diff --git a/teressa-copeland-homes/src/app/api/documents/[id]/prepare/route.ts b/teressa-copeland-homes/src/app/api/documents/[id]/prepare/route.ts
index 98763ad..c0c477c 100644
--- a/teressa-copeland-homes/src/app/api/documents/[id]/prepare/route.ts
+++ b/teressa-copeland-homes/src/app/api/documents/[id]/prepare/route.ts
@@ -3,6 +3,7 @@ import { db } from '@/lib/db';
 import { documents } from '@/lib/db/schema';
 import { eq } from 'drizzle-orm';
 import { preparePdf } from '@/lib/pdf/prepare-document';
+import { logAuditEvent } from '@/lib/signing/audit';
 import path from 'node:path';
 
 const UPLOADS_DIR = path.join(process.cwd(), 'uploads');
@@ -54,5 +55,7 @@ export async function POST(
     .where(eq(documents.id, id))
     .returning();
 
+  await logAuditEvent({ documentId: id, eventType: 'document_prepared' });
+
   return Response.json(updated);
 }
diff --git a/teressa-copeland-homes/src/app/api/documents/[id]/send/route.ts b/teressa-copeland-homes/src/app/api/documents/[id]/send/route.ts
new file mode 100644
index 0000000..530ac4e
--- /dev/null
+++ b/teressa-copeland-homes/src/app/api/documents/[id]/send/route.ts
@@ -0,0 +1,61 @@
+import { NextResponse } from 'next/server';
+import { auth } from '@/lib/auth';
+import { db } from '@/lib/db';
+import { documents, clients } from '@/lib/db/schema';
+import { eq } from 'drizzle-orm';
+import { createSigningToken } from '@/lib/signing/token';
+import { sendSigningRequestEmail } from '@/lib/signing/signing-mailer';
+import { logAuditEvent } from '@/lib/signing/audit';
+
+export async function POST(
+  _req: Request,
+  { params }: { params: Promise<{ id: string }> }
+) {
+  const session = await auth();
+  if (!session) return new Response('Unauthorized', { status: 401 });
+
+  const { id } = await params;
+
+  try {
+    const doc = await db.query.documents.findFirst({
+      where: eq(documents.id, id),
+    });
+    if (!doc) return NextResponse.json({ error: 'Document not found' }, { status: 404 });
+    if (!doc.preparedFilePath)
+      return NextResponse.json({ error: 'Document not yet prepared' }, { status: 422 });
+    if (doc.status === 'Signed')
+      return NextResponse.json({ error: 'Already signed' }, { status: 409 });
+
+    // Resolve recipient: prefer assignedClientId, fall back to clientId
+    const clientId = doc.assignedClientId ?? doc.clientId;
+    const client = await db.query.clients.findFirst({ where: eq(clients.id, clientId) });
+    if (!client) return NextResponse.json({ error: 'Client not found' }, { status: 422 });
+
+    const { token, expiresAt } = await createSigningToken(doc.id);
+    const baseUrl = process.env.NEXT_PUBLIC_BASE_URL ?? 'http://localhost:3000';
+    const signingUrl = `${baseUrl}/sign/${token}`;
+
+    await sendSigningRequestEmail({
+      to: client.email,
+      clientName: client.name,
+      documentName: doc.name,
+      signingUrl,
+      expiresAt,
+    });
+
+    await logAuditEvent({ documentId: doc.id, eventType: 'email_sent' });
+
+    // Update status to Sent (skip if already Sent or Signed to avoid downgrade)
+    if (doc.status === 'Draft') {
+      await db
+        .update(documents)
+        .set({ status: 'Sent', sentAt: new Date() })
+        .where(eq(documents.id, id));
+    }
+
+    return NextResponse.json({ ok: true, expiresAt: expiresAt.toISOString() });
+  } catch (err) {
+    console.error('[send] error:', err);
+    return NextResponse.json({ error: 'Failed to send signing email' }, { status: 502 });
+  }
+}