From 4563b4d76d769db7c3f5c6d9bcfeefa0eef07e5a Mon Sep 17 00:00:00 2001
From: Joakim Persson <joakim.persson@icloud.com>
Date: Sat, 11 Jul 2026 15:26:23 +0200
Subject: [PATCH] feat: warn at shell startup if Mac host SSH is not reachable

Adds a _devbox_check_host_ssh() check to ~/.bash_aliases (baked into
the image). On first bash session of each container it tries a quick
SSH probe to the Mac host; if it fails it prints a clear one-time
warning with the exact two steps needed to fix it:

  1. Enable Remote Login in macOS System Settings
  2. echo '<public key>' >> ~/.ssh/authorized_keys

The check is guarded:
  - only runs inside a container (/.dockerenv)
  - only when the jump key exists (~/.ssh-local/devbox_jump_ed25519.pub)
  - only once per container lifetime (/tmp flag, cleared on recreate)

After --force-recreate the key changes, the flag is gone, and the
check runs again on the first bash window. Subsequent windows are
silent.
---
 rootfs/home/developer/.bash_aliases | 32 +++++++++++++++++++++++++++++
 1 file changed, 32 insertions(+)

diff --git a/rootfs/home/developer/.bash_aliases b/rootfs/home/developer/.bash_aliases
index c11ab13..b17e5ae 100644
--- a/rootfs/home/developer/.bash_aliases
+++ b/rootfs/home/developer/.bash_aliases
@@ -54,6 +54,38 @@ alias gs='git status'
 alias gd='git diff'
 alias gl='git log --oneline --graph --decorate -20'
 
+# ── Host SSH reachability check (once per container lifetime) ───────────────
+# Warns at first shell startup if the Mac host is not reachable via SSH.
+# Only runs inside a container, only if the jump key exists, and only once
+# per container lifetime (/tmp flag is cleared on recreate).
+_devbox_check_host_ssh() {
+  [ -f "/.dockerenv" ] || return 0
+  local ssh_cfg="$HOME/.ssh-local/config"
+  [ -f "$ssh_cfg" ] || return 0
+  local key_pub="$HOME/.ssh-local/devbox_jump_ed25519.pub"
+  [ -f "$key_pub" ] || return 0
+  local flag="/tmp/.devbox_host_ssh_ok"
+  [ -f "$flag" ] && return 0
+  if ssh -F "$ssh_cfg" \
+        -o BatchMode=yes \
+        -o ConnectTimeout=2 \
+        -o StrictHostKeyChecking=accept-new \
+        mac true 2>/dev/null; then
+    touch "$flag"
+    return 0
+  fi
+  local pub_key
+  pub_key=$(cat "$key_pub")
+  printf '\n\033[1;33m⚠  devbox: Mac host not reachable via SSH\033[0m\n'
+  printf '   Some tools use SSH to run commands on the Mac host.\n'
+  printf '   Fix (run both on the Mac):\n\n'
+  printf '   \033[1mStep 1\033[0m  System Settings → General → Sharing → Remote Login → ON\n\n'
+  printf '   \033[1mStep 2\033[0m  echo '"'"'%s'"'"' >> ~/.ssh/authorized_keys\n' "$pub_key"
+  printf '\n   Then open a new shell in the container to verify.\n\n'
+}
+_devbox_check_host_ssh
+unset -f _devbox_check_host_ssh
+
 # ── LAN access via the host (dssh) ───────────────────────────────────
 # When running on a VM-backed host (macOS OrbStack / Docker Desktop), the
 # entrypoint's setup-lan-access.sh generates ~/.ssh-local/config so the host