diff --git a/Projects/UOContent.Tests/Tests/Mobiles/AI/DebugMessageTimingTests.cs b/Projects/UOContent.Tests/Tests/Mobiles/AI/DebugMessageTimingTests.cs
new file mode 100644
index 000000000..042628b79
--- /dev/null
+++ b/Projects/UOContent.Tests/Tests/Mobiles/AI/DebugMessageTimingTests.cs
@@ -0,0 +1,145 @@
+using System.Collections.Generic;
+using System.Globalization;
+using Server;
+using Server.Mobiles;
+using Server.Mobiles.AI.BaseAI;
+using Xunit;
+
+namespace UOContent.Tests.Mobiles.AI;
+
+[Collection("Sequential UOContent Tests")]
+public class DebugMessageTimingTests
+{
+    public static IEnumerable<object[]> DeadlineCases()
+    {
+        (long Now, long Deadline, bool Due)[] clocks =
+        [
+            (99, 100, false), (100, 100, true), (101, 100, true),
+            (-101, -100, false), (-100, -100, true), (-99, -100, true),
+            (long.MaxValue - 10, long.MinValue + 10, false),
+            (long.MinValue + 10, long.MaxValue - 10, true)
+        ];
+
+        foreach (var (now, deadline, due) in clocks)
+        {
+            foreach (var withProvider in new[] { false, true })
+            {
+                foreach (var debug in new[] { false, true })
+                {
+                    yield return [now, deadline, due, withProvider, debug];
+                }
+            }
+        }
+    }
+
+    [Theory]
+    [MemberData(nameof(DeadlineCases))]
+    public void Handler_EmitsOnlyWhenDebugEnabledAndDue(
+        long now, long deadline, bool due, bool withProvider, bool debug)
+    {
+        var previousTick = Core.TickCount;
+        var pet = new PetTestStub();
+        var ai = pet.AIObject;
+        pet.Debug = debug;
+        ai.NextDebugMessage = deadline;
+        Core._tickCount = now;
+        var handler = withProvider
+            ? new DebugInterpolatedStringHandler(6, 1, CultureInfo.InvariantCulture, ai)
+            : new DebugInterpolatedStringHandler(6, 1, ai);
+
+        try
+        {
+            handler.AppendLiteral("value ");
+            handler.AppendFormatted(42);
+            Assert.Equal(debug && due ? "value 42" : "", handler.Text.ToString());
+
+            ai.DebugSayFormatted(ref handler, 50);
+            Assert.Equal(debug && due ? unchecked(now + 50) : deadline, ai.NextDebugMessage);
+            Assert.True(handler.Text.IsEmpty);
+        }
+        finally
+        {
+            handler.Clear();
+            Core._tickCount = previousTick;
+            pet.Delete();
+        }
+    }
+
+    [Theory]
+    [InlineData(false)]
+    [InlineData(true)]
+    public void Handler_RearmedCooldown_WaitsAcrossWrap(bool withProvider)
+    {
+        var previousTick = Core.TickCount;
+        var pet = new PetTestStub { Debug = true };
+        var ai = pet.AIObject;
+
+        try
+        {
+            Core._tickCount = long.MaxValue - 10;
+            ai.NextDebugMessage = Core.TickCount;
+            Emit(ai, withProvider);
+            var deadline = ai.NextDebugMessage;
+            Assert.Equal(long.MinValue + 39, deadline);
+
+            Core._tickCount = long.MaxValue - 9;
+            Emit(ai, withProvider);
+            Assert.Equal(deadline, ai.NextDebugMessage);
+
+            Core._tickCount = deadline - 1;
+            Emit(ai, withProvider);
+            Assert.Equal(deadline, ai.NextDebugMessage);
+
+            Core._tickCount = deadline;
+            Emit(ai, withProvider);
+            Assert.Equal(deadline + 50, ai.NextDebugMessage);
+        }
+        finally
+        {
+            Core._tickCount = previousTick;
+            pet.Delete();
+        }
+    }
+
+    [Fact]
+    public void InterpolatedCall_UsesHandlerAcrossWrap()
+    {
+        var previousTick = Core.TickCount;
+        var pet = new PetTestStub { Debug = true };
+        var ai = pet.AIObject;
+
+        try
+        {
+            Core._tickCount = long.MaxValue - 10;
+            ai.NextDebugMessage = long.MinValue + 10;
+            var value = 42;
+            ai.DebugSayFormatted($"value {value}", 50);
+            Assert.Equal(long.MinValue + 10, ai.NextDebugMessage);
+
+            Core._tickCount = long.MinValue + 10;
+            ai.DebugSayFormatted($"value {value}", 50);
+            Assert.Equal(long.MinValue + 60, ai.NextDebugMessage);
+        }
+        finally
+        {
+            Core._tickCount = previousTick;
+            pet.Delete();
+        }
+    }
+
+    private static void Emit(BaseAI ai, bool withProvider)
+    {
+        var handler = withProvider
+            ? new DebugInterpolatedStringHandler(5, 0, CultureInfo.InvariantCulture, ai)
+            : new DebugInterpolatedStringHandler(5, 0, ai);
+        try
+        {
+            handler.AppendLiteral("debug");
+            ai.DebugSayFormatted(ref handler, 50);
+        }
+        finally
+        {
+            handler.Clear();
+        }
+    }
+}
diff --git a/Projects/UOContent/Mobiles/AI/BaseAI/DebugInterpolatedStringHandler.cs b/Projects/UOContent/Mobiles/AI/BaseAI/DebugInterpolatedStringHandler.cs
index 05630d2f8..03c0f1a1e 100644
--- a/Projects/UOContent/Mobiles/AI/BaseAI/DebugInterpolatedStringHandler.cs
+++ b/Projects/UOContent/Mobiles/AI/BaseAI/DebugInterpolatedStringHandler.cs
@@ -56,7 +56,7 @@ public ref struct DebugInterpolatedStringHandler
     /// <remarks>This is intended to be called only by compiler-generated code. Arguments are not validated as they'd otherwise be for members intended to be used directly.</remarks>
     public DebugInterpolatedStringHandler(int literalLength, int formattedCount, Mobiles.BaseAI ai)
     {
-        _debugActive = ai.Mobile?.Debug == true && Core.TickCount >= ai.NextDebugMessage;
+        _debugActive = ai.Mobile?.Debug == true && Core.TickCount - ai.NextDebugMessage >= 0;
 
         if (_debugActive)
         {
@@ -79,7 +79,7 @@ public ref struct DebugInterpolatedStringHandler
     /// <remarks>This is intended to be called only by compiler-generated code. Arguments are not validated as they'd otherwise be for members intended to be used directly.</remarks>
     public DebugInterpolatedStringHandler(int literalLength, int formattedCount, IFormatProvider? provider, Mobiles.BaseAI ai)
     {
-        _debugActive = ai.Mobile?.Debug == true && Core.TickCount >= ai.NextDebugMessage;
+        _debugActive = ai.Mobile?.Debug == true && Core.TickCount - ai.NextDebugMessage >= 0;
 
         if (_debugActive)
         {