When transitioning from Windows to macOS for system administration, finding a proper WinSCP replacement becomes critical. WinSCP's killer features were:

• SCP/SFTP file transfers with persistent connections
• Integrated text editor with auto-sync on save
• Transparent sudo elevation for editing protected files
• GUI convenience without terminal gymnastics

After testing 15+ apps, these stand out for technical users:

1. ForkLift (Best All-Around)

The Swiss Army knife for macOS file management with advanced remote capabilities:

# Sample ForkLift remote connection setup:
{
  "name": "Production Server",
  "host": "192.168.1.100",
  "protocol": "sftp",
  "port": 22,
  "username": "admin",
  "authentication": "keyfile",
  "privateKey": "/Users/me/.ssh/id_rsa",
  "remotePath": "/var/www/html"
}

2. Transmit (Best for Power Users)

Panic's Transmit offers superior sudo integration through its "Elevate" feature:

# Transmit's sudo workflow:
1. Connect via SFTP as regular user
2. Right-click → "Elevate" → Enter sudo password
3. Edit /etc/nginx/nginx.conf directly
4. Changes save with correct permissions

3. Cyberduck (Best Free Option)

While open-source, it requires CLI workarounds for sudo:

# Cyberduck workaround:
$ sudo chown $USER /etc/hosts
# Edit file in Cyberduck
$ sudo chown root /etc/hosts

For true WinSCP-like behavior, combine these tools with:

SSH Config Snippets

Host production
  HostName server.example.com
  User deploy
  IdentityFile ~/.ssh/production_key
  RemoteForward 52698 127.0.0.1:52698

Automated Permission Handling

#!/bin/bash
# pre-edit.sh
TARGET_FILE="$1"
BACKUP_OWNER=$(stat -f "%Su" "$TARGET_FILE")
sudo chown $USER "$TARGET_FILE"

Pair with a corresponding post-edit script to restore permissions.

For developers preferring their own editors:

VSCode Remote-SSH Extension

// settings.json
{
  "remote.SSH.showLoginTerminal": true,
  "remote.SSH.enableRemoteCommand": true,
  "remote.SSH.remotePlatform": {
    "production-server": "linux"
  }
}

sshfs + Local Editor

# Mount remote filesystem with sudo access
sshfs -o allow_other,defer_permissions user@host:/remote/path /local/mount
# Edit with Sublime Text/Atom/VSCode
# Unmount when done
umount /local/mount

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After switching from Windows to macOS for system administration, finding a proper GUI SCP client with sudo capabilities becomes critical. WinSCP's perfect combination of these features makes it particularly hard to replace:

• SCP/SFTP file transfer with automatic sync
• Built-in text editor with syntax highlighting
• Transparent sudo file editing without manual chown
• Session management and GUI convenience

1. ForkLift (Premium)

# Example of setting up ForkLift for sudo operations:
1. Install ForkLift from App Store
2. Configure SFTP connection with admin credentials
3. Enable "Use sudo for remote operations" in Preferences
4. When editing protected files, it will automatically prompt for sudo password

Key advantages:

• Dual-pane file manager with SCP/SFTP support
• Mount remote directories as local volumes
• Scriptable through AppleScript

2. Cyberduck (Free + Paid CLI)

# Using Cyberduck CLI for automated sudo operations:
duck --username admin --password pass --sudo sftp://example.com/path/to/file

Notable features:

• Open source base with commercial extensions
• Integrated with external editors like BBEdit/VSCode
• Supports bookmarking and connection profiles

3. Transmit (Premium with Free Trial)

The most professional option with advanced features:

• Full sudo support through "Edit as Administrator" context menu
• Delta sync for efficient large file transfers
• Deep integration with macOS Keychain

For apps without built-in sudo support, consider these technical solutions:

# SSH config snippet for transparent sudo:
Host myserver
    HostName example.com
    User myuser
    RemoteCommand echo "mypassword" | sudo -S cat /dev/null && /bin/bash -l
    RequestTTY force

Or mount remote filesystems locally using sshfs:

# Mount remote directory with sudo access:
sshfs -o allow_other,defer_permissions user@host:/remote/path /local/mountpoint

For developers preferring their own editors (VSCode, Sublime, etc.):

# VSCode SFTP extension config example:
{
    "name": "Production Server",
    "host": "example.com",
    "protocol": "sftp",
    "port": 22,
    "username": "user",
    "remotePath": "/var/www/",
    "uploadOnSave": true,
    "sudo": true,
    "sudoPassword": "mypassword"
}

Remember to never store plaintext passwords - use SSH keys and macOS Keychain whenever possible.