diff --git a/server/src/test/java/org/opensearch/index/translog/RemoteFsTimestampAwareTranslogTests.java b/server/src/test/java/org/opensearch/index/translog/RemoteFsTimestampAwareTranslogTests.java
index 6cac02ebaa15b..0995f2e75a17a 100644
--- a/server/src/test/java/org/opensearch/index/translog/RemoteFsTimestampAwareTranslogTests.java
+++ b/server/src/test/java/org/opensearch/index/translog/RemoteFsTimestampAwareTranslogTests.java
@@ -1505,4 +1505,22 @@ public void testTrimUnreferencedReadersNoPermits() throws Exception {
             );
         }, 30, TimeUnit.SECONDS);
     }
+
+    public void testTrimUnreferencedReadersFailAlwaysRepo() throws Exception {
+        ArrayList<Translog.Operation> ops = new ArrayList<>();
+
+        addToTranslogAndListAndUpload(translog, ops, new Translog.Index("0", 0, primaryTerm.get(), new byte[] { 1 }));
+        addToTranslogAndListAndUpload(translog, ops, new Translog.Index("1", 1, primaryTerm.get(), new byte[] { 1 }));
+        addToTranslogAndListAndUpload(translog, ops, new Translog.Index("2", 2, primaryTerm.get(), new byte[] { 1 }));
+        addToTranslogAndListAndUpload(translog, ops, new Translog.Index("3", 3, primaryTerm.get(), new byte[] { 1 }));
+
+        translog.setMinSeqNoToKeep(2);
+        RemoteStoreSettings.setPinnedTimestampsLookbackInterval(TimeValue.ZERO);
+        updatePinnedTimstampTask.run();
+
+        fail.failAlways();
+        translog.trimUnreferencedReaders();
+
+        assertBusy(() -> assertTrue(translog.isRemoteGenerationDeletionPermitsAvailable()));
+    }
 }
diff --git a/server/src/test/java/org/opensearch/index/translog/RemoteFsTranslogTests.java b/server/src/test/java/org/opensearch/index/translog/RemoteFsTranslogTests.java
index 03c77a9a83f57..190af714d5764 100644
--- a/server/src/test/java/org/opensearch/index/translog/RemoteFsTranslogTests.java
+++ b/server/src/test/java/org/opensearch/index/translog/RemoteFsTranslogTests.java
@@ -20,6 +20,7 @@
 import org.opensearch.cluster.metadata.RepositoryMetadata;
 import org.opensearch.cluster.service.ClusterService;
 import org.opensearch.common.blobstore.BlobContainer;
+import org.opensearch.common.blobstore.BlobMetadata;
 import org.opensearch.common.blobstore.BlobPath;
 import org.opensearch.common.blobstore.BlobStore;
 import org.opensearch.common.blobstore.fs.FsBlobContainer;
@@ -32,6 +33,7 @@
 import org.opensearch.common.util.concurrent.AbstractRunnable;
 import org.opensearch.common.util.concurrent.ConcurrentCollections;
 import org.opensearch.common.util.io.IOUtils;
+import org.opensearch.core.action.ActionListener;
 import org.opensearch.core.common.bytes.BytesArray;
 import org.opensearch.core.common.unit.ByteSizeUnit;
 import org.opensearch.core.common.unit.ByteSizeValue;
@@ -1965,6 +1967,28 @@ public void writeBlobAtomic(final String blobName, final InputStream inputStream
             }
             super.writeBlobAtomic(blobName, inputStream, blobSize, failIfAlreadyExists);
         }
+
+        @Override
+        public void listBlobsByPrefixInSortedOrder(
+            String blobNamePrefix,
+            int limit,
+            BlobNameSortOrder blobNameSortOrder,
+            ActionListener<List<BlobMetadata>> listener
+        ) {
+            if (fail.fail()) {
+                listener.onFailure(new RuntimeException("blob container throwing error"));
+                return;
+            }
+            if (slowDown.getSleepSeconds() > 0) {
+                try {
+                    Thread.sleep(slowDown.getSleepSeconds() * 1000L);
+                } catch (InterruptedException e) {
+                    listener.onFailure(new RuntimeException(e));
+                    return;
+                }
+            }
+            super.listBlobsByPrefixInSortedOrder(blobNamePrefix, limit, blobNameSortOrder, listener);
+        }
     }
 
     class TranslogThread extends Thread {