diff --git a/packages/http-client-java/generator/http-client-generator-core/src/main/java/com/microsoft/typespec/http/client/generator/core/util/CodeNamer.java b/packages/http-client-java/generator/http-client-generator-core/src/main/java/com/microsoft/typespec/http/client/generator/core/util/CodeNamer.java
index 060ddea7165..b97f4296944 100644
--- a/packages/http-client-java/generator/http-client-generator-core/src/main/java/com/microsoft/typespec/http/client/generator/core/util/CodeNamer.java
+++ b/packages/http-client-java/generator/http-client-generator-core/src/main/java/com/microsoft/typespec/http/client/generator/core/util/CodeNamer.java
@@ -94,6 +94,15 @@ public static String getEnumMemberName(String name) {
             return name;
         }
 
+        // Special handling for inputs that start with special characters followed by numbers
+        if (name.length() > 1 && !Character.isLetterOrDigit(name.charAt(0)) && Character.isDigit(name.charAt(1))) {
+            // Convert the first character to its word form
+            String firstCharReplacement = getBasicLatinCharacter(name.charAt(0));
+            if (firstCharReplacement != null) {
+                name = firstCharReplacement + "_" + name.substring(1);
+            }
+        }
+
         // trim leading and trailing '_'
         if ((name.startsWith("_") || name.endsWith("_")) && !name.chars().allMatch(c -> c == '_')) {
             StringBuilder sb = new StringBuilder(name);
diff --git a/packages/http-client-java/generator/http-client-generator-core/src/test/java/com/microsoft/typespec/http/client/generator/core/util/CodeNamerTests.java b/packages/http-client-java/generator/http-client-generator-core/src/test/java/com/microsoft/typespec/http/client/generator/core/util/CodeNamerTests.java
index 705b42c36e0..4d51c183364 100644
--- a/packages/http-client-java/generator/http-client-generator-core/src/test/java/com/microsoft/typespec/http/client/generator/core/util/CodeNamerTests.java
+++ b/packages/http-client-java/generator/http-client-generator-core/src/test/java/com/microsoft/typespec/http/client/generator/core/util/CodeNamerTests.java
@@ -32,6 +32,12 @@ public void testEnumMemberName() {
 
         Assertions.assertEquals("ONE_ZEROMINUTELY", CodeNamer.getEnumMemberName("_10minutely"));
 
+        Assertions.assertEquals("DOLLAR_SIGN_100_GIFT_CARD", CodeNamer.getEnumMemberName("$100 Gift Card"));
+
+        Assertions.assertEquals("PERCENT_SIGN_50_OFF", CodeNamer.getEnumMemberName("%50 Off"));
+
+        Assertions.assertEquals("NUMBER_SIGN_10_TRENDING", CodeNamer.getEnumMemberName("#10 Trending"));
+
         Assertions.assertEquals("_", CodeNamer.getEnumMemberName("_"));
     }
 }