diff --git a/src/Neo.CLI/CLI/MainService.Wallet.cs b/src/Neo.CLI/CLI/MainService.Wallet.cs
index 7c0c197b3..71df6c3ef 100644
--- a/src/Neo.CLI/CLI/MainService.Wallet.cs
+++ b/src/Neo.CLI/CLI/MainService.Wallet.cs
@@ -11,8 +11,10 @@
 
 using Akka.Actor;
 using Neo.ConsoleService;
+using Neo.Cryptography;
 using Neo.Extensions;
 using Neo.Json;
+using Neo.Network.P2P;
 using Neo.Network.P2P.Payloads;
 using Neo.Persistence;
 using Neo.Sign;
@@ -23,7 +25,9 @@
 using Neo.Wallets.NEP6;
 using System.Numerics;
 using System.Security.Cryptography;
+using System.Text;
 using static Neo.SmartContract.Helper;
+using ECCurve = Neo.Cryptography.ECC.ECCurve;
 using ECPoint = Neo.Cryptography.ECC.ECPoint;
 
 namespace Neo.CLI;
@@ -470,8 +474,8 @@ private void OnListKeyCommand()
     /// <summary>
     /// Process "sign" command
     /// </summary>
-    /// <param name="jsonObjectToSign">Json object to sign</param>
-    [ConsoleCommand("sign", Category = "Wallet Commands")]
+    /// <param name="jsonObjectToSign">The json string that records the transaction information</param>
+    [ConsoleCommand("sign transaction", Category = "Wallet Commands")]
     private void OnSignCommand(JObject jsonObjectToSign)
     {
         if (NoWallet()) return;
@@ -503,6 +507,77 @@ private void OnSignCommand(JObject jsonObjectToSign)
         }
     }
 
+    /// <summary>
+    /// Process "sign message" command
+    /// </summary>
+    /// <param name="message">Message to sign</param>
+    [ConsoleCommand("sign message", Category = "Wallet Commands")]
+    private void OnSignMessageCommand(string message)
+    {
+        if (NoWallet()) return;
+
+        string password = ReadUserInput("password", true);
+        if (password.Length == 0)
+        {
+            ConsoleHelper.Info("Cancelled");
+            return;
+        }
+        if (!CurrentWallet!.VerifyPassword(password))
+        {
+            ConsoleHelper.Error("Incorrect password");
+            return;
+        }
+
+        var saltBytes = new byte[16];
+        RandomNumberGenerator.Fill(saltBytes);
+        var saltHex = saltBytes.ToHexString().ToLowerInvariant();
+
+        var paramBytes = Encoding.UTF8.GetBytes(saltHex + message);
+
+        byte[] payload;
+        using (var ms = new MemoryStream())
+        using (var w = new BinaryWriter(ms, Encoding.UTF8, true))
+        {
+            // We add these 4 bytes to prevent the signature from being a valid transaction
+            w.Write((byte)0x01);
+            w.Write((byte)0x00);
+            w.Write((byte)0x01);
+            w.Write((byte)0xF0);
+            // Write the actual message to sign
+            w.WriteVarBytes(paramBytes);
+            // We add these 2 bytes to prevent the signature from being a valid transaction
+            w.Write((ushort)0);
+            w.Flush();
+            payload = ms.ToArray();
+        }
+
+        ConsoleHelper.Info("Signed Payload: ", $"{Environment.NewLine}{payload.ToHexString()}");
+        Console.WriteLine();
+        ConsoleHelper.Info("    Curve: ", "secp256r1");
+        ConsoleHelper.Info("Algorithm: ", "payload = 010001f0 + VarBytes(Salt + Message) + 0000");
+        ConsoleHelper.Info("Algorithm: ", "Sign(SHA256(network || Hash256(payload)))");
+        ConsoleHelper.Info("           ", "See the online documentation for details on how to verify this signature.");
+        ConsoleHelper.Info("           ", "https://developers.neo.org/docs/n3/node/cli/cli#sign_message");
+        Console.WriteLine();
+        ConsoleHelper.Info("Generated signatures:");
+        Console.WriteLine();
+
+        var hash = new UInt256(Crypto.Hash256(payload));
+        var signData = hash.GetSignData(NeoSystem.Settings.Network);
+
+        foreach (WalletAccount account in CurrentWallet.GetAccounts().Where(p => p.HasKey))
+        {
+            var key = account.GetKey();
+            var signature = Crypto.Sign(signData, key!.PrivateKey, ECCurve.Secp256r1);
+
+            ConsoleHelper.Info("    Address: ", account.Address);
+            ConsoleHelper.Info("  PublicKey: ", key.PublicKey.EncodePoint(true).ToHexString());
+            ConsoleHelper.Info("  Signature: ", signature.ToHexString());
+            ConsoleHelper.Info("       Salt: ", saltHex);
+            Console.WriteLine();
+        }
+    }
+
     /// <summary>
     /// Process "send" command
     /// </summary>
@@ -761,4 +836,5 @@ private void SignAndSendTx(DataCache snapshot, Transaction tx)
             ConsoleHelper.Info("Incomplete signature:\n", $"{context}");
         }
     }
+    internal Func<string, bool, string> ReadUserInput { get; set; } = ConsoleHelper.ReadUserInput;
 }
diff --git a/src/Neo.ConsoleService/ConsoleServiceBase.cs b/src/Neo.ConsoleService/ConsoleServiceBase.cs
index a329d1cc0..eb0b46e20 100644
--- a/src/Neo.ConsoleService/ConsoleServiceBase.cs
+++ b/src/Neo.ConsoleService/ConsoleServiceBase.cs
@@ -125,6 +125,7 @@ internal bool OnCommand(string commandLine)
         var possibleHelp = "";
         var tokens = commandLine.Tokenize();
         var availableCommands = new List<(ConsoleCommandMethod Command, object?[] Arguments)>();
+
         foreach (var entries in _verbs.Values)
         {
             foreach (var command in entries)
@@ -133,6 +134,7 @@ internal bool OnCommand(string commandLine)
                 if (consumed <= 0) continue;
 
                 var args = tokens.Skip(consumed).ToList().Trim();
+
                 try
                 {
                     if (args.Any(u => u.IsIndicator))
@@ -170,7 +172,8 @@ internal bool OnCommand(string commandLine)
 
         // Show Ambiguous call
         var ambiguousCommands = availableCommands.Select(u => u.Command.Key).Distinct().ToList();
-        throw new ArgumentException($"Ambiguous calls for: {string.Join(',', ambiguousCommands)}");
+        var ambiguousCommandsQuoted = ambiguousCommands.Select(u => $"'{u}'").ToList();
+        throw new ArgumentException($"Ambiguous calls for: {string.Join(',', ambiguousCommandsQuoted)}");
     }
 
     private bool TryProcessValue(Type parameterType, IList<CommandToken> args, bool consumeAll, out object? value)
diff --git a/tests/Neo.CLI.Tests/TestUtils.cs b/tests/Neo.CLI.Tests/TestUtils.cs
new file mode 100644
index 000000000..1036a5627
--- /dev/null
+++ b/tests/Neo.CLI.Tests/TestUtils.cs
@@ -0,0 +1,32 @@
+// Copyright (C) 2015-2025 The Neo Project.
+//
+// TestUtils.cs file belongs to the neo project and is free
+// software distributed under the MIT software license, see the
+// accompanying file LICENSE in the main directory of the
+// repository or http://www.opensource.org/licenses/mit-license.php
+// for more details.
+//
+// Redistribution and use in source and binary forms with or without
+// modifications are permitted.
+
+using Neo.Json;
+using Neo.Wallets.NEP6;
+
+namespace Neo.CLI.Tests;
+
+public static partial class TestUtils
+{
+    public static NEP6Wallet GenerateTestWallet(string password)
+    {
+        var wallet = new JObject()
+        {
+            ["name"] = "noname",
+            ["version"] = new Version("1.0").ToString(),
+            ["scrypt"] = new ScryptParameters(2, 1, 1).ToJson(),
+            ["accounts"] = new JArray(),
+            ["extra"] = null
+        };
+        Assert.AreEqual("{\"name\":\"noname\",\"version\":\"1.0\",\"scrypt\":{\"n\":2,\"r\":1,\"p\":1},\"accounts\":[],\"extra\":null}", wallet.ToString());
+        return new NEP6Wallet(null, password, TestProtocolSettings.Default, wallet);
+    }
+}
diff --git a/tests/Neo.CLI.Tests/UT_MainService_Wallet.cs b/tests/Neo.CLI.Tests/UT_MainService_Wallet.cs
new file mode 100644
index 000000000..a81b6c55f
--- /dev/null
+++ b/tests/Neo.CLI.Tests/UT_MainService_Wallet.cs
@@ -0,0 +1,189 @@
+// Copyright (C) 2015-2025 The Neo Project.
+//
+// UT_MainService_Wallet.cs file belongs to the neo project and is free
+// software distributed under the MIT software license, see the
+// accompanying file LICENSE in the main directory of the
+// repository or http://www.opensource.org/licenses/mit-license.php
+// for more details.
+//
+// Redistribution and use in source and binary forms with or without
+// modifications are permitted.
+
+using System.Reflection;
+
+namespace Neo.CLI.Tests;
+
+[TestClass]
+public class UT_MainService_Wallet
+{
+    private NeoSystem _neoSystem;
+
+    [TestInitialize]
+    public void TestSetup()
+    {
+        _neoSystem = TestBlockchain.GetSystem();
+    }
+
+    [TestMethod]
+    public void TestOnSignMessageCommand()
+    {
+        var walletPassword = "test_pwd";
+        var output = CreateWalletAngSignMessage(walletPassword);
+
+        // Basic headers
+        Assert.IsFalse(string.IsNullOrWhiteSpace(output), "Output from sign message command should not be empty");
+        Assert.Contains("Signed Payload", output, "Output should containt the signed payload");
+        Assert.Contains("Algorithm", output, "Output should describe the algorithm used");
+        Assert.Contains("Generated signatures", output, "Output should contain signatures header");
+
+        // Sign block
+        Assert.Contains("Address", output, "Output should contain at least one address");
+        Assert.Contains("PublicKey", output, "Output should contain the public key");
+        Assert.Contains("Signature", output, "Output should contain the signature");
+        Assert.Contains("Salt", output, "Output should contain the salt used");
+
+        // Check Salt
+        var salt = ExtractHexValue(output, "Salt:");
+        Assert.IsNotNull(salt, "Salt hex should be present in the output");
+        Assert.AreEqual(32, salt!.Length, "Salt should be 16 bytes (32 hex chars)");
+        Assert.IsTrue(IsHexString(salt!), "Salt should be valid hex");
+    }
+    [TestMethod]
+    public void TestOnSignMessageCommandWithoutPassword()
+    {
+        var output = CreateWalletAngSignMessage(string.Empty);
+
+        Assert.IsFalse(string.IsNullOrWhiteSpace(output), "Output should not be empty");
+        Assert.Contains("Cancelled", output, "Output should contain cancellation message");
+    }
+    [TestMethod]
+    public void TestOnSignMessageCommandWrongPassword()
+    {
+        var walletPassword = "invalid_pwd";
+        var output = CreateWalletAngSignMessage(walletPassword);
+
+        Assert.IsFalse(string.IsNullOrWhiteSpace(output), "Output should not be empty");
+        Assert.Contains("Incorrect password", output, "Output should contain incorrect password");
+        Assert.DoesNotContain("Signed Payload", output, "Output should not containt signed payload");
+        Assert.DoesNotContain("Generated signatures", output, "Output should not containt signatures");
+    }
+    [TestMethod]
+    public void TestOnSignMessageCommandWithoutAccount()
+    {
+        var walletPassword = "test_pwd";
+        var output = CreateWalletAngSignMessage(walletPassword, false);
+
+        Assert.IsFalse(string.IsNullOrWhiteSpace(output), "Output should not be empty");
+        Assert.Contains("Signed Payload", output, "Output should containt signed payload");
+        Assert.Contains("Generated signatures", output, "Output should containt signatures");
+        Assert.DoesNotContain("Address:", output, "Output should not containt Address");
+        Assert.DoesNotContain("PublicKey:", output, "Output should not containt PublicKey");
+        Assert.DoesNotContain("Signature:", output, "Output should not containt Signature");
+        Assert.DoesNotContain("Salt:", output, "Output should not containt Salt");
+    }
+    private string CreateWalletAngSignMessage(string userPassword, bool withAccount = true)
+    {
+        var walletPassword = "test_pwd";
+        var message = "this is a test to sign";
+
+        var wallet = TestUtils.GenerateTestWallet(walletPassword);
+        if (withAccount)
+        {
+            var account = wallet.CreateAccount();
+            Assert.IsNotNull(account, "Wallet.CreateAccount() should create an account");
+        }
+
+        var service = new MainService();
+
+        TrySet(service, "NeoSystem", _neoSystem);
+        TrySetField(service, "_neoSystem", _neoSystem);
+        TrySet(service, "CurrentWallet", wallet);
+        TrySetField(service, "_currentWallet", wallet);
+
+        var readInputProp = service.GetType().GetProperty(
+            "ReadUserInput",
+            BindingFlags.Instance | BindingFlags.Public | BindingFlags.NonPublic);
+
+        Assert.IsNotNull(readInputProp, "ReadUserInput property not found on MainService");
+
+        Func<string, bool, string> fakeReadInput = (label, isPassword) =>
+        {
+            Assert.AreEqual("password", label);
+            Assert.IsTrue(isPassword);
+            return userPassword;
+        };
+
+        readInputProp!.SetValue(service, fakeReadInput);
+
+        var originalOut = Console.Out;
+        using var outputWriter = new StringWriter();
+        Console.SetOut(outputWriter);
+
+        try
+        {
+            InvokeNonPublic(service, "OnSignMessageCommand", message);
+        }
+        finally
+        {
+            Console.SetOut(originalOut);
+        }
+
+        return outputWriter.ToString();
+    }
+    private static string ExtractHexValue(string output, string label)
+    {
+        var index = output.IndexOf(label, StringComparison.OrdinalIgnoreCase);
+        if (index < 0)
+            return null;
+
+        var start = index + label.Length;
+        var endOfLine = output.IndexOfAny(new[] { '\r', '\n' }, start);
+        if (endOfLine < 0)
+            endOfLine = output.Length;
+
+        var value = output[start..endOfLine].Trim();
+        return string.IsNullOrEmpty(value) ? null : value;
+    }
+    private static bool IsHexString(string value)
+    {
+        foreach (var c in value)
+        {
+            var isHex =
+                (c >= '0' && c <= '9') ||
+                (c >= 'a' && c <= 'f') ||
+                (c >= 'A' && c <= 'F');
+
+            if (!isHex) return false;
+        }
+
+        return true;
+    }
+    private static void TrySet(object target, string propertyName, object value)
+    {
+        var prop = target.GetType().GetProperty(
+            propertyName,
+            BindingFlags.Instance | BindingFlags.Public | BindingFlags.NonPublic
+        );
+
+        prop?.SetValue(target, value);
+    }
+    private static void TrySetField(object target, string fieldName, object value)
+    {
+        var field = target.GetType().GetField(
+            fieldName,
+            BindingFlags.Instance | BindingFlags.Public | BindingFlags.NonPublic
+        );
+
+        field?.SetValue(target, value);
+    }
+    private static void InvokeNonPublic(object target, string methodName, params object[] args)
+    {
+        var method = target.GetType().GetMethod(
+            methodName,
+            BindingFlags.Instance | BindingFlags.Public | BindingFlags.NonPublic
+        );
+
+        Assert.IsNotNull(method, $"Method '{methodName}' not found on type '{target.GetType().FullName}'.");
+        method.Invoke(target, args);
+    }
+}