VMTests.swift
+++ b/tests/VMTests.swift
@@ -95,7 +95,7 @@ func testVMRunAndStop() async throws {
     
     // Test running VM
     let runTask = Task {
-        try await vm.run(noDisplay: false, sharedDirectories: [], mount: nil)
+        try await vm.run(noDisplay: false, sharedDirectories: [], mount: nil, vncPort: 0)
     }
     
     // Give the VM time to start