diff --git a/src/app/OperationalSessionSetup.cpp b/src/app/OperationalSessionSetup.cpp
index 7b5d70919f2a8a..0b68c12c96a7dd 100644
--- a/src/app/OperationalSessionSetup.cpp
+++ b/src/app/OperationalSessionSetup.cpp
@@ -702,10 +702,43 @@ void OperationalSessionSetup::NotifyRetryHandlers(CHIP_ERROR error, const Reliab
 
 void OperationalSessionSetup::NotifyRetryHandlers(CHIP_ERROR error, System::Clock::Seconds16 timeoutEstimate)
 {
-    for (auto * item = mConnectionRetry.First(); item && item != &mConnectionRetry; item = item->mNext)
+    // We have to be very careful here: Calling into these handlers might in
+    // theory destroy the Callback objects involved, but unlike the
+    // succcess/failure cases we don't want to just clear the handlers from our
+    // list when we are calling them, because we might need to call a given
+    // handler more than once.
+    //
+    // To handle this we:
+    //
+    // 1) Snapshot the list of handlers up front, so if any of the handlers
+    //    triggers an AddRetryHandler with some other handler that does not
+    //    affect the list we plan to notify here.
+    //
+    // 2) When planning to notify a handler move it to a new list that contains
+    //    just that handler.  This way if it gets canceled as part of the
+    //    notification we can tell it has been canceled.
+    //
+    // 3) If notifying the handler does not cancel it, add it back to our list
+    //    of handlers so we will notify it on future retries.
+
+    Cancelable retryHandlerListSnapshot;
+    mConnectionRetry.DequeueAll(retryHandlerListSnapshot);
+
+    while (retryHandlerListSnapshot.mNext != &retryHandlerListSnapshot)
     {
-        auto cb = Callback::Callback<OnDeviceConnectionRetry>::FromCancelable(item);
+        auto * cb = Callback::Callback<OnDeviceConnectionRetry>::FromCancelable(retryHandlerListSnapshot.mNext);
+
+        Callback::CallbackDeque currentCallbackHolder;
+        currentCallbackHolder.Enqueue(cb->Cancel());
+
         cb->mCall(cb->mContext, mPeerId, error, timeoutEstimate);
+
+        if (currentCallbackHolder.mNext != &currentCallbackHolder)
+        {
+            // Callback has not been canceled as part of the call, so is still
+            // supposed to be registered with us.
+            AddRetryHandler(cb);
+        }
     }
 }
 #endif // CHIP_DEVICE_CONFIG_ENABLE_AUTOMATIC_CASE_RETRIES