diff --git a/app/Classes/VATUSAMoodle.php b/app/Classes/VATUSAMoodle.php
index 652bba2..24a7e85 100644
--- a/app/Classes/VATUSAMoodle.php
+++ b/app/Classes/VATUSAMoodle.php
@@ -53,6 +53,12 @@ class VATUSAMoodle extends MoodleRest
 
     private $isTest;
 
+    /** @var array|null Memoized result of getCategories() for the lifetime of this instance */
+    private $categoriesCache = null;
+
+    /** @var int Seconds to bound each Moodle HTTP request to */
+    private const HTTP_TIMEOUT_SECONDS = 30;
+
     /**
      * VATUSAMoodle constructor.
      *
@@ -91,6 +97,32 @@ public function setSSO(bool $isSSO = true)
         }
     }
 
+    /**
+     * Make the request, with a bounded HTTP timeout.
+     *
+     * The vendored MoodleRest::request() uses file_get_contents()/stream contexts with no
+     * explicit timeout, so it silently falls back to PHP's default_socket_timeout ini
+     * (60s, not guaranteed). Scope an explicit timeout tightly around each individual call
+     * rather than setting it once for the process, since default_socket_timeout is a
+     * process-global ini setting also consulted by predis (CACHE_DRIVER=redis).
+     *
+     * @param string      $function
+     * @param array|null  $parameters
+     * @param string      $method
+     *
+     * @return mixed
+     * @throws \Exception
+     */
+    public function request($function, $parameters = null, $method = self::METHOD_GET)
+    {
+        $previous = ini_set('default_socket_timeout', self::HTTP_TIMEOUT_SECONDS);
+        try {
+            return parent::request($function, $parameters, $method);
+        } finally {
+            ini_set('default_socket_timeout', $previous);
+        }
+    }
+
     /**
      * Get all Cohorts
      * @return mixed
@@ -124,7 +156,11 @@ public function getCohortMembers(): array
      */
     public function getCategories()
     {
-        return $this->request("core_course_get_categories");
+        if ($this->categoriesCache === null) {
+            $this->categoriesCache = $this->request("core_course_get_categories");
+        }
+
+        return $this->categoriesCache;
     }
 
     /**
diff --git a/app/Console/Kernel.php b/app/Console/Kernel.php
index 192fa85..a0063e2 100644
--- a/app/Console/Kernel.php
+++ b/app/Console/Kernel.php
@@ -4,6 +4,8 @@
 
 use Illuminate\Console\Scheduling\Schedule;
 use Illuminate\Foundation\Console\Kernel as ConsoleKernel;
+use Illuminate\Support\Facades\Cache;
+use Illuminate\Support\Facades\Log;
 
 class Kernel extends ConsoleKernel
 {
@@ -30,18 +32,32 @@ class Kernel extends ConsoleKernel
      */
     protected function schedule(Schedule $schedule)
     {
-        // Helper function to create a 'before' hook closure with the command name
+        // Helper function to create a 'before' hook closure with the command name.
+        // Records the start time in cache (not a shared closure variable) because
+        // runInBackground() events run their 'after' hook in a separate, freshly-booted
+        // `schedule:finish` process with no memory in common with this one.
         $createBeforeHook = function (string $commandName) {
             return function () use ($commandName) {
-                // Use logger() or Log::info() etc.
                 logger("Starting scheduled task: {$commandName}");
+                Cache::put("schedule:started:{$commandName}", now(), now()->addHours(6));
             };
         };
 
-        // Helper function to create an 'after' hook closure with the command name
-        $createAfterHook = function (string $commandName) {
-            return function () use ($commandName) {
-                logger("Finished scheduled task: {$commandName}");
+        // Helper function to create an 'after' hook closure with the command name.
+        // $warnAfterMinutes, when given, logs a WARN if the run exceeded that duration —
+        // used for commands with a withoutOverlapping() lock window to catch a run
+        // approaching that window before it starts stacking overlapping instances.
+        $createAfterHook = function (string $commandName, ?int $warnAfterMinutes = null) {
+            return function () use ($commandName, $warnAfterMinutes) {
+                $startedAt = Cache::pull("schedule:started:{$commandName}");
+                $elapsedMinutes = $startedAt ? round(now()->diffInSeconds($startedAt) / 60, 1) : null;
+
+                logger("Finished scheduled task: {$commandName}" .
+                    ($elapsedMinutes !== null ? " ({$elapsedMinutes} min)" : ""));
+
+                if ($warnAfterMinutes !== null && $elapsedMinutes !== null && $elapsedMinutes > $warnAfterMinutes) {
+                    Log::warning("Scheduled task {$commandName} took {$elapsedMinutes} minutes, exceeding the {$warnAfterMinutes}-minute warn threshold.");
+                }
             };
         };
 
@@ -60,7 +76,7 @@ protected function schedule(Schedule $schedule)
             ->runInBackground()
             ->withoutOverlapping(120)
             ->before($createBeforeHook($commandName))
-            ->after($createAfterHook($commandName));
+            ->after($createAfterHook($commandName, 90));
 
         $commandName = 'vatsim:flights';
         $schedule->command($commandName)
@@ -86,7 +102,7 @@ protected function schedule(Schedule $schedule)
             ->withoutOverlapping(60)
             ->runInBackground()
             ->before($createBeforeHook($commandName))
-            ->after($createAfterHook($commandName));
+            ->after($createAfterHook($commandName, 45));
 
         $commandName = "controller:eligibility";
         $schedule->command($commandName)