diff --git a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/AutoUpdateUtils.java b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/AutoUpdateUtils.java
new file mode 100644
index 0000000000000..c138ddf5718c2
--- /dev/null
+++ b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/AutoUpdateUtils.java
@@ -0,0 +1,84 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+package org.elasticsearch.xpack.esql;
+
+import org.apache.logging.log4j.util.StringBuilders;
+
+import java.io.BufferedReader;
+import java.io.BufferedWriter;
+import java.io.FileReader;
+import java.io.FileWriter;
+import java.io.IOException;
+import java.nio.file.Files;
+import java.nio.file.Paths;
+
+import static java.nio.file.StandardCopyOption.REPLACE_EXISTING;
+
+public class AutoUpdateUtils {
+    // TODO: CLI option.
+    public static boolean isAutoUpdating = false;
+
+    // TODO: handle more than one update at a time.
+    private static void handleAutoUpdate(String expected, String actual, String fileName, int lineNumber) throws IOException {
+        var expLineCount = expected.chars().filter(ch -> ch == '\n').count() + 1;
+
+        var outFilePath = Files.createTempFile("autoupdate-", "");
+        var writer = new BufferedWriter(new FileWriter(outFilePath.toString()));
+        var reader = new BufferedReader(new FileReader(fileName));
+        for (int li = 0;; li++) {
+            var line = reader.readLine();
+            if (line == null) {
+                break;
+            }
+            if (li < lineNumber || li >= lineNumber + expLineCount) {
+                writer.write(line + "\n");
+            } else if (li == lineNumber) {
+                var actualLines = actual.split("\n");
+                for (int actualLineId = 0; actualLineId < actualLines.length; actualLineId++) {
+                    var sb = new StringBuilder(actualLines[actualLineId]);
+                    StringBuilders.escapeJson(sb, 0);
+                    writer.write(sb.toString());
+                    if (actualLineId + 1 < actualLines.length) {
+                        writer.write("\n");
+                    }
+                }
+                writer.write(line.stripLeading() + "\n");
+            }
+        }
+        reader.close();
+        writer.close();
+        Files.move(outFilePath, Paths.get(fileName), REPLACE_EXISTING);
+    }
+
+    public static void assertStr(String expected, String actual) {
+        if (expected.equals(actual)) {
+            return;
+        }
+        assert AutoUpdateUtils.isAutoUpdating;
+
+        final var stacktrace = Thread.currentThread().getStackTrace();
+        assert stacktrace.length > 2;
+        final var callerFrame = stacktrace[2];
+
+        try {
+            final String cn = callerFrame.getClassName().replace('.', '/') + ".class";
+            final var uri = Class.forName(callerFrame.getClassName()).getClassLoader().getResource(cn);
+            assert uri != null;
+
+            // Navigate from .class to .java source file.
+            final var fileName = uri.toString()
+                .replace(".class", ".java")
+                .replace("file:", "")
+                .replace("/build/classes/java/test/", "/src/test/java/");
+
+            handleAutoUpdate(expected, actual, fileName, callerFrame.getLineNumber());
+        } catch (Exception e) {
+            throw new RuntimeException("Encountered an error while auto-updating: " + e.getMessage());
+        }
+    }
+}
diff --git a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/analysis/AnalyzerTests.java b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/analysis/AnalyzerTests.java
index e94fff4c682f1..815b0352e43dc 100644
--- a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/analysis/AnalyzerTests.java
+++ b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/analysis/AnalyzerTests.java
@@ -18,6 +18,7 @@
 import org.elasticsearch.index.analysis.IndexAnalyzers;
 import org.elasticsearch.logging.LogManager;
 import org.elasticsearch.test.ESTestCase;
+import org.elasticsearch.xpack.esql.AutoUpdateUtils;
 import org.elasticsearch.xpack.esql.EsqlTestUtils;
 import org.elasticsearch.xpack.esql.LoadMapping;
 import org.elasticsearch.xpack.esql.VerificationException;
@@ -47,7 +48,6 @@
 import org.elasticsearch.xpack.esql.expression.function.aggregate.Max;
 import org.elasticsearch.xpack.esql.expression.function.aggregate.Min;
 import org.elasticsearch.xpack.esql.expression.function.fulltext.Match;
-import org.elasticsearch.xpack.esql.expression.function.fulltext.MatchOperator;
 import org.elasticsearch.xpack.esql.expression.function.fulltext.MultiMatch;
 import org.elasticsearch.xpack.esql.expression.function.fulltext.QueryString;
 import org.elasticsearch.xpack.esql.expression.function.grouping.Bucket;
@@ -2878,19 +2878,22 @@ public void testInvalidNamedParamsForIdentifierPatterns() {
     public void testFromEnrichAndMatchColonUsage() {
         LogicalPlan plan = analyze("""
             from *:test
-            | EVAL x = to_string(languages)
-            | ENRICH _any:languages ON x
+            | EVAL y = to_string(languages)
+            | ENRICH _any:languages ON y
             | WHERE first_name: "Anna"
             """, "mapping-default.json");
-        var limit = as(plan, Limit.class);
-        var filter = as(limit.child(), Filter.class);
-        var match = as(filter.condition(), MatchOperator.class);
-        var enrich = as(filter.child(), Enrich.class);
-        assertEquals(enrich.mode(), Enrich.Mode.ANY);
-        assertEquals(enrich.policy().getMatchField(), "language_code");
-        var eval = as(enrich.child(), Eval.class);
-        var esRelation = as(eval.child(), EsRelation.class);
-        assertEquals(esRelation.indexPattern(), "test");
+
+        AutoUpdateUtils.isAutoUpdating = true;
+        AutoUpdateUtils.assertStr(
+            """
+                Limit[1000[INTEGER],false]
+                \\_Filter[:(first_name{f}#8,Anna[KEYWORD])]
+                  \\_Enrich[ANY,languages[KEYWORD],y{r}#4,{\"match\":{\"indices\":[],\"match_field\":\"language_code\",\"enrich_fields\":[\"language_nam
+                e\"]}},{=languages_idx},[language_name{r}#32]]
+                    \\_Eval[[TOSTRING(languages{f}#14) AS y#4]]
+                      \\_EsRelation[test][avg_worked_seconds{f}#23, birth_date{f}#11, emp_no{..]""",
+            plan.toString()
+        );
     }
 
     public void testFunctionNamedParamsAsFunctionArgument() {