diff --git a/compiler/src/generators/typescript-state-machine.ts b/compiler/src/generators/typescript-state-machine.ts
index f080866..184c3f7 100644
--- a/compiler/src/generators/typescript-state-machine.ts
+++ b/compiler/src/generators/typescript-state-machine.ts
@@ -333,9 +333,12 @@ function emitAction(action: ActionNode, stateVarNames: Set<string>, mapVarNames:
       case 'assign': {
         const target = cleanName(stmt.target);
         const expr = rewriteExpr(stmt.expr, stateVarNames, mapVarNames, localNames, stateEnumName, knownStateValues);
-        const mapBracketMatch = target.match(/^(\w+)\[([^\]]+)\]$/);
+        // Handle Map bracket assignment: mapVar[index] := value -> this.mapVar.set(index, value)
+        // Support nested brackets by finding the outermost [ ] pair
+        const mapBracketMatch = target.match(/^(\w+)\[([\s\S]+)\]$/);
         if (mapBracketMatch && mapVarNames.has(mapBracketMatch[1])) {
-          bodyParts.push(`    this.${mapBracketMatch[1]}.set(${mapBracketMatch[2]}, ${expr});`);
+          const indexExpr = rewriteExpr(mapBracketMatch[2], stateVarNames, mapVarNames, localNames, stateEnumName, knownStateValues);
+          bodyParts.push(`    this.${mapBracketMatch[1]}.set(${indexExpr}, ${expr});`);
         } else {
           bodyParts.push(`    this.${target} = ${expr};`);
         }
@@ -416,13 +419,19 @@ function rewriteExpr(expr: string, stateVarNames: Set<string>, mapVarNames: Set<
   });
 
   // Step 3b: Replace identifiers that are state variables but not local params
+  // Track if previous token was 'this.' to avoid double-prefixing
   const tokens = ts.split(/([\s\(\)\[\]{}+\-*/=<>!&|.,;:'"`]+)/);
+  let prevWasThisDot = false;
   const result = tokens.map(tok => {
     if (/^[a-zA-Z_]\w*\.\w+$/.test(tok)) return tok; // already has dot (enum ref)
     if (/^(true|false|null|undefined|\d+|\w+\.\w+)$/.test(tok)) return tok;
+    if (tok === 'this') { prevWasThisDot = true; return tok; }
+    if (tok === '.') { prevWasThisDot = true; return tok; }
+    if (prevWasThisDot) { prevWasThisDot = false; return tok; } // skip if preceded by this.
     if (/^[a-zA-Z_]\w*$/.test(tok) && shouldPrefix(tok)) {
       return `this.${tok}`;
     }
+    prevWasThisDot = false;
     return tok;
   }).join('')
     // Undo this. prefix on identifiers after bracket access
@@ -478,6 +487,28 @@ function rewriteExpr(expr: string, stateVarNames: Set<string>, mapVarNames: Set<
   //     "not isOn" -> "!this.isOn"  (will be prefixed by step 3)
   ts = ts.replace(/\bnot\s+/g, '!');
 
+  // 5d2: and -> &&, or -> ||  (logical operators)
+  ts = ts.replace(/\band\b/g, '&&').replace(/\bor\b/g, '||');
+
+  // 5d3: Strip SpeckDL comments (// ...) before TS processing
+  ts = ts.replace(/\/\/.*$/gm, '');
+
+  // 5d4: [a..b] range syntax -> array literal [a, a+1, ..., b]
+  ts = ts.replace(/\[(\d+)\.\.(\d+)\]/g, (match, a, b) => {
+    const start = parseInt(a);
+    const end = parseInt(b);
+    const values = [];
+    for (let i = start; i <= end; i++) values.push(i);
+    return `[${values.join(', ')}]`;
+  });
+
+  // 5d5: Map literals {k: v} for Map type assignments
+  //     If target is a Map var, convert {k: v} to new Map([[k, v]])
+  ts = ts.replace(/\{(\d+):\s*([^}]+)\}/g, (match, k, v) => {
+    // Only convert if it looks like a Map literal (single key:value pair with number key)
+    return `new Map([[${k}, ${v}]])`;
+  });
+
   // 5e: Clean up trailing empty comparisons (===) — expression has no RHS after old() removal
   //     "accounts[t.from].debits_posted ===" -> "accounts[t.from].debits_posted === accounts[t.from].debits_posted"
   ts = ts.replace(/(\S+)\s*===\s*$/g, '$1 === $1');
@@ -491,10 +522,17 @@ function rewriteExpr(expr: string, stateVarNames: Set<string>, mapVarNames: Set<
   for (const mapVar of mapVarNames) {
     // Match: mapVar[expr] where mapVar is a known Map state variable
     // Handle both bare mapVar[...] and this.mapVar[...]
+    // The inner expr needs rewriting for this-prefixing
     const barePattern = new RegExp('\\b(' + mapVar + ')\\[([^\\]]+)\\]', 'g');
-    ts = ts.replace(barePattern, '$1.get($2)!');
+    ts = ts.replace(barePattern, (match, varName, innerExpr) => {
+      const rewrittenInner = rewriteExpr(innerExpr, stateVarNames, mapVarNames, localNames, stateEnumName, knownStateValues);
+      return `${varName}.get(${rewrittenInner})!`;
+    });
     const thisPattern = new RegExp('\\b(this\\.' + mapVar + ')\\[([^\\]]+)\\]', 'g');
-    ts = ts.replace(thisPattern, '$1.get($2)!');
+    ts = ts.replace(thisPattern, (match, varName, innerExpr) => {
+      const rewrittenInner = rewriteExpr(innerExpr, stateVarNames, mapVarNames, localNames, stateEnumName, knownStateValues);
+      return `${varName}.get(${rewrittenInner})!`;
+    });
   }
   // 5h: .size() -> .size  (Set/Map size property, not a method in JS)
   ts = ts.replace(/\.size\(\)/g, '.size');
@@ -571,13 +609,15 @@ function tsType(t: any, speckName: string = '', enumMap?: Map<string, string[]>)
   }
   if (t.type === 'ident') {
     const rawName = cleanName(t.name); // strip trailing comma
+    // Map known identifier types to concrete TS types BEFORE checking enum
+    if (rawName === 'Integer') return 'number';
+    if (rawName === 'Boolean') return 'boolean';
+    if (rawName === 'Nat') return 'number';
     // Check if this ident maps to a known enum interface
     if (enumMap && enumMap.has(rawName)) {
       return `${speckName}${rawName}`;
     }
-    // Map known identifier types to concrete TS types
     if (rawName === 'IssueState') return 'IssueWorkflowState';
-    if (rawName === 'Nat') return 'number';
     // Opaque interfaces become 'any' for now
     if (rawName === 'AST' || rawName === 'ArtifactMap') return 'any';
     return rawName;