Cannot Pair Visual Studio on Windows with Mac via SSH for Xamarin/iOS Build

Question

I'm trying to pair Visual Studio 2022 (Windows) with a Mac for building a .NET MAUI or Xamarin.iOS project. I have full terminal access on the Mac, and I've already enabled Remote Login (SSH) on it. I can successfully connect from Windows terminal using:

ssh [email protected].###.###

What I've done:

Generated SSH keys on Windows via: ssh-keygen -t rsa -b 4096.
Copied the public key (id_rsa.pub) into ~/.ssh/authorized_keys on the Mac using nano.
Set permissions:
- chmod 700 ~/.ssh
- chmod 600 ~/.ssh/authorized_keys
Verified the key is in place and correctly formatted.
Ran ssh -v [email protected].###.### — it authenticates with the key, no password needed.

The problem is that Visual Studio still fails to pair with the Mac.

It shows: Error: An error occurred while generating the SSH keys. Please check that the environment is properly configured. Sometimes, it fails silently with no pairing success after "Add Mac."

Polyariz · Accepted Answer · 2025-07-06 18:26:17Z

Problem: Visual Studio 2022 fails to pair with Mac running macOS Ventura/Sonoma/Sequoia with error "An error occurred while generating the SSH keys" even though manual SSH connection works.

Root Cause

Modern macOS versions use OpenSSH 9.0+ which disabled RSA SHA-1 signatures by default, breaking Visual Studio's SSH key generation.

Solution: Manual SSH Key Generation

On Mac:

Enable Remote Login: System Settings → General → Sharing → Remote Login (ON)
Generate compatible SSH keys:

ssh-keygen -t ecdsa -b 521 -f ./id_ecdsa -q
# Enter a passphrase when prompted (required!)

On Windows:

rmdir /s /q "%LOCALAPPDATA%\Xamarin\MonoTouch"
# Create .ssh folder if it doesn't exist
if not exist "C:\Users\%USERNAME%\.ssh" mkdir "C:\Users\%USERNAME%\.ssh"
# Copy both id_ecdsa and id_ecdsa.pub from Mac to this folder

Restart Visual Studio and try pairing. VS will prompt for Mac credentials and SSH passphrase.

If you get dotnet runtime error after SSH connects:

# On Mac, install .NET SDK
brew install --cask dotnet

The manual ECDSA key generation bypasses Visual Studio's broken RSA key generation and works with modern macOS SSH servers.

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Cannot Pair Visual Studio on Windows with Mac via SSH for Xamarin/iOS Build

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Root Cause

Solution: Manual SSH Key Generation

If you get dotnet runtime error after SSH connects:

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Collectives™ on Stack Overflow

1 Answer 1

Root Cause

Solution: Manual SSH Key Generation

If you get dotnet runtime error after SSH connects:

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