diff --git a/docs/changelog/122326.yaml b/docs/changelog/122326.yaml
new file mode 100644
index 0000000000000..91c71041d58fc
--- /dev/null
+++ b/docs/changelog/122326.yaml
@@ -0,0 +1,5 @@
+pr: 122326
+summary: System Index Migration Failure Results in a Non-Recoverable State
+area: Infra/Core
+type: bug
+issues: []
diff --git a/modules/reindex/src/internalClusterTest/java/org/elasticsearch/migration/FeatureMigrationIT.java b/modules/reindex/src/internalClusterTest/java/org/elasticsearch/migration/FeatureMigrationIT.java
index ee95ce5513820..efca437d14eb4 100644
--- a/modules/reindex/src/internalClusterTest/java/org/elasticsearch/migration/FeatureMigrationIT.java
+++ b/modules/reindex/src/internalClusterTest/java/org/elasticsearch/migration/FeatureMigrationIT.java
@@ -277,7 +277,6 @@ public void testMigrateIndexWithWriteBlock() throws Exception {
         });
     }
 
-    @AwaitsFix(bugUrl = "ES-10666") // This test uncovered an existing issue
     public void testIndexBlockIsRemovedWhenAliasRequestFails() throws Exception {
         createSystemIndexForDescriptor(INTERNAL_UNMANAGED);
         ensureGreen();
diff --git a/server/src/main/java/org/elasticsearch/upgrades/SystemIndexMigrator.java b/server/src/main/java/org/elasticsearch/upgrades/SystemIndexMigrator.java
index cdd466c567e8b..9947606470178 100644
--- a/server/src/main/java/org/elasticsearch/upgrades/SystemIndexMigrator.java
+++ b/server/src/main/java/org/elasticsearch/upgrades/SystemIndexMigrator.java
@@ -207,49 +207,14 @@ public void run(SystemIndexMigrationTaskState taskState) {
         }
 
         // Kick off our callback "loop" - finishIndexAndLoop calls back into prepareNextIndex
-        cleanUpPreviousMigration(
-            taskState,
-            clusterState,
-            state -> prepareNextIndex(state, state2 -> migrateSingleIndex(state2, this::finishIndexAndLoop), stateFeatureName)
-        );
-    }
-
-    private void cleanUpPreviousMigration(
-        SystemIndexMigrationTaskState taskState,
-        ClusterState currentState,
-        Consumer<ClusterState> listener
-    ) {
         logger.debug("cleaning up previous migration, task state: [{}]", taskState == null ? "null" : Strings.toString(taskState));
-        if (taskState != null && taskState.getCurrentIndex() != null) {
-            SystemIndexMigrationInfo migrationInfo;
-            try {
-                migrationInfo = SystemIndexMigrationInfo.fromTaskState(
-                    taskState,
-                    systemIndices,
-                    currentState.metadata(),
-                    indexScopedSettings
-                );
-            } catch (Exception e) {
-                markAsFailed(e);
-                return;
-            }
-            final String newIndexName = migrationInfo.getNextIndexName();
-            logger.info("removing index [{}] from previous incomplete migration", newIndexName);
-
-            migrationInfo.createClient(baseClient)
-                .admin()
-                .indices()
-                .prepareDelete(newIndexName)
-                .execute(ActionListener.wrap(ackedResponse -> {
-                    if (ackedResponse.isAcknowledged()) {
-                        logger.debug("successfully removed index [{}]", newIndexName);
-                        clearResults(clusterService, ActionListener.wrap(listener::accept, this::markAsFailed));
-                    }
-                }, this::markAsFailed));
-        } else {
-            logger.debug("no incomplete index to remove");
-            clearResults(clusterService, ActionListener.wrap(listener::accept, this::markAsFailed));
-        }
+        clearResults(
+            clusterService,
+            ActionListener.wrap(
+                state -> prepareNextIndex(state2 -> migrateSingleIndex(state2, this::finishIndexAndLoop), stateFeatureName),
+                this::markAsFailed
+            )
+        );
     }
 
     private void finishIndexAndLoop(BulkByScrollResponse bulkResponse) {
@@ -289,11 +254,7 @@ private void finishIndexAndLoop(BulkByScrollResponse bulkResponse) {
                 }, this::markAsFailed)
             );
         } else {
-            prepareNextIndex(
-                clusterService.state(),
-                state2 -> migrateSingleIndex(state2, this::finishIndexAndLoop),
-                lastMigrationInfo.getFeatureName()
-            );
+            prepareNextIndex(state2 -> migrateSingleIndex(state2, this::finishIndexAndLoop), lastMigrationInfo.getFeatureName());
         }
     }
 
@@ -303,7 +264,6 @@ private void recordIndexMigrationSuccess(SystemIndexMigrationInfo lastMigrationI
             SingleFeatureMigrationResult.success(),
             ActionListener.wrap(state -> {
                 prepareNextIndex(
-                    state,
                     clusterState -> migrateSingleIndex(clusterState, this::finishIndexAndLoop),
                     lastMigrationInfo.getFeatureName()
                 );
@@ -312,7 +272,7 @@ private void recordIndexMigrationSuccess(SystemIndexMigrationInfo lastMigrationI
         updateTask.submit(clusterService);
     }
 
-    private void prepareNextIndex(ClusterState clusterState, Consumer<ClusterState> listener, String lastFeatureName) {
+    private void prepareNextIndex(Consumer<ClusterState> listener, String lastFeatureName) {
         synchronized (migrationQueue) {
             assert migrationQueue != null;
             if (migrationQueue.isEmpty()) {
@@ -424,7 +384,7 @@ private void migrateSingleIndex(ClusterState clusterState, Consumer<BulkByScroll
         logger.info("migrating index [{}] from feature [{}] to new index [{}]", oldIndexName, migrationInfo.getFeatureName(), newIndexName);
         ActionListener<BulkByScrollResponse> innerListener = ActionListener.wrap(listener::accept, this::markAsFailed);
         try {
-            createIndex(migrationInfo, innerListener.delegateFailureAndWrap((delegate, shardsAcknowledgedResponse) -> {
+            createIndexRetryOnFailure(migrationInfo, innerListener.delegateFailureAndWrap((delegate, shardsAcknowledgedResponse) -> {
                 logger.debug(
                     "while migrating [{}] , got create index response: [{}]",
                     oldIndexName,
@@ -509,6 +469,8 @@ private void migrateSingleIndex(ClusterState clusterState, Consumer<BulkByScroll
     }
 
     private void createIndex(SystemIndexMigrationInfo migrationInfo, ActionListener<ShardsAcknowledgedResponse> listener) {
+        logger.info("creating new system index [{}] from feature [{}]", migrationInfo.getNextIndexName(), migrationInfo.getFeatureName());
+
         final CreateIndexClusterStateUpdateRequest createRequest = new CreateIndexClusterStateUpdateRequest(
             "migrate-system-index",
             migrationInfo.getNextIndexName(),
@@ -534,6 +496,35 @@ private void createIndex(SystemIndexMigrationInfo migrationInfo, ActionListener<
         );
     }
 
+    private void createIndexRetryOnFailure(SystemIndexMigrationInfo migrationInfo, ActionListener<ShardsAcknowledgedResponse> listener) {
+        createIndex(migrationInfo, listener.delegateResponse((l, e) -> {
+            logger.warn("createIndex failed, retrying after removing index [{}] from previous attempt", migrationInfo.getNextIndexName());
+            deleteIndex(migrationInfo, ActionListener.wrap(cleanupResponse -> createIndex(migrationInfo, l.delegateResponse((l3, e3) -> {
+                logger.error(
+                    "createIndex failed after retrying, aborting system index migration. index: " + migrationInfo.getNextIndexName(),
+                    e3
+                );
+                l.onFailure(e3);
+            })), e2 -> {
+                logger.error("deleteIndex failed, aborting system index migration. index: " + migrationInfo.getNextIndexName(), e2);
+                l.onFailure(e2);
+            }));
+        }));
+    }
+
+    private <T> void deleteIndex(SystemIndexMigrationInfo migrationInfo, ActionListener<AcknowledgedResponse> listener) {
+        logger.info("removing index [{}] from feature [{}]", migrationInfo.getNextIndexName(), migrationInfo.getFeatureName());
+        String newIndexName = migrationInfo.getNextIndexName();
+        baseClient.admin().indices().prepareDelete(newIndexName).execute(ActionListener.wrap(ackedResponse -> {
+            if (ackedResponse.isAcknowledged()) {
+                logger.info("successfully removed index [{}]", newIndexName);
+                listener.onResponse(ackedResponse);
+            } else {
+                listener.onFailure(new ElasticsearchException("Failed to acknowledge index deletion for [" + newIndexName + "]"));
+            }
+        }, listener::onFailure));
+    }
+
     private void setAliasAndRemoveOldIndex(SystemIndexMigrationInfo migrationInfo, ActionListener<IndicesAliasesResponse> listener) {
         final IndicesAliasesRequestBuilder aliasesRequest = migrationInfo.createClient(baseClient).admin().indices().prepareAliases();
         aliasesRequest.removeIndex(migrationInfo.getCurrentIndexName());