diff --git a/supabase/functions/inbound-bill-email/index.ts b/supabase/functions/inbound-bill-email/index.ts
index 6c1d661..dc96c05 100644
--- a/supabase/functions/inbound-bill-email/index.ts
+++ b/supabase/functions/inbound-bill-email/index.ts
@@ -14,10 +14,15 @@ const corsHeaders = {
 
 function extractEmail(raw: string | null): { email: string | null; name: string | null } {
   if (!raw) return { email: null, name: null }
-  // Match "Name <email@x.com>" or just "email@x.com"
-  const m = raw.match(/(?:"?([^"<]*)"?\s*)?<?([^\s<>]+@[^\s<>]+)>?/)
-  if (!m) return { email: null, name: null }
-  return { email: m[2].trim().toLowerCase(), name: (m[1] || '').trim() || null }
+  // Prefer the address inside <...>; otherwise take the first bare email token.
+  // (A greedy "Name" group mis-splits bare addresses like invoices@x.com -> s@x.com.)
+  const angle = raw.match(/<([^<>\s]+@[^<>\s]+)>/)
+  const email = angle?.[1] ?? raw.match(/[^\s<>,;]+@[^\s<>,;]+/)?.[0] ?? null
+  const nameM = raw.match(/^\s*"?([^"<]+?)"?\s*</)
+  return {
+    email: email ? email.trim().toLowerCase() : null,
+    name: nameM ? (nameM[1].trim() || null) : null,
+  }
 }
 
 async function arrayBufferToBase64(buf: ArrayBuffer): Promise<string> {
@@ -127,9 +132,31 @@ Deno.serve(async (req) => {
     }
   }
 
-  // Look up sender → association mapping
+  // Determine the target association: first by the RECIPIENT alias
+  // (<alias>@bills.avriamail.com), then by the SENDER's vendor mapping.
   let mappedAssociationId: string | null = null
   let mappedVendorId: string | null = null
+
+  // Recipient local-part from the SMTP envelope (most reliable), falling back to
+  // the To header. e.g. "ashleymanor@bills.avriamail.com" -> alias "ashleymanor".
+  let recipientLocal: string | null = null
+  try {
+    const env = JSON.parse(formData.get('envelope')?.toString() ?? '{}')
+    const envTo = Array.isArray(env?.to) ? env.to[0] : null
+    recipientLocal = (envTo ?? toRaw ?? '').toString().match(/([^\s<>@]+)@/)?.[1]?.toLowerCase() ?? null
+    if (recipientLocal) recipientLocal = recipientLocal.split('+')[0]
+  } catch (_) { /* ignore malformed envelope */ }
+  if (recipientLocal) {
+    const { data: assoc } = await supabase
+      .from('associations')
+      .select('id')
+      .ilike('inbound_alias', recipientLocal)
+      .limit(1)
+    if (assoc && assoc.length > 0) mappedAssociationId = assoc[0].id as string
+  }
+
+  // Sender → vendor/association mapping (sets the vendor, and the association too
+  // if the recipient alias didn't resolve one).
   if (fromEmail) {
     const { data: mappings } = await supabase
       .from('vendor_email_mappings')
@@ -137,8 +164,8 @@ Deno.serve(async (req) => {
       .eq('email', fromEmail)
       .limit(1)
     if (mappings && mappings.length > 0) {
-      mappedAssociationId = mappings[0].association_id as string
       mappedVendorId = (mappings[0].vendor_id as string) ?? null
+      if (!mappedAssociationId) mappedAssociationId = mappings[0].association_id as string
     }
   }
 
@@ -187,7 +214,16 @@ Deno.serve(async (req) => {
     const { data, error } = await supabase.functions.invoke('parse-invoice', {
       body: { pdf_base64: pdfBase64, filename: pdfFile?.name ?? 'invoice.pdf' },
     })
-    if (error) throw error
+    if (error) {
+      // Surface the function's actual error body (e.g. "PDF too large…") instead
+      // of the generic "non-2xx status code" wrapper.
+      let detail = error.message
+      try {
+        const body = await (error as { context?: Response }).context?.json()
+        if (body?.error) detail = body.error
+      } catch (_) { /* keep generic message */ }
+      throw new Error(detail)
+    }
     parsed = (data as { data?: Record<string, unknown> })?.data ?? null
   } catch (err) {
     parseError = err instanceof Error ? err.message : String(err)
diff --git a/supabase/functions/parse-invoice/index.ts b/supabase/functions/parse-invoice/index.ts
index ff4c16d..5de1616 100644
--- a/supabase/functions/parse-invoice/index.ts
+++ b/supabase/functions/parse-invoice/index.ts
@@ -82,6 +82,19 @@ Deno.serve(async (req) => {
       });
     }
 
+    // Guard against oversized/scanned PDFs that the AI gateway rejects with an
+    // opaque error. The caller (inbound-bill-email) still keeps the attachment
+    // in the inbox for manual entry when this returns an error.
+    const approxBytes = Math.floor((pdf_base64.length * 3) / 4);
+    const sizeMB = approxBytes / (1024 * 1024);
+    const MAX_MB = 18;
+    if (sizeMB > MAX_MB) {
+      return new Response(
+        JSON.stringify({ error: `PDF too large to auto-parse (${sizeMB.toFixed(1)} MB; limit ${MAX_MB} MB). Saved to the inbox for manual entry.` }),
+        { status: 413, headers: { ...corsHeaders, "Content-Type": "application/json" } },
+      );
+    }
+
     const prompt = `You are a meticulous invoice data extraction AI. Analyze the provided PDF invoice carefully — examine EVERY page and EVERY line item, including continuation pages, sub-totals, and tables. Do not skip or summarize line items; capture each one individually exactly as it appears.
 
 CRITICAL RULES:
@@ -162,11 +175,17 @@ Return ONLY valid JSON (no markdown, no code blocks, no commentary) with this ex
 
     if (!response.ok) {
       const errText = await response.text();
-      console.error("AI Gateway error:", errText);
-      return new Response(JSON.stringify({ error: `AI processing failed: ${response.status}` }), {
-        status: 502,
-        headers: { ...corsHeaders, "Content-Type": "application/json" },
-      });
+      console.error("AI Gateway error:", response.status, errText);
+      const snippet = errText.replace(/\s+/g, " ").slice(0, 300);
+      const hint = response.status === 429 || response.status === 402
+        ? " (AI gateway rate/credit limit)"
+        : response.status === 413 || /too large|payload|size/i.test(errText)
+        ? " (PDF too large for the AI gateway — saved to inbox for manual entry)"
+        : "";
+      return new Response(
+        JSON.stringify({ error: `AI gateway error ${response.status}${hint}: ${snippet || "no detail"}` }),
+        { status: 502, headers: { ...corsHeaders, "Content-Type": "application/json" } },
+      );
     }
 
     const aiResult = await response.json();