1password-tailscale

name	1password-tailscale
description	Use when SSHing into remote machines, looking up credentials, renaming Tailscale devices, or accessing services on the tailnet. Symptoms - SSH auth failures, too many authentication failures, command not found tailscale, need to find credentials for remote machines.

1Password + Tailscale System

Infra config: Machine names, IPs, and credentials come from ~/.claude/infra.toml. See ~/.claude/infra.toml.example for the template. Load vars in scripts with source ~/.claude/skills/lib/infra-load.sh.

Overview

Joe's infrastructure uses 1Password CLI (op) for credential management and Tailscale for networking between machines. SSH is configured to use the 1Password agent, which introduces specific quirks that must be handled correctly.

Quick Reference

Tailscale CLI

The tailscale command is available two ways:

Method	Path	Notes
App Store app	/Applications/Tailscale.app/Contents/MacOS/Tailscale	Always available on macOS machines. tailscale ssh NOT available on App Store builds.
Homebrew CLI	tailscale (in PATH)	Installed on $INFRA_DEV_HOST. Provides tailscale ssh if using standalone build.

QUIRK: The bare tailscale command may not be in PATH on remote macOS machines. Always try the full app path as fallback:

# Try short form first, fall back to app path
tailscale status 2>/dev/null || /Applications/Tailscale.app/Contents/MacOS/Tailscale status

Common Tailscale Operations

# View all devices
tailscale status

# Rename a device (run ON that device)
tailscale set --hostname=new-name

# Get detailed info (tailnet name, self info)
tailscale status --json | python3 -c "import sys,json; d=json.load(sys.stdin); print(d.get('MagicDNSSuffix',''))"

1Password CLI

Accounts

Joe has two 1Password accounts:

Account	Use
$INFRA_OP_PERSONAL	Personal — SSH keys, machine credentials, personal services
toptal.1password.com	Work — work-related credentials

IMPORTANT: Always specify --account=$INFRA_OP_PERSONAL for infrastructure/machine credentials. The default account may be the work one.

Vaults (Personal Account)

Vault	Contents
Personal	General credentials, some SSH keys
cli	SSH keys, API credentials, programmatic access items

QUIRK: Items may be in either vault. If you can't find an item, search without vault filter first:

op item list --account=$INFRA_OP_PERSONAL

Then check which vault it's in:

op item get "<item-name>" --account=$INFRA_OP_PERSONAL --format=json | python3 -c "import sys,json; print(json.load(sys.stdin).get('vault',{}).get('name',''))"

Finding Credentials

Search by keyword — item titles don't always match device names:

op item list --account=$INFRA_OP_PERSONAL --format=json | python3 -c "
import sys,json
items=json.load(sys.stdin)
for i in items:
    title = i.get('title','').lower()
    if any(k in title for k in ['keyword1','keyword2']):
        print(f\"{i['title']} ({i.get('category','')}) [{i.get('id','')}]\")
"

Extracting SSH Private Keys

CRITICAL QUIRK: op read outputs SSH keys in a format that ssh -i rejects ("invalid format" or "Load key: invalid format"). You MUST extract keys via JSON:

# ❌ WRONG — produces invalid key format
op read "op://vault/item/private key" > /tmp/key

# ✅ CORRECT — extract via JSON with --reveal
op item get "<item-id>" --account=$INFRA_OP_PERSONAL --reveal --format=json | python3 -c "
import sys, json
item = json.load(sys.stdin)
for f in item.get('fields', []):
    if f.get('label') == 'private key':
        print(f.get('value', ''))
" > /tmp/key
chmod 600 /tmp/key

Always clean up temp key files after use:

rm -f /tmp/key

SSH with 1Password Agent

The "Too Many Authentication Failures" Problem

The 1Password SSH agent offers ALL stored SSH keys to the server. If you have many keys (Joe has 5+), the server rejects the connection before finding the right one.

Fix: Bypass the 1Password agent and specify the key directly:

ssh -o IdentitiesOnly=yes -o IdentityAgent=none -i /path/to/extracted/key user@host "command"

SSH Config

The global SSH config routes all connections through 1Password:

Host *
    IdentityAgent "~/Library/Group Containers/2BUA8C4S2C.com.1password/t/agent.sock"

This is why -o IdentityAgent=none is needed when using a specific key file.

Password-Based SSH

For machines that use password auth, use sshpass (installed via Homebrew):

sshpass -p 'password' ssh -o IdentitiesOnly=yes -o IdentityAgent=none user@host "command"

For commands requiring sudo:

sshpass -p 'password' ssh -o IdentitiesOnly=yes -o IdentityAgent=none user@host "sudo -S command" <<< 'password'

Known 1Password Items (Dotfiles)

Item	Vault	Use
age-key-dotfiles	cli	age private key for sops secrets in the dotfiles repo — auto-restored to ~/.config/sops/age/keys.txt by setup-secrets.sh if missing

To manually restore or back up the age key:

# Restore key from 1Password
op item get "age-key-dotfiles" --account=$INFRA_OP_PERSONAL --fields notesPlain > ~/.config/sops/age/keys.txt
chmod 600 ~/.config/sops/age/keys.txt

# Save updated key to 1Password (creates new item)
op item create --category "Secure Note" --title "age-key-dotfiles" \
  "notesPlain=$(cat ~/.config/sops/age/keys.txt)" --account=$INFRA_OP_PERSONAL

Machine Credentials

Known Machines

Machine	Tailscale IP	SSH User	Auth Method	1Password Item
$INFRA_MAC_MINI_HOST	(see infra.toml)	$INFRA_MAC_MINI_USER	SSH key (1Password agent)	"rentamac" (secure note), "Rent a Mac" (login)
$INFRA_VPS_HOST	$INFRA_VPS_IP	$INFRA_VPS_USER	Password	$INFRA_VPS_OP_ITEM (login, Personal vault)
$INFRA_DEV_HOST	$INFRA_DEV_IP	$INFRA_DEV_USER	Local	N/A

Connecting to Each Machine

$INFRA_MAC_MINI_HOST:

ssh $INFRA_MAC_MINI_USER@$INFRA_MAC_MINI_ADDR "command"

$INFRA_VPS_HOST:

source ~/.claude/skills/lib/infra-load.sh
sshpass -p "$(op item get $INFRA_VPS_OP_ITEM --account=$INFRA_OP_PERSONAL --fields password --reveal)" \
  ssh -o IdentitiesOnly=yes -o IdentityAgent=none -o PreferredAuthentications=password \
  $INFRA_VPS_USER@$INFRA_VPS_IP "command"

op run on m5-max: Shell Env Has Mixed op:// References

CRITICAL: The shell environment on $INFRA_DEV_HOST has many op:// references already set (ANTHROPIC_API_KEY, OPENAI_API_KEY, FIRECRAWL_API_KEY, etc. — all pointing to Personal or cli vaults in $INFRA_OP_PERSONAL). When you run op run --account=toptal.1password.com, it tries to resolve ALL op:// references in the current environment, including those personal vault ones — and fails.

Rule: Always use --account=$INFRA_OP_PERSONAL with --env-file=~/.secrets. Never use the toptal account from an interactive shell — the shell env and ~/.secrets only reference personal vaults.

~/.secrets is the canonical op:// env file — all cli and Personal vault references, no work vault refs.

# ✅ CORRECT — personal account + ~/.secrets
op run --account=$INFRA_OP_PERSONAL --env-file=~/.secrets -- <command>

# ❌ WRONG — toptal account can't resolve op://Personal/... or op://cli/... refs
op run --account=toptal.1password.com --env-file some.env -- <command>

If a tool has its own .env with op://Employee/... (toptal vaults), ignore it — the equivalent key is already in ~/.secrets pointing to the personal vault.

direnv + op run: How Shell Env Is Loaded

The shell env on $INFRA_DEV_HOST is loaded by direnv via /Users/joe/dev/.envrc (and per-project .envrc files that call source_up). The parent .envrc runs op run --account=$INFRA_OP_PERSONAL --env-file=~/.secrets -- env and exports all resolved secrets into the shell.

~/.secrets is the canonical secret file — op:// references for all CLI/Personal vault keys. When you need a secret available in shell (and therefore in mise run, uv run, etc.), it must be in ~/.secrets.

ANTHROPIC_API_KEY — canonical reference

ANTHROPIC_API_KEY="op://Personal/<api-key-item>/ANTHROPIC_API_KEY"

QUIRK: The cli vault has an item called Anthropic API Key whose credential field contains sk-ant-oat01-... — an OAuth token, not an API key. This resolves successfully via op run but is rejected by the Anthropic API with "Invalid API key". Always use the Personal/vps-anthropic-api item.

Reloading after changing ~/.secrets

After editing ~/.secrets, run direnv reload (or cd out and back in) to re-export the new values:

direnv reload
# or
cd .. && cd -

If mise run doesn't see env vars

mise run inherits the shell environment, so direnv must be loaded in the calling shell. If running from a shell without direnv (e.g., a CI script, a nushell subprocess, or a run_in_background Bash tool call), source the env manually:

eval "$(op run --account=$INFRA_OP_PERSONAL --env-file=~/.secrets -- env | grep -E '^(ANTHROPIC|OPENAI|GEMINI)' | sed 's/^/export /')"

Common Mistakes

Mistake	Fix
Using bare tailscale on remote macOS	Use /Applications/Tailscale.app/Contents/MacOS/Tailscale
SSH failing with "too many auth failures"	Add -o IdentitiesOnly=yes -o IdentityAgent=none -i /path/to/key
op read for SSH keys gives invalid format	Use op item get --reveal --format=json and extract via python
Searching wrong 1Password account	Always specify --account=my.1password.com for infra
Assuming item title matches device name	Search broadly, then filter — titles are inconsistent
tailscale ssh on macOS App Store build	Not available — use regular ssh instead
Forgetting to clean up temp key files	Always rm -f /tmp/keyfile after use
sudo over SSH without TTY	Use sudo -S command <<< 'password' or avoid sudo when possible
op run --account=toptal from interactive shell	Shell has op://Personal/... env vars; use --account=$INFRA_OP_PERSONAL instead
op://cli/Anthropic API Key/credential	Returns OAuth token (oat01), not API key — use the Personal vault API key item
env vars missing in mise run	direnv must be loaded in the calling shell; check with direnv status