diff --git a/ruby/bindings/InitRubyBindings.cpp b/ruby/bindings/InitRubyBindings.cpp
index 5afa3be03c7..0d0a7702170 100644
--- a/ruby/bindings/InitRubyBindings.cpp
+++ b/ruby/bindings/InitRubyBindings.cpp
@@ -534,10 +534,23 @@ if RbConfig::CONFIG['arch'] =~ /x64-mswin64/
 end
 
 # load embedded ruby gems
+# This loads :/ruby/gems/3.2.0/specifications/default
 require 'rubygems'
 require 'rubygems/version'
 Gem::Platform.local
 
+# Note that we have three standard locations where we have gemspecs
+#
+# 1. This is the Ruby-built in stuff (eg; csv, fileutils, irb, json, reline, etc)
+#':/ruby/gems/3.2.0/specifications/default',
+#
+# 2. This is the Ruby-built in stuff that's brought in via gems/bundled_gems (https://github.com/ruby/ruby/blob/f91480d7a671b1b114270a4b5e4d3c5aa6dabce9/gems/bundled_gems)
+# (rbs, debug, matrix, rexml, etc)
+#  ':/ruby/gems/3.2.0/specifications',
+#
+# 3. Where we have the openstudio-gems gemspecs (openstudio-standards, etc)
+#':/ruby/3.2.0/specifications',
+
 if original_arch
   RbConfig::CONFIG['arch'] = original_arch
 end
@@ -545,6 +558,7 @@ end
 
     openstudio::evalString(initScript);
 
+#ifndef _WIN32  // no io/console available
     const std::string irbPatch = R"ruby(if $logger.trace?
 require 'irb'
 require 'irb/lc/error'
@@ -655,6 +669,7 @@ end
 end)ruby";
 
     openstudio::evalString(irbPatch);
+#endif
   }
 
   void setupEmbeddedGemsClearEnvVars() {
diff --git a/ruby/engine/embedded_help.rb b/ruby/engine/embedded_help.rb
index c1322e3f25f..6e0c5f9d7f4 100644
--- a/ruby/engine/embedded_help.rb
+++ b/ruby/engine/embedded_help.rb
@@ -36,7 +36,7 @@ def self.get_absolute_path(p)
       end
       absolute_path = ':' + absolute_path
     else
-      absolute_path = File.expand_path p2
+      absolute_path = File.expand_path p
     end
     return absolute_path
   end
@@ -626,8 +626,10 @@ def self.[](*args)
     end
   end
 
-  def self.glob(pattern, *args, **options)
+  def self.glob(pattern, _flags = 0, flags: _flags, base: nil, sort: true)
 
+    debug = false
+    # debug = !base.nil? && base.start_with?(':/ruby/gems/3.2.0/specifications/default')
     pattern_array = []
     if pattern.is_a? String
       pattern_array = [pattern]
@@ -637,45 +639,71 @@ def self.glob(pattern, *args, **options)
       pattern_array = pattern
     end
 
-    #puts "Dir.glob pattern = #{pattern}, pattern_array = #{pattern_array}, args = #{args}, options = #{options}"
-    override_args_extglob = false
-
-    result = []
-    pattern_array.each do |pattern|
+    pattern_has_embedded = pattern_array.any? {|p| p.to_s.chars.first == ':'}
+    base_has_embedded = (!base.nil? && base.to_s.chars.first == ':')
+    if !pattern_has_embedded && !base_has_embedded
+      # puts "Original glob"
+      return self.original_glob(pattern, flags: flags, base: base, sort: sort)
+    end
 
-      if pattern.to_s.chars.first == ':'
+    absolute_base = if base.nil?
+                      nil
+                    else
+                      OpenStudio.get_absolute_path(base)
+                    end
+    if debug
+      puts "pattern_array=#{pattern_array}"
+      puts "base=#{base}"
+      puts "flags=#{flags}"
+      puts "pattern_has_embedded=#{pattern_has_embedded}"
+      puts "base_has_embedded=#{base_has_embedded}"
+      puts "absolute_base=#{absolute_base}"
+    end
 
-        # DLM: seems like this is needed for embedded paths, possibly due to leading ':' character?
-        override_args_extglob = true
+    # DLM: seems like this is needed for embedded paths, possibly due to leading ':' character?
+    # JM (2025): Seems like fnmatch behaves differently than Dir.glob
+    # fnmatch specifically needs EXTGLOB to allow patterns like '{a,b}' while
+    # glob seems to allow that directly
+    override_args_extglob = true
 
-        #puts "searching embedded files for #{pattern}"
-        absolute_pattern = OpenStudio.get_absolute_path(pattern)
-        #puts "absolute_pattern #{absolute_pattern}"
+    flags = flags | File::FNM_EXTGLOB if override_args_extglob
+    result = []
+    pattern_array.each do |pattern|
 
-        EmbeddedScripting::fileNames.each do |name|
-          absolute_path = OpenStudio.get_absolute_path(name)
+      absolute_pattern = if pattern.to_s.chars.first == ':'
+                           OpenStudio.get_absolute_path(pattern)
+                         elsif !base.nil?
+                           File.expand_path(pattern, base)
+                         else
+                           pattern
+                         end
+      if debug
+        puts "searching embedded files for #{pattern}"
+        puts "absolute_pattern #{absolute_pattern}"
+      end
 
-          if override_args_extglob
-            if File.fnmatch( absolute_pattern, absolute_path, File::FNM_EXTGLOB )
-              #puts "#{absolute_path} is a match!"
-              result << absolute_path
-            end
-          else
-            if File.fnmatch( absolute_pattern, absolute_path, *args, **options )
-              #puts "#{absolute_path} is a match!"
-              result << absolute_path
-            end
+      EmbeddedScripting::fileNames.each do |name|
+        absolute_path = OpenStudio.get_absolute_path(name)
+        if base_has_embedded
+          next unless absolute_path.start_with?(absolute_base)
+          if debug
+            puts "name=#{name}, absolute_path=#{absolute_path}"
+            puts "absolute_path.start_with?(absolute_base)=#{absolute_path.start_with?(absolute_base)}"
           end
-
         end
 
-      else
-        if override_args_extglob
-          result.concat(self.original_glob(pattern, File::FNM_EXTGLOB))
-        else
-          result.concat(self.original_glob(pattern, *args, **options))
+        #if override_args_extglob
+        # if File.fnmatch( absolute_pattern, absolute_path, File::FNM_EXTGLOB )
+        if File.fnmatch(absolute_pattern, absolute_path, flags)
+          #puts "#{absolute_path} is a match!"
+          result << absolute_path
         end
       end
+
+    end
+
+    if debug
+      puts result
     end
 
     if block_given?
diff --git a/src/cli/CMakeLists.txt b/src/cli/CMakeLists.txt
index d424ca2874d..cf114be99a0 100644
--- a/src/cli/CMakeLists.txt
+++ b/src/cli/CMakeLists.txt
@@ -120,6 +120,10 @@ if(BUILD_TESTING)
     COMMAND $<TARGET_FILE:openstudio> ruby_version
   )
 
+  add_test(NAME OpenStudioCLI.ruby_version_trace
+    COMMAND $<TARGET_FILE:openstudio> --loglevel Trace ruby_version
+  )
+
   add_test(NAME OpenStudioCLI.python_version
     COMMAND $<TARGET_FILE:openstudio> python_version
   )