diff --git a/CHANGELOG.md b/CHANGELOG.md
index a3242d589..d7510d88d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,7 @@ All notable changes to this project will be documented in this file.
 ## [Unreleased]
 
 - Hide files starting with `.` in the timeline
+- Prevent automatically retrying failed indexing jobs
 
 ## [v6.2.2] - 2024-01-10
 
diff --git a/appinfo/routes.php b/appinfo/routes.php
index 294dc958f..6da9a71ee 100644
--- a/appinfo/routes.php
+++ b/appinfo/routes.php
@@ -96,6 +96,7 @@ function w($base, $param)
         ['name' => 'Admin#getSystemStatus', 'url' => '/api/system-status', 'verb' => 'GET'],
         ['name' => 'Admin#getSystemConfig', 'url' => '/api/system-config', 'verb' => 'GET'],
         ['name' => 'Admin#setSystemConfig', 'url' => '/api/system-config/{key}', 'verb' => 'PUT'],
+        ['name' => 'Admin#getFailureLogs', 'url' => '/api/failure-logs', 'verb' => 'GET'],
         ['name' => 'Admin#placesSetup', 'url' => '/api/occ/places-setup', 'verb' => 'POST'],
 
         // Service worker and assets
diff --git a/lib/Command/Index.php b/lib/Command/Index.php
index 0b07455e6..39b884f1f 100644
--- a/lib/Command/Index.php
+++ b/lib/Command/Index.php
@@ -42,6 +42,7 @@ class IndexOpts
     public ?string $user = null;
     public ?string $folder = null;
     public ?string $group = null;
+    public bool $retry = false;
     public bool $skipCleanup = false;
 
     public function __construct(InputInterface $input)
@@ -50,7 +51,8 @@ public function __construct(InputInterface $input)
         $this->clear = (bool) $input->getOption('clear');
         $this->user = $input->getOption('user');
         $this->folder = $input->getOption('folder');
-        $this->skipCleanup = $input->getOption('skip-cleanup');
+        $this->retry = (bool) $input->getOption('retry');
+        $this->skipCleanup = (bool) $input->getOption('skip-cleanup');
         $this->group = $input->getOption('group');
     }
 }
@@ -82,6 +84,7 @@ protected function configure(): void
             ->addOption('folder', null, InputOption::VALUE_REQUIRED, 'Index only the specified folder (relative to the user\'s root)')
             ->addOption('force', 'f', InputOption::VALUE_NONE, 'Force refresh of existing index entries')
             ->addOption('clear', null, InputOption::VALUE_NONE, 'Clear all existing index entries')
+            ->addOption('retry', 'r', InputOption::VALUE_NONE, 'Retry indexing of failed files')
             ->addOption('skip-cleanup', null, InputOption::VALUE_NONE, 'Skip cleanup step (removing index entries with missing files)')
         ;
     }
@@ -109,6 +112,7 @@ protected function execute(InputInterface $input, OutputInterface $output): int
             // Perform steps based on opts
             $this->checkClear();
             $this->checkForce();
+            $this->checkRetry();
 
             // Run the indexer
             $this->runIndex();
@@ -118,6 +122,9 @@ protected function execute(InputInterface $input, OutputInterface $output): int
                 $this->indexer->cleanupStale();
             }
 
+            // Warn about skipped files
+            $this->warnRetry();
+
             return 0;
         } catch (\Exception $e) {
             $this->output->writeln("<error>{$e->getMessage()}</error>".PHP_EOL);
@@ -161,10 +168,31 @@ protected function checkForce(): void
         }
 
         $this->output->writeln('Forcing refresh of existing index entries');
-
         $this->tw->orphanAll();
     }
 
+    /**
+     * Check and act on the retry option if set.
+     */
+    protected function checkRetry(): void
+    {
+        if (!$this->opts->retry) {
+            return;
+        }
+
+        $this->output->writeln("<info>Retrying indexing of failed files</info>");
+        $this->tw->clearAllFailures();
+    }
+
+    /**
+     * Warn about skipped files (called at the end of indexing).
+     */
+    protected function warnRetry(): void {
+        if ($count = $this->tw->countFailures()) {
+            $this->output->writeln("Indexing skipped for ${count} failed files, use --retry to try again");
+        }
+    }
+
     /**
      * Run the indexer.
      */
diff --git a/lib/Controller/AdminController.php b/lib/Controller/AdminController.php
index ccaab81bf..14ab67e0b 100644
--- a/lib/Controller/AdminController.php
+++ b/lib/Controller/AdminController.php
@@ -85,6 +85,7 @@ public function getSystemStatus(): Http\Response
         return Util::guardEx(function () {
             $config = \OC::$server->get(\OCP\IConfig::class);
             $index = \OC::$server->get(\OCA\Memories\Service\Index::class);
+            $tw = \OC::$server->get(\OCA\Memories\Db\TimelineWrite::class);
 
             // Build status array
             $status = [];
@@ -107,6 +108,7 @@ public function getSystemStatus(): Http\Response
 
             // Check number of indexed files
             $status['indexed_count'] = $index->getIndexedCount();
+            $status['failure_count'] = $tw->countFailures();
 
             // Automatic indexing stats
             $jobStart = (int) $config->getAppValue(Application::APPNAME, 'last_index_job_start', (string) 0);
@@ -178,6 +180,29 @@ public function getSystemStatus(): Http\Response
         });
     }
 
+    /**
+     * @AdminRequired
+     *
+     * @NoCSRFRequired
+     */
+    public function getFailureLogs(): Http\Response {
+        return Util::guardExDirect(static function (Http\IOutput $out) {
+            $tw = \OC::$server->get(\OCA\Memories\Db\TimelineWrite::class);
+
+            $out->setHeader('Content-Type: text/plain');
+            $out->setHeader('X-Accel-Buffering: no');
+            $out->setHeader('Cache-Control: no-cache');
+
+            foreach ($tw->listFailures() as $log) {
+                $fileid = str_pad((string) $log['fileid'], 12, ' ', STR_PAD_RIGHT); // size
+                $mtime = $log['mtime'];
+                $reason = $log['reason'];
+
+                $out->setOutput("{$fileid}[{$mtime}]\t{$reason}\n");
+            }
+        });
+    }
+
     /**
      * @AdminRequired
      *
diff --git a/lib/Db/TimelineWrite.php b/lib/Db/TimelineWrite.php
index 666de699c..eb56dc19c 100644
--- a/lib/Db/TimelineWrite.php
+++ b/lib/Db/TimelineWrite.php
@@ -11,7 +11,7 @@
 use OCP\IDBConnection;
 use OCP\Lock\ILockingProvider;
 
-const DELETE_TABLES = ['memories', 'memories_livephoto', 'memories_places'];
+const DELETE_TABLES = ['memories', 'memories_livephoto', 'memories_places', 'memories_failures'];
 const TRUNCATE_TABLES = ['memories_mapclusters'];
 
 class TimelineWrite
@@ -19,6 +19,7 @@ class TimelineWrite
     use TimelineWriteMap;
     use TimelineWriteOrphans;
     use TimelineWritePlaces;
+    use TimelineWriteFailures;
 
     public function __construct(
         protected IDBConnection $connection,
@@ -182,7 +183,15 @@ public function processFile(
             $query->insert('memories')->values($params);
         }
 
-        return $query->executeStatement() > 0;
+        // Execute query
+        $updated = $query->executeStatement() > 0;
+
+        // Clear failures if successful
+        if ($updated) {
+            $this->clearFailures($file);
+        }
+
+        return $updated;
     }
 
     /**
diff --git a/lib/Db/TimelineWriteFailures.php b/lib/Db/TimelineWriteFailures.php
new file mode 100644
index 000000000..4ad8d7c98
--- /dev/null
+++ b/lib/Db/TimelineWriteFailures.php
@@ -0,0 +1,93 @@
+<?php
+
+declare(strict_types=1);
+
+namespace OCA\Memories\Db;
+
+use OCP\DB\QueryBuilder\IQueryBuilder;
+use OCP\Files\File;
+use OCP\IDBConnection;
+
+trait TimelineWriteFailures
+{
+    protected IDBConnection $connection;
+
+    /**
+     * Mark a file as failed indexing.
+     * The file will not be re-indexed until it changes.
+     *
+     * @param File $file The file that failed indexing
+     * @param string $reason The reason for the failure
+     */
+    public function markFailed(File $file, string $reason): void
+    {
+        // Add file path to reason
+        $reason .= " ({$file->getPath()})";
+
+        // Remove all previous failures for this file
+        $this->connection->beginTransaction();
+        $this->clearFailures($file);
+
+        // Add the failure to the database
+        $query = $this->connection->getQueryBuilder();
+        $query->insert('memories_failures')
+            ->values([
+                'fileid' => $query->createNamedParameter($file->getId(), IQueryBuilder::PARAM_INT),
+                'mtime' => $query->createNamedParameter($file->getMtime(), IQueryBuilder::PARAM_INT),
+                'reason' => $query->createNamedParameter($reason, IQueryBuilder::PARAM_STR),
+            ])
+            ->executeStatement()
+        ;
+        $this->connection->commit();
+    }
+
+    /**
+     * Mark a file as successfully indexed.
+     * The entry will be removed from the failures table.
+     *
+     * @param File $file The file that was successfully indexed
+     */
+    public function clearFailures(File $file): void
+    {
+        $query = $this->connection->getQueryBuilder();
+        $query->delete('memories_failures')
+            ->where($query->expr()->eq('fileid', $query->createNamedParameter($file->getId(), IQueryBuilder::PARAM_INT)))
+            ->executeStatement()
+        ;
+    }
+
+    /**
+     * Get the count of failed files.
+     */
+    public function countFailures(): int
+    {
+        $query = $this->connection->getQueryBuilder();
+        $query->select($query->createFunction('COUNT(fileid)'))
+            ->from('memories_failures')
+        ;
+        return (int) $query->executeQuery()->fetchOne();
+    }
+
+    /**
+     * Get the list of failures.
+     */
+    public function listFailures(): array
+    {
+        return $this->connection->getQueryBuilder()
+            ->select('*')
+            ->from('memories_failures')
+            ->executeQuery()
+            ->fetchAll();
+        ;
+    }
+
+    /**
+     * Clear all failures from the database.
+     */
+    public function clearAllFailures(): void
+    {
+        // Delete all entries and reset autoincrement counter
+        $this->connection->executeStatement(
+            $this->connection->getDatabasePlatform()->getTruncateTableSQL('*PREFIX*memories_failures', false));
+    }
+}
\ No newline at end of file
diff --git a/lib/Migration/Version602003Date20240310203729.php b/lib/Migration/Version602003Date20240310203729.php
new file mode 100644
index 000000000..300f61bca
--- /dev/null
+++ b/lib/Migration/Version602003Date20240310203729.php
@@ -0,0 +1,75 @@
+<?php
+
+declare(strict_types=1);
+
+/**
+ * @copyright Copyright (c) 2023 Varun Patil <radialapps@gmail.com>
+ * @author Varun Patil <radialapps@gmail.com>
+ * @license GNU AGPL version 3 or any later version
+ *
+ * This program is free software: you can redistribute it and/or modify
+ * it under the terms of the GNU Affero General Public License as
+ * published by the Free Software Foundation, either version 3 of the
+ * License, or (at your option) any later version.
+ *
+ * This program is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+ * GNU Affero General Public License for more details.
+ *
+ * You should have received a copy of the GNU Affero General Public License
+ * along with this program. If not, see <http://www.gnu.org/licenses/>.
+ */
+
+namespace OCA\Memories\Migration;
+
+use OCP\DB\ISchemaWrapper;
+use OCP\DB\Types;
+use OCP\Migration\IOutput;
+use OCP\Migration\SimpleMigrationStep;
+
+class Version602003Date20240310203729 extends SimpleMigrationStep
+{
+    /**
+     * @param Closure(): ISchemaWrapper $schemaClosure
+     */
+    public function preSchemaChange(IOutput $output, \Closure $schemaClosure, array $options): void {}
+
+    /**
+     * @param \Closure(): ISchemaWrapper $schemaClosure
+     */
+    public function changeSchema(IOutput $output, \Closure $schemaClosure, array $options): ?ISchemaWrapper
+    {
+        /** @var ISchemaWrapper $schema */
+        $schema = $schemaClosure();
+
+        if (!$schema->hasTable('memories_failures')) {
+            $table = $schema->createTable('memories_failures');
+            $table->addColumn('id', 'integer', [
+                'autoincrement' => true,
+                'notnull' => true,
+            ]);
+            $table->addColumn('fileid', Types::BIGINT, [
+                'notnull' => true,
+                'length' => 20,
+            ]);
+            $table->addColumn('mtime', Types::BIGINT, [
+                'notnull' => true,
+                'length' => 20,
+            ]);
+			$table->addColumn('reason', 'text', [
+                'notnull' => false,
+            ]);
+
+            $table->setPrimaryKey(['id']);
+            $table->addIndex(['fileid', 'mtime'], 'memories_fail_fid_mt_idx');
+        }
+
+        return $schema;
+    }
+
+    /**
+     * @param Closure(): ISchemaWrapper $schemaClosure
+     */
+    public function postSchemaChange(IOutput $output, \Closure $schemaClosure, array $options): void {}
+}
diff --git a/lib/Service/Index.php b/lib/Service/Index.php
index 6c337c6b1..58f8702f4 100644
--- a/lib/Service/Index.php
+++ b/lib/Service/Index.php
@@ -150,17 +150,24 @@ public function indexFolder(Folder $folder): void
             ;
 
             // Filter out files that are already indexed
-            $addFilter = static function (string $table, string $alias) use (&$query): void {
+            $addFilter = static function (
+                string $table,
+                string $alias,
+                bool $orphan = true,
+            ) use (&$query): void {
                 $query->leftJoin('f', $table, $alias, $query->expr()->andX(
                     $query->expr()->eq('f.fileid', "{$alias}.fileid"),
                     $query->expr()->eq('f.mtime', "{$alias}.mtime"),
-                    $query->expr()->eq("{$alias}.orphan", $query->expr()->literal(0)),
+                    $orphan
+                        ? $query->expr()->eq("{$alias}.orphan", $query->expr()->literal(0))
+                        : $query->expr()->literal(1),
                 ));
 
                 $query->andWhere($query->expr()->isNull("{$alias}.fileid"));
             };
             $addFilter('memories', 'm');
             $addFilter('memories_livephoto', 'lp');
+            $addFilter('memories_failures', 'fail', false);
 
             // Get file IDs to actually index
             $fileIds = $query->executeQuery()->fetchAll(\PDO::FETCH_COLUMN);
@@ -201,6 +208,7 @@ public function indexFile(File $file): void
             $this->log("Skipping file {$path} due to lock", true);
         } catch (\Exception $e) {
             $this->error("Failed to index file {$path}: {$e->getMessage()}");
+            $this->tw->markFailed($file, $e->getMessage());
         } finally {
             $this->tempManager->clean();
         }
diff --git a/src/components/admin/AdminTypes.ts b/src/components/admin/AdminTypes.ts
index 4f54aeb63..b7e213eb5 100644
--- a/src/components/admin/AdminTypes.ts
+++ b/src/components/admin/AdminTypes.ts
@@ -48,6 +48,7 @@ export type ISystemStatus = {
 
   bad_encryption: boolean;
   indexed_count: number;
+  failure_count: number;
   mimes: string[];
   imagick: string | false;
   gis_type: number;
diff --git a/src/components/admin/sections/Indexing.vue b/src/components/admin/sections/Indexing.vue
index 8e6c31ce9..58bdb7e08 100644
--- a/src/components/admin/sections/Indexing.vue
+++ b/src/components/admin/sections/Indexing.vue
@@ -4,30 +4,16 @@
 
     <template v-if="status">
       <NcNoteCard :type="status.indexed_count > 0 ? 'success' : 'warning'">
-        {{
-          t('memories', '{n} media files have been indexed', {
-            n: status.indexed_count,
-          })
-        }}
+        {{ t('memories', '{n} media files have been indexed', { n: status.indexed_count }) }}
       </NcNoteCard>
       <NcNoteCard :type="status.last_index_job_status_type">
-        {{
-          t('memories', 'Automatic Indexing status: {status}', {
-            status: status.last_index_job_status,
-          })
-        }}
+        {{ t('memories', 'Automatic Indexing status: {status}', { status: status.last_index_job_status }) }}
       </NcNoteCard>
       <NcNoteCard v-if="status.last_index_job_start" :type="status.last_index_job_duration ? 'success' : 'warning'">
-        {{
-          t('memories', 'Last index job was run {t} seconds ago.', {
-            t: status.last_index_job_start,
-          })
-        }}
+        {{ t('memories', 'Last index job was run {t} seconds ago.', { t: status.last_index_job_start }) }}
         {{
           status.last_index_job_duration
-            ? t('memories', 'It took {t} seconds to complete.', {
-                t: status.last_index_job_duration,
-              })
+            ? t('memories', 'It took {t} seconds to complete.', { t: status.last_index_job_duration })
             : t('memories', 'It is still running or was interrupted.')
         }}
       </NcNoteCard>
@@ -99,25 +85,42 @@
       />
     </p>
 
-    {{ t('memories', 'For advanced usage, perform a run of indexing by running:') }}
-    <br />
-    <code>occ memories:index</code>
-    <br />
-    {{ t('memories', 'Run index in parallel with 4 threads:') }}
-    <br />
-    <code>bash -c 'for i in {1..4}; do (occ memories:index &amp;); done'</code>
-    <br />
-    {{ t('memories', 'Force re-indexing of all files:') }}
-    <br />
-    <code>occ memories:index --force</code>
-    <br />
-    {{ t('memories', 'You can limit indexing by user and/or folder:') }}
-    <br />
-    <code>occ memories:index --user=admin --folder=/Photos/</code>
-    <br />
-    {{ t('memories', 'Clear all existing index tables:') }}
-    <br />
-    <code>occ memories:index --clear</code>
+    <div>
+      {{ t('memories', 'For advanced usage, perform a run of indexing by running:') }}
+      <br />
+      <code>occ memories:index</code>
+      <br />
+      {{ t('memories', 'Run index in parallel with 4 threads:') }}
+      <br />
+      <code>bash -c 'for i in {1..4}; do (occ memories:index &amp;); done'</code>
+      <br />
+      {{ t('memories', 'Force re-indexing of all files:') }}
+      <br />
+      <code>occ memories:index --force</code>
+      <br />
+      {{ t('memories', 'You can limit indexing by user and/or folder:') }}
+      <br />
+      <code>occ memories:index --user=admin --folder=/Photos/</code>
+      <br />
+      {{ t('memories', 'Clear all existing index tables:') }}
+      <br />
+      <code>occ memories:index --clear</code>
+    </div>
+
+    <div v-if="status && status.failure_count > 0">
+      <NcNoteCard type="warning">
+        {{ t('memories', '{n} media files failed indexing and were skipped', { n: status.failure_count }) }}
+      </NcNoteCard>
+
+      {{ t('memories', 'Files that failed indexing will not be indexed again unless they change.') }}
+      {{ t('memories', 'You can manually retry files that failed indexing.') }}
+      <br />
+      <code>occ memories:index --retry</code>
+
+      <NcButton @click="openFailureLogs()" style="margin-top: 4px">
+        {{ t('memories', 'View failure logs') }}
+      </NcButton>
+    </div>
   </div>
 </template>
 
@@ -125,6 +128,7 @@
 import { defineComponent } from 'vue';
 
 import { translate as t } from '@services/l10n';
+import { API } from '@services/API';
 
 import AdminMixin from '../AdminMixin';
 
@@ -132,5 +136,11 @@ export default defineComponent({
   name: 'Indexing',
   title: t('memories', 'Media Indexing'),
   mixins: [AdminMixin],
+
+  methods: {
+    openFailureLogs() {
+      return window.open(API.FAILURE_LOGS());
+    },
+  },
 });
 </script>
diff --git a/src/components/admin/sections/Places.vue b/src/components/admin/sections/Places.vue
index ae071041c..d7ccb2a65 100644
--- a/src/components/admin/sections/Places.vue
+++ b/src/components/admin/sections/Places.vue
@@ -13,9 +13,7 @@
         >
           {{
             status.gis_count > 0
-              ? t('memories', 'Database is populated with {n} geometries.', {
-                  n: status.gis_count,
-                })
+              ? t('memories', 'Database is populated with {n} geometries.', { n: status.gis_count })
               : t('memories', 'Geometry table has not been created.')
           }}
           {{
diff --git a/src/services/API.ts b/src/services/API.ts
index 0ce33cf00..07fcd6605 100644
--- a/src/services/API.ts
+++ b/src/services/API.ts
@@ -198,6 +198,10 @@ export class API {
     return gen(`${BASE}/system-status`);
   }
 
+  static FAILURE_LOGS() {
+    return gen(`${BASE}/failure-logs`);
+  }
+
   static OCC_PLACES_SETUP() {
     return gen(`${BASE}/occ/places-setup`);
   }