- ssh-config-key-management: add Windows OpenSSH admin user key auth section (administrators_authorized_keys, BOM-free writing, ACL requirements) - windows-openssh-wsl-default-shell: add bash.exe as recommended fix (Option 1), demote PowerShell to Option 2, add shell-not-found diagnostic tip - windows-sshd-stops-after-reboot: fix stale wsl.exe reference to bash.exe - index/README: update Recently Updated table and article descriptions Co-Authored-By: Claude Opus 4.6 (1M context) <noreply@anthropic.com>
185 lines
6.2 KiB
Markdown
185 lines
6.2 KiB
Markdown
---
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title: SSH Config and Key Management
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domain: linux
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category: networking
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tags:
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- ssh
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- keys
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- security
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- linux
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- remote-access
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status: published
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created: 2026-03-08
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updated: 2026-04-07T21:55
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---
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# SSH Config and Key Management
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SSH is how you get into remote servers. Key-based authentication is safer than passwords and, once set up, faster too. The `~/.ssh/config` file is what turns SSH from something you type long commands for into something that actually works the way you want.
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## The Short Answer
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```bash
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# Generate a key (use ed25519 — it's faster and more secure than RSA now)
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ssh-keygen -t ed25519 -C "yourname@hostname"
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# Copy the public key to a server
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ssh-copy-id user@server-ip
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# SSH using a specific key
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ssh -i ~/.ssh/id_ed25519 user@server-ip
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```
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## Key Generation
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```bash
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# ed25519 — preferred
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ssh-keygen -t ed25519 -C "home-laptop"
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# RSA 4096 — use this if the server is old and doesn't support ed25519
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ssh-keygen -t rsa -b 4096 -C "home-laptop"
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```
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The `-C` comment is just a label — use something that tells you which machine the key came from. Comes in handy when you look at `authorized_keys` on a server and need to know what's what.
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Keys land in `~/.ssh/`:
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- `id_ed25519` — private key. **Never share this.**
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- `id_ed25519.pub` — public key. This is what you put on servers.
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## Copying Your Key to a Server
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```bash
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# Easiest way
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ssh-copy-id user@server-ip
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# If the server is on a non-standard port
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ssh-copy-id -p 2222 user@server-ip
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# Manual way (if ssh-copy-id isn't available)
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cat ~/.ssh/id_ed25519.pub | ssh user@server-ip "mkdir -p ~/.ssh && cat >> ~/.ssh/authorized_keys"
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```
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After copying, test that key auth works before doing anything else, especially before disabling password auth.
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## SSH Config File
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`~/.ssh/config` lets you define aliases for servers so you can type `ssh myserver` instead of `ssh -i ~/.ssh/id_ed25519 -p 2222 admin@192.168.1.50`.
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```
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# ~/.ssh/config
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# Home server
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Host homelab
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HostName 192.168.1.50
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User admin
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IdentityFile ~/.ssh/id_ed25519
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Port 22
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# Remote VPS
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Host vps
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HostName vps.yourdomain.com
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User ubuntu
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IdentityFile ~/.ssh/vps_key
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Port 2222
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# Jump host pattern — SSH through a bastion to reach internal servers
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Host internal-server
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HostName 10.0.0.50
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User admin
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ProxyJump bastion.yourdomain.com
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# Default settings for all hosts
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Host *
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ServerAliveInterval 60
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ServerAliveCountMax 3
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IdentityFile ~/.ssh/id_ed25519
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```
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After saving, `ssh homelab` connects with all those settings automatically.
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## Managing Multiple Keys
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One key per machine you connect from is reasonable. One key per server you connect to is overkill for personal use but correct for anything sensitive.
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```bash
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# List keys loaded in the SSH agent
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ssh-add -l
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# Add a key to the agent (so you don't type the passphrase every time)
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ssh-add ~/.ssh/id_ed25519
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# On macOS, persist the key in Keychain
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ssh-add --apple-use-keychain ~/.ssh/id_ed25519
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```
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The SSH agent stores decrypted keys in memory for the session. You enter the passphrase once and the agent handles authentication for the rest of the session.
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## Server-Side: Authorized Keys
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Public keys live in `~/.ssh/authorized_keys` on the server. One key per line.
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```bash
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# Check permissions — wrong permissions break SSH key auth silently
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chmod 700 ~/.ssh
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chmod 600 ~/.ssh/authorized_keys
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```
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If key auth isn't working and the config looks right, permissions are the first thing to check.
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## Gotchas & Notes
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- **Permissions must be right.** SSH ignores `authorized_keys` if the file or directory is world-writable. `chmod 700 ~/.ssh` and `chmod 600 ~/.ssh/authorized_keys` are required.
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- **ed25519 over RSA.** ed25519 keys are shorter, faster, and currently considered more secure. Use them unless you have a compatibility reason not to.
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- **Add a passphrase to your private key.** If your machine is compromised, an unprotected private key gives the attacker access to everything it's authorized on. A passphrase mitigates that.
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- **`ServerAliveInterval` in your config** keeps connections from timing out on idle sessions. Saves you from the annoyance of reconnecting after stepping away.
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- **Never put private keys in cloud storage, Git repos, or Docker images.** It happens more than you'd think.
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## Windows OpenSSH: Admin User Key Auth
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Windows OpenSSH has a separate key file for users in the `Administrators` group. Regular `~/.ssh/authorized_keys` is **ignored** for admin users unless the `Match Group administrators` block in `sshd_config` is disabled.
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### Where keys go
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| User type | Key file |
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|---|---|
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| Regular user | `C:\Users\<user>\.ssh\authorized_keys` |
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| Admin user | `C:\ProgramData\ssh\administrators_authorized_keys` |
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### Setup (elevated PowerShell)
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1. **Enable the Match block** in `C:\ProgramData\ssh\sshd_config` — both lines must be uncommented:
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```
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Match Group administrators
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AuthorizedKeysFile __PROGRAMDATA__/ssh/administrators_authorized_keys
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```
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2. **Write the key file without BOM** — PowerShell 5 defaults to UTF-16LE or UTF-8 with BOM, both of which OpenSSH silently rejects:
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```powershell
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[System.IO.File]::WriteAllText(
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"C:\ProgramData\ssh\administrators_authorized_keys",
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"ssh-ed25519 AAAA... user@hostname`n",
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[System.Text.UTF8Encoding]::new($false)
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)
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```
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3. **Lock down permissions** — OpenSSH requires strict ACLs:
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```powershell
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icacls "C:\ProgramData\ssh\administrators_authorized_keys" /inheritance:r /grant "SYSTEM:(F)" /grant "Administrators:(F)"
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```
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4. **Restart sshd:**
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```powershell
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Restart-Service sshd
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```
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### Troubleshooting
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- If key auth silently fails, check `Get-WinEvent -LogName OpenSSH/Operational -MaxEvents 10`
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- Common cause: BOM in the key file or `sshd_config` — PowerShell file-writing commands are the usual culprit
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- If the log says `User not allowed because shell does not exist`, the `DefaultShell` registry path is wrong — see [WSL default shell troubleshooting](../../05-troubleshooting/networking/windows-openssh-wsl-default-shell-breaks-remote-commands.md)
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## See Also
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- [linux-server-hardening-checklist](../../02-selfhosting/security/linux-server-hardening-checklist.md)
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- [managing-linux-services-systemd-ansible](../process-management/managing-linux-services-systemd-ansible.md)
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