diff --git a/CHANGELOG.md b/CHANGELOG.md
index 280e9fa7..f4bb5060 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -17,6 +17,7 @@ changes you may need to make.
 
 - **BREAKING**: Minimum required Sonarr version increased to `3.0.9.1549` (Previous minimum version
   was `3.0.4.1098`).
+- **BREAKING**: Old boolean syntax for `reset_unmatched_scores` is no longer supported.
 
 ## [5.4.3] - 2023-09-16
 
diff --git a/src/Recyclarr.TrashLib.Config/Parsing/ConfigParser.cs b/src/Recyclarr.TrashLib.Config/Parsing/ConfigParser.cs
index c5707d38..ba027667 100644
--- a/src/Recyclarr.TrashLib.Config/Parsing/ConfigParser.cs
+++ b/src/Recyclarr.TrashLib.Config/Parsing/ConfigParser.cs
@@ -47,18 +47,25 @@ public class ConfigParser
             _log.Debug(e, "Exception while parsing config file");
 
             var line = e.Start.Line;
-            switch (e.InnerException)
+
+            var contextualMsg = ConfigContextualMessages.GetContextualErrorFromException(e);
+            if (contextualMsg is not null)
+            {
+                _log.Error("Exception at line {Line}: {Msg}", line, contextualMsg);
+            }
+            else
             {
-                case InvalidCastException:
-                    _log.Error("Incompatible value assigned/used at line {Line}: {Msg}", line,
-                        e.InnerException.Message);
-                    break;
+                switch (e.InnerException)
+                {
+                    case InvalidCastException:
+                        _log.Error("Incompatible value assigned/used at line {Line}: {Msg}", line,
+                            e.InnerException.Message);
+                        break;
 
-                default:
-                    var msg = ConfigContextualMessages.GetContextualErrorFromException(e) ??
-                        e.InnerException?.Message ?? e.Message;
-                    _log.Error("Exception at line {Line}: {Msg}", line, msg);
-                    break;
+                    default:
+                        _log.Error("Exception at line {Line}: {Msg}", line, e.InnerException?.Message ?? e.Message);
+                        break;
+                }
             }
         }
 
diff --git a/src/Recyclarr.TrashLib.Config/Parsing/ConfigYamlDataObjects.cs b/src/Recyclarr.TrashLib.Config/Parsing/ConfigYamlDataObjects.cs
index 9689e699..26a2c9e8 100644
--- a/src/Recyclarr.TrashLib.Config/Parsing/ConfigYamlDataObjects.cs
+++ b/src/Recyclarr.TrashLib.Config/Parsing/ConfigYamlDataObjects.cs
@@ -1,7 +1,5 @@
-using System.ComponentModel;
 using System.Diagnostics.CodeAnalysis;
 using JetBrains.Annotations;
-using Recyclarr.TrashLib.Config.Parsing.BackwardCompatibility;
 using Recyclarr.TrashLib.Config.Parsing.PostProcessing.ConfigMerging;
 using YamlDotNet.Serialization;
 
@@ -45,13 +43,8 @@ public record QualityProfileQualityConfigYaml
 }
 
 [UsedImplicitly(ImplicitUseTargetFlags.WithMembers)]
-[TypeConverter(typeof(ResetUnmatchedScoresYamlTypeConverter))]
 public record ResetUnmatchedScoresConfigYaml
 {
-    // This exists so that we know if this value came from the legacy 'true|false' value.
-    [YamlIgnore]
-    public bool FromBool { get; set; }
-
     public bool? Enabled { get; init; }
     public IReadOnlyCollection<string>? Except { get; init; }
 }
diff --git a/src/Recyclarr.TrashLib.Config/Parsing/ConfigYamlDataObjectsValidation.cs b/src/Recyclarr.TrashLib.Config/Parsing/ConfigYamlDataObjectsValidation.cs
index 74e64345..70bba0c3 100644
--- a/src/Recyclarr.TrashLib.Config/Parsing/ConfigYamlDataObjectsValidation.cs
+++ b/src/Recyclarr.TrashLib.Config/Parsing/ConfigYamlDataObjectsValidation.cs
@@ -93,13 +93,6 @@ public class ResetUnmatchedScoresConfigYamlValidator : AbstractValidator<ResetUn
         RuleFor(x => x.Enabled)
             .NotNull()
             .WithMessage("Under `reset_unmatched_scores`, the `enabled` property is required.");
-
-        RuleFor(x => x.FromBool)
-            .Must(x => !x) // must be false
-            .WithMessage(
-                "Using true/false with `reset_unmatched_scores` is deprecated. " +
-                "See: https://recyclarr.dev/wiki/upgrade-guide/v6.0/#reset-scores")
-            .WithSeverity(Severity.Warning);
     }
 }
 
diff --git a/src/Recyclarr.TrashLib.Config/Parsing/ErrorHandling/ConfigContextualMessages.cs b/src/Recyclarr.TrashLib.Config/Parsing/ErrorHandling/ConfigContextualMessages.cs
index d06557ab..969a3558 100644
--- a/src/Recyclarr.TrashLib.Config/Parsing/ErrorHandling/ConfigContextualMessages.cs
+++ b/src/Recyclarr.TrashLib.Config/Parsing/ErrorHandling/ConfigContextualMessages.cs
@@ -6,7 +6,17 @@ public static class ConfigContextualMessages
 {
     public static string? GetContextualErrorFromException(YamlException e)
     {
-        if (e.Message.Contains(
+        return LookupMessage(e.Message) ?? LookupMessage(e.InnerException?.Message);
+    }
+
+    private static string? LookupMessage(string? msg)
+    {
+        if (msg is null)
+        {
+            return null;
+        }
+
+        if (msg.Contains(
             "Property 'reset_unmatched_scores' not found on type " +
             $"'{typeof(QualityScoreConfigYaml).FullName}'"))
         {
@@ -16,6 +26,14 @@ public static class ConfigContextualMessages
                 "See: https://recyclarr.dev/wiki/upgrade-guide/v5.0/#reset-unmatched-scores";
         }
 
+        if (msg.Contains(
+            $"Invalid cast from 'System.String' to '{typeof(ResetUnmatchedScoresConfigYaml).FullName}'"))
+        {
+            return
+                "Using true/false with `reset_unmatched_scores` is no longer supported. " +
+                "See: https://recyclarr.dev/wiki/upgrade-guide/v6.0/#reset-scores";
+        }
+
         return null;
     }
 }
diff --git a/src/Recyclarr.TrashLib/Settings/SettingsContextualMessages.cs b/src/Recyclarr.TrashLib/Settings/SettingsContextualMessages.cs
index aa17ed1d..d76fab50 100644
--- a/src/Recyclarr.TrashLib/Settings/SettingsContextualMessages.cs
+++ b/src/Recyclarr.TrashLib/Settings/SettingsContextualMessages.cs
@@ -6,7 +6,17 @@ public static class SettingsContextualMessages
 {
     public static string? GetContextualErrorFromException(YamlException e)
     {
-        if (e.Message.Contains(
+        return LookupMessage(e.Message) ?? LookupMessage(e.InnerException?.Message);
+    }
+
+    private static string? LookupMessage(string? msg)
+    {
+        if (msg is null)
+        {
+            return null;
+        }
+
+        if (msg.Contains(
             "Property 'repository' not found on type " +
             $"'{typeof(SettingsValues).FullName}'"))
         {
diff --git a/src/Recyclarr.TrashLib/Settings/SettingsProvider.cs b/src/Recyclarr.TrashLib/Settings/SettingsProvider.cs
index 30431d76..badc0347 100644
--- a/src/Recyclarr.TrashLib/Settings/SettingsProvider.cs
+++ b/src/Recyclarr.TrashLib/Settings/SettingsProvider.cs
@@ -40,7 +40,7 @@ public class SettingsProvider : ISettingsProvider
             _log.Debug(e, "Exception while parsing settings file");
 
             var line = e.Start.Line;
-            var msg = SettingsContextualMessages.GetContextualErrorFromException(e);
+            var msg = SettingsContextualMessages.GetContextualErrorFromException(e) ?? e.Message;
             _log.Error("Exception while parsing settings.yml at line {Line}: {Msg}", line, msg);
 
             throw;