diff --git a/CHANGELOG.md b/CHANGELOG.md
index c3dd7202..333a3855 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -18,6 +18,8 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/).
   - This bug made it difficult to "stop" a channel after previewing it
 - Fix bug where deco default filler would never use hardware acceleration
 - Fix deleting local libraries with MySql backend
+- Fix `Scaling Behavior` `Crop` when content is smaller than FFmpeg Profile resolution
+  - Now, content will properly scale beyond the desired resolution before cropping
 
 ## [0.8.8-beta] - 2024-09-19
 ### Added
diff --git a/ErsatzTV.Core.Tests/FFmpeg/FFmpegPlaybackSettingsCalculatorTests.cs b/ErsatzTV.Core.Tests/FFmpeg/FFmpegPlaybackSettingsCalculatorTests.cs
index 3a052ea4..97413780 100644
--- a/ErsatzTV.Core.Tests/FFmpeg/FFmpegPlaybackSettingsCalculatorTests.cs
+++ b/ErsatzTV.Core.Tests/FFmpeg/FFmpegPlaybackSettingsCalculatorTests.cs
@@ -356,6 +356,66 @@ public class FFmpegPlaybackSettingsCalculatorTests
             actual.PadToDesiredResolution.Should().BeTrue();
         }
 
+        [Test]
+        public void Should_ScaleBeyondMinSize_ForCrop_ForTransportStream()
+        {
+            FFmpegProfile ffmpegProfile = TestProfile() with
+            {
+                Resolution = new Resolution { Width = 1280, Height = 720 },
+                ScalingBehavior = ScalingBehavior.Crop
+            };
+
+            var version = new MediaVersion { Width = 944, Height = 720, SampleAspectRatio = "1:1" };
+
+            FFmpegPlaybackSettings actual = FFmpegPlaybackSettingsCalculator.CalculateSettings(
+                StreamingMode.TransportStream,
+                ffmpegProfile,
+                version,
+                new MediaStream(),
+                new MediaStream(),
+                DateTimeOffset.Now,
+                DateTimeOffset.Now,
+                TimeSpan.Zero,
+                TimeSpan.Zero,
+                false,
+                None);
+
+            IDisplaySize scaledSize = actual.ScaledSize.IfNone(new MediaVersion { Width = 0, Height = 0 });
+            scaledSize.Width.Should().Be(1280);
+            scaledSize.Height.Should().Be(976);
+            actual.PadToDesiredResolution.Should().BeFalse();
+        }
+
+        [Test]
+        public void Should_ScaleDownToMinSize_ForCrop_ForTransportStream()
+        {
+            FFmpegProfile ffmpegProfile = TestProfile() with
+            {
+                Resolution = new Resolution { Width = 1280, Height = 720 },
+                ScalingBehavior = ScalingBehavior.Crop
+            };
+
+            var version = new MediaVersion { Width = 1920, Height = 816, SampleAspectRatio = "1:1" };
+
+            FFmpegPlaybackSettings actual = FFmpegPlaybackSettingsCalculator.CalculateSettings(
+                StreamingMode.TransportStream,
+                ffmpegProfile,
+                version,
+                new MediaStream(),
+                new MediaStream(),
+                DateTimeOffset.Now,
+                DateTimeOffset.Now,
+                TimeSpan.Zero,
+                TimeSpan.Zero,
+                false,
+                None);
+
+            IDisplaySize scaledSize = actual.ScaledSize.IfNone(new MediaVersion { Width = 0, Height = 0 });
+            scaledSize.Width.Should().Be(1694);
+            scaledSize.Height.Should().Be(720);
+            actual.PadToDesiredResolution.Should().BeFalse();
+        }
+
         [Test]
         public void Should_NotPadToDesiredResolution_When_UnscaledContentIsUnderSized_ForHttpLiveStreaming()
         {
diff --git a/ErsatzTV.Core/FFmpeg/FFmpegLibraryProcessService.cs b/ErsatzTV.Core/FFmpeg/FFmpegLibraryProcessService.cs
index 02f0f3c8..3721080f 100644
--- a/ErsatzTV.Core/FFmpeg/FFmpegLibraryProcessService.cs
+++ b/ErsatzTV.Core/FFmpeg/FFmpegLibraryProcessService.cs
@@ -335,8 +335,24 @@ public class FFmpegLibraryProcessService : IFFmpegProcessService
 
         if (channel.FFmpegProfile.ScalingBehavior is ScalingBehavior.Crop)
         {
-            paddedSize = ffmpegVideoStream.SquarePixelFrameSizeForCrop(
-                new FrameSize(channel.FFmpegProfile.Resolution.Width, channel.FFmpegProfile.Resolution.Height));
+            bool isTooSmallToCrop = videoVersion.Height < channel.FFmpegProfile.Resolution.Height ||
+                                    videoVersion.Width < channel.FFmpegProfile.Resolution.Width;
+
+            // if any dimension is smaller than the crop, scale beyond the crop (beyond the target resolution)
+            if (isTooSmallToCrop)
+            {
+                foreach (IDisplaySize size in playbackSettings.ScaledSize)
+                {
+                    scaledSize = new FrameSize(size.Width, size.Height);
+                }
+
+                paddedSize = scaledSize;
+            }
+            else
+            {
+                paddedSize = ffmpegVideoStream.SquarePixelFrameSizeForCrop(
+                    new FrameSize(channel.FFmpegProfile.Resolution.Width, channel.FFmpegProfile.Resolution.Height));
+            }
 
             cropSize = new FrameSize(
                 channel.FFmpegProfile.Resolution.Width,
diff --git a/ErsatzTV.Core/FFmpeg/FFmpegPlaybackSettingsCalculator.cs b/ErsatzTV.Core/FFmpeg/FFmpegPlaybackSettingsCalculator.cs
index 65d747f1..addffcb0 100644
--- a/ErsatzTV.Core/FFmpeg/FFmpegPlaybackSettingsCalculator.cs
+++ b/ErsatzTV.Core/FFmpeg/FFmpegPlaybackSettingsCalculator.cs
@@ -99,7 +99,7 @@ public static class FFmpegPlaybackSettingsCalculator
                 }
 
                 IDisplaySize sizeAfterScaling = result.ScaledSize.IfNone(videoVersion);
-                if (!sizeAfterScaling.IsSameSizeAs(ffmpegProfile.Resolution))
+                if (!sizeAfterScaling.IsSameSizeAs(ffmpegProfile.Resolution) && ffmpegProfile.ScalingBehavior is not ScalingBehavior.Crop)
                 {
                     result.PadToDesiredResolution = true;
                 }
@@ -229,7 +229,8 @@ public static class FFmpegPlaybackSettingsCalculator
     private static bool NeedToScale(FFmpegProfile ffmpegProfile, MediaVersion version) =>
         IsIncorrectSize(ffmpegProfile.Resolution, version) ||
         IsTooLarge(ffmpegProfile.Resolution, version) ||
-        IsOddSize(version);
+        IsOddSize(version) ||
+        TooSmallToCrop(ffmpegProfile, version);
 
     private static bool IsIncorrectSize(IDisplaySize desiredResolution, MediaVersion version) =>
         IsAnamorphic(version) ||
@@ -243,6 +244,16 @@ public static class FFmpegPlaybackSettingsCalculator
     private static bool IsOddSize(MediaVersion version) =>
         version.Height % 2 == 1 || version.Width % 2 == 1;
 
+    private static bool TooSmallToCrop(FFmpegProfile ffmpegProfile, MediaVersion version)
+    {
+        if (ffmpegProfile.ScalingBehavior is not ScalingBehavior.Crop)
+        {
+            return false;
+        }
+
+        return version.Height < ffmpegProfile.Resolution.Height || version.Width < ffmpegProfile.Resolution.Width;
+    }
+
     private static DisplaySize CalculateScaledSize(FFmpegProfile ffmpegProfile, MediaVersion version)
     {
         IDisplaySize sarSize = SARSize(version);
@@ -256,12 +267,20 @@ public static class FFmpegPlaybackSettingsCalculator
         int hh1 = hw1 * q / p;
         int hh2 = targetSize.Height;
         int hw2 = targetSize.Height * p / q;
-        if (hh1 <= targetSize.Height)
+
+        // crop needs to return whichever version has *both* dimensions >= required
+        // because it will never pad
+        if (ffmpegProfile.ScalingBehavior is ScalingBehavior.Crop)
         {
-            return new DisplaySize(hw1, hh1);
+            if (hw1 >= targetSize.Width && hh1 >= targetSize.Height)
+            {
+                return new DisplaySize(hw1, hh1);
+            }
+
+            return new DisplaySize(hw2, hh2);
         }
 
-        return new DisplaySize(hw2, hh2);
+        return hh1 <= targetSize.Height ? new DisplaySize(hw1, hh1) : new DisplaySize(hw2, hh2);
     }
 
     private static int Gcd(int a, int b)