diff --git a/compiler/src/generators/typescript-state-machine.ts b/compiler/src/generators/typescript-state-machine.ts
index b4cfeaa..f7aa068 100644
--- a/compiler/src/generators/typescript-state-machine.ts
+++ b/compiler/src/generators/typescript-state-machine.ts
@@ -542,10 +542,14 @@ function rewriteExpr(expr: string, stateVarNames: Set<string>, mapVarNames: Set<
   ts = ts.replace(/\.size\(\)/g, '.size');
 
   // 5i: SpeckDL conditional expression: if cond: a else b -> cond ? a : b
-  // Use a careful regex that matches word boundaries and stops at expression end
-  // Pattern: if <cond>: <then> else <else>
-  // Where cond, then, else are balanced expressions (no unbalanced braces at top level)
-  ts = ts.replace(/\bif\s+((?:[^{}:()]|\([^)]*\)|\{[^}]*\})+):\s*((?:[^{};]|\{[^}]*\})+)\s+else\s+((?:[^{};]|\{[^}]*\})+)(?=[;)}\],\s]|$)/g, '($1 ? $2 : $3)');
+  // Simpler approach: match if <cond>: <then> else <else>
+  // where cond doesn't contain { } : and then/else don't contain ; or }
+  let prev2;
+  do {
+    prev2 = ts;
+    // Match if followed by non-special chars, colon, then clause, else, else clause
+    ts = ts.replace(/\bif\s+([^{}:]+):\s*([^{};]+)\s+else\s+([^{};\n]+)/g, '($1 ? $2 : $3)');
+  } while (ts !== prev2);
 
   return ts.trim();
 }