From 23a42cda46d65397872f62ee9b8b10549e29ebea Mon Sep 17 00:00:00 2001
From: Tom Hicks <headhunter3@gmail.com>
Date: Mon, 7 Sep 2026 18:09:09 -0700
Subject: [PATCH] Cleans up ruby script.

---
 .rc.d/ruby.sh | 106 +++++++++++++++++++++++++++++++++++++++++++++++---
 1 file changed, 100 insertions(+), 6 deletions(-)

diff --git a/.rc.d/ruby.sh b/.rc.d/ruby.sh
index 28d7385..ae13101 100755
--- a/.rc.d/ruby.sh
+++ b/.rc.d/ruby.sh
@@ -1,6 +1,100 @@
-# Ruby
-if [[ $(command -v rbenv) ]]; then
-  eval "$(rbenv init -)"
-  export PATH="$HOME/.gem/ruby/3.0.0/bin:$PATH"
-  export RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix openssl@1.1)"
-fi
+# Setup Ruby environment: version managers (rbenv, chruby, rvm), Homebrew Ruby, and gem bin paths
+_setup_ruby() {
+    [ -n "$ZSH_VERSION" ] && setopt localoptions nonomatch nullglob
+
+    _add_to_path() {
+        [ -d "$1" ] || return 0
+        case ":$PATH:" in
+            *":$1:"*) ;;
+            *) PATH="$1:$PATH"; export PATH ;;
+        esac
+    }
+
+    _ruby_manager_active=0
+
+    # 1. Check for rbenv (prefer managed Ruby)
+    if [ -d "$HOME/.rbenv/bin" ]; then
+        _add_to_path "$HOME/.rbenv/bin"
+    fi
+    if command -v rbenv >/dev/null 2>&1; then
+        eval "$(rbenv init - 2>/dev/null)"
+        _ruby_manager_active=1
+
+        # Fast OpenSSL detection for ruby-build without calling slow `brew --prefix`
+        if [ -z "$RUBY_CONFIGURE_OPTS" ]; then
+            for _ssl_dir in \
+                "/opt/homebrew/opt/openssl@3" \
+                "/opt/homebrew/opt/openssl@1.1" \
+                "/usr/local/opt/openssl@3" \
+                "/usr/local/opt/openssl@1.1"
+            do
+                if [ -d "$_ssl_dir" ]; then
+                    export RUBY_CONFIGURE_OPTS="--with-openssl-dir=$_ssl_dir"
+                    break
+                fi
+            done
+        fi
+    fi
+
+    # 2. Check for chruby
+    if [ "$_ruby_manager_active" -eq 0 ]; then
+        for _chruby_sh in \
+            "/opt/homebrew/opt/chruby/share/chruby/chruby.sh" \
+            "/usr/local/share/chruby/chruby.sh" \
+            "/usr/share/chruby/chruby.sh"
+        do
+            if [ -r "$_chruby_sh" ]; then
+                \. "$_chruby_sh"
+                [ -r "${_chruby_sh%/*}/auto.sh" ] && \. "${_chruby_sh%/*}/auto.sh"
+                _ruby_manager_active=1
+                break
+            fi
+        done
+    fi
+
+    # 3. Check for RVM
+    if [ "$_ruby_manager_active" -eq 0 ]; then
+        if [ -s "$HOME/.rvm/scripts/rvm" ]; then
+            \. "$HOME/.rvm/scripts/rvm"
+            _ruby_manager_active=1
+        fi
+    fi
+
+    # 4. If no version manager is active, fallback to Homebrew keg-only Ruby or standard locations
+    # (Avoids Apple's deprecated /usr/bin/ruby on macOS when Homebrew Ruby is installed)
+    if [ "$_ruby_manager_active" -eq 0 ]; then
+        for _brew_ruby in $(
+            for _r in /opt/homebrew/opt/ruby/bin \
+                      /opt/homebrew/opt/ruby@*/bin \
+                      /usr/local/opt/ruby/bin \
+                      /usr/local/opt/ruby@*/bin; do
+                [ -x "$_r/ruby" ] && echo "$_r"
+            done | sort -V -r 2>/dev/null
+        ); do
+            _add_to_path "$_brew_ruby"
+            break
+        done
+    fi
+
+    # 5. Add user gem binaries to PATH (dynamically resolved, not hardcoded to a fixed version)
+    if command -v ruby >/dev/null 2>&1; then
+        _gem_user_bin="$(ruby -e 'puts Gem.user_dir' 2>/dev/null)/bin"
+        if [ -n "$_gem_user_bin" ] && [ -d "$_gem_user_bin" ]; then
+            _add_to_path "$_gem_user_bin"
+        fi
+        unset _gem_user_bin
+
+        for _gbin in $(
+            for _gd in "$HOME/.gem/ruby"/*/bin "$HOME/.local/share/gem/ruby"/*/bin; do
+                [ -d "$_gd" ] && echo "$_gd"
+            done | sort -V -r 2>/dev/null
+        ); do
+            _add_to_path "$_gbin"
+            break
+        done
+    fi
+
+    unset _ruby_manager_active
+}
+_setup_ruby
+unset -f _setup_ruby _add_to_path