diff --git a/docs/user-manual/playlists.md b/docs/user-manual/playlists.md
index 693cd6f68..d13cd3da1 100644
--- a/docs/user-manual/playlists.md
+++ b/docs/user-manual/playlists.md
@@ -37,7 +37,7 @@ Smart blocks are automatically filled with media files from the LibreTime librar
 To create a smart block, click the **Smartblocks** button on the left sidebar, and select **New** from the toolbar. Like a playlist, smart blocks can have a title and description, which you can edit. This helps you find relevant smart blocks in searches.
 
 Fill out the smart block's **Name**, **Search Criteria**, and **Limit to** sections. The search criteria can be any one of LibreTime's metadata categories, such as **Title**, **Creator** or **Genre**. The modifier depends on whether the metadata in question contains letters or numbers. For example, **Title** has modifiers including _contains_ and _starts with_, whereas the modifiers for **BPM** include _is greater than_ and _is in the range_.
-To filter tracks using today's date information, use the `now{}` macro. Format characters are listed in the [php documentation](https://www.php.net/manual/en/datetime.format.php). For example, to filter to tracks with a **Title** that ends in `Instrumental Jan 2024` where `Jan 2024` is the current month and year, add a criteria for **Title** with a modifier of **ends with** and a value of `Instrumental now{M Y}`. The macro uses the configured station timezone to resolve dates and times.
+To filter tracks using today's date information, use the `now{}` macro. Format characters are listed in the [php documentation](https://www.php.net/manual/en/datetime.format.php). For example, to filter to tracks with a **Title** that ends in `Instrumental Jan 2024` where `Jan 2024` is the current month and year, add a criteria for **Title** with a modifier of **ends with** and a value of `Instrumental now{M Y}`. The macro uses the configured station timezone to resolve dates and times. For dynamic autoloading smart blocks the datetime used is the start datetime of the show. In all other cases the current datetime is used.
 
 If you have a large number of files which meet the criteria that you specify, you may wish to limit the duration of the smart block using the **Limit to** field, so that it fits within the show you have in mind. Select **hours**, **minutes** or **items** from the drop-down menu, and click the **Generate** button again, if it's a static smart block. Then click the **Save** button.
 
diff --git a/legacy/application/models/Block.php b/legacy/application/models/Block.php
index dc3cfd457..859f52546 100644
--- a/legacy/application/models/Block.php
+++ b/legacy/application/models/Block.php
@@ -1295,9 +1295,9 @@ SQL;
         }
     }
 
-    public function getListOfFilesUnderLimit($show = null)
+    public function getListOfFilesUnderLimit($show = null, $showStartTime = null)
     {
-        $info = $this->getListofFilesMeetCriteria($show);
+        $info = $this->getListofFilesMeetCriteria($show, $showStartTime);
         $files = $info['files'];
         $limit = $info['limit'];
         $repeat = $info['repeat_tracks'] == 1;
@@ -1480,13 +1480,14 @@ SQL;
         return $storedCrit;
     }
 
-    private function resolveDate($value, $timeZone)
+    private function resolveDate($value, ?DateTime $resolveTo, string $timeZone)
     {
         if (!is_string($value)) {
             return $value;
         }
 
-        $dt = new DateTime('now', new DateTimeZone($timeZone));
+        $dt = $resolveTo ?: new DateTime('now');
+        $dt->setTimezone(new DateTimeZone($timeZone));
 
         return preg_replace_callback(
             '/now{(.*?)}/',
@@ -1496,7 +1497,7 @@ SQL;
     }
 
     // this function return list of propel object
-    public function getListofFilesMeetCriteria($showLimit = null)
+    public function getListofFilesMeetCriteria($showLimit = null, $showStartTime = null)
     {
         $storedCrit = $this->getCriteria();
 
@@ -1563,7 +1564,7 @@ SQL;
                         $spCriteriaExtra = $criteria['extra'];
                     }
 
-                    $spCriteriaValue = $this->resolveDate($spCriteriaValue, $timeZone);
+                    $spCriteriaValue = $this->resolveDate($spCriteriaValue, $showStartTime, $timeZone);
 
                     if ($spCriteriaModifier == CriteriaModifier::STARTS_WITH) {
                         $spCriteriaValue = "{$spCriteriaValue}%";
diff --git a/legacy/application/models/Scheduler.php b/legacy/application/models/Scheduler.php
index a4de230e6..9c0b80d21 100644
--- a/legacy/application/models/Scheduler.php
+++ b/legacy/application/models/Scheduler.php
@@ -219,6 +219,7 @@ final class Application_Model_Scheduler
         // if there is a show we need to set a show limit to pass to smart blocks in case they use time remaining
         $showInstance = new Application_Model_ShowInstance($show);
         $showLimit = $showInstance->getSecondsRemaining();
+        $showStart = $showInstance->getShowInstanceStart(null);
         $originalShowLimit = $showLimit;
 
         $files = [];
@@ -286,7 +287,7 @@ final class Application_Model_Scheduler
                     } else {
                         $defaultFadeIn = Application_Model_Preference::GetDefaultFadeIn();
                         $defaultFadeOut = Application_Model_Preference::GetDefaultFadeOut();
-                        $dynamicFiles = $bl->getListOfFilesUnderLimit($showLimit);
+                        $dynamicFiles = $bl->getListOfFilesUnderLimit($showLimit, $showStart);
                         foreach ($dynamicFiles as $f) {
                             $fileId = $f['id'];
                             $file = CcFilesQuery::create()->findPk($fileId);
@@ -347,7 +348,7 @@ final class Application_Model_Scheduler
             } else {
                 $defaultFadeIn = Application_Model_Preference::GetDefaultFadeIn();
                 $defaultFadeOut = Application_Model_Preference::GetDefaultFadeOut();
-                $dynamicFiles = $bl->getListOfFilesUnderLimit($showLimit);
+                $dynamicFiles = $bl->getListOfFilesUnderLimit($showLimit, $showStart);
                 foreach ($dynamicFiles as $f) {
                     $fileId = $f['id'];
                     $file = CcFilesQuery::create()->findPk($fileId);