diff --git a/buildSrc/src/main/resources/checkstyle.xml b/buildSrc/src/main/resources/checkstyle.xml
index 867ff3751cb06..c6e8a8c3d3527 100644
--- a/buildSrc/src/main/resources/checkstyle.xml
+++ b/buildSrc/src/main/resources/checkstyle.xml
@@ -1,7 +1,7 @@
 <?xml version="1.0"?>
 <!DOCTYPE module PUBLIC
-          "-//Puppy Crawl//DTD Check Configuration 1.3//EN"
-          "http://www.puppycrawl.com/dtds/configuration_1_3.dtd">
+    "-//Puppy Crawl//DTD Check Configuration 1.3//EN"
+    "http://www.puppycrawl.com/dtds/configuration_1_3.dtd">
 
 <module name="Checker">
   <property name="charset" value="UTF-8" />
@@ -10,12 +10,16 @@
     <property name="file" value="${config_loc}/checkstyle_suppressions.xml" />
   </module>
 
-  <!-- Checks Java files and forbids empty Javadoc comments -->
+  <module name="SuppressWarningsFilter" />
+
+  <!-- Checks Java files and forbids empty Javadoc comments. -->
+  <!-- Although you can use the "JavadocStyle" rule for this, it considers Javadoc -->
+  <!-- that only contains a "@return" line to be empty. -->
   <module name="RegexpMultiline">
-    <property name="id" value="EmptyJavadoc"/>
-    <property name="format" value="\/\*[\s\*]*\*\/"/>
-    <property name="fileExtensions" value="java"/>
-    <property name="message" value="Empty javadoc comments are forbidden"/>
+    <property name="id" value="EmptyJavadoc" />
+    <property name="format" value="\/\*[\s\*]*\*\/" />
+    <property name="fileExtensions" value="java" />
+    <property name="message" value="Empty javadoc comments are forbidden" />
   </module>
 
   <!--
@@ -25,18 +29,21 @@
     such snippets.
   -->
   <module name="org.elasticsearch.gradle.checkstyle.SnippetLengthCheck">
-    <property name="id" value="SnippetLength"/>
-    <property name="max" value="76"/>
+    <property name="id" value="SnippetLength" />
+    <property name="max" value="76" />
+  </module>
+
+  <!-- Its our official line length! See checkstyle_suppressions.xml for the files that don't pass this. For now we
+    suppress the check there but enforce it everywhere else. This prevents the list from getting longer even if it is
+    unfair. -->
+  <module name="LineLength">
+    <property name="max" value="140" />
+    <property name="ignorePattern" value="^ *\* *https?://[^ ]+$" />
   </module>
 
   <module name="TreeWalker">
-    <!-- Its our official line length! See checkstyle_suppressions.xml for the files that don't pass this. For now we
-      suppress the check there but enforce it everywhere else. This prevents the list from getting longer even if it is
-      unfair. -->
-    <module name="LineLength">
-      <property name="max" value="140"/>
-      <property name="ignorePattern" value="^ *\* *https?://[^ ]+$"/>
-    </module>
+    <!-- Make the @SuppressWarnings annotations available to Checkstyle -->
+    <module name="SuppressWarningsHolder" />
 
     <module name="AvoidStarImport" />
 
@@ -45,15 +52,19 @@
 
     <!-- Non-inner classes must be in files that match their names. -->
     <module name="OuterTypeFilename" />
+
     <!-- No line wraps inside of import and package statements. -->
     <module name="NoLineWrap" />
+
     <!-- only one statement per line should be allowed -->
-    <module name="OneStatementPerLine"/>
+    <module name="OneStatementPerLine" />
+
     <!-- Each java file has only one outer class -->
     <module name="OneTopLevelClass" />
+
     <!-- The suffix L is preferred, because the letter l (ell) is often
-    hard to distinguish from the digit 1 (one). -->
-    <module name="UpperEll"/>
+      hard to distinguish from the digit 1 (one). -->
+    <module name="UpperEll" />
 
     <module name="EqualsHashCode" />
 
@@ -82,7 +93,7 @@
     <module name="RedundantModifier" />
     <!-- Checks that all java files have a package declaration and that it
       lines up with the directory structure. -->
-    <module name="PackageDeclaration"/>
+    <module name="PackageDeclaration" />
 
     <!-- We don't use Java's builtin serialization and we suppress all warning
       about it. The flip side of that coin is that we shouldn't _try_ to use
@@ -104,21 +115,19 @@
 
     <!-- Forbid equality comparisons with `true` -->
     <module name="DescendantToken">
-      <property name="tokens" value="EQUAL"/>
-      <property name="limitedTokens" value="LITERAL_TRUE"/>
-      <property name="maximumNumber" value="0"/>
-      <property name="maximumDepth" value="1"/>
-      <message key="descendant.token.max" value="Do not check for equality with 'true', since it is implied"/>
+      <property name="id" value="EqualityWithTrue" />
+      <property name="tokens" value="EQUAL" />
+      <property name="limitedTokens" value="LITERAL_TRUE" />
+      <property name="maximumNumber" value="0" />
+      <property name="maximumDepth" value="1" />
+      <message key="descendant.token.max" value="Do not check for equality with 'true', since it is implied" />
     </module>
 
-    <!-- Forbid using '!' for logical negations in favour of checking
-         against 'false' explicitly. -->
-    <!-- This is disabled for now because there are many, many violations,
-         hence the rule is reporting at the "warning" severity. -->
-
+    <!-- Forbid using '!' for logical negations in favour of checking against 'false' explicitly. -->
+    <!-- This is disabled for now because there are many violations, hence the rule is reporting at the "warning" severity. -->
     <!--
     <module name="DescendantToken">
-      <property name="severity" value="warning"/>
+      <property name="id" value="BooleanNegation" />
       <property name="tokens" value="EXPR"/>
       <property name="limitedTokens" value="LNOT"/>
       <property name="maximumNumber" value="0"/>
diff --git a/buildSrc/src/main/resources/checkstyle_ide_fragment.xml b/buildSrc/src/main/resources/checkstyle_ide_fragment.xml
new file mode 100644
index 0000000000000..e4d80a1549396
--- /dev/null
+++ b/buildSrc/src/main/resources/checkstyle_ide_fragment.xml
@@ -0,0 +1,48 @@
+<?xml version="1.0"?>
+<!DOCTYPE module PUBLIC
+    "-//Puppy Crawl//DTD Check Configuration 1.3//EN"
+    "http://www.puppycrawl.com/dtds/configuration_1_3.dtd">
+
+<!-- There are some rules that we only want to enable in an IDE. These  -->
+<!-- are extracted to a separate file, and merged into the IDE-specific -->
+<!-- Checkstyle config by the `:configureIdeCheckstyle` task.           -->
+
+<module name="IdeFragment">
+    <!-- Forbid using '!' for logical negations in favour of checking against 'false' explicitly. -->
+    <!-- This is only reported in the IDE for now because there are many violations -->
+    <module name="DescendantToken">
+        <property name="id" value="BooleanNegation" />
+        <property name="tokens" value="EXPR"/>
+        <property name="limitedTokens" value="LNOT"/>
+        <property name="maximumNumber" value="0"/>
+        <property name="maximumDepth" value="1"/>
+        <message
+            key="descendant.token.max"
+            value="Do not negate boolean expressions with '!', but check explicitly with '== false' as it is more explicit"/>
+    </module>
+
+    <module name="MissingJavadocMethod">
+        <property name="severity" value="warning" />
+        <!-- Exclude short methods from this check - we don't want to have to document getters -->
+        <property name="minLineCount" value="2" />
+        <message key="javadoc.missing" value="Public methods should be documented" />
+    </module>
+
+    <module name="MissingJavadocPackage">
+        <property name="severity" value="warning"/>
+        <message
+            key="package.javadoc.missing"
+            value="A description and other related documentation for a package should be written up in the package-info.java" />
+    </module>
+
+    <module name="MissingJavadocType">
+        <property name="severity" value="warning"/>
+        <message key="javadoc.missing" value="Types should explain their purpose" />
+    </module>
+
+    <!-- Public methods must have JavaDoc -->
+    <module name="JavadocMethod">
+        <property name="severity" value="warning"/>
+        <property name="scope" value="public"/>
+    </module>
+</module>
diff --git a/buildSrc/version.properties b/buildSrc/version.properties
index 13927e31914a0..b28936d20964e 100644
--- a/buildSrc/version.properties
+++ b/buildSrc/version.properties
@@ -4,7 +4,7 @@ lucene            = 8.8.0-snapshot-737cb9c49b0
 bundled_jdk_vendor = adoptopenjdk
 bundled_jdk = 15.0.1+9
 
-checkstyle = 8.20
+checkstyle = 8.39
 
 # optional dependencies
 spatial4j         = 0.7
diff --git a/gradle/ide.gradle b/gradle/ide.gradle
index dbab6c140bcf4..3ef2efab6dd50 100644
--- a/gradle/ide.gradle
+++ b/gradle/ide.gradle
@@ -1,9 +1,9 @@
 import org.elasticsearch.gradle.info.BuildParams
-import org.jetbrains.gradle.ext.Remote
 import org.jetbrains.gradle.ext.JUnit
+
 import java.nio.file.Files
-import java.nio.file.StandardCopyOption
 import java.nio.file.Paths
+import java.nio.file.StandardCopyOption
 
 buildscript {
   repositories {
@@ -29,9 +29,11 @@ tasks.register('configureIdeCheckstyle') {
   description = 'Generated a suitable checkstyle config for IDEs'
 
   String checkstyleConfig = 'buildSrc/src/main/resources/checkstyle.xml'
+  String checkstyleSuppressions = 'buildSrc/src/main/resources/checkstyle_suppressions.xml'
+  String checkstyleIdeFragment = 'buildSrc/src/main/resources/checkstyle_ide_fragment.xml'
   String checkstyleIdeConfig = "$rootDir/checkstyle_ide.xml"
 
-  inputs.files(file(checkstyleConfig))
+  inputs.files(file(checkstyleConfig), file(checkstyleIdeFragment))
   outputs.files(file(checkstyleIdeConfig))
 
   doLast {
@@ -41,28 +43,33 @@ tasks.register('configureIdeCheckstyle') {
       Paths.get(file(checkstyleIdeConfig).getPath()),
       StandardCopyOption.REPLACE_EXISTING
     )
+
+    // There are some rules that we only want to enable in an IDE. These
+    // are extracted to a separate file, and merged into the IDE-specific
+    // Checkstyle config.
+    Node xmlFragment = parseXml(checkstyleIdeFragment)
+
     // Edit the copy so that IntelliJ can copy with it
     modifyXml(checkstyleIdeConfig, { xml ->
       // Remove this module since it is implemented with custom code
       xml.module.findAll { it.'@name' == 'org.elasticsearch.gradle.checkstyle.SnippetLengthCheck' }.each { it.parent().remove(it) }
 
-      // Move the line length check because the IDE thinks it can't belong under a TreeWalker. Moving the
-      // configuration in the main file causes the command-line Checkstyle task to fail ¯\_(ツ)_/¯
+      // Add all the nodes from the fragment file
       Node treeWalker = xml.module.find { it.'@name' == 'TreeWalker' }
-      Node lineLength = treeWalker.module.find { it.'@name' == 'LineLength' }
-      treeWalker.remove(lineLength)
-      xml.append(lineLength)
+      xmlFragment.module.each { treeWalker.append(it) }
 
       // Change the checkstyle config to inline the path to the
       // suppressions config. This removes a configuration step when using
       // the checkstyle config in an IDE.
       Node suppressions = xml.module.find { it.'@name' == 'SuppressionFilter' }
-      suppressions.property.findAll { it.'@name' == 'file' }.each { it.'@value' = "buildSrc/src/main/resources/checkstyle_suppressions.xml" }
+      suppressions.property.findAll { it.'@name' == 'file' }.each { it.'@value' = checkstyleSuppressions }
     },
       "<!DOCTYPE module PUBLIC\n" +
       "  \"-//Puppy Crawl//DTD Check Configuration 1.3//EN\"\n" +
       "  \"http://www.puppycrawl.com/dtds/configuration_1_3.dtd\">\n" +
-      "<!-- Generated automatically from ${checkstyleConfig} - do not edit this file directly. -->\n"
+      "<!-- Generated automatically from the following - do not edit this file directly. -->\n" +
+      "<!--     ${checkstyleConfig} -->\n" +
+      "<!--     ${checkstyleIdeFragment} -->\n"
     )
   }
 }
@@ -172,12 +179,10 @@ if (System.getProperty('idea.active') == 'true') {
  * but before the XML document, e.g. a doctype or comment
  */
 void modifyXml(Object path, Action<? super Node> action, String preface = null) {
-  File xmlFile = project.file(path)
-  XmlParser xmlParser = new XmlParser(false, true, true)
-  xmlParser.setFeature("http://apache.org/xml/features/nonvalidating/load-external-dtd", false)
-  Node xml = xmlParser.parse(xmlFile)
+  Node xml = parseXml(path)
   action.execute(xml)
 
+  File xmlFile = project.file(path)
   xmlFile.withPrintWriter { writer ->
     def printer = new XmlNodePrinter(writer)
     printer.namespaceAware = true
@@ -190,3 +195,11 @@ void modifyXml(Object path, Action<? super Node> action, String preface = null)
     printer.print(xml)
   }
 }
+
+Node parseXml(Object path) {
+  File xmlFile = project.file(path)
+  XmlParser xmlParser = new XmlParser(false, true, true)
+  xmlParser.setFeature("http://apache.org/xml/features/nonvalidating/load-external-dtd", false)
+  Node xml = xmlParser.parse(xmlFile)
+  return xml
+}