diff --git a/oak-examples/standalone/pom.xml b/oak-examples/standalone/pom.xml
index 20d52710f77..15997f084e1 100644
--- a/oak-examples/standalone/pom.xml
+++ b/oak-examples/standalone/pom.xml
@@ -212,7 +212,7 @@
       <version>1.0.2</version>
     </dependency>
     <dependency>
-      <groupId>org.codehaus.groovy</groupId>
+      <groupId>org.apache.groovy</groupId>
       <artifactId>groovy</artifactId>
       <version>${groovy.version}</version>
     </dependency>
diff --git a/oak-examples/webapp/pom.xml b/oak-examples/webapp/pom.xml
index 8ae44c82229..e6753a902e1 100644
--- a/oak-examples/webapp/pom.xml
+++ b/oak-examples/webapp/pom.xml
@@ -143,7 +143,7 @@
       <version>1.0.2</version>
     </dependency>
     <dependency>
-      <groupId>org.codehaus.groovy</groupId>
+      <groupId>org.apache.groovy</groupId>
       <artifactId>groovy</artifactId>
       <version>${groovy.version}</version>
     </dependency>
diff --git a/oak-parent/pom.xml b/oak-parent/pom.xml
index 39755b83c34..d4555aad08d 100644
--- a/oak-parent/pom.xml
+++ b/oak-parent/pom.xml
@@ -70,7 +70,7 @@
     <testcontainers.version>2.0.5</testcontainers.version>
     <pax-exam.version>4.14.0</pax-exam.version>
     <pax-url.version>2.6.17</pax-url.version>
-    <groovy.version>3.0.25</groovy.version>
+    <groovy.version>4.0.33</groovy.version>
     <netty.version>4.1.136.Final</netty.version>
     <aws.sdk.version>2.36.3</aws.sdk.version>
     <!-- determines the bytecode version (i.e. the minimum JRE required to run the build artifact) -->
@@ -240,7 +240,7 @@
         <plugin>
           <groupId>org.codehaus.gmavenplus</groupId>
           <artifactId>gmavenplus-plugin</artifactId>
-          <version>3.0.2</version>
+          <version>4.3.1</version>
         </plugin>
         <plugin>
           <artifactId>maven-deploy-plugin</artifactId>
diff --git a/oak-run/pom.xml b/oak-run/pom.xml
index 2b7dca92ba9..429b812b3d4 100644
--- a/oak-run/pom.xml
+++ b/oak-run/pom.xml
@@ -34,6 +34,7 @@
     <jetty.version>9.4.53.v20231009</jetty.version>
     <!--
       Size History:
+      + 4 MB (Groovy 3.0.25 -> 4.0.33, OAK-12355)
       + 88 MB (Ben-manes Caffeine, OAK-12148)
       + 87 MB (Aws Sdk 2.x, OAK-11935)
       + 84 MB (RDB/Tomcat, OAK-10752)
@@ -53,7 +54,7 @@
       + 41 MB build failing on the release profile (OAK-6250)
       + 38 MB. Initial value. Current 35MB plus a 10%
     -->
-    <max.jar.size>92274688</max.jar.size>
+    <max.jar.size>96274688</max.jar.size>
   </properties>
 
   <build>
@@ -273,28 +274,24 @@
       <artifactId>jopt-simple</artifactId>
     </dependency>
     <dependency>
-      <groupId>org.codehaus.groovy</groupId>
+      <groupId>org.apache.groovy</groupId>
       <artifactId>groovy</artifactId>
       <version>${groovy.version}</version>
-      <classifier>indy</classifier>
     </dependency>
     <dependency>
-      <groupId>org.codehaus.groovy</groupId>
+      <groupId>org.apache.groovy</groupId>
       <artifactId>groovy-json</artifactId>
       <version>${groovy.version}</version>
-      <classifier>indy</classifier>
     </dependency>
     <dependency>
-      <groupId>org.codehaus.groovy</groupId>
+      <groupId>org.apache.groovy</groupId>
       <artifactId>groovy-cli-picocli</artifactId>
       <version>${groovy.version}</version>
-      <classifier>indy</classifier>
     </dependency>
     <dependency>
-      <groupId>org.codehaus.groovy</groupId>
+      <groupId>org.apache.groovy</groupId>
       <artifactId>groovy-groovysh</artifactId>
       <version>${groovy.version}</version>
-      <classifier>indy</classifier>
     </dependency>
     <dependency>
       <groupId>org.mongodb</groupId>
diff --git a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/GroovyConsole.groovy b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/GroovyConsole.groovy
index 904ab15a609..f50238c2c84 100644
--- a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/GroovyConsole.groovy
+++ b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/GroovyConsole.groovy
@@ -23,21 +23,51 @@ import groovy.transform.TypeCheckingMode
 import jline.Terminal
 import jline.TerminalFactory
 import jline.console.history.FileHistory
+import org.apache.jackrabbit.oak.console.commands.CdCommand
+import org.apache.jackrabbit.oak.console.commands.CheckpointCommand
+import org.apache.jackrabbit.oak.console.commands.ExportCommand
+import org.apache.jackrabbit.oak.console.commands.ExportRelevantDocumentsCommand
+import org.apache.jackrabbit.oak.console.commands.LsCommand
+import org.apache.jackrabbit.oak.console.commands.LsdDocumentCommand
+import org.apache.jackrabbit.oak.console.commands.LuceneCommand
+import org.apache.jackrabbit.oak.console.commands.OakHelpCommand
+import org.apache.jackrabbit.oak.console.commands.PnCommand
+import org.apache.jackrabbit.oak.console.commands.PrintDocumentCommand
+import org.apache.jackrabbit.oak.console.commands.RefreshCommand
+import org.apache.jackrabbit.oak.console.commands.RetrieveCommand
 import org.apache.jackrabbit.oak.run.commons.Utils
-import org.apache.jackrabbit.oak.console.commands.*
 import org.apache.jackrabbit.oak.plugins.document.DocumentNodeStore
+import org.apache.groovy.groovysh.AnsiDetector
+import org.apache.groovy.groovysh.ExitNotification
+import org.apache.groovy.groovysh.Groovysh
+import org.apache.groovy.groovysh.InteractiveShellRunner
+import org.apache.groovy.groovysh.Command as ShellCommand
+import org.apache.groovy.groovysh.commands.AliasCommand
+import org.apache.groovy.groovysh.commands.ClearCommand
+import org.apache.groovy.groovysh.commands.DisplayCommand
+import org.apache.groovy.groovysh.commands.DocCommand
+import org.apache.groovy.groovysh.commands.EditCommand
+import org.apache.groovy.groovysh.commands.ExitCommand
+import org.apache.groovy.groovysh.commands.HistoryCommand
+import org.apache.groovy.groovysh.commands.ImportCommand
+import org.apache.groovy.groovysh.commands.InspectCommand
+import org.apache.groovy.groovysh.commands.LoadCommand
+import org.apache.groovy.groovysh.commands.PurgeCommand
+import org.apache.groovy.groovysh.commands.RecordCommand
+import org.apache.groovy.groovysh.commands.RegisterCommand
+import org.apache.groovy.groovysh.commands.SaveCommand
+import org.apache.groovy.groovysh.commands.SetCommand
+import org.apache.groovy.groovysh.commands.ShowCommand
 import org.codehaus.groovy.runtime.StackTraceUtils
-import org.codehaus.groovy.tools.shell.*
-import org.codehaus.groovy.tools.shell.Command as ShellCommand
-import org.codehaus.groovy.tools.shell.commands.*
 import org.codehaus.groovy.tools.shell.util.Logger
+import org.codehaus.groovy.tools.shell.IO
 import org.codehaus.groovy.tools.shell.util.Preferences
 import org.fusesource.jansi.Ansi
 import org.fusesource.jansi.AnsiConsole
 import org.fusesource.jansi.AnsiRenderer
 
 /**
- * Some part of logic is based on usage in org.codehaus.groovy.tools.shell.Main
+ * Some part of logic is based on usage in org.apache.groovy.tools.shell.Main
  */
 @CompileStatic
 class GroovyConsole {
@@ -175,7 +205,7 @@ class GroovyConsole {
                 throw new IllegalStateException("Error hook is not set")
             }
             if (cause instanceof MissingPropertyException) {
-                if (cause.type && cause.type.canonicalName == Interpreter.SCRIPT_FILENAME) {
+                if (cause.type && cause.type.canonicalName == "groovysh_evaluate") {
                     io.err.println("@|bold,red Unknown property|@: " + cause.property)
                     return
                 }
diff --git a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/CdCommand.groovy b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/CdCommand.groovy
index 98811828811..b62f6017393 100644
--- a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/CdCommand.groovy
+++ b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/CdCommand.groovy
@@ -22,9 +22,9 @@ import jline.console.completer.Completer
 import org.apache.jackrabbit.oak.commons.PathUtils
 import org.apache.jackrabbit.oak.commons.collections.IterableUtils
 import org.apache.jackrabbit.oak.console.ConsoleSession
-import org.codehaus.groovy.tools.shell.CommandSupport
-import org.codehaus.groovy.tools.shell.Groovysh
-import org.codehaus.groovy.tools.shell.util.SimpleCompletor
+import org.apache.groovy.groovysh.CommandSupport
+import org.apache.groovy.groovysh.Groovysh
+import org.apache.groovy.groovysh.util.SimpleCompleter
 
 class CdCommand extends CommandSupport{
     public static final String COMMAND_NAME = 'change-dir'
@@ -35,7 +35,7 @@ class CdCommand extends CommandSupport{
 
     @Override
     protected List<Completer> createCompleters() {
-        SimpleCompletor completor = new SimpleCompletor(){
+        SimpleCompleter completor = new SimpleCompleter(){
             @Override
             SortedSet getCandidates() {
                 SortedSet<String> names = new TreeSet<String>()
diff --git a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/CheckpointCommand.groovy b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/CheckpointCommand.groovy
index a50f7c51568..20610ddf6e1 100644
--- a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/CheckpointCommand.groovy
+++ b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/CheckpointCommand.groovy
@@ -20,8 +20,8 @@ package org.apache.jackrabbit.oak.console.commands
 
 import groovy.transform.CompileStatic
 import org.apache.jackrabbit.oak.console.ConsoleSession
-import org.codehaus.groovy.tools.shell.CommandSupport
-import org.codehaus.groovy.tools.shell.Groovysh
+import org.apache.groovy.groovysh.CommandSupport
+import org.apache.groovy.groovysh.Groovysh
 
 import java.util.concurrent.TimeUnit
 
diff --git a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/ExportCommand.groovy b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/ExportCommand.groovy
index 5a4772f9c2b..a94d30f7f0d 100644
--- a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/ExportCommand.groovy
+++ b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/ExportCommand.groovy
@@ -22,8 +22,8 @@ package org.apache.jackrabbit.oak.console.commands
 import org.apache.jackrabbit.oak.commons.PathUtils
 import org.apache.jackrabbit.oak.console.ConsoleSession
 import org.apache.jackrabbit.oak.exporter.NodeStateSerializer
-import org.codehaus.groovy.tools.shell.CommandSupport
-import org.codehaus.groovy.tools.shell.Groovysh
+import org.apache.groovy.groovysh.CommandSupport
+import org.apache.groovy.groovysh.Groovysh
 import groovy.cli.picocli.CliBuilder
 
 class ExportCommand extends CommandSupport{
diff --git a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/ExportRelevantDocumentsCommand.groovy b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/ExportRelevantDocumentsCommand.groovy
index b5eabf11d98..13b665d3969 100644
--- a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/ExportRelevantDocumentsCommand.groovy
+++ b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/ExportRelevantDocumentsCommand.groovy
@@ -25,8 +25,8 @@ import org.apache.jackrabbit.oak.plugins.document.DocumentNodeStore
 import org.apache.jackrabbit.oak.plugins.document.DocumentStore
 import org.apache.jackrabbit.oak.plugins.document.NodeDocument
 import org.apache.jackrabbit.oak.plugins.document.util.Utils
-import org.codehaus.groovy.tools.shell.CommandSupport
-import org.codehaus.groovy.tools.shell.Groovysh
+import org.apache.groovy.groovysh.CommandSupport
+import org.apache.groovy.groovysh.Groovysh
 import groovy.cli.picocli.CliBuilder
 
 class ExportRelevantDocumentsCommand extends CommandSupport {
diff --git a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/LsCommand.groovy b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/LsCommand.groovy
index fd38c33f78c..54cb55763a3 100644
--- a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/LsCommand.groovy
+++ b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/LsCommand.groovy
@@ -21,8 +21,8 @@ package org.apache.jackrabbit.oak.console.commands
 import groovy.transform.CompileStatic
 import org.apache.jackrabbit.oak.commons.collections.IterableUtils
 import org.apache.jackrabbit.oak.console.ConsoleSession
-import org.codehaus.groovy.tools.shell.CommandSupport
-import org.codehaus.groovy.tools.shell.Groovysh
+import org.apache.groovy.groovysh.CommandSupport
+import org.apache.groovy.groovysh.Groovysh
 
 @CompileStatic
 class LsCommand extends CommandSupport{
diff --git a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/LsdDocumentCommand.groovy b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/LsdDocumentCommand.groovy
index 55ec16eb842..964ecc1f642 100644
--- a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/LsdDocumentCommand.groovy
+++ b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/LsdDocumentCommand.groovy
@@ -24,8 +24,8 @@ import org.apache.jackrabbit.oak.plugins.document.DocumentNodeStore
 import org.apache.jackrabbit.oak.plugins.document.NodeDocument
 import org.apache.jackrabbit.oak.plugins.document.Path
 import org.apache.jackrabbit.oak.plugins.document.util.Utils
-import org.codehaus.groovy.tools.shell.CommandSupport
-import org.codehaus.groovy.tools.shell.Groovysh
+import org.apache.groovy.groovysh.CommandSupport
+import org.apache.groovy.groovysh.Groovysh
 
 import static org.apache.jackrabbit.oak.plugins.document.Collection.NODES
 
diff --git a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/LuceneCommand.groovy b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/LuceneCommand.groovy
index dbea3e1bb79..00ddbcc4757 100644
--- a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/LuceneCommand.groovy
+++ b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/LuceneCommand.groovy
@@ -35,8 +35,8 @@ import org.apache.lucene.index.DirectoryReader
 import org.apache.lucene.store.Directory
 import org.apache.lucene.store.FSDirectory
 import org.apache.lucene.store.IOContext
-import org.codehaus.groovy.tools.shell.ComplexCommandSupport
-import org.codehaus.groovy.tools.shell.Groovysh
+import org.apache.groovy.groovysh.ComplexCommandSupport
+import org.apache.groovy.groovysh.Groovysh
 import org.apache.jackrabbit.oak.spi.state.NodeBuilder as OakNodeBuilder
 
 
diff --git a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/OakHelpCommand.groovy b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/OakHelpCommand.groovy
index 703d409b887..814039cf80b 100644
--- a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/OakHelpCommand.groovy
+++ b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/OakHelpCommand.groovy
@@ -18,13 +18,13 @@
  */
 package org.apache.jackrabbit.oak.console.commands
 
-import org.codehaus.groovy.tools.shell.Command
-import org.codehaus.groovy.tools.shell.CommandSupport
-import org.codehaus.groovy.tools.shell.Groovysh
-import org.codehaus.groovy.tools.shell.completion.CommandNameCompleter
+import org.apache.groovy.groovysh.Command
+import org.apache.groovy.groovysh.CommandSupport
+import org.apache.groovy.groovysh.Groovysh
+import org.apache.groovy.groovysh.completion.CommandNameCompleter
 
 /**
- * Copy of org.codehaus.groovy.tools.shell.commands.HelpCommand to customize
+ * Copy of org.apache.groovy.tools.shell.commands.HelpCommand to customize
  * the banner
  */
 class OakHelpCommand extends CommandSupport{
diff --git a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/PnCommand.groovy b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/PnCommand.groovy
index 987b6df5dd7..0d01370db0f 100644
--- a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/PnCommand.groovy
+++ b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/PnCommand.groovy
@@ -21,8 +21,8 @@ package org.apache.jackrabbit.oak.console.commands
 import groovy.transform.CompileStatic
 import org.apache.jackrabbit.oak.console.ConsoleSession
 import org.apache.jackrabbit.oak.nodestate.NodeStateHelper
-import org.codehaus.groovy.tools.shell.CommandSupport
-import org.codehaus.groovy.tools.shell.Groovysh
+import org.apache.groovy.groovysh.CommandSupport
+import org.apache.groovy.groovysh.Groovysh
 
 @CompileStatic
 class PnCommand extends CommandSupport{
diff --git a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/PrintDocumentCommand.groovy b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/PrintDocumentCommand.groovy
index 1cf646a86c5..820e8698eb3 100644
--- a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/PrintDocumentCommand.groovy
+++ b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/PrintDocumentCommand.groovy
@@ -23,8 +23,8 @@ import org.apache.jackrabbit.oak.console.ConsoleSession
 import org.apache.jackrabbit.oak.plugins.document.DocumentNodeStore
 import org.apache.jackrabbit.oak.plugins.document.NodeDocument
 import org.apache.jackrabbit.oak.plugins.document.util.Utils
-import org.codehaus.groovy.tools.shell.CommandSupport
-import org.codehaus.groovy.tools.shell.Groovysh
+import org.apache.groovy.groovysh.CommandSupport
+import org.apache.groovy.groovysh.Groovysh
 import org.json.simple.JSONObject
 import org.json.simple.JSONValue
 
diff --git a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/RefreshCommand.groovy b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/RefreshCommand.groovy
index 8691296490d..b7edf1f3475 100644
--- a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/RefreshCommand.groovy
+++ b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/RefreshCommand.groovy
@@ -20,8 +20,8 @@ package org.apache.jackrabbit.oak.console.commands
 
 import groovy.transform.CompileStatic
 import org.apache.jackrabbit.oak.console.ConsoleSession
-import org.codehaus.groovy.tools.shell.ComplexCommandSupport
-import org.codehaus.groovy.tools.shell.Groovysh
+import org.apache.groovy.groovysh.ComplexCommandSupport
+import org.apache.groovy.groovysh.Groovysh
 
 @CompileStatic
 class RefreshCommand extends ComplexCommandSupport{
diff --git a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/RetrieveCommand.groovy b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/RetrieveCommand.groovy
index 682f2e6765b..9433dc17346 100644
--- a/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/RetrieveCommand.groovy
+++ b/oak-run/src/main/groovy/org/apache/jackrabbit/oak/console/commands/RetrieveCommand.groovy
@@ -20,8 +20,8 @@ package org.apache.jackrabbit.oak.console.commands
 
 import groovy.transform.CompileStatic
 import org.apache.jackrabbit.oak.console.ConsoleSession
-import org.codehaus.groovy.tools.shell.CommandSupport
-import org.codehaus.groovy.tools.shell.Groovysh
+import org.apache.groovy.groovysh.CommandSupport
+import org.apache.groovy.groovysh.Groovysh
 
 @CompileStatic
 class RetrieveCommand extends CommandSupport{