diff --git a/src/Sentry.NLog/SentryTarget.cs b/src/Sentry.NLog/SentryTarget.cs
index 596c895d4a..d2a2eaf6c8 100644
--- a/src/Sentry.NLog/SentryTarget.cs
+++ b/src/Sentry.NLog/SentryTarget.cs
@@ -11,6 +11,7 @@ public sealed partial class SentryTarget : TargetWithContext
 
     private readonly ISystemClock _clock;
     private readonly UninitializedSdkWarning _uninitializedSdkWarning;
+    private bool _reportedUnsupportedSdkSetting;
 
     internal static readonly string AdditionalGroupingKeyProperty = "AdditionalGroupingKey";
 
@@ -76,7 +77,7 @@ internal SentryTarget(
     public Layout? Dsn
     {
         get => null;
-        set => throw new NotSupportedException(ConfigurationExtensions.ObsoleteDsnOverload);
+        set => throw ReportUnsupportedSdkSetting();
     }
 
     /// <summary>
@@ -87,7 +88,13 @@ public Layout? Dsn
     public bool InitializeSdk
     {
         get => false;
-        set => throw new NotSupportedException(ConfigurationExtensions.ObsoleteDsnOverload);
+        set
+        {
+            if (value)
+            {
+                throw ReportUnsupportedSdkSetting();
+            }
+        }
     }
 
     /// <summary>
@@ -181,6 +188,18 @@ public SentryNLogUser? User
         set => Options.User = value;
     }
 
+    // NLog discards the exception unless throwConfigExceptions is on. Report once: a v6 config may set both.
+    private NotSupportedException ReportUnsupportedSdkSetting()
+    {
+        if (!_reportedUnsupportedSdkSetting)
+        {
+            _reportedUnsupportedSdkSetting = true;
+            _uninitializedSdkWarning.WriteToStandardError("Sentry: " + ConfigurationExtensions.ObsoleteDsnOverload);
+        }
+
+        return new NotSupportedException(ConfigurationExtensions.ObsoleteDsnOverload);
+    }
+
     /// <inheritdoc />
     protected override void InitializeTarget()
     {
diff --git a/test/Sentry.NLog.Tests/SentryTargetConfigurationBindingTests.cs b/test/Sentry.NLog.Tests/SentryTargetConfigurationBindingTests.cs
index a25df0ed93..b367f2b9e4 100644
--- a/test/Sentry.NLog.Tests/SentryTargetConfigurationBindingTests.cs
+++ b/test/Sentry.NLog.Tests/SentryTargetConfigurationBindingTests.cs
@@ -33,6 +33,12 @@ public void LoadConfiguration_WithTargetSettings_DoesNotThrow()
         Assert.Null(LoadConfiguration("minimumEventLevel='Warn' includeEventPropertiesAsTags='true'"));
     }
 
+    [Fact]
+    public void LoadConfiguration_WithInitializeSdkFalse_DoesNotThrow()
+    {
+        Assert.Null(LoadConfiguration("initializeSdk='false'"));
+    }
+
     [Theory]
     [InlineData(2)]
     [InlineData(3)]
@@ -67,6 +73,55 @@ public void AddSentry_DsnOverload_IsObsoleteAsError(int parameterCount)
         Assert.True(obsolete!.IsError);
     }
 
+    [Fact]
+    public void Dsn_WhenSet_WritesMigrationMessageToStandardError()
+    {
+        var standardError = new List<string>();
+
+        Set(GetTarget(standardError), "Dsn", (Layout)ValidDsn);
+
+        Assert.Contains(ConfigurationExtensions.ObsoleteDsnOverload, Assert.Single(standardError));
+    }
+
+    [Fact]
+    public void InitializeSdk_WhenSetToTrue_WritesMigrationMessageToStandardError()
+    {
+        var standardError = new List<string>();
+
+        Set(GetTarget(standardError), "InitializeSdk", true);
+
+        Assert.Contains(ConfigurationExtensions.ObsoleteDsnOverload, Assert.Single(standardError));
+    }
+
+    [Fact]
+    public void InitializeSdk_WhenSetToFalse_WritesNothing()
+    {
+        var standardError = new List<string>();
+
+        Set(GetTarget(standardError), "InitializeSdk", false);
+
+        Assert.Empty(standardError);
+    }
+
+    [Fact]
+    public void ReportUnsupportedSdkSetting_BothSettingsOnOneTarget_WritesOnce()
+    {
+        var standardError = new List<string>();
+        var target = GetTarget(standardError);
+
+        Set(target, "Dsn", (Layout)ValidDsn);
+        Set(target, "InitializeSdk", true);
+
+        Assert.Single(standardError);
+    }
+
+    private static SentryTarget GetTarget(List<string> standardError) =>
+        new(new SentryNLogOptions(), () => Substitute.For<IHub>(), new MockClock(),
+            new UninitializedSdkWarning { WriteToStandardError = standardError.Add });
+
+    private static void Set(SentryTarget target, string property, object value) =>
+        Record.Exception(() => typeof(SentryTarget).GetProperty(property)!.SetValue(target, value));
+
     private static MethodInfo DsnOverload(int parameterCount) => typeof(ConfigurationExtensions)
         .GetMethods(BindingFlags.Public | BindingFlags.Static)
         .Single(m => m.Name == nameof(ConfigurationExtensions.AddSentry)