diff --git a/CLI/CleanupPendingUploadsCommand.php b/CLI/CleanupPendingUploadsCommand.php
new file mode 100644
index 00000000..8772c015
--- /dev/null
+++ b/CLI/CleanupPendingUploadsCommand.php
@@ -0,0 +1,100 @@
+<?php
+
+declare(strict_types=1);
+
+namespace openvk\CLI;
+
+use Symfony\Component\Console\Command\Command;
+use Symfony\Component\Console\Input\InputInterface;
+use Symfony\Component\Console\Input\InputOption;
+use Symfony\Component\Console\Output\OutputInterface;
+
+class CleanupPendingUploadsCommand extends Command
+{
+    protected static $defaultName = "cleanup-pending-uploads";
+
+    public function __construct()
+    {
+        parent::__construct();
+    }
+
+    protected function configure(): void
+    {
+        $this->setDescription("Cleanup pending photo uploads older than specified time")
+             ->addOption(
+                 "max-age",
+                 "a",
+                 InputOption::VALUE_OPTIONAL,
+                 "Maximum age in hours (default: 24)",
+                 24
+             )
+             ->addOption(
+                 "dry-run",
+                 "d",
+                 InputOption::VALUE_NONE,
+                 "Show what would be deleted without actually deleting"
+             );
+    }
+
+    protected function execute(InputInterface $input, OutputInterface $output): int
+    {
+        $maxAge = (int) $input->getOption("max-age");
+        $dryRun = $input->getOption("dry-run");
+
+        $photoFolder = __DIR__ . "/../tmp/api-storage/photos";
+
+        if (!is_dir($photoFolder)) {
+            $output->writeln("<error>Photo upload directory not found: {$photoFolder}</error>");
+            return Command::FAILURE;
+        }
+
+        $output->writeln("<info>Scanning for pending uploads older than {$maxAge} hours...</info>");
+
+        $cutoffTime = time() - ($maxAge * 3600);
+        $deletedCount = 0;
+        $totalSize = 0;
+
+        $files = glob($photoFolder . "/*_*.oct");
+
+        foreach ($files as $file) {
+            $fileTime = filemtime($file);
+
+            if ($fileTime < $cutoffTime) {
+                $fileSize = filesize($file);
+                $totalSize += $fileSize;
+
+                if ($dryRun) {
+                    $age = round((time() - $fileTime) / 3600, 1);
+                    $output->writeln("<comment>Would delete: " . basename($file) . " (age: {$age}h, size: " . $this->formatBytes($fileSize) . ")</comment>");
+                } else {
+                    if (unlink($file)) {
+                        $deletedCount++;
+                        $output->writeln("<info>Deleted: " . basename($file) . "</info>");
+                    } else {
+                        $output->writeln("<error>Failed to delete: " . basename($file) . "</error>");
+                    }
+                }
+            }
+        }
+
+        if ($dryRun) {
+            $output->writeln("<info>Dry run completed. Would delete {$deletedCount} files (" . $this->formatBytes($totalSize) . ")</info>");
+        } else {
+            $output->writeln("<info>Cleanup completed. Deleted {$deletedCount} files (" . $this->formatBytes($totalSize) . ")</info>");
+        }
+
+        return Command::SUCCESS;
+    }
+
+    private function formatBytes(int $bytes): string
+    {
+        $units = ['B', 'KB', 'MB', 'GB'];
+        $bytes = max($bytes, 0);
+        $pow = floor(($bytes ? log($bytes) : 0) / log(1024));
+        $pow = min($pow, count($units) - 1);
+
+        $bytes /= pow(1024, $pow);
+
+        return round($bytes, 2) . ' ' . $units[$pow];
+    }
+}
diff --git a/CLI/README.md b/CLI/README.md
new file mode 100644
index 00000000..1b66610d
--- /dev/null
+++ b/CLI/README.md
@@ -0,0 +1,40 @@
+# OpenVK CLI Commands
+
+This directory contains command-line utilities for OpenVK management.
+
+## Available Commands
+
+### cleanup-pending-uploads
+Automatically removes pending photo uploads older than the specified time.
+
+**Usage:**
+```bash
+# Clean up uploads older than 24 hours (default)
+php openvkctl cleanup-pending-uploads
+
+# Clean up uploads older than 1 hour
+php openvkctl cleanup-pending-uploads --max-age=1
+
+# Dry run to see what would be deleted
+php openvkctl cleanup-pending-uploads --dry-run
+```
+
+**Options:**
+- `--max-age`, `-a`: Maximum age in hours (default: 24)
+- `--dry-run`, `-d`: Show what would be deleted without actually deleting
+
+**Cron Setup:**
+To automatically clean up pending uploads daily, add to your crontab:
+```bash
+# Clean up pending uploads daily at 2 AM
+0 2 * * * cd /path/to/openvk && php openvkctl cleanup-pending-uploads
+```
+
+### build-images
+Rebuilds photo thumbnails and image sizes.
+
+### fetch-toncoin-transactions
+Fetches Toncoin transactions for payment processing.
+
+### upgrade
+Performs database upgrades and migrations.
\ No newline at end of file
diff --git a/Web/Presenters/VKAPIPresenter.php b/Web/Presenters/VKAPIPresenter.php
index 2ab0818a..008e98c9 100644
--- a/Web/Presenters/VKAPIPresenter.php
+++ b/Web/Presenters/VKAPIPresenter.php
@@ -126,8 +126,14 @@ final class VKAPIPresenter extends OpenVKPresenter
         $maxFiles = OPENVK_ROOT_CONF["openvk"]["preferences"]["uploads"]["api"]["maxFilesPerDomain"];
         $usrFiles = sizeof(glob("$folder/$data[USER]_*.oct"));
         if ($usrFiles >= $maxFiles) {
+            $pendingInfo = $this->getPendingUploadInfo($folder, $data["USER"]);
             header("HTTP/1.1 507 Insufficient Storage");
-            exit("There are $maxFiles pending already. Please save them before uploading more :3");
+            header("Content-Type: application/json");
+            exit(json_encode([
+                "error" => "insufficient_storage",
+                "error_description" => "There are $maxFiles pending already. Please save them before uploading more :3",
+                "pending_uploads" => $pendingInfo,
+            ]));
         }
 
         # Not multifile
@@ -166,8 +172,14 @@ final class VKAPIPresenter extends OpenVKPresenter
                     unlink($f);
                 }
 
+                $pendingInfo = $this->getPendingUploadInfo($folder, $data["USER"]);
                 header("HTTP/1.1 507 Insufficient Storage");
-                exit("There are $maxFiles pending already. Please save them before uploading more :3");
+                header("Content-Type: application/json");
+                exit(json_encode([
+                    "error" => "insufficient_storage",
+                    "error_description" => "There are $maxFiles pending already. Please save them before uploading more :3",
+                    "pending_uploads" => $pendingInfo,
+                ]));
             }
 
             $files[++$usrFiles] = move_uploaded_file($file["tmp_name"], "$folder/$data[USER]_$usrFiles.oct");
@@ -194,6 +206,30 @@ final class VKAPIPresenter extends OpenVKPresenter
         ]));
     }
 
+    private function getPendingUploadInfo(string $folder, string $userId): array
+    {
+        $pendingFiles = glob("$folder/$userId" . "_*.oct");
+        $pendingInfo = [];
+
+        foreach ($pendingFiles as $file) {
+            $filename = basename($file);
+            $uploadId = str_replace([$userId . "_", ".oct"], "", $filename);
+            $fileTime = filemtime($file);
+            $fileSize = filesize($file);
+            $ageHours = round((time() - $fileTime) / 3600, 1);
+
+            $pendingInfo[] = [
+                "upload_id" => $uploadId,
+                "filename" => $filename,
+                "size" => $fileSize,
+                "age_hours" => $ageHours,
+                "uploaded_at" => date("Y-m-d H:i:s", $fileTime),
+            ];
+        }
+
+        return $pendingInfo;
+    }
+
     public function renderRoute(string $object, string $method): void
     {
         $callback = $this->queryParam("callback");
diff --git a/openvkctl b/openvkctl
index 13b02d45..dd1f08cc 100755
--- a/openvkctl
+++ b/openvkctl
@@ -13,5 +13,6 @@ $application = new Application();
 $application->add(new CLI\UpgradeCommand());
 $application->add(new CLI\RebuildImagesCommand());
 $application->add(new CLI\FetchToncoinTransactions());
+$application->add(new CLI\CleanupPendingUploadsCommand());
 
 $application->run();