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Add support for SSH private key passphrase #73

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Add support for SSH private key passphrase #73

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Copilot AI commented Oct 20, 2025 •
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This PR implements comprehensive support for SSH private key passphrases, addressing issue requirements for automatic detection, secure caching, and user prompting.

Problem

The extension previously failed when users had password-protected SSH private keys, as it attempted to load keys without providing passphrases. This prevented developers from using encrypted SSH keys for secure remote debugging.

Solution

Automatic Encryption Detection

Implemented robust detection for encrypted SSH keys supporting both traditional PEM and modern OpenSSH formats:

// Detects traditional PEM format
if (keyContent.Contains("ENCRYPTED") || keyContent.Contains("Proc-Type: 4,ENCRYPTED"))
    return true;

// Detects OpenSSH format with base64-encoded algorithms
if (keyContent.Contains("CmFlczI1Ni1jdHI"))  // aes256-ctr
    return true;

Secure Passphrase Management

Created a singleton service that securely manages passphrases using SecureString with proper disposal patterns:

private readonly ConcurrentDictionary<string, SecureString> passphraseCache = new();

public void ClearCachedPassphrase(string privateKeyFilePath)
{
    if (passphraseCache.TryRemove(normalizedPath, out var securePassphrase))
    {
        securePassphrase?.Dispose();
    }
}

User Experience

Added a clean WPF dialog that prompts users for passphrases when needed, with validation and clear messaging. Passphrases are cached for the Visual Studio session lifetime, so users only need to enter them once per solution load.

Error Handling

Enhanced the SSH client creation logic to gracefully handle encryption detection and fallback scenarios:

try
{
    return new PrivateKeyFile(privateKeyFilePath);
}
catch (Exception ex) when (ex is InvalidOperationException || ex is SshException)
{
    if (SecureShellKeyUtilities.IsPrivateKeyEncrypted(privateKeyFilePath))
    {
        // Prompt for passphrase and retry
    }
}

Key Features

  • Automatic Detection: No user configuration required - automatically detects encrypted keys
  • Session Caching: Passphrases cached securely until Visual Studio closes
  • Multiple Formats: Supports RSA, Ed25519, ECDSA keys in both PEM and OpenSSH formats
  • Security: Uses SecureString for in-memory protection with proper disposal
  • Backward Compatibility: Zero impact on existing unencrypted key workflows

Testing

Added comprehensive unit tests for encryption detection and manual verification with real SSH keys. The implementation correctly identifies encrypted vs unencrypted keys across multiple formats and handles edge cases gracefully.

This change enables developers to use industry-standard encrypted SSH keys while maintaining the extension's ease of use and security best practices.

Warning

Firewall rules blocked me from connecting to one or more addresses (expand for details)

I tried to connect to the following addresses, but was blocked by firewall rules:

  • 0psvsblobprodwus2145.vsblob.vsassets.io
    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: dotnet build --verbosity quiet (dns block)
    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
  • 77wvsblobprodwus2160.vsblob.vsassets.io
    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: dotnet build --verbosity quiet (dns block)
    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: dotnet build --verbosity quiet (dns block)
    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: dotnet build --verbosity quiet (dns block)
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    • Triggering command: /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/.dotnet/dotnet restore --no-dependencies /home/REDACTED/work/RemoteDebuggerLaunchExtension/RemoteDebuggerLaunchExtension/RemoteDebuggerLauncherExtension.sln --packages /home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/packages /p:DisableImplicitNuGetFallbackFolder=true --verbosity normal /p:TargetFrameworkRootPath=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot /p:NetCoreTargetingPackRoot=/home/REDACTED/work/RemoteDebuggerLaunchExtension/.codeql-scratch/dbs/csharp/working/emptyFakeDotnetRoot (dns block)
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    • Triggering command: dotnet build --verbosity quiet (dns block)
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    • Triggering command: dotnet build --verbosity quiet (dns block)
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    • Triggering command: dotnet build --verbosity quiet (dns block)
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Original prompt

This section details on the original issue you should resolve

<issue_title>Add support for SSH private key passphrase</issue_title>
<issue_description>As a developer I want to protect my SSH private key with a passphrase.
The extension shall detect that the private key is protected and ask for the passphrase.

  • The shall be cached for the time the visual studio solution is loaded.
  • The passphrase shall be kept secure while in memory</issue_description>

Comments on the Issue (you are @copilot in this section)

Fixes #16

✨ Let Copilot coding agent set things up for you — coding agent works faster and does higher quality work when set up for your repo.

Copilot AI and others added 5 commits October 20, 2025 15:00
@MichaelKoster70
Add SSH private key passphrase support infrastructure
f58648f 
Co-authored-by: MichaelKoster70 <12211710+MichaelKoster70@users.noreply.github.com>
@MichaelKoster70
Improve SSH passphrase handling with better error detection and lifec…
1a3542a 
…ycle management

Co-authored-by: MichaelKoster70 <12211710+MichaelKoster70@users.noreply.github.com>
@MichaelKoster70
Fix code review issues: proper SecureString disposal and remove fragi…
265a508 
…le exception matching

Co-authored-by: MichaelKoster70 <12211710+MichaelKoster70@users.noreply.github.com>
@MichaelKoster70
Fix SSH key encryption detection with proper base64 algorithm matching
d3d98da 
Co-authored-by: MichaelKoster70 <12211710+MichaelKoster70@users.noreply.github.com>
@MichaelKoster70
Final code review fixes: improve robustness of none pattern counting …
04b3156 
…and add explanatory comments

Co-authored-by: MichaelKoster70 <12211710+MichaelKoster70@users.noreply.github.com>
Copilot AI changed the title [WIP] Add support for SSH private key passphrase Add support for SSH private key passphrase Oct 20, 2025
Copilot AI requested a review from MichaelKoster70 October 20, 2025 15:21
Copilot finished work on behalf of MichaelKoster70 October 20, 2025 15:21
MichaelKoster70
MichaelKoster70 requested changes Oct 20, 2025
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src/Extension/RemoteDebuggerLauncher/RemoteOperations/SecureShellPassphraseDialog.xaml Outdated
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@MichaelKoster70 MichaelKoster70 Oct 20, 2025

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Move this and all UI related files to RemoteDebuggerLauncherUI

src/Extension/RemoteDebuggerLauncher/RemoteOperations/SecureShellPassphraseDialog.xaml.cs Outdated
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@MichaelKoster70 MichaelKoster70 Oct 20, 2025

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Move to the RemoteDebuggerLauncherUI project

MichaelKoster70
MichaelKoster70 requested changes Oct 20, 2025
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src/Extension/RemoteDebuggerLauncher/RemoteOperations/SecureShellPassphraseDialog.xaml Outdated
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@MichaelKoster70 MichaelKoster70 Oct 20, 2025

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Use the MVVM pattern as in all the other dialogs

@MichaelKoster70 MichaelKoster70 marked this pull request as ready for review October 20, 2025 16:56
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@MichaelKoster70 MichaelKoster70 MichaelKoster70 requested changes

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Add support for SSH private key passphrase

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@MichaelKoster70