diff --git a/apps/Backend/src/ai/cdt-lookup.ts b/apps/Backend/src/ai/cdt-lookup.ts
index 58602a7d..095442e3 100644
--- a/apps/Backend/src/ai/cdt-lookup.ts
+++ b/apps/Backend/src/ai/cdt-lookup.ts
@@ -17,6 +17,8 @@ interface CdtMatch {
   code: string;
   description: string;
   input: string;
+  toothNumber?: string;
+  toothSurface?: string;
 }
 
 // Load once at module init
@@ -215,6 +217,23 @@ const DIRECT_CODE_MAP: Record<string, string> = {
   "implant crown":          "D6058",
 };
 
+/**
+ * Extract tooth number and surface from any input containing "#NN" (1-32).
+ * e.g. "#29 OB" → { toothNumber: "29", toothSurface: "OB" }
+ * e.g. "extraction #14" → { toothNumber: "14" }
+ */
+function extractToothSurface(input: string): { toothNumber?: string; toothSurface?: string } {
+  const m = input.match(/#(\d{1,2})(?:\s+([A-Za-z]{1,5}))?/);
+  if (!m) return {};
+  const toothNum = parseInt(m[1]!, 10);
+  if (toothNum < 1 || toothNum > 32) return {};
+  const surfaces = (m[2] ?? "").toUpperCase();
+  return {
+    toothNumber: String(toothNum),
+    ...(surfaces && /^[OMDBLFIV]+$/.test(surfaces) ? { toothSurface: surfaces } : {}),
+  };
+}
+
 // Composite filling tooth classification
 const FRONT_TEETH = new Set([6, 7, 8, 9, 10, 11, 22, 23, 24, 25, 26, 27]);
 const BACK_TEETH  = new Set([1, 2, 3, 4, 5, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 28, 29, 30, 31, 32]);
@@ -249,7 +268,7 @@ function parseCompositeCode(input: string): CdtMatch | null {
   }
 
   const row = ALL_CODES.find((r) => r["Procedure Code"] === code);
-  return { code, description: row?.Description ?? code, input };
+  return { code, description: row?.Description ?? code, input, toothNumber: String(toothNum), toothSurface: surfaces.toUpperCase() };
 }
 
 /**
@@ -326,28 +345,30 @@ export function lookupCdtCodes(
 
   return procedureNames.map((name) => {
     const cleaned = name.trim().toLowerCase();
+    // Extract tooth# from "#NN" notation — applies to any procedure
+    const toothInfo = extractToothSurface(name);
 
     // 1. Custom alias exact match (highest priority)
     if (customMap[cleaned]) {
       const code = customMap[cleaned]!;
       const row = ALL_CODES.find((r) => r["Procedure Code"].toUpperCase() === code);
-      return { code, description: row?.Description ?? code, input: name };
+      return { code, description: row?.Description ?? code, input: name, ...toothInfo };
     }
 
-    // 2. Composite filling by tooth# and surfaces (e.g. "#29 OB", "composite #8 MO")
+    // 2. Composite filling by tooth# and surfaces — also determines CDT code from tooth position
     const compositeMatch = parseCompositeCode(name);
-    if (compositeMatch) return compositeMatch;
+    if (compositeMatch) return compositeMatch; // already carries toothNumber/toothSurface
 
     // 3. Hardcoded direct code map (short abbreviations / codes not in MH schedule)
     if (DIRECT_CODE_MAP[cleaned]) {
       const code = DIRECT_CODE_MAP[cleaned]!;
       const row = ALL_CODES.find((r) => r["Procedure Code"].toUpperCase() === code);
-      return { code, description: row?.Description ?? code, input: name };
+      return { code, description: row?.Description ?? code, input: name, ...toothInfo };
     }
 
-    // 3. Hardcoded alias + keyword search
+    // 4. Hardcoded alias + keyword search
     const match = matchOne(name);
-    if (match) return match;
+    if (match) return { ...match, ...toothInfo };
 
     return {
       code: null,
diff --git a/apps/Backend/src/ai/internal-chat-workflow.ts b/apps/Backend/src/ai/internal-chat-workflow.ts
index e5b9d354..323bd2a3 100644
--- a/apps/Backend/src/ai/internal-chat-workflow.ts
+++ b/apps/Backend/src/ai/internal-chat-workflow.ts
@@ -436,7 +436,7 @@ async function handleCheckAndClaim(
       siteKey,
       autoCheck: siteKeyToAutoCheck(siteKey),
       cdtResults,
-      matchedCodes: matched.map((r) => ({ code: r.code!, description: r.description })),
+      matchedCodes: matched.map((r) => ({ code: r.code!, description: r.description, toothNumber: r.toothNumber, toothSurface: r.toothSurface })),
     },
   };
 }
@@ -518,7 +518,7 @@ async function handleClaimOnly(
           actionData: {
             patient,
             siteKey: resolveSiteKey(patient.insuranceProvider ?? null, c.insuranceHint ?? null) ?? "MH",
-            matchedCodes: matched.map((r) => ({ code: r.code!, description: r.description })),
+            matchedCodes: matched.map((r) => ({ code: r.code!, description: r.description, toothNumber: r.toothNumber, toothSurface: r.toothSurface })),
             options: [
               { label: fmtUTC(sorted[0]), appointmentId: sorted[0].id, serviceDate: isoUTC(sorted[0]) },
               { label: fmtUTC(sorted[1]), appointmentId: sorted[1].id, serviceDate: isoUTC(sorted[1]) },
@@ -561,7 +561,7 @@ async function handleClaimOnly(
       siteKey,
       serviceDate,
       appointmentId,
-      matchedCodes: matched.map((r) => ({ code: r.code!, description: r.description })),
+      matchedCodes: matched.map((r) => ({ code: r.code!, description: r.description, toothNumber: r.toothNumber, toothSurface: r.toothSurface })),
     },
   };
 }
diff --git a/apps/Frontend/src/components/claims/claim-form.tsx b/apps/Frontend/src/components/claims/claim-form.tsx
index 74f67252..e9c196a1 100755
--- a/apps/Frontend/src/components/claims/claim-form.tsx
+++ b/apps/Frontend/src/components/claims/claim-form.tsx
@@ -496,7 +496,7 @@ export function ClaimForm({
     if (!raw) return;
     try {
       const { codes, serviceDate } = JSON.parse(raw) as {
-        codes: { code: string; description: string }[];
+        codes: { code: string; description: string; toothNumber?: string; toothSurface?: string }[];
         serviceDate?: string;
       };
       sessionStorage.removeItem("chatbot_claim_prefill");
@@ -515,7 +515,13 @@ export function ClaimForm({
         const updatedLines = [...prev.serviceLines];
         codes.forEach((c, i) => {
           if (i < updatedLines.length) {
-            updatedLines[i] = { ...updatedLines[i]!, procedureCode: c.code, procedureDate: date };
+            updatedLines[i] = {
+              ...updatedLines[i]!,
+              procedureCode: c.code,
+              procedureDate: date,
+              ...(c.toothNumber ? { toothNumber: c.toothNumber } : {}),
+              ...(c.toothSurface ? { toothSurface: c.toothSurface } : {}),
+            };
           }
         });
         return { ...prev, serviceLines: updatedLines };