diff --git a/CHANGELOG.md b/CHANGELOG.md
index 24a1af9e..85f4f06c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -36,6 +36,16 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/).
 - Synchronize Plex "network" metadata for Plex show libraries
   - Shows will have new `network` search field
   - Episodes will have new `show_network` search field
+- YAML playout: add `stop_before_end` setting to `pad_until` and `duration` instructions
+  - When `stop_before_end: false`, content can run over the desired time before executing the next instruction
+- YAML playout: add `offline_tail` setting to `pad_until` instruction
+  - This can be used to stop primary content before the desired time (`stop_before_end: true` and `offline_tail: false`)
+  - You can then have a second `pad_until` with the same target time and different content
+- YAML playout: make `tomorrow` an expression on `pad_until` instruction
+  - `true` and `false` still work as normal
+  - The current time (as a decimal) can also be used in the expression, e.g. `now > 23`
+    - `now = hours + minutes / 60.0 + seconds / 3600.0`
+    - So `10:30 AM` would be `10.5`, `10:45 PM` would be `22.75`, etc
 
 ### Changed
 - Allow `Other Video` libraries and `Image` libraries to use the same folders
diff --git a/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutDurationHandler.cs b/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutDurationHandler.cs
index dda79095..8df67e6d 100644
--- a/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutDurationHandler.cs
+++ b/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutDurationHandler.cs
@@ -28,6 +28,12 @@ public class YamlPlayoutDurationHandler(EnumeratorCache enumeratorCache) : YamlP
             return false;
         }
 
+        if (duration.StopBeforeEnd == false && duration.OfflineTail)
+        {
+            logger.LogError("offline_tail must be false when stop_before_end is false");
+            return false;
+        }
+
         DateTimeOffset targetTime = context.CurrentTime.Add(timeSpan);
 
         Option<IMediaCollectionEnumerator> maybeEnumerator = await GetContentEnumerator(
@@ -49,6 +55,7 @@ public class YamlPlayoutDurationHandler(EnumeratorCache enumeratorCache) : YamlP
                 instruction.Content,
                 duration.Fallback,
                 targetTime,
+                duration.StopBeforeEnd,
                 duration.DiscardAttempts,
                 duration.Trim,
                 duration.OfflineTail,
@@ -68,6 +75,7 @@ public class YamlPlayoutDurationHandler(EnumeratorCache enumeratorCache) : YamlP
         string contentKey,
         string fallbackContentKey,
         DateTimeOffset targetTime,
+        bool stopBeforeEnd,
         int discardAttempts,
         bool trim,
         bool offlineTail,
@@ -97,7 +105,7 @@ public class YamlPlayoutDurationHandler(EnumeratorCache enumeratorCache) : YamlP
                     //DisableWatermarks = !allowWatermarks
                 };
 
-                if (remainingToFill - itemDuration >= TimeSpan.Zero)
+                if (remainingToFill - itemDuration >= TimeSpan.Zero || !stopBeforeEnd)
                 {
                     context.Playout.Items.Add(playoutItem);
                     context.AdvanceGuideGroup();
@@ -195,6 +203,11 @@ public class YamlPlayoutDurationHandler(EnumeratorCache enumeratorCache) : YamlP
             }
         }
 
+        if (!stopBeforeEnd)
+        {
+            return context.CurrentTime;
+        }
+
         return offlineTail ? targetTime : context.CurrentTime;
     }
 }
diff --git a/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutPadToNextHandler.cs b/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutPadToNextHandler.cs
index 7121ff33..d547db31 100644
--- a/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutPadToNextHandler.cs
+++ b/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutPadToNextHandler.cs
@@ -57,6 +57,7 @@ public class YamlPlayoutPadToNextHandler(EnumeratorCache enumeratorCache) : Yaml
                 padToNext.Content,
                 padToNext.Fallback,
                 targetTime,
+                false,
                 padToNext.DiscardAttempts,
                 padToNext.Trim,
                 offlineTail: true,
diff --git a/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutPadUntilHandler.cs b/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutPadUntilHandler.cs
index 2acc2306..f46f0ee0 100644
--- a/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutPadUntilHandler.cs
+++ b/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutPadUntilHandler.cs
@@ -29,7 +29,17 @@ public class YamlPlayoutPadUntilHandler(EnumeratorCache enumeratorCache) : YamlP
 
             if (timeOnly > result)
             {
-                if (padUntil.Tomorrow)
+                var expression = new NCalc.Expression(padUntil.Tomorrow);
+                expression.EvaluateParameter += (name, e) =>
+                {
+                    e.Result = name switch
+                    {
+                        "now" => timeOnly.Hour + timeOnly.Minute / 60.0 + timeOnly.Second / 3600.0,
+                        _ => e.Result
+                    };
+                };
+
+                if (expression.Evaluate() as bool? == true)
                 {
                     // this is wrong when offset changes
                     dayOnly = dayOnly.AddDays(1);
@@ -67,9 +77,10 @@ public class YamlPlayoutPadUntilHandler(EnumeratorCache enumeratorCache) : YamlP
                 padUntil.Content,
                 padUntil.Fallback,
                 targetTime,
+                padUntil.StopBeforeEnd,
                 padUntil.DiscardAttempts,
                 padUntil.Trim,
-                offlineTail: true,
+                padUntil.OfflineTail,
                 GetFillerKind(padUntil),
                 padUntil.CustomTitle,
                 enumerator,
diff --git a/ErsatzTV.Core/Scheduling/YamlScheduling/Models/YamlPlayoutDurationInstruction.cs b/ErsatzTV.Core/Scheduling/YamlScheduling/Models/YamlPlayoutDurationInstruction.cs
index 2c982734..714015b2 100644
--- a/ErsatzTV.Core/Scheduling/YamlScheduling/Models/YamlPlayoutDurationInstruction.cs
+++ b/ErsatzTV.Core/Scheduling/YamlScheduling/Models/YamlPlayoutDurationInstruction.cs
@@ -15,4 +15,7 @@ public class YamlPlayoutDurationInstruction : YamlPlayoutInstruction
 
     [YamlMember(Alias = "discard_attempts", ApplyNamingConventions = false)]
     public int DiscardAttempts { get; set; }
+
+    [YamlMember(Alias = "stop_before_end", ApplyNamingConventions = false)]
+    public bool StopBeforeEnd { get; set; } = true;
 }
diff --git a/ErsatzTV.Core/Scheduling/YamlScheduling/Models/YamlPlayoutPadUntilInstruction.cs b/ErsatzTV.Core/Scheduling/YamlScheduling/Models/YamlPlayoutPadUntilInstruction.cs
index 5f9f4255..a26059a9 100644
--- a/ErsatzTV.Core/Scheduling/YamlScheduling/Models/YamlPlayoutPadUntilInstruction.cs
+++ b/ErsatzTV.Core/Scheduling/YamlScheduling/Models/YamlPlayoutPadUntilInstruction.cs
@@ -7,12 +7,18 @@ public class YamlPlayoutPadUntilInstruction : YamlPlayoutInstruction
     [YamlMember(Alias = "pad_until", ApplyNamingConventions = false)]
     public string PadUntil { get; set; }
 
-    public bool Tomorrow { get; set; }
+    public string Tomorrow { get; set; }
 
     public bool Trim { get; set; }
 
+    [YamlMember(Alias = "offline_tail", ApplyNamingConventions = false)]
+    public bool OfflineTail { get; set; }
+
     public string Fallback { get; set; }
 
     [YamlMember(Alias = "discard_attempts", ApplyNamingConventions = false)]
     public int DiscardAttempts { get; set; }
+
+    [YamlMember(Alias = "stop_before_end", ApplyNamingConventions = false)]
+    public bool StopBeforeEnd { get; set; } = true;
 }