diff --git a/docs/LOOT Metadata Syntax.html b/docs/LOOT Metadata Syntax.html
index be32cc12..ba691202 100644
--- a/docs/LOOT Metadata Syntax.html	
+++ b/docs/LOOT Metadata Syntax.html	
@@ -422,7 +422,7 @@ nav: 0
 <table>
     <thead><tr><th>Key Name<th>Data Type<th>Required<th>Notes
     <tbody>
-        <tr><td><code>name</code><td>string<td>&#x2713;<td>Can be an exact plugin filename or a regular expression plugin filename. If the period that precedes the file extension has been escaped (eg. <code>\.esp</code>, <code>\.esm</code>), the string is treated as a regular expression, otherwise it is treated as an exact filename.
+        <tr><td><code>name</code><td>string<td>&#x2713;<td>Can be an exact plugin filename or a regular expression plugin filename. If the filename contains any of the characters <code>:\*?|</code>, the string will be treated as a regular expression, otherwise it will be treated as an exact filename. For example, <code>Example\.esm</code> will be treated as a regular expression, as it contains a <code>\</code> character.
         <tr><td><code>enabled</code><td>boolean<td>&#x2717;<td>Enables or disables use of the plugin object. Used for user rules, but no reason to use it in the masterlist. If unspecified, defaults to <code>true</code>.
         <tr><td><code>priority</code><td>integer<td>&#x2717;<td>Modifies plugin position relative to others that change one or more of the same records, but which are otherwise unrelated (ie. neither plugin lists the other as a master, requirement, or in its <code>after</code> list). Plugins that don't change any of the same records are not compared, unless:
             <ul>
@@ -598,6 +598,7 @@ msg:
         <tr><td>Location <code>ver</code> key<td colspan="3">Yes<td>No
         <tr><td>Location <code>name</code> key<td colspan="3">No<td>Yes
         <tr><td><code>many("<var>regex</var>")</code> condition function<td colspan="3">No<td>Yes
+        <tr><td>Regex plugin entries<td colspan="3">Must end with <code>\.esp</code> or <code>\.esm</code>.<td>Must contain any of <code>:\*?|</code>
 </table>
 
 <h2 id="license">License</h2>
diff --git a/src/backend/metadata/plugin_metadata.cpp b/src/backend/metadata/plugin_metadata.cpp
index dce08b9b..a45b3561 100644
--- a/src/backend/metadata/plugin_metadata.cpp
+++ b/src/backend/metadata/plugin_metadata.cpp
@@ -355,7 +355,10 @@ namespace loot {
     }
 
     bool PluginMetadata::IsRegexPlugin() const {
-        return boost::iends_with(name, "\\.esm") || boost::iends_with(name, "\\.esp");
+        // Treat as regex if the plugin filename contains any of ":\*?|" as
+        // they are not valid Windows filename characters, but have meaning
+        // in regexes.
+        return strpbrk(name.c_str(), ":\\*?|") != nullptr;
     }
 
     bool PluginMetadata::IsPriorityExplicit() const {
diff --git a/src/tests/backend/metadata/test_plugin_metadata.h b/src/tests/backend/metadata/test_plugin_metadata.h
index a3f4b627..dcb2daaa 100644
--- a/src/tests/backend/metadata/test_plugin_metadata.h
+++ b/src/tests/backend/metadata/test_plugin_metadata.h
@@ -601,19 +601,19 @@ TEST_F(PluginMetadata, IsRegexPlugin) {
     EXPECT_FALSE(pm.IsRegexPlugin());
 
     pm = loot::PluginMetadata("Blank[[:blank:]]- Different.esm");
-    EXPECT_FALSE(pm.IsRegexPlugin());
+    EXPECT_TRUE(pm.IsRegexPlugin());
 
     pm = loot::PluginMetadata("Blank\\.esm");
     EXPECT_TRUE(pm.IsRegexPlugin());
 
     pm = loot::PluginMetadata("Blank - (Different )*Master Dependent.esm");
-    EXPECT_FALSE(pm.IsRegexPlugin());
+    EXPECT_TRUE(pm.IsRegexPlugin());
 
     pm = loot::PluginMetadata("Blank - (Different )?Master Dependent.esm");
-    EXPECT_FALSE(pm.IsRegexPlugin());
+    EXPECT_TRUE(pm.IsRegexPlugin());
 
     pm = loot::PluginMetadata("Blank.es(p|m)");
-    EXPECT_FALSE(pm.IsRegexPlugin());
+    EXPECT_TRUE(pm.IsRegexPlugin());
 }
 
 TEST_F(PluginMetadata, YamlEmitter) {