diff --git a/src/SMAPI.Tests/Core/AssetNameTests.cs b/src/SMAPI.Tests/Core/AssetNameTests.cs
index fdaa2c01..2d546ec7 100644
--- a/src/SMAPI.Tests/Core/AssetNameTests.cs
+++ b/src/SMAPI.Tests/Core/AssetNameTests.cs
@@ -265,6 +265,25 @@ namespace SMAPI.Tests.Core
             return name.StartsWith(otherAssetName, allowPartialWord: true, allowSubfolder: allowSubfolder);
         }
 
+        // The enumerator strips the trailing path separator, so each of these cases has to be handled on each branch.
+        [TestCase("Mods/SomeMod", "Mods/", false, ExpectedResult = true)]
+        [TestCase("Mods/SomeMod", "Mods", false, ExpectedResult = false)]
+        [TestCase("Mods/Jasper/Data", "Mods/Jas/", false, ExpectedResult = false)]
+        [TestCase("Mods/Jasper/Data", "Mods/Jas", false, ExpectedResult = false)]
+        [TestCase("Mods/Jas", "Mods/Jas/", false, ExpectedResult = false)]
+        [TestCase("Mods/Jas", "Mods/Jas", false, ExpectedResult = true)]
+        public bool StartsWith_PrefixHasSeparator(string mainAssetName, string otherAssetName, bool allowSubfolder)
+        {
+            // arrange
+            mainAssetName = PathUtilities.NormalizeAssetName(mainAssetName);
+
+            // act
+            AssetName name = AssetName.Parse(mainAssetName, _ => null);
+
+            // assert value
+            return name.StartsWith(otherAssetName, allowPartialWord: true, allowSubfolder: allowSubfolder);
+        }
+
 
         /****
         ** GetHashCode
diff --git a/src/SMAPI/Framework/Content/AssetName.cs b/src/SMAPI/Framework/Content/AssetName.cs
index 99968299..8355f9ec 100644
--- a/src/SMAPI/Framework/Content/AssetName.cs
+++ b/src/SMAPI/Framework/Content/AssetName.cs
@@ -162,8 +162,14 @@ namespace StardewModdingAPI.Framework.Content
                     if (prefixHasMore)
                         return false;
 
-                    // match if subfolder paths are fine (e.g. prefix 'Data/Events' with target 'Data/Events/Beach')
-                    return allowSubfolder;
+                    // match: every segment in the prefix matched and subfolders are allowed (e.g. prefix 'Data/Events' with target 'Data/Events/Beach')
+                    if (allowSubfolder)
+                        return true;
+
+                    // Special case: the prefix ends with a path separator, but subfolders aren't allowed. This case
+                    // matches if there's no further path separator in the asset name *after* the current separator.
+                    // For example, the prefix 'A/B/' matches 'A/B/C' but not 'A/B/C/D'.
+                    return pathSeparators.Contains(trimmedPrefix[^1]) && curParts.Remainder.Length == 0;
                 }
 
                 // previous segments matched exactly and both reached the end