diff --git a/ApplySyntax.py b/ApplySyntax.py
index ec3c052..ad6a247 100755
--- a/ApplySyntax.py
+++ b/ApplySyntax.py
@@ -224,7 +224,7 @@ def update_extenstions(lst):
     ext_map = {}
 
     # Walk the entries
-    for entry in SETTINGS.get("default_syntaxes", []) + SETTINGS.get("syntaxes", []):
+    for entry in SETTINGS.get("syntaxes", []) + SETTINGS.get("default_syntaxes", []):
         # Grab the extensions from each relevant rule
         ext = []
         if "extensions" in entry:
@@ -544,8 +544,9 @@ def extension_matches(self, rule):
         extensions = rule.get('extensions', [])
         file_name = os.path.basename(self.file_name).lower()
         for extension in extensions:
-            dot_file_match = extension.startswith('.') and extension == file_name
-            if dot_file_match or file_name.endswith('.' + extension):
+            ext = extension.lower()
+            dot_file_match = ext.startswith('.') and ext == file_name
+            if dot_file_match or file_name.endswith('.' + ext):
                 match = True
                 break
         return match
diff --git a/CHANGES.md b/CHANGES.md
index 9f9335b..e1ba381 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -1,3 +1,7 @@
+## ApplySyntax 2.5.4
+
+- **FIX**: Fix extension compare and order of evaluation.
+
 ## ApplySyntax 2.5.3
 
 - **FIX**: Use proper Bash syntax.
diff --git a/docs/src/markdown/usage.md b/docs/src/markdown/usage.md
index 468d40c..e48d1ab 100644
--- a/docs/src/markdown/usage.md
+++ b/docs/src/markdown/usage.md
@@ -58,7 +58,7 @@ The `extensions` attribute is used to define extensions to apply a syntax to.  `
 
 An added benefit of `extensions`, if you are using ST3 and set [`add_exts_to_lang_settings`](#add-extensions-to-language-settings) to `true`, is that ApplySyntax will add the extensions to the specified syntax language's settings file in your `User` folder.  By doing this, Sublime Text will be able to show the associated icon for the file type in the sidebar.  Apply syntax will also create a file `ApplySyntax.ext-list` in your `User` folder and track which extension it added so that if you remove a rule, ApplySyntax will only remove the extensions it added to the language file in question. If you do not like this functionality, you can simply disable `add_exts_to_lang_settings` by setting it to `false`.
 
-!!! note "Note":
+!!! note "Note"
     `add_exts_to_lang_settings` will not be applied to `extensions` found in a [project specific rule](#project-specific-rules), as project specific rules are not global, but the effects of `add_exts_to_lang_settings` are global.
 
 ### Match
diff --git a/support.py b/support.py
index 608d819..db696eb 100644
--- a/support.py
+++ b/support.py
@@ -5,7 +5,7 @@
 import webbrowser
 import re
 
-__version__ = "2.5.3"
+__version__ = "2.5.4"
 __pc_name__ = 'ApplySyntax'
 
 CSS = '''