diff --git a/plexus-compiler-its/pom.xml b/plexus-compiler-its/pom.xml
index 3fa5a7e62..e2ac1b1d7 100644
--- a/plexus-compiler-its/pom.xml
+++ b/plexus-compiler-its/pom.xml
@@ -15,7 +15,7 @@
 
   <properties>
     <junit.version>4.13.2</junit.version>
-    <javaVersion>17</javaVersion>
+    <javaVersion>21</javaVersion>
     <maven.deploy.skip>true</maven.deploy.skip>
   </properties>
 
diff --git a/plexus-compiler-its/src/main/it/error-prone-compiler/pom.xml b/plexus-compiler-its/src/main/it/error-prone-compiler/pom.xml
index a50cee55d..5a8896259 100644
--- a/plexus-compiler-its/src/main/it/error-prone-compiler/pom.xml
+++ b/plexus-compiler-its/src/main/it/error-prone-compiler/pom.xml
@@ -49,6 +49,7 @@
           <fork>true</fork>
           <compilerArgs>
             <arg>-XDcompilePolicy=simple</arg>
+            <arg>-XDaddTypeAnnotationsToSymbol=true</arg>
             <arg>-Xplugin:ErrorProne</arg>
             <arg>--should-stop=ifError=FLOW</arg>
             <arg>-J--add-exports=jdk.compiler/com.sun.tools.javac.api=ALL-UNNAMED</arg>
diff --git a/plexus-compiler-its/src/main/it/issues-351/pom.xml b/plexus-compiler-its/src/main/it/issues-351/pom.xml
index 15ffe11a6..5eb49dd2f 100644
--- a/plexus-compiler-its/src/main/it/issues-351/pom.xml
+++ b/plexus-compiler-its/src/main/it/issues-351/pom.xml
@@ -55,6 +55,7 @@
             <arg>-J--add-opens=jdk.compiler/com.sun.tools.javac.code=ALL-UNNAMED</arg>
             <arg>-J--add-opens=jdk.compiler/com.sun.tools.javac.comp=ALL-UNNAMED</arg>
             <arg>-XDcompilePolicy=simple</arg>
+            <arg>-XDaddTypeAnnotationsToSymbol=true</arg>
             <arg>--should-stop=ifError=FLOW</arg>
             <arg>-Xplugin:ErrorProne
               -Xep:DeadException:WARN</arg>
diff --git a/plexus-compilers/plexus-compiler-javac-errorprone/pom.xml b/plexus-compilers/plexus-compiler-javac-errorprone/pom.xml
index f8e96af38..60e51ba00 100644
--- a/plexus-compilers/plexus-compiler-javac-errorprone/pom.xml
+++ b/plexus-compilers/plexus-compiler-javac-errorprone/pom.xml
@@ -16,7 +16,7 @@
     See https://errorprone.info</description>
 
   <properties>
-    <javaVersion>17</javaVersion>
+    <javaVersion>21</javaVersion>
   </properties>
 
   <dependencies>
diff --git a/plexus-compilers/plexus-compiler-javac-errorprone/src/site/markdown/index.md b/plexus-compilers/plexus-compiler-javac-errorprone/src/site/markdown/index.md
index aa7f27659..efc5dbf5a 100644
--- a/plexus-compilers/plexus-compiler-javac-errorprone/src/site/markdown/index.md
+++ b/plexus-compilers/plexus-compiler-javac-errorprone/src/site/markdown/index.md
@@ -6,4 +6,4 @@ with error-prone static analysis checks enabled.
 
 See https://errorprone.info
 
-**Requires** `JDK 17+`
+**Requires** `JDK 21+`
diff --git a/plexus-compilers/plexus-compiler-javac-errorprone/src/test/java/org/codehaus/plexus/compiler/javac/JavacErrorProneCompilerTest.java b/plexus-compilers/plexus-compiler-javac-errorprone/src/test/java/org/codehaus/plexus/compiler/javac/JavacErrorProneCompilerTest.java
index 2e6eb9a2a..553e06af6 100644
--- a/plexus-compilers/plexus-compiler-javac-errorprone/src/test/java/org/codehaus/plexus/compiler/javac/JavacErrorProneCompilerTest.java
+++ b/plexus-compilers/plexus-compiler-javac-errorprone/src/test/java/org/codehaus/plexus/compiler/javac/JavacErrorProneCompilerTest.java
@@ -17,7 +17,8 @@ protected int expectedWarnings() {
         String javaVersion = getJavaVersion();
         if (javaVersion.startsWith("1.8")) {
             return 1;
-        } else if (javaVersion.contains("21") || javaVersion.contains("25")) {
+        } else if (Runtime.version().feature() >= 21) {
+            // javac 21 and later also warn that -source 8 and -target 8 are obsolete
             return 5;
         }
         return 2;
diff --git a/pom.xml b/pom.xml
index a001176cd..d9241c184 100644
--- a/pom.xml
+++ b/pom.xml
@@ -46,7 +46,7 @@
     <redirectTestOutputToFile>true</redirectTestOutputToFile>
     <project.build.outputTimestamp>2026-09-09T11:47:52Z</project.build.outputTimestamp>
     <aspectj.version>1.9.21</aspectj.version>
-    <errorprone.version>2.37.0</errorprone.version>
+    <errorprone.version>2.50.0</errorprone.version>
     <eclipse.sisu.version>1.1.0</eclipse.sisu.version>
     <trimStackTrace>false</trimStackTrace>
     <preparationGoals>clean install</preparationGoals>