diff --git a/MultiversalDiplomacy/Script/AdjudicationQueryScriptHandler.cs b/MultiversalDiplomacy/Script/AdjudicationQueryScriptHandler.cs
index 683089b..32f63aa 100644
--- a/MultiversalDiplomacy/Script/AdjudicationQueryScriptHandler.cs
+++ b/MultiversalDiplomacy/Script/AdjudicationQueryScriptHandler.cs
@@ -35,7 +35,8 @@ public class AdjudicationQueryScriptHandler(World world, bool strict = false) :
                 break;
 
             case "assert":
-                return HandleAssertion(args[1]);
+                if (!EvaluateAssertion(args[1])) return Strict ? null : this;
+                break;
 
             case "status":
                 throw new NotImplementedException();
@@ -49,19 +50,48 @@ public class AdjudicationQueryScriptHandler(World world, bool strict = false) :
         return this;
     }
 
-    private AdjudicationQueryScriptHandler? HandleAssertion(string assertion)
+    private bool EvaluateAssertion(string assertion)
     {
-        // Simple assertions
-        switch (assertion)
+        var args = assertion.Split(' ', 2, StringSplitOptions.RemoveEmptyEntries);
+
+        switch (args[0])
         {
             case "true":
-                return this;
+                return true;
 
             case "false":
-                return null;
+                return false;
+
+            case "order-valid":
+                // Assert order was valid
+
+            case "order-invalid":
+                // Assert order was invalid
+
+            case "has-past":
+                // Assert a timeline's past
+
+            case "holds":
+                // Assert a unit successfully held
+
+            case "dislodged":
+                // Assert a unit was dislodged
+
+            case "moves":
+                // Assert a unit successfully moved
+
+            case "no-move":
+                // Assert a unit did not move
+
+            case "supports":
+                // Assert a unit's support was given
+
+            case "cut":
+                // Assert a unit's support was cut
+
+            default:
+                Console.WriteLine($"Unknown assertion \"{args[0]}\"");
+                return !Strict;
         }
-            
-        Console.WriteLine("Order lookup not implemented yet");
-        return this;
     }
 }
diff --git a/MultiversalDiplomacyTests/ReplTest.cs b/MultiversalDiplomacyTests/ReplTest.cs
index 5feed37..2460201 100644
--- a/MultiversalDiplomacyTests/ReplTest.cs
+++ b/MultiversalDiplomacyTests/ReplTest.cs
@@ -86,4 +86,179 @@ public class ReplTest
 
         repl["assert false"].AssertClosed();
     }
+
+    [Test]
+    public void AssertInvalidOrder()
+    {
+        var repl = StandardRepl();
+
+        repl["""
+        unit Germany A Mun
+        ---
+        Germany A Mun - Mars
+        ---
+        """].AssertReady();
+
+        // Assertion should pass for an invalid order
+        repl["assert order-invalid Mun"].AssertReady();
+        // Assertion should fail for an invalid order
+        repl["assert order-valid Mun"].AssertClosed();
+    }
+
+    [Test]
+    public void AssertValidOrder()
+    {
+        var repl = StandardRepl();
+
+        repl["""
+        unit Germany A Mun
+        ---
+        Germany A Mun - Tyr
+        ---
+        """].AssertReady();
+
+        // Assertion should pass for a valid order
+        repl["assert order-valid Mun"].AssertReady();
+        // Assertion should fail for a valid order
+        repl["assert order-invalid Mun"].AssertClosed();
+    }
+
+    [Test]
+    public void AssertSeasonPast()
+    {
+        var repl = StandardRepl();
+
+        repl["""
+        unit England F London
+        ---
+        ---
+        """].AssertReady();
+
+        // Assertion should pass for a season's past
+        repl["assert has-past a1>a0"].AssertReady();
+        // Assertion should fail for an incorrect past
+        repl["assert has-past a0>a1"].AssertClosed();
+    }
+
+    [Test]
+    public void AssertHolds()
+    {
+        var repl = StandardRepl();
+
+        repl["""
+        unit Germany A Mun
+        unit Austria A Tyr
+        ---
+        Germany Mun - Tyr
+        ---
+        """].AssertReady();
+
+        // Assertion should pass for a repelled move
+        repl["assert holds Tyr"].AssertReady();
+        // Assertion should fail for a repelled move
+        repl["assert dislodged Tyr"].AssertClosed();
+    }
+
+    [Test]
+    public void AssertDislodged()
+    {
+        var repl = StandardRepl();
+
+        repl["""
+        unit Germany A Mun
+        unit Germany A Boh
+        unit Austria A Tyr
+        ---
+        Germany Mun - Tyr
+        Germany Boh s Mun - Tyr
+        ---
+        """].AssertReady();
+
+        // Assertion should pass for a dislodge
+        repl["assert dislodged Tyr"].AssertReady();
+        // Assertion should fail for a repelled move
+        repl["assert holds Tyr"].AssertClosed();
+    }
+
+    [Test]
+    public void AssertMoves()
+    {
+        var repl = StandardRepl();
+
+        repl["""
+        unit Germany A Mun
+        ---
+        Germany Mun - Tyr
+        ---
+        """].AssertReady();
+
+        // Assertion should pass for a move
+        repl["assert moves Mun"].AssertReady();
+        // Assertion should fail for a successful move
+        repl["assert no-move Mun"].AssertClosed();
+    }
+
+    [Test]
+    public void AssertRepelled()
+    {
+        var repl = StandardRepl();
+
+        repl["""
+        unit Germany A Mun
+        unit Austria A Tyr
+        ---
+        Germany Mun - Tyr
+        ---
+        """].AssertReady();
+
+        // Assertion should pass for a repelled move
+        repl["assert no-move Mun"].AssertReady();
+        // Assertion should fail for no move
+        repl["assert moves Mun"].AssertClosed();
+    }
+
+    [Test]
+    public void AssertSupports()
+    {
+        var repl = StandardRepl();
+
+        repl["""
+        unit Germany A Mun
+        unit Germany A Boh
+        unit Austria A Tyr
+        ---
+        Germany:
+        Mun - Tyr
+        Boh s Mun - Tyr
+        ---
+        """].AssertReady();
+
+        // `supports` and `cut` are opposites
+        repl["assert supports Boh"].AssertReady();
+        repl["assert cut Boh"].AssertClosed();
+    }
+
+    [Test]
+    public void AssertCutSupport()
+    {
+        var repl = StandardRepl();
+
+        repl["""
+        unit Germany A Mun
+        unit Germany A Boh
+        unit Austria A Tyr
+        unit Italy A Vienna
+        ---
+        Germany:
+        Mun - Tyr
+        Boh s Mun - Tyr
+
+        Italy Vienna - Boh
+        ---
+        """].AssertReady();
+
+        // `supports` and `cut` are opposites
+        repl["assert cut Boh"].AssertReady();
+        repl["assert supports Boh"].AssertClosed();
+    }
 }