feat(guide): add 'a' (always) option for automatic updates

- Add 'a' option to upgrade prompt that installs immediately AND enables
  auto-update for future runs (no more prompting for that tool)
- Add set_auto_update.sh script to manage auto_update flag on tools
- Fix npm_global.sh to use @latest suffix to force latest version
- Fix ruby-build version detection to use --version instead of git log
- Update install_ruby.sh fallback to Ruby 4.0.0 (now stable)
- Enable auto_update for claude and prettier per user selection

Author: CybotTM

catalog/claude.json

@@ -3,13 +3,13 @@
   "category": "ai",
   "install_method": "npm_global",
   "description": "Anthropic's Claude Code CLI - AI-powered development assistant",
-  "homepage": "https://claude.com/claude-code",
-  "github_repo": "anthropics/claude-code",
+  "homepage": "https://www.npmjs.com/package/@anthropic-ai/claude-code",
   "binary_name": "claude",
   "package_name": "@anthropic-ai/claude-code",
   "guide": {
     "display_name": "Claude Code",
     "install_action": "upgrade",
     "order": 400
-  }
+  },
+  "auto_update": true
 }

catalog/prettier.json

@@ -5,5 +5,6 @@
   "description": "Opinionated code formatter",
   "homepage": "https://prettier.io",
   "package_name": "prettier",
-  "notes": "Prettier is a JavaScript/Node.js tool installed via npm"
+  "notes": "Prettier is a JavaScript/Node.js tool installed via npm",
+  "auto_update": true
 }

catalog/ruby-build.json

@@ -7,7 +7,7 @@
   "github_repo": "rbenv/ruby-build",
   "binary_name": "ruby-build",
   "clone_path": "~/.rbenv/plugins/ruby-build",
-  "version_command": "cd ~/.rbenv/plugins/ruby-build && git log -1 --format='%s' | grep -oP 'ruby-build \\K[0-9]+'",
+  "version_command": "~/.rbenv/plugins/ruby-build/bin/ruby-build --version | grep -oE '[0-9]+'",
   "notes": "Installs as rbenv plugin. Requires rbenv to be installed first.",
   "guide": {
     "display_name": "ruby-build",

scripts/guide.sh

@@ -134,6 +134,7 @@ process_tool() {
   local install_action="$(catalog_get_guide_property "$tool" install_action "")"
   local description="$(catalog_get_property "$tool" description)"
   local homepage="$(catalog_get_property "$tool" homepage)"
+  local auto_update="$(catalog_get_property "$tool" auto_update)"
 
   # Check if up-to-date
   if [ -n "$is_up_to_date" ] && [ -n "$installed" ]; then
@@ -144,6 +145,36 @@ process_tool() {
     return 0
   fi
 
+  # Check if auto_update is enabled - install without prompting
+  if [ "$auto_update" = "true" ]; then
+    printf "\n==> %s %s [auto-update]\n" "$icon" "$display"
+    printf "    installed: %s via %s\n" "${installed:-<none>}" "${method:-unknown}"
+    printf "    target:    %s\n" "$(osc8 "$url" "${latest:-<unknown>}")"
+    printf "    auto-updating...\n"
+
+    # Build install command from catalog metadata
+    local install_cmd="install_tool.sh $tool"
+    if [ -n "$install_action" ]; then
+      install_cmd="install_tool.sh $tool $install_action"
+    elif [ -n "$installed" ]; then
+      install_cmd="install_tool.sh $tool update"
+    fi
+
+    # Execute the install
+    if [ "$tool" = "python" ]; then
+      UV_PYTHON_SPEC="$latest" "$ROOT"/scripts/$install_cmd || true
+    elif [ "$tool" = "ruby" ]; then
+      RUBY_VERSION="$latest" "$ROOT"/scripts/$install_cmd || true
+    else
+      "$ROOT"/scripts/$install_cmd || true
+    fi
+
+    # Re-audit with fresh collection for this specific tool
+    CLI_AUDIT_JSON=1 CLI_AUDIT_COLLECT=1 CLI_AUDIT_MERGE=1 "$CLI" audit.py "$tool" >/dev/null 2>&1 || true
+    AUDIT_JSON="$(cd "$ROOT" && CLI_AUDIT_JSON=1 CLI_AUDIT_RENDER=1 "$CLI" audit.py || true)"
+    return 0
+  fi
+
   # Prompt for installation/update
   printf "\n==> %s %s\n" "$icon" "$display"
   [ -n "$description" ] && printf "    %s\n" "$description"
@@ -164,6 +195,7 @@ process_tool() {
   # Prompt with options explained
   printf "    Options:\n"
   printf "      y = Install/upgrade now\n"
+  printf "      a = Always update (install now + auto-update in future)\n"
   printf "      N = Skip (ask again next time)\n"
   if [ -n "$installed" ]; then
     printf "      s = Skip version %s (ask again if newer available)\n" "$latest"
@@ -173,7 +205,7 @@ process_tool() {
     printf "      p = Never install (permanently skip this tool)\n"
   fi
 
-  local prompt_text="Install/update? [y/N/s/p] "
+  local prompt_text="Install/update? [y/a/N/s/p] "
 
   local ans=""
   if [ -t 0 ]; then
@@ -218,6 +250,41 @@ process_tool() {
         fi
       fi
       ;;
+    [Aa])
+      # Install/upgrade AND enable auto-update for future
+      printf "    Enabling auto-update for future upgrades...\n"
+      "$ROOT"/scripts/set_auto_update.sh "$tool" true >/dev/null 2>&1 || true
+
+      # Handle tool-specific version environment variables
+      local upgrade_success_a=0
+      if [ "$tool" = "python" ]; then
+        UV_PYTHON_SPEC="$latest" "$ROOT"/scripts/$install_cmd && upgrade_success_a=1 || true
+      elif [ "$tool" = "ruby" ]; then
+        RUBY_VERSION="$latest" "$ROOT"/scripts/$install_cmd && upgrade_success_a=1 || true
+      else
+        "$ROOT"/scripts/$install_cmd && upgrade_success_a=1 || true
+      fi
+
+      # Re-audit with fresh collection for this specific tool
+      CLI_AUDIT_JSON=1 CLI_AUDIT_COLLECT=1 CLI_AUDIT_MERGE=1 "$CLI" audit.py "$tool" >/dev/null 2>&1 || true
+      AUDIT_JSON="$(cd "$ROOT" && CLI_AUDIT_JSON=1 CLI_AUDIT_RENDER=1 "$CLI" audit.py || true)"
+
+      # Check if upgrade succeeded
+      local new_installed_a="$(json_field "$tool" installed)"
+      if [ "$upgrade_success_a" = "0" ] || [ "$new_installed_a" = "$installed" ]; then
+        printf "\n    ⚠️  Upgrade did not succeed (version unchanged)\n"
+        printf "    Auto-update is still enabled - will try again next time.\n"
+      else
+        printf "    ✓ Auto-update enabled. This tool will update automatically in future.\n"
+        # Remove any existing pin
+        if catalog_has_tool "$tool"; then
+          local existing_pin_a="$(catalog_get_property "$tool" pinned_version)"
+          if [ -n "$existing_pin_a" ]; then
+            "$ROOT"/scripts/unpin_version.sh "$tool" || true
+          fi
+        fi
+      fi
+      ;;
     [Ss])
       # Skip this specific version
       printf "    Skipping version %s (will prompt again if newer version available)\n" "$latest"

scripts/install_ruby.sh

@@ -34,8 +34,8 @@ ensure_rbenv_loaded() {
 
 get_latest_ruby_version() {
   ensure_rbenv
-  # Get latest stable Ruby version from rbenv
-  rbenv install --list 2>/dev/null | grep -E '^\s*[0-9]+\.[0-9]+\.[0-9]+$' | tail -1 | tr -d ' ' || echo "3.3.6"
+  # Get latest stable Ruby version from rbenv (MRI Ruby only, excludes jruby/mruby/truffleruby)
+  rbenv install --list 2>/dev/null | grep -E '^\s*[0-9]+\.[0-9]+\.[0-9]+$' | tail -1 | tr -d ' ' || echo "4.0.0"
 }
 
 install_ruby() {

scripts/installers/npm_global.sh

@@ -57,19 +57,22 @@ fi
 echo "[$TOOL] Installing package globally via $PKG_MANAGER: $PACKAGE_NAME" >&2
 case "$PKG_MANAGER" in
   pnpm)
-    pnpm add -g "$PACKAGE_NAME" || {
+    # Use @latest to ensure we get the newest version
+    pnpm add -g "${PACKAGE_NAME}@latest" || {
       echo "[$TOOL] Error: pnpm install failed" >&2
       exit 1
     }
     ;;
   npm)
-    npm install -g "$PACKAGE_NAME" || {
+    # Use @latest to ensure we get the newest version (bypasses npm cache issues)
+    npm install -g "${PACKAGE_NAME}@latest" || {
       echo "[$TOOL] Error: npm install failed" >&2
       exit 1
     }
     ;;
   yarn)
-    yarn global add "$PACKAGE_NAME" || {
+    # Use @latest to ensure we get the newest version
+    yarn global add "${PACKAGE_NAME}@latest" || {
       echo "[$TOOL] Error: yarn install failed" >&2
       exit 1
     }

scripts/set_auto_update.sh

@@ -0,0 +1,57 @@
+#!/usr/bin/env bash
+# set_auto_update.sh - Enable/disable automatic updates for a tool
+set -euo pipefail
+
+DIR="$(cd "$(dirname "${BASH_SOURCE[0]}")" && pwd)"
+ROOT="$(cd "$DIR/.." && pwd)"
+
+TOOL="${1:-}"
+VALUE="${2:-true}"  # true or false
+
+if [ -z "$TOOL" ]; then
+  echo "Usage: $0 TOOL_NAME [true|false]" >&2
+  echo "" >&2
+  echo "Enable or disable automatic updates for a tool." >&2
+  echo "When enabled, 'make upgrade' will update the tool without asking." >&2
+  echo "" >&2
+  echo "Examples:" >&2
+  echo "  $0 prettier         # Enable auto-update for prettier" >&2
+  echo "  $0 prettier true    # Enable auto-update for prettier" >&2
+  echo "  $0 prettier false   # Disable auto-update for prettier" >&2
+  exit 1
+fi
+
+CATALOG_FILE="$ROOT/catalog/$TOOL.json"
+if [ ! -f "$CATALOG_FILE" ]; then
+  echo "Error: Tool '$TOOL' not found in catalog" >&2
+  exit 1
+fi
+
+# Normalize value
+case "$VALUE" in
+  true|1|yes|on) VALUE="true" ;;
+  false|0|no|off) VALUE="false" ;;
+  *)
+    echo "Error: Invalid value '$VALUE'. Use 'true' or 'false'" >&2
+    exit 1
+    ;;
+esac
+
+if [ "$VALUE" = "true" ]; then
+  echo "Enabling automatic updates for '$TOOL'..."
+  TMP_FILE=$(mktemp)
+  jq '. + {auto_update: true}' "$CATALOG_FILE" > "$TMP_FILE"
+  mv "$TMP_FILE" "$CATALOG_FILE"
+  echo "✓ Auto-update enabled for '$TOOL'"
+  echo ""
+  echo "This tool will be automatically updated during 'make upgrade' without prompting."
+  echo "To disable: $0 $TOOL false"
+else
+  echo "Disabling automatic updates for '$TOOL'..."
+  TMP_FILE=$(mktemp)
+  jq 'del(.auto_update)' "$CATALOG_FILE" > "$TMP_FILE"
+  mv "$TMP_FILE" "$CATALOG_FILE"
+  echo "✓ Auto-update disabled for '$TOOL'"
+  echo ""
+  echo "You will be prompted before updating this tool."
+fi