diff --git a/docs/changelog/109173.yaml b/docs/changelog/109173.yaml
new file mode 100644
index 0000000000000..9f4f73a6f74c8
--- /dev/null
+++ b/docs/changelog/109173.yaml
@@ -0,0 +1,5 @@
+pr: 109173
+summary: Wrap "Pattern too complex" exception into an `IllegalArgumentException`
+area: Mapping
+type: bug
+issues: []
diff --git a/modules/analysis-common/src/yamlRestTest/resources/rest-api-spec/test/analysis-common/50_char_filters.yml b/modules/analysis-common/src/yamlRestTest/resources/rest-api-spec/test/analysis-common/50_char_filters.yml
index 67e68428c07c7..76f17dddd3f0e 100644
--- a/modules/analysis-common/src/yamlRestTest/resources/rest-api-spec/test/analysis-common/50_char_filters.yml
+++ b/modules/analysis-common/src/yamlRestTest/resources/rest-api-spec/test/analysis-common/50_char_filters.yml
@@ -27,6 +27,33 @@
     - length: { tokens: 1 }
     - match:  { tokens.0.token: "replacedSample 6 sample1" }
 
+---
+"pattern_replace error handling (too complex pattern)":
+  - do:
+      catch: bad_request
+      indices.create:
+        index: test_too_complex_regex_pattern
+        body:
+          settings:
+            index:
+              analysis:
+                analyzer:
+                  my_analyzer:
+                    tokenizer: standard
+                    char_filter:
+                      - my_char_filter
+                char_filter:
+                  my_char_filter:
+                    type: "pattern_replace"
+                    # This pattern intentionally uses special characters designed to throw an error.
+                    # It's expected that the pattern may not render correctly.
+                    pattern: "(\\d+)-(?=\\d\nͭͭͭͭͭͭͭͭͭͭͭͭͭͭͭ"
+                    flags: CASE_INSENSITIVE|MULTILINE|DOTALL|UNICODE_CASE|CANON_EQ
+                    replacement: "_$1"
+  - match: { status: 400 }
+  - match: { error.type: illegal_argument_exception }
+  - match: { error.reason: "Too complex regex pattern" }
+
 ---
 "mapping":
     - do:
diff --git a/server/src/main/java/org/elasticsearch/common/regex/Regex.java b/server/src/main/java/org/elasticsearch/common/regex/Regex.java
index 039f484f1ebca..983144c7cee89 100644
--- a/server/src/main/java/org/elasticsearch/common/regex/Regex.java
+++ b/server/src/main/java/org/elasticsearch/common/regex/Regex.java
@@ -230,8 +230,26 @@ public static boolean simpleMatch(final List<String> patterns, final String str)
     }
 
     public static Pattern compile(String regex, String flags) {
-        int pFlags = flags == null ? 0 : flagsFromString(flags);
-        return Pattern.compile(regex, pFlags);
+        try {
+            int pFlags = flags == null ? 0 : flagsFromString(flags);
+            return Pattern.compile(regex, pFlags);
+        } catch (OutOfMemoryError e) {
+            if (e.getMessage().equals("Pattern too complex")) {
+                // Normally, we do try to handle OutOfMemoryError errors, as they typically indicate the JVM is not healthy.
+                //
+                // In the context of Pattern::compile, an OutOfMemoryError can occur if the pattern is too complex.
+                // In this case, the OutOfMemoryError is thrown by a pre-check rather than actual memory exhaustion.
+                //
+                // Because the JVM has not encountered a real memory issue, we can treat this as a recoverable exception by wrapping
+                // the original OutOfMemoryError in an IllegalArgumentException.
+                //
+                // For additional details, see:
+                // - https://bugs.openjdk.org/browse/JDK-8300207
+                // - https://github.com/openjdk/jdk/commit/030b071db1fb6197a2633a04b20aa95432a903bc
+                throw new IllegalArgumentException("Too complex regex pattern", e);
+            }
+            throw e;
+        }
     }
 
     public static int flagsFromString(String flags) {