diff --git a/graalpython/com.oracle.graal.python.test/src/tests/unittest_tags/test_contextlib.txt b/graalpython/com.oracle.graal.python.test/src/tests/unittest_tags/test_contextlib.txt
index 21bf666890..565bf67268 100644
--- a/graalpython/com.oracle.graal.python.test/src/tests/unittest_tags/test_contextlib.txt
+++ b/graalpython/com.oracle.graal.python.test/src/tests/unittest_tags/test_contextlib.txt
@@ -51,8 +51,10 @@ test.test_contextlib.TestExitStack.test_dont_reraise_RuntimeError @ darwin-arm64
 test.test_contextlib.TestExitStack.test_enter_context @ darwin-arm64,linux-aarch64,linux-aarch64-github,linux-x86_64,linux-x86_64-github,win32-AMD64,win32-AMD64-github
 test.test_contextlib.TestExitStack.test_enter_context_errors @ darwin-arm64,linux-aarch64,linux-aarch64-github,linux-x86_64,linux-x86_64-github,win32-AMD64,win32-AMD64-github
 test.test_contextlib.TestExitStack.test_excessive_nesting @ darwin-arm64,linux-aarch64,linux-aarch64-github,linux-x86_64,linux-x86_64-github,win32-AMD64,win32-AMD64-github
+test.test_contextlib.TestExitStack.test_exit_exception_chaining @ darwin-arm64,linux-aarch64,linux-aarch64-github,linux-x86_64,linux-x86_64-github,win32-AMD64,win32-AMD64-github
 test.test_contextlib.TestExitStack.test_exit_exception_chaining_reference @ darwin-arm64,linux-aarch64,linux-aarch64-github,linux-x86_64,linux-x86_64-github,win32-AMD64,win32-AMD64-github
 test.test_contextlib.TestExitStack.test_exit_exception_chaining_suppress @ darwin-arm64,linux-aarch64,linux-aarch64-github,linux-x86_64,linux-x86_64-github,win32-AMD64,win32-AMD64-github
+test.test_contextlib.TestExitStack.test_exit_exception_explicit_none_context @ darwin-arm64,linux-aarch64,linux-aarch64-github,linux-x86_64,linux-x86_64-github,win32-AMD64,win32-AMD64-github
 test.test_contextlib.TestExitStack.test_exit_exception_non_suppressing @ darwin-arm64,linux-aarch64,linux-aarch64-github,linux-x86_64,linux-x86_64-github,win32-AMD64,win32-AMD64-github
 test.test_contextlib.TestExitStack.test_exit_exception_traceback @ darwin-arm64,linux-aarch64,linux-aarch64-github,linux-x86_64,linux-x86_64-github,win32-AMD64,win32-AMD64-github
 test.test_contextlib.TestExitStack.test_exit_exception_with_correct_context @ darwin-arm64,linux-aarch64,linux-aarch64-github,linux-x86_64,linux-x86_64-github,win32-AMD64,win32-AMD64-github
diff --git a/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/nodes/bytecode/PBytecodeRootNode.java b/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/nodes/bytecode/PBytecodeRootNode.java
index fef50c8cca..e4b7724903 100644
--- a/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/nodes/bytecode/PBytecodeRootNode.java
+++ b/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/nodes/bytecode/PBytecodeRootNode.java
@@ -3453,6 +3453,9 @@ private void chainPythonExceptions(VirtualFrame virtualFrame, MutableLoopData mu
     }
 
     private void chainPythonExceptions(PException current, PException context) {
+        if (current.isReraised()) {
+            return;
+        }
         if (chainExceptionsNode == null) {
             CompilerDirectives.transferToInterpreterAndInvalidate();
             chainExceptionsNode = insert(ChainExceptionsNode.create());
diff --git a/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/nodes/bytecode_dsl/PBytecodeDSLRootNode.java b/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/nodes/bytecode_dsl/PBytecodeDSLRootNode.java
index 46868c9eca..09e5ecb375 100644
--- a/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/nodes/bytecode_dsl/PBytecodeDSLRootNode.java
+++ b/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/nodes/bytecode_dsl/PBytecodeDSLRootNode.java
@@ -901,7 +901,7 @@ public AbstractTruffleException interceptTruffleException(AbstractTruffleExcepti
                 getCaughtExceptionNode = insert(ExceptionStateNodes.GetCaughtExceptionNode.create());
             }
             AbstractTruffleException context = getCaughtExceptionNode.execute(frame);
-            if (context instanceof PException pe2) {
+            if (context instanceof PException pe2 && !pe.isReraised()) {
                 if (chainExceptionsNode == null) {
                     CompilerDirectives.transferToInterpreterAndInvalidate();
                     chainExceptionsNode = insert(ChainExceptionsNode.create());
diff --git a/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/runtime/exception/PException.java b/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/runtime/exception/PException.java
index 77f6d7f945..89c9f4a2ba 100644
--- a/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/runtime/exception/PException.java
+++ b/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/runtime/exception/PException.java
@@ -116,6 +116,7 @@ public final class PException extends AbstractTruffleException {
     private int catchBci;
     private boolean reified = false;
     private boolean skipFirstTracebackFrame;
+    private boolean reraised;
 
     // See the docs of MaterializeLazyTracebackNode
     private int tracebackFrameCount;
@@ -436,6 +437,7 @@ public void notifyAddedTracebackFrame(boolean visible) {
     public PException getExceptionForReraise(boolean rootNodeVisible) {
         ensureReified();
         PException pe = PException.fromObject(pythonException, getLocation(), false);
+        pe.reraised = true;
         if (pe.getUnreifiedException() instanceof PBaseExceptionGroup grp) {
             grp.setContainsReraises(true);
         }
@@ -603,6 +605,10 @@ public void dontTraceOnReraise() {
         shouldTrace = true;
     }
 
+    public boolean isReraised() {
+        return reraised;
+    }
+
     @TruffleBoundary
     public static PException raiseUnboundLocalException(BytecodeNode bytecodeNode, LocalVariable localVariable) {
         Object info = localVariable.getInfo();