diff --git a/vscode-extension-ashes/Requirements.md b/vscode-extension-ashes/Requirements.md
index 61a401f6..b990ed01 100644
--- a/vscode-extension-ashes/Requirements.md
+++ b/vscode-extension-ashes/Requirements.md
@@ -275,7 +275,7 @@ Based on the Escoria core documentation, ASHES supports the following language f
 **FR-9.6: Indentation Validation**
 - The extension MUST enforce tab-based indentation (not spaces) as required by ASHES
 - The extension MUST detect mixed tabs and spaces
-- The extension MUST warn about excessive indentation (more than 3 levels)
+- The extension MUST allow deep indentation for complex nested structures
 - The extension MUST validate proper indentation for control flow blocks
 - The extension MUST validate that events are at the top level (no indentation)
 - The extension MUST validate proper indentation for dialog blocks and choices
diff --git a/vscode-extension-ashes/src/syntaxValidator.ts b/vscode-extension-ashes/src/syntaxValidator.ts
index 4ca812b0..dc35634f 100644
--- a/vscode-extension-ashes/src/syntaxValidator.ts
+++ b/vscode-extension-ashes/src/syntaxValidator.ts
@@ -386,10 +386,14 @@ export class ASHESSyntaxValidator {
                 const conditionText = conditionMatch[2].trim();
                 
                 // Check for proper inventory check patterns: "item" in inventory
-                const inventoryMatch = conditionText.match(/([^"]*)\s+in\s+inventory/);
+                const inventoryMatch = conditionText.match(/"([^"]*)"\s+in\s+inventory/);
                 if (inventoryMatch) {
-                    const itemPart = inventoryMatch[1].trim();
-                    if (!itemPart.startsWith('"') || !itemPart.endsWith('"')) {
+                    // The pattern already matches quoted strings, so this is valid
+                    // No need to check for quotes since the regex already requires them
+                } else {
+                    // Check if there's an inventory check without proper quotes
+                    const unquotedInventoryMatch = conditionText.match(/([^"]*)\s+in\s+inventory/);
+                    if (unquotedInventoryMatch) {
                         const inventoryIndex = conditionText.indexOf('in inventory');
                         diagnostics.push({
                             range: new vscode.Range(lineNumber, line.indexOf(conditionText) + inventoryIndex, lineNumber, line.indexOf(conditionText) + inventoryIndex + 'in inventory'.length),
@@ -608,15 +612,15 @@ export class ASHESSyntaxValidator {
             if (prevIndentMatch) {
                 const prevIndent = prevIndentMatch[1].length;
                 
-                // Check for excessive indentation (more than 3 levels deep)
-                if (currentIndent > 3) {
-                    diagnostics.push({
-                        range: new vscode.Range(lineNumber, 0, lineNumber, currentIndent),
-                        message: "Excessive indentation detected (more than 3 levels)",
-                        severity: vscode.DiagnosticSeverity.Warning,
-                        code: 'excessive-indentation'
-                    });
-                }
+                // Note: Removed excessive indentation limit to allow deeper nesting
+                // if (currentIndent > 3) {
+                //     diagnostics.push({
+                //         range: new vscode.Range(lineNumber, 0, lineNumber, currentIndent),
+                //         message: "Excessive indentation detected (more than 3 levels)",
+                //         severity: vscode.DiagnosticSeverity.Warning,
+                //         code: 'excessive-indentation'
+                //     });
+                // }
             }
         }
 
diff --git a/vscode-extension-ashes/syntaxes/ashes.tmLanguage.json b/vscode-extension-ashes/syntaxes/ashes.tmLanguage.json
index 174e2498..47e42f3e 100644
--- a/vscode-extension-ashes/syntaxes/ashes.tmLanguage.json
+++ b/vscode-extension-ashes/syntaxes/ashes.tmLanguage.json
@@ -286,11 +286,39 @@
             },
             {
               "include": "#numbers"
+            },
+            {
+              "include": "#keywords"
+            },
+            {
+              "include": "#variables"
+            },
+            {
+              "include": "#conditional-expressions"
             }
           ]
         }
       ]
     },
+    "conditional-expressions": {
+      "patterns": [
+        {
+          "name": "meta.conditional-expression.ashes",
+          "match": "\\b([a-zA-Z_][a-zA-Z0-9_]*)\\s*(==|!=|<=|>=|<|>)\\s*([a-zA-Z_][a-zA-Z0-9_]*|\\d+)\\b",
+          "captures": {
+            "1": {
+              "name": "variable.other.conditional.ashes"
+            },
+            "2": {
+              "name": "keyword.operator.comparison.ashes"
+            },
+            "3": {
+              "name": "variable.other.conditional.ashes"
+            }
+          }
+        }
+      ]
+    },
     "strings": {
       "patterns": [
         {
@@ -361,7 +389,7 @@
         },
         {
           "name": "keyword.other.ashes",
-          "match": "\\b(in|is|active)\\b"
+          "match": "\\b(in|is|active|inventory)\\b"
         }
       ]
     },