diff --git a/Content.Tests/DMProject/Tests/Expression/edge_comparison.dm b/Content.Tests/DMProject/Tests/Expression/edge_comparison.dm
index 069fc4aaae..27c5a815ef 100644
--- a/Content.Tests/DMProject/Tests/Expression/edge_comparison.dm
+++ b/Content.Tests/DMProject/Tests/Expression/edge_comparison.dm
@@ -1,18 +1,20 @@
 
 /proc/RunTest()
+	// null violates the holy trichotomy here, with how it compares to an empty string.
+	ASSERT( (null > "") == 0 )
 	ASSERT( (null >= "") == 1 )
+	ASSERT( (null == "") == 0 )
 	ASSERT( (null <= "") == 1 )
+	ASSERT( (null < "") == 0 )
 
 	ASSERT( (null > 5) == 0 )
 	ASSERT( (null > -5) == 1 )
 	ASSERT( (null > "abc") == 0 )
-	ASSERT( (null > "") == 0 )
 	ASSERT( (null > null) == 0 )
 
 	ASSERT( (null < 5) == 1 )
 	ASSERT( (null < -5) == 0 )
 	ASSERT( (null < "abc") == 1 )
-	ASSERT( (null < "") == 0 )
 	ASSERT( (null < null) == 0 )
 
 	ASSERT( (0.15 <= null) == 0)
diff --git a/DMCompiler/DM/Expressions/Binary.cs b/DMCompiler/DM/Expressions/Binary.cs
index 8679fa8c53..c05a7d3d4c 100644
--- a/DMCompiler/DM/Expressions/Binary.cs
+++ b/DMCompiler/DM/Expressions/Binary.cs
@@ -35,6 +35,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.Add();
@@ -60,6 +65,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.Subtract();
@@ -85,6 +95,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.Multiply();
@@ -110,6 +125,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.Divide();
@@ -125,7 +145,7 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
         }
 
         if (lhs is Number lhsNum && rhs is Number rhsNum) {
-            constant = new Number(Location, lhsNum.Value % rhsNum.Value);
+            constant = new Number(Location, (int)lhsNum.Value % (int)rhsNum.Value);
         } else {
             constant = null;
             return false;
@@ -135,6 +155,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.Modulus();
@@ -163,6 +188,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.ModulusModulus();
@@ -188,6 +218,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.Power();
@@ -213,6 +248,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.BitShiftLeft();
@@ -238,6 +278,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.BitShiftRight();
@@ -265,6 +310,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.BinaryAnd();
@@ -290,6 +340,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.BinaryXor();
@@ -315,6 +370,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.BinaryOr();
@@ -378,6 +438,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.GreaterThan();
@@ -387,6 +452,11 @@ public override void EmitPushValue(ExpressionContext ctx) {
 // x >= y
 internal sealed class GreaterThanOrEqual(Location location, DMExpression lhs, DMExpression rhs) : BinaryOp(location, lhs, rhs) {
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.GreaterThanOrEqual();
@@ -414,6 +484,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
 // x < y
 internal sealed class LessThan(Location location, DMExpression lhs, DMExpression rhs) : BinaryOp(location, lhs, rhs) {
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.LessThan();
@@ -441,6 +516,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
 // x <= y
 internal sealed class LessThanOrEqual(Location location, DMExpression lhs, DMExpression rhs) : BinaryOp(location, lhs, rhs) {
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         LHS.EmitPushValue(ctx);
         RHS.EmitPushValue(ctx);
         ctx.Proc.LessThanOrEqual();
@@ -485,6 +565,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         string endLabel = ctx.Proc.NewLabelName();
 
         LHS.EmitPushValue(ctx);
@@ -512,6 +597,21 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (LHS.TryAsConstant(ctx.Compiler, out var lhs)) {
+            if (lhs.IsTruthy()) {
+                if (RHS.TryAsConstant(ctx.Compiler, out var constant)) {
+                    constant.EmitPushValue(ctx);
+                    return;
+                }
+
+                RHS.EmitPushValue(ctx);
+                return;
+            }
+
+            lhs.EmitPushValue(ctx);
+            return;
+        }
+
         string endLabel = ctx.Proc.NewLabelName();
 
         LHS.EmitPushValue(ctx);
diff --git a/DMCompiler/DM/Expressions/Builtins.cs b/DMCompiler/DM/Expressions/Builtins.cs
index 6988c48c54..02f9a0accb 100644
--- a/DMCompiler/DM/Expressions/Builtins.cs
+++ b/DMCompiler/DM/Expressions/Builtins.cs
@@ -709,6 +709,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         expr.EmitPushValue(ctx);
         ctx.Proc.Sin();
     }
@@ -734,6 +739,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         expr.EmitPushValue(ctx);
         ctx.Proc.Cos();
     }
@@ -759,6 +769,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         expr.EmitPushValue(ctx);
         ctx.Proc.Tan();
     }
@@ -789,6 +804,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         expr.EmitPushValue(ctx);
         ctx.Proc.ArcSin();
     }
@@ -819,6 +839,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         expr.EmitPushValue(ctx);
         ctx.Proc.ArcCos();
     }
@@ -844,6 +869,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         expr.EmitPushValue(ctx);
         ctx.Proc.ArcTan();
     }
@@ -873,6 +903,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         xExpr.EmitPushValue(ctx);
         yExpr.EmitPushValue(ctx);
         ctx.Proc.ArcTan2();
@@ -904,6 +939,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         expr.EmitPushValue(ctx);
         ctx.Proc.Sqrt();
     }
@@ -946,6 +986,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         expr.EmitPushValue(ctx);
         if (baseExpr == null) {
             ctx.Proc.LogE();
@@ -976,6 +1021,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         expr.EmitPushValue(ctx);
         ctx.Proc.Abs();
     }
diff --git a/DMCompiler/DM/Expressions/Ternary.cs b/DMCompiler/DM/Expressions/Ternary.cs
index c5b874a89b..8c5ba9afba 100644
--- a/DMCompiler/DM/Expressions/Ternary.cs
+++ b/DMCompiler/DM/Expressions/Ternary.cs
@@ -22,6 +22,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         string cLabel = ctx.Proc.NewLabelName();
         string endLabel = ctx.Proc.NewLabelName();
 
diff --git a/DMCompiler/DM/Expressions/Unary.cs b/DMCompiler/DM/Expressions/Unary.cs
index f6b07c94fb..4de2a46821 100644
--- a/DMCompiler/DM/Expressions/Unary.cs
+++ b/DMCompiler/DM/Expressions/Unary.cs
@@ -18,6 +18,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         Expr.EmitPushValue(ctx);
         ctx.Proc.Negate();
     }
@@ -33,6 +38,11 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         Expr.EmitPushValue(ctx);
         ctx.Proc.Not();
     }
@@ -44,11 +54,16 @@ public override bool TryAsConstant(DMCompiler compiler, [NotNullWhen(true)] out
         if (!Expr.TryAsConstant(compiler, out constant) || constant is not Number constantNum)
             return false;
 
-        constant = new Number(Location, ~(int)constantNum.Value);
+        constant = new Number(Location, (~(int)constantNum.Value) & 0xFFFFFF);
         return true;
     }
 
     public override void EmitPushValue(ExpressionContext ctx) {
+        if (TryAsConstant(ctx.Compiler, out var constant)) {
+            constant.EmitPushValue(ctx);
+            return;
+        }
+
         Expr.EmitPushValue(ctx);
         ctx.Proc.BinaryNot();
     }