diff --git a/.changeset/every-moose-kick.md b/.changeset/every-moose-kick.md
new file mode 100644
index 0000000000..a845151cc8
--- /dev/null
+++ b/.changeset/every-moose-kick.md
@@ -0,0 +1,2 @@
+---
+---
diff --git a/server/public/admin-org-detail.html b/server/public/admin-org-detail.html
index abb1e6a177..0676d408ae 100644
--- a/server/public/admin-org-detail.html
+++ b/server/public/admin-org-detail.html
@@ -1356,6 +1356,25 @@ <h4 style="margin-top: var(--space-4); margin-bottom: var(--space-3); font-size:
           </div>
         </div>
 
+        <!-- Draft Review Section (shown after billing details, before sending) -->
+        <div id="invoiceDraftReview" style="display: none;">
+          <div style="background: var(--color-info-50); border: 1px solid var(--color-info-200); border-radius: var(--radius-md); padding: var(--space-4); margin-bottom: var(--space-4);">
+            <strong style="color: var(--color-info-700);">Review Invoice Draft</strong>
+            <p style="margin: var(--space-2) 0 0; font-size: var(--text-sm); color: var(--color-text-secondary);">
+              Please review all details before sending. The invoice will be emailed to the contact.
+            </p>
+          </div>
+
+          <div id="draftReviewContent" style="background: var(--color-bg-subtle); border-radius: var(--radius-md); padding: var(--space-4); margin-bottom: var(--space-4);">
+            <!-- Populated by JavaScript -->
+          </div>
+
+          <div id="draftMissingFields" style="display: none; background: var(--color-warning-50); border: 1px solid var(--color-warning-200); border-radius: var(--radius-md); padding: var(--space-3); margin-bottom: var(--space-4);">
+            <strong style="color: var(--color-warning-700); font-size: var(--text-sm);">Missing Information</strong>
+            <ul id="missingFieldsList" style="margin: var(--space-2) 0 0; padding-left: var(--space-4); font-size: var(--text-sm); color: var(--color-warning-700);"></ul>
+          </div>
+        </div>
+
         <!-- Success Message -->
         <div id="invoiceResult" style="display: none;">
           <div style="background: var(--color-success-50); border: 1px solid var(--color-success-200); border-radius: var(--radius-md); padding: var(--space-4); margin-bottom: var(--space-4);">
@@ -1372,6 +1391,8 @@ <h4 style="margin-top: var(--space-4); margin-bottom: var(--space-3); font-size:
 
         <div class="modal-actions">
           <button type="button" class="btn btn-secondary" onclick="closeInvoiceModal()">Close</button>
+          <button type="button" class="btn btn-secondary" id="backToEditBtn" style="display: none;" onclick="backToEditInvoice()">Edit Details</button>
+          <button type="button" class="btn btn-primary" id="prepareDraftBtn" style="display: none;" onclick="prepareDraft()">Prepare Draft</button>
           <button type="submit" class="btn btn-primary" id="sendInvoiceBtn" style="display: none;">Send Invoice</button>
         </div>
       </form>
@@ -3351,8 +3372,11 @@ <h2 id="discountModalTitle">Set Discount</h2>
       document.getElementById('invoiceProducts').innerHTML = 'Loading products...';
       document.getElementById('invoiceProductSection').style.display = 'block';
       document.getElementById('invoiceBillingSection').style.display = 'none';
+      document.getElementById('invoiceDraftReview').style.display = 'none';
       document.getElementById('invoiceResult').style.display = 'none';
       document.getElementById('sendInvoiceBtn').style.display = 'none';
+      document.getElementById('prepareDraftBtn').style.display = 'none';
+      document.getElementById('backToEditBtn').style.display = 'none';
       document.getElementById('invoiceForm').reset();
 
       // Pre-fill from org data
@@ -3375,6 +3399,9 @@ <h2 id="discountModalTitle">Set Discount</h2>
         const data = await response.json();
         const invoiceableProducts = data.products.filter(p => p.is_invoiceable);
 
+        // Sort products by price (lowest first for better UX)
+        invoiceableProducts.sort((a, b) => (a.amount_cents || 0) - (b.amount_cents || 0));
+
         renderInvoiceProducts(invoiceableProducts);
       } catch (error) {
         console.error('Error loading products:', error);
@@ -3383,6 +3410,53 @@ <h2 id="discountModalTitle">Set Discount</h2>
       }
     }
 
+    function getRecommendedInvoiceProduct(products) {
+      // Get the org's revenue tier
+      let orgRevenueTier = orgData?.revenue_tier;
+
+      // If no revenue_tier set, try to derive from enrichment data
+      if (!orgRevenueTier && orgData?.enrichment_revenue_range) {
+        const rangeMap = {
+          'under $1m': 'under_1m',
+          '$1m-$5m': '1m_5m',
+          '$5m-$50m': '5m_50m',
+          '$50m-$250m': '50m_250m',
+          '$250m-$1b': '250m_1b',
+          'over $1b': '1b_plus'
+        };
+        const lowerRange = orgData.enrichment_revenue_range.toLowerCase();
+        for (const [key, value] of Object.entries(rangeMap)) {
+          if (lowerRange.includes(key.replace('$', '').replace('-', ' to '))) {
+            orgRevenueTier = value;
+            break;
+          }
+        }
+      }
+
+      if (!orgRevenueTier) return null;
+
+      // Find products that match the org's revenue tier
+      const matchingProducts = products.filter(p => {
+        if (!p.revenue_tiers || p.revenue_tiers.length === 0) return true;
+        return p.revenue_tiers.includes(orgRevenueTier);
+      });
+
+      // Return highest priced matching product (same logic as pricing section)
+      if (matchingProducts.length > 0) {
+        return matchingProducts.reduce((a, b) => (b.amount_cents || 0) > (a.amount_cents || 0) ? b : a);
+      }
+      return null;
+    }
+
+    function calculateDiscountedPrice(amountCents) {
+      if (orgData?.discount_percent) {
+        return Math.round(amountCents * (1 - orgData.discount_percent / 100));
+      } else if (orgData?.discount_amount_cents) {
+        return Math.max(0, amountCents - orgData.discount_amount_cents);
+      }
+      return amountCents;
+    }
+
     function renderInvoiceProducts(products) {
       const container = document.getElementById('invoiceProducts');
 
@@ -3391,54 +3465,277 @@ <h2 id="discountModalTitle">Set Discount</h2>
         return;
       }
 
-      container.innerHTML = products.map(product => {
-        const price = new Intl.NumberFormat('en-US', {
+      const recommendedProduct = getRecommendedInvoiceProduct(products);
+      const hasDiscount = orgData?.discount_percent || orgData?.discount_amount_cents;
+
+      // Show discount info at top if applicable
+      let headerHtml = '';
+      if (hasDiscount) {
+        const discountText = orgData.discount_percent
+          ? `${orgData.discount_percent}% discount`
+          : `${formatPriceCurrency(orgData.discount_amount_cents)} discount`;
+        headerHtml = `
+          <div style="margin-bottom: var(--space-3); padding: var(--space-2) var(--space-3); background: var(--color-success-50); border-radius: var(--radius-md); border: 1px solid var(--color-success-200);">
+            <span style="color: var(--color-success-700); font-weight: var(--font-medium);">
+              ${discountText} will be applied
+            </span>
+          </div>
+        `;
+      }
+
+      container.innerHTML = headerHtml + products.map(product => {
+        const listPrice = product.amount_cents || 0;
+        const netPrice = hasDiscount ? calculateDiscountedPrice(listPrice) : listPrice;
+
+        const listPriceFormatted = new Intl.NumberFormat('en-US', {
           style: 'currency',
-          currency: 'USD'
-        }).format(product.amount_cents / 100);
+          currency: 'USD',
+          minimumFractionDigits: 0,
+          maximumFractionDigits: 0
+        }).format(listPrice / 100);
+
+        const netPriceFormatted = new Intl.NumberFormat('en-US', {
+          style: 'currency',
+          currency: 'USD',
+          minimumFractionDigits: 0,
+          maximumFractionDigits: 0
+        }).format(netPrice / 100);
 
         const interval = product.billing_interval ? `/${product.billing_interval}` : '';
         const displayName = escapeHtml(product.display_name || product.product_name);
         const lookupKey = escapeHtml(product.lookup_key);
         const description = product.description ? escapeHtml(product.description) : '';
+        const isRecommended = recommendedProduct && product.lookup_key === recommendedProduct.lookup_key;
+
+        // Build price display
+        let priceHtml;
+        if (hasDiscount && listPrice !== netPrice) {
+          priceHtml = `
+            <span style="text-decoration: line-through; color: var(--color-text-muted); margin-right: var(--space-2);">${listPriceFormatted}</span>
+            <span style="color: var(--color-success-600); font-weight: var(--font-semibold);">${netPriceFormatted}${interval}</span>
+          `;
+        } else {
+          priceHtml = `<span style="color: var(--color-brand); font-weight: var(--font-semibold);">${listPriceFormatted}${interval}</span>`;
+        }
+
+        // Build recommended badge
+        const recommendedBadge = isRecommended
+          ? `<span style="display: inline-block; margin-left: var(--space-2); padding: 2px 8px; font-size: var(--text-xs); background: var(--color-brand); color: white; border-radius: var(--radius-full);">Recommended</span>`
+          : '';
+
+        const borderColor = isRecommended ? 'var(--color-brand)' : 'var(--color-border)';
+        const borderWidth = isRecommended ? '2px' : '1px';
 
         return `
-          <button type="button" class="product-select-btn" onclick="selectInvoiceProduct('${lookupKey}', '${displayName}', ${product.amount_cents})" style="
+          <button type="button" class="product-select-btn"
+            data-lookup-key="${lookupKey}"
+            data-display-name="${displayName}"
+            data-amount="${listPrice}"
+            data-border-color="${borderColor}"
+            style="
             display: block;
             width: 100%;
             text-align: left;
             padding: var(--space-3);
             margin-bottom: var(--space-2);
-            border: 1px solid var(--color-border);
+            border: ${borderWidth} solid ${borderColor};
             border-radius: var(--radius-md);
             background: var(--color-bg-card);
             cursor: pointer;
             transition: var(--transition-all);
-          " onmouseover="this.style.borderColor='var(--color-brand)'" onmouseout="this.style.borderColor='var(--color-border)'">
-            <strong>${displayName}</strong>
+          ">
+            <strong>${displayName}</strong>${recommendedBadge}
             <br>
-            <span style="color: var(--color-brand); font-weight: var(--font-semibold);">${price}${interval}</span>
+            ${priceHtml}
             ${description ? `<br><span style="font-size: var(--text-xs); color: var(--color-text-muted);">${description}</span>` : ''}
           </button>
         `;
       }).join('');
+
+      // Add event listeners to avoid XSS from inline onclick
+      container.querySelectorAll('.product-select-btn').forEach(btn => {
+        btn.addEventListener('click', () => {
+          selectInvoiceProduct(
+            btn.dataset.lookupKey,
+            btn.dataset.displayName,
+            parseInt(btn.dataset.amount, 10)
+          );
+        });
+        btn.addEventListener('mouseover', () => {
+          btn.style.borderColor = 'var(--color-brand)';
+        });
+        btn.addEventListener('mouseout', () => {
+          btn.style.borderColor = btn.dataset.borderColor;
+        });
+      });
     }
 
     function selectInvoiceProduct(lookupKey, productName, amountCents) {
       selectedInvoiceProduct = { lookupKey, productName, amountCents };
 
-      const price = new Intl.NumberFormat('en-US', {
+      const hasDiscount = orgData?.discount_percent || orgData?.discount_amount_cents;
+      const netPrice = hasDiscount ? calculateDiscountedPrice(amountCents) : amountCents;
+
+      const listPriceFormatted = new Intl.NumberFormat('en-US', {
         style: 'currency',
-        currency: 'USD'
+        currency: 'USD',
+        minimumFractionDigits: 0,
+        maximumFractionDigits: 0
       }).format(amountCents / 100);
 
+      const netPriceFormatted = new Intl.NumberFormat('en-US', {
+        style: 'currency',
+        currency: 'USD',
+        minimumFractionDigits: 0,
+        maximumFractionDigits: 0
+      }).format(netPrice / 100);
+
+      let priceDisplay;
+      if (hasDiscount && amountCents !== netPrice) {
+        priceDisplay = `
+          <span style="text-decoration: line-through; color: var(--color-text-muted);">${listPriceFormatted}</span>
+          <span style="color: var(--color-success-600); font-weight: var(--font-semibold); margin-left: var(--space-2);">${netPriceFormatted}</span>
+        `;
+      } else {
+        priceDisplay = `<span style="color: var(--color-brand);">${listPriceFormatted}</span>`;
+      }
+
       document.getElementById('selectedProductDisplay').innerHTML = `
-        <strong>${productName}</strong> - <span style="color: var(--color-brand);">${price}</span>
+        <strong>${productName}</strong> - ${priceDisplay}
       `;
 
       document.getElementById('invoiceProductSection').style.display = 'none';
       document.getElementById('invoiceBillingSection').style.display = 'block';
-      document.getElementById('sendInvoiceBtn').style.display = 'inline-block';
+      document.getElementById('invoiceDraftReview').style.display = 'none';
+      document.getElementById('prepareDraftBtn').style.display = 'inline-block';
+      document.getElementById('sendInvoiceBtn').style.display = 'none';
+      document.getElementById('backToEditBtn').style.display = 'none';
+    }
+
+    function prepareDraft() {
+      // Collect all invoice data for review
+      const contactName = document.getElementById('invoiceContactName').value;
+      const contactEmail = document.getElementById('invoiceContactEmail').value;
+      const companyName = document.getElementById('invoiceCompanyName').value;
+      const addressLine1 = document.getElementById('invoiceAddressLine1').value;
+      const addressLine2 = document.getElementById('invoiceAddressLine2').value;
+      const city = document.getElementById('invoiceCity').value;
+      const state = document.getElementById('invoiceState').value;
+      const postalCode = document.getElementById('invoicePostalCode').value;
+      const country = document.getElementById('invoiceCountry').value;
+
+      // Check for missing required fields
+      const missingFields = [];
+      if (!contactName) missingFields.push('Contact Name');
+      if (!contactEmail) missingFields.push('Contact Email');
+      if (!companyName) missingFields.push('Company Name');
+      if (!addressLine1) missingFields.push('Street Address');
+      if (!city) missingFields.push('City');
+      if (!state) missingFields.push('State/Province');
+      if (!postalCode) missingFields.push('Postal Code');
+      if (!country) missingFields.push('Country');
+
+      // Calculate pricing
+      const hasDiscount = orgData?.discount_percent || orgData?.discount_amount_cents;
+      const listPrice = selectedInvoiceProduct.amountCents;
+      const netPrice = hasDiscount ? calculateDiscountedPrice(listPrice) : listPrice;
+
+      const listPriceFormatted = new Intl.NumberFormat('en-US', {
+        style: 'currency', currency: 'USD', minimumFractionDigits: 0, maximumFractionDigits: 0
+      }).format(listPrice / 100);
+
+      const netPriceFormatted = new Intl.NumberFormat('en-US', {
+        style: 'currency', currency: 'USD', minimumFractionDigits: 0, maximumFractionDigits: 0
+      }).format(netPrice / 100);
+
+      // Build discount info
+      let discountHtml = '';
+      if (hasDiscount && listPrice !== netPrice) {
+        const discountText = orgData.discount_percent
+          ? `${orgData.discount_percent}% discount`
+          : `${formatPriceCurrency(orgData.discount_amount_cents)} off`;
+        const savingsFormatted = new Intl.NumberFormat('en-US', {
+          style: 'currency', currency: 'USD', minimumFractionDigits: 0, maximumFractionDigits: 0
+        }).format((listPrice - netPrice) / 100);
+        discountHtml = `
+          <div style="margin-top: var(--space-2); padding: var(--space-2); background: var(--color-success-50); border-radius: var(--radius-sm);">
+            <span style="color: var(--color-success-700); font-size: var(--text-sm);">
+              ${discountText} applied (saves ${savingsFormatted})
+            </span>
+          </div>
+        `;
+      }
+
+      // Build address display
+      const addressParts = [addressLine1];
+      if (addressLine2) addressParts.push(addressLine2);
+      addressParts.push(`${city}, ${state} ${postalCode}`);
+      addressParts.push(country);
+      const fullAddress = addressParts.filter(Boolean).join('<br>');
+
+      // Populate review content
+      document.getElementById('draftReviewContent').innerHTML = `
+        <div style="display: grid; grid-template-columns: 1fr 1fr; gap: var(--space-4);">
+          <div>
+            <div style="font-size: var(--text-xs); color: var(--color-text-muted); text-transform: uppercase; margin-bottom: var(--space-1);">Company</div>
+            <div style="font-weight: var(--font-semibold);">${escapeHtml(companyName) || '<em style="color: var(--color-error-500);">Not provided</em>'}</div>
+          </div>
+          <div>
+            <div style="font-size: var(--text-xs); color: var(--color-text-muted); text-transform: uppercase; margin-bottom: var(--space-1);">Contact</div>
+            <div style="font-weight: var(--font-semibold);">${escapeHtml(contactName) || '<em style="color: var(--color-error-500);">Not provided</em>'}</div>
+            <div style="color: var(--color-text-secondary); font-size: var(--text-sm);">${escapeHtml(contactEmail) || '<em style="color: var(--color-error-500);">Not provided</em>'}</div>
+          </div>
+        </div>
+
+        <hr style="margin: var(--space-4) 0; border: none; border-top: 1px solid var(--color-border);">
+
+        <div style="display: grid; grid-template-columns: 1fr 1fr; gap: var(--space-4);">
+          <div>
+            <div style="font-size: var(--text-xs); color: var(--color-text-muted); text-transform: uppercase; margin-bottom: var(--space-1);">Product</div>
+            <div style="font-weight: var(--font-semibold);">${escapeHtml(selectedInvoiceProduct.productName)}</div>
+          </div>
+          <div>
+            <div style="font-size: var(--text-xs); color: var(--color-text-muted); text-transform: uppercase; margin-bottom: var(--space-1);">Amount</div>
+            ${hasDiscount && listPrice !== netPrice
+              ? `<div><span style="text-decoration: line-through; color: var(--color-text-muted);">${listPriceFormatted}</span> <span style="color: var(--color-success-600); font-weight: var(--font-semibold);">${netPriceFormatted}</span></div>`
+              : `<div style="font-weight: var(--font-semibold);">${listPriceFormatted}</div>`
+            }
+            ${discountHtml}
+          </div>
+        </div>
+
+        <hr style="margin: var(--space-4) 0; border: none; border-top: 1px solid var(--color-border);">
+
+        <div>
+          <div style="font-size: var(--text-xs); color: var(--color-text-muted); text-transform: uppercase; margin-bottom: var(--space-1);">Billing Address</div>
+          <div style="line-height: 1.5;">${fullAddress || '<em style="color: var(--color-error-500);">Not provided</em>'}</div>
+        </div>
+      `;
+
+      // Show/hide missing fields warning
+      const missingFieldsDiv = document.getElementById('draftMissingFields');
+      const missingFieldsList = document.getElementById('missingFieldsList');
+      if (missingFields.length > 0) {
+        missingFieldsList.innerHTML = missingFields.map(f => `<li>${f}</li>`).join('');
+        missingFieldsDiv.style.display = 'block';
+      } else {
+        missingFieldsDiv.style.display = 'none';
+      }
+
+      // Update UI state
+      document.getElementById('invoiceBillingSection').style.display = 'none';
+      document.getElementById('invoiceDraftReview').style.display = 'block';
+      document.getElementById('prepareDraftBtn').style.display = 'none';
+      document.getElementById('backToEditBtn').style.display = 'inline-block';
+      document.getElementById('sendInvoiceBtn').style.display = missingFields.length === 0 ? 'inline-block' : 'none';
+    }
+
+    function backToEditInvoice() {
+      document.getElementById('invoiceDraftReview').style.display = 'none';
+      document.getElementById('invoiceBillingSection').style.display = 'block';
+      document.getElementById('prepareDraftBtn').style.display = 'inline-block';
+      document.getElementById('backToEditBtn').style.display = 'none';
+      document.getElementById('sendInvoiceBtn').style.display = 'none';
     }
 
     async function submitInvoice(event) {
@@ -3468,6 +3765,11 @@ <h2 id="discountModalTitle">Set Discount</h2>
         }
       };
 
+      // Include coupon_id if the org has a discount configured
+      if (orgData?.stripe_coupon_id) {
+        data.coupon_id = orgData.stripe_coupon_id;
+      }
+
       try {
         const response = await fetch(`/api/admin/prospects/${orgId}/invoice`, {
           method: 'POST',
@@ -3484,7 +3786,9 @@ <h2 id="discountModalTitle">Set Discount</h2>
 
         if (result.success && result.invoice_url) {
           document.getElementById('invoiceBillingSection').style.display = 'none';
+          document.getElementById('invoiceDraftReview').style.display = 'none';
           document.getElementById('sendInvoiceBtn').style.display = 'none';
+          document.getElementById('backToEditBtn').style.display = 'none';
           document.getElementById('invoiceUrl').value = result.invoice_url;
           document.getElementById('invoiceResult').style.display = 'block';
 
diff --git a/server/public/dashboard.html b/server/public/dashboard.html
index 2c432dbdda..26fbb00a38 100644
--- a/server/public/dashboard.html
+++ b/server/public/dashboard.html
@@ -1613,6 +1613,11 @@ <h3>Join the Agentic Advertising Organization</h3>
         const customerType = org.is_personal ? 'individual' : 'company';
         const revenueTier = org.revenue_tier || '';
 
+        // Get discount info from billing data
+        const discountPercent = org.billing?.discount_percent || null;
+        const discountAmountCents = org.billing?.discount_amount_cents || null;
+        const hasDiscount = discountPercent || discountAmountCents;
+
         // Fetch products filtered by customer type and revenue tier
         const url = new URL('/api/billing-products', window.location.origin);
         url.searchParams.set('customer_type', customerType);
@@ -1637,25 +1642,70 @@ <h3>Join the Agentic Advertising Organization</h3>
           return;
         }
 
+        // Helper to calculate discounted price
+        function calculateDiscountedPrice(amountCents) {
+          if (discountPercent) {
+            return Math.round(amountCents * (1 - discountPercent / 100));
+          } else if (discountAmountCents) {
+            return Math.max(0, amountCents - discountAmountCents);
+          }
+          return amountCents;
+        }
+
+        // Build discount banner if applicable
+        let discountBanner = '';
+        if (hasDiscount) {
+          const discountText = discountPercent
+            ? `${discountPercent}% discount`
+            : formatCurrency(discountAmountCents) + ' discount';
+          discountBanner = `
+            <div style="margin-bottom: 16px; padding: 12px 16px; background: linear-gradient(135deg, var(--color-success-50), var(--color-success-100)); border-radius: 8px; border: 1px solid var(--color-success-200); text-align: center;">
+              <span style="color: var(--color-success-700); font-weight: 600;">
+                Your organization has a ${discountText} applied to membership
+              </span>
+            </div>
+          `;
+        }
+
         // Render product cards
         const productCards = products.map(product => {
-          const price = formatCurrency(product.amount_cents, product.currency);
+          const listPrice = product.amount_cents;
+          const netPrice = hasDiscount ? calculateDiscountedPrice(listPrice) : listPrice;
+          const listPriceFormatted = formatCurrency(listPrice, product.currency);
+          const netPriceFormatted = formatCurrency(netPrice, product.currency);
           const interval = product.billing_interval === 'year' ? '/year' : product.billing_interval === 'month' ? '/month' : '';
           const isSubscription = product.billing_type === 'subscription';
 
-          return `
-            <div class="product-card" style="border: 2px solid var(--color-border); border-radius: 12px; padding: 24px; text-align: center; transition: all 0.2s; cursor: pointer;"
-                 onmouseover="this.style.borderColor='var(--aao-primary)'; this.style.boxShadow='0 4px 12px rgba(102, 126, 234, 0.15)';"
-                 onmouseout="this.style.borderColor='var(--color-border)'; this.style.boxShadow='none';">
-              <h3 style="margin: 0 0 8px 0; font-size: 18px; color: var(--color-text-heading);">${escapeHtml(product.display_name)}</h3>
-              ${product.description ? `<p style="margin: 0 0 16px 0; font-size: 14px; color: var(--color-text-secondary);">${escapeHtml(product.description)}</p>` : ''}
+          // Build price display
+          let priceDisplay;
+          if (hasDiscount && listPrice !== netPrice) {
+            priceDisplay = `
               <div style="margin: 16px 0;">
-                <span style="font-size: 32px; font-weight: 700; color: var(--color-text-heading);">${price}</span>
+                <div style="margin-bottom: 4px;">
+                  <span style="font-size: 18px; text-decoration: line-through; color: var(--color-text-muted);">${listPriceFormatted}</span>
+                </div>
+                <span style="font-size: 32px; font-weight: 700; color: var(--color-success-600);">${netPriceFormatted}</span>
                 <span style="font-size: 14px; color: var(--color-text-secondary);">${interval}</span>
               </div>
+            `;
+          } else {
+            priceDisplay = `
+              <div style="margin: 16px 0;">
+                <span style="font-size: 32px; font-weight: 700; color: var(--color-text-heading);">${listPriceFormatted}</span>
+                <span style="font-size: 14px; color: var(--color-text-secondary);">${interval}</span>
+              </div>
+            `;
+          }
+
+          return `
+            <div class="product-card" style="border: 2px solid var(--color-border); border-radius: 12px; padding: 24px; text-align: center; transition: all 0.2s; cursor: pointer;">
+              <h3 style="margin: 0 0 8px 0; font-size: 18px; color: var(--color-text-heading);">${escapeHtml(product.display_name)}</h3>
+              ${product.description ? `<p style="margin: 0 0 16px 0; font-size: 14px; color: var(--color-text-secondary);">${escapeHtml(product.description)}</p>` : ''}
+              ${priceDisplay}
               <button
-                onclick="startCheckout('${product.price_id}', '${org.id}')"
-                class="btn btn-primary"
+                data-price-id="${escapeHtml(product.price_id)}"
+                data-org-id="${escapeHtml(org.id)}"
+                class="btn btn-primary checkout-btn"
                 style="width: 100%; padding: 12px 24px; font-size: 16px;"
               >
                 ${isSubscription ? 'Subscribe' : 'Purchase'}
@@ -1665,10 +1715,28 @@ <h3 style="margin: 0 0 8px 0; font-size: 18px; color: var(--color-text-heading);
         }).join('');
 
         container.innerHTML = `
+          ${discountBanner}
           <div style="display: grid; grid-template-columns: repeat(auto-fit, minmax(250px, 1fr)); gap: 20px; margin-bottom: 20px;">
             ${productCards}
           </div>
         `;
+
+        // Add event listeners to avoid XSS from inline handlers
+        container.querySelectorAll('.product-card').forEach(card => {
+          card.addEventListener('mouseover', () => {
+            card.style.borderColor = 'var(--aao-primary)';
+            card.style.boxShadow = '0 4px 12px rgba(102, 126, 234, 0.15)';
+          });
+          card.addEventListener('mouseout', () => {
+            card.style.borderColor = 'var(--color-border)';
+            card.style.boxShadow = 'none';
+          });
+        });
+        container.querySelectorAll('.checkout-btn').forEach(btn => {
+          btn.addEventListener('click', () => {
+            startCheckout(btn.dataset.priceId, btn.dataset.orgId);
+          });
+        });
       } catch (error) {
         console.error('Error loading products:', error);
         container.innerHTML = `
@@ -2673,6 +2741,10 @@ <h3 style="margin: 0 0 8px 0; color: var(--color-text-heading);">Create Your Pro
                       is_personal: billingData.is_personal,
                       suggested_company_type: billingData.suggested_company_type,
                       suggested_revenue_tier: billingData.suggested_revenue_tier,
+                      // Discount info
+                      discount_percent: billingData.discount_percent,
+                      discount_amount_cents: billingData.discount_amount_cents,
+                      stripe_promotion_code: billingData.stripe_promotion_code,
                     },
                     stripeCustomerId: billingData.stripe_customer_id,
                     customerSessionSecret: billingData.customer_session_secret,
@@ -3303,6 +3375,385 @@ <h3 style="margin: 0 0 8px 0; color: var(--color-text-heading);">Create Your Pro
         window.history.replaceState({}, '', newUrl);
       }
     });
+
+    // =========================================================================
+    // Invoice Request Modal Functions (Two-Step Draft Process)
+    // =========================================================================
+
+    let invoiceProducts = [];
+    let selectedInvoiceProductData = null;
+
+    function openInvoiceRequestModal(options = {}) {
+      const modal = document.getElementById('invoiceRequestModal');
+      const productSelect = document.getElementById('invoice-product');
+
+      // Reset modal state
+      document.getElementById('invoiceFormSection').style.display = 'block';
+      document.getElementById('invoiceDraftReviewSection').style.display = 'none';
+      document.getElementById('invoiceSuccessSection').style.display = 'none';
+      document.getElementById('invoiceFormError').style.display = 'none';
+      document.getElementById('invoiceRequestForm').reset();
+      document.getElementById('prepareDraftInvoiceBtn').style.display = 'inline-block';
+      document.getElementById('backToEditInvoiceBtn').style.display = 'none';
+      document.getElementById('sendInvoiceRequestBtn').style.display = 'none';
+
+      // Pre-fill company name if provided
+      if (options.companyName) {
+        document.getElementById('invoice-company').value = options.companyName;
+      }
+
+      // Load products and populate dropdown
+      loadInvoiceProducts(options.selectedProduct);
+
+      modal.style.display = 'flex';
+      document.getElementById('invoice-company').focus();
+    }
+
+    async function loadInvoiceProducts(preSelectedKey) {
+      const productSelect = document.getElementById('invoice-product');
+
+      try {
+        const response = await fetch('/api/products');
+        if (!response.ok) throw new Error('Failed to load products');
+
+        const data = await response.json();
+        invoiceProducts = (data.products || []).filter(p => p.billing_type === 'subscription' && p.is_invoiceable);
+
+        // Sort by price
+        invoiceProducts.sort((a, b) => (a.amount_cents || 0) - (b.amount_cents || 0));
+
+        // Check if org has discount
+        const hasDiscount = currentOrg?.billing?.discount_percent || currentOrg?.billing?.discount_amount_cents;
+
+        productSelect.innerHTML = '<option value="">Select a product...</option>';
+        invoiceProducts.forEach(product => {
+          const listPrice = product.amount_cents || 0;
+          const netPrice = hasDiscount ? calculateInvoiceDiscountedPrice(listPrice) : listPrice;
+          const priceText = hasDiscount && netPrice !== listPrice
+            ? `${formatInvoiceCurrency(netPrice)}/year (was ${formatInvoiceCurrency(listPrice)})`
+            : `${formatInvoiceCurrency(listPrice)}/year`;
+          productSelect.innerHTML += `<option value="${product.lookup_key}">${escapeHtml(product.display_name)} - ${priceText}</option>`;
+        });
+
+        // Pre-select if specified
+        if (preSelectedKey) {
+          productSelect.value = preSelectedKey;
+        }
+      } catch (error) {
+        console.error('Error loading products:', error);
+        productSelect.innerHTML = '<option value="">Failed to load products</option>';
+      }
+    }
+
+    function calculateInvoiceDiscountedPrice(amountCents) {
+      if (currentOrg?.billing?.discount_percent) {
+        return Math.round(amountCents * (1 - currentOrg.billing.discount_percent / 100));
+      } else if (currentOrg?.billing?.discount_amount_cents) {
+        return Math.max(0, amountCents - currentOrg.billing.discount_amount_cents);
+      }
+      return amountCents;
+    }
+
+    function formatInvoiceCurrency(cents) {
+      return new Intl.NumberFormat('en-US', {
+        style: 'currency', currency: 'USD', minimumFractionDigits: 0, maximumFractionDigits: 0
+      }).format(cents / 100);
+    }
+
+    function closeInvoiceRequestModal() {
+      document.getElementById('invoiceRequestModal').style.display = 'none';
+      selectedInvoiceProductData = null;
+    }
+
+    function prepareDraftInvoice() {
+      // Collect form data
+      const companyName = document.getElementById('invoice-company').value;
+      const contactName = document.getElementById('invoice-contact').value;
+      const contactEmail = document.getElementById('invoice-email').value;
+      const lookupKey = document.getElementById('invoice-product').value;
+      const addressLine1 = document.getElementById('invoice-address1').value;
+      const addressLine2 = document.getElementById('invoice-address2').value;
+      const city = document.getElementById('invoice-city').value;
+      const state = document.getElementById('invoice-state').value;
+      const postalCode = document.getElementById('invoice-postal').value;
+      const country = document.getElementById('invoice-country').value;
+
+      // Find selected product
+      const product = invoiceProducts.find(p => p.lookup_key === lookupKey);
+      if (!product) {
+        document.getElementById('invoiceFormError').textContent = 'Please select a product';
+        document.getElementById('invoiceFormError').style.display = 'block';
+        return;
+      }
+
+      // Check for missing required fields
+      const missingFields = [];
+      if (!companyName) missingFields.push('Company Name');
+      if (!contactName) missingFields.push('Contact Name');
+      if (!contactEmail) missingFields.push('Billing Email');
+      if (!addressLine1) missingFields.push('Address Line 1');
+      if (!city) missingFields.push('City');
+      if (!state) missingFields.push('State/Province');
+      if (!postalCode) missingFields.push('Postal Code');
+      if (!country) missingFields.push('Country');
+
+      // Store selected product data
+      selectedInvoiceProductData = { product, lookupKey };
+
+      // Calculate pricing
+      const hasDiscount = currentOrg?.billing?.discount_percent || currentOrg?.billing?.discount_amount_cents;
+      const listPrice = product.amount_cents || 0;
+      const netPrice = hasDiscount ? calculateInvoiceDiscountedPrice(listPrice) : listPrice;
+
+      // Build discount info
+      let discountHtml = '';
+      if (hasDiscount && listPrice !== netPrice) {
+        const discountText = currentOrg.billing.discount_percent
+          ? `${currentOrg.billing.discount_percent}% discount`
+          : `${formatInvoiceCurrency(currentOrg.billing.discount_amount_cents)} off`;
+        const savings = formatInvoiceCurrency(listPrice - netPrice);
+        discountHtml = `
+          <div style="margin-top: 8px; padding: 8px; background: var(--color-success-50); border-radius: 4px;">
+            <span style="color: var(--color-success-700); font-size: 13px;">${discountText} applied (saves ${savings})</span>
+          </div>
+        `;
+      }
+
+      // Build address display
+      const addressParts = [addressLine1];
+      if (addressLine2) addressParts.push(addressLine2);
+      addressParts.push(`${city}, ${state} ${postalCode}`);
+      addressParts.push(country);
+      const fullAddress = addressParts.filter(Boolean).join('<br>');
+
+      // Populate draft review content
+      document.getElementById('invoiceDraftReviewContent').innerHTML = `
+        <div style="display: grid; grid-template-columns: 1fr 1fr; gap: 16px; margin-bottom: 16px;">
+          <div>
+            <div style="font-size: 11px; color: var(--color-text-muted); text-transform: uppercase; margin-bottom: 4px;">Company</div>
+            <div style="font-weight: 600;">${escapeHtml(companyName) || '<em style="color: var(--color-error-500);">Not provided</em>'}</div>
+          </div>
+          <div>
+            <div style="font-size: 11px; color: var(--color-text-muted); text-transform: uppercase; margin-bottom: 4px;">Contact</div>
+            <div style="font-weight: 600;">${escapeHtml(contactName) || '<em style="color: var(--color-error-500);">Not provided</em>'}</div>
+            <div style="color: var(--color-text-secondary); font-size: 13px;">${escapeHtml(contactEmail) || '<em style="color: var(--color-error-500);">Not provided</em>'}</div>
+          </div>
+        </div>
+
+        <hr style="margin: 16px 0; border: none; border-top: 1px solid var(--color-border);">
+
+        <div style="display: grid; grid-template-columns: 1fr 1fr; gap: 16px; margin-bottom: 16px;">
+          <div>
+            <div style="font-size: 11px; color: var(--color-text-muted); text-transform: uppercase; margin-bottom: 4px;">Product</div>
+            <div style="font-weight: 600;">${escapeHtml(product.display_name)}</div>
+          </div>
+          <div>
+            <div style="font-size: 11px; color: var(--color-text-muted); text-transform: uppercase; margin-bottom: 4px;">Amount</div>
+            ${hasDiscount && listPrice !== netPrice
+              ? `<div><span style="text-decoration: line-through; color: var(--color-text-muted);">${formatInvoiceCurrency(listPrice)}</span> <span style="color: var(--color-success-600); font-weight: 600;">${formatInvoiceCurrency(netPrice)}/year</span></div>`
+              : `<div style="font-weight: 600;">${formatInvoiceCurrency(listPrice)}/year</div>`
+            }
+            ${discountHtml}
+          </div>
+        </div>
+
+        <hr style="margin: 16px 0; border: none; border-top: 1px solid var(--color-border);">
+
+        <div>
+          <div style="font-size: 11px; color: var(--color-text-muted); text-transform: uppercase; margin-bottom: 4px;">Billing Address</div>
+          <div style="line-height: 1.5;">${fullAddress || '<em style="color: var(--color-error-500);">Not provided</em>'}</div>
+        </div>
+      `;
+
+      // Show/hide missing fields warning
+      const missingFieldsDiv = document.getElementById('invoiceMissingFields');
+      if (missingFields.length > 0) {
+        missingFieldsDiv.innerHTML = `<strong style="font-size: 13px;">Missing Information:</strong> ${missingFields.join(', ')}`;
+        missingFieldsDiv.style.display = 'block';
+      } else {
+        missingFieldsDiv.style.display = 'none';
+      }
+
+      // Update UI state
+      document.getElementById('invoiceFormSection').style.display = 'none';
+      document.getElementById('invoiceDraftReviewSection').style.display = 'block';
+      document.getElementById('prepareDraftInvoiceBtn').style.display = 'none';
+      document.getElementById('backToEditInvoiceBtn').style.display = 'inline-block';
+      document.getElementById('sendInvoiceRequestBtn').style.display = missingFields.length === 0 ? 'inline-block' : 'none';
+    }
+
+    function backToEditInvoiceRequest() {
+      document.getElementById('invoiceDraftReviewSection').style.display = 'none';
+      document.getElementById('invoiceFormSection').style.display = 'block';
+      document.getElementById('prepareDraftInvoiceBtn').style.display = 'inline-block';
+      document.getElementById('backToEditInvoiceBtn').style.display = 'none';
+      document.getElementById('sendInvoiceRequestBtn').style.display = 'none';
+    }
+
+    async function submitInvoiceRequest(event) {
+      event.preventDefault();
+
+      const submitBtn = document.getElementById('sendInvoiceRequestBtn');
+      const errorDiv = document.getElementById('invoiceFormError');
+
+      submitBtn.disabled = true;
+      submitBtn.textContent = 'Sending...';
+      errorDiv.style.display = 'none';
+
+      const form = document.getElementById('invoiceRequestForm');
+      const formData = new FormData(form);
+
+      const requestData = {
+        companyName: formData.get('companyName'),
+        contactName: formData.get('contactName'),
+        contactEmail: formData.get('contactEmail'),
+        lookupKey: formData.get('lookupKey'),
+        billingAddress: {
+          line1: formData.get('line1'),
+          line2: formData.get('line2') || undefined,
+          city: formData.get('city'),
+          state: formData.get('state'),
+          postal_code: formData.get('postal_code'),
+          country: formData.get('country'),
+        },
+      };
+
+      try {
+        const response = await fetch('/api/invoice-request', {
+          method: 'POST',
+          headers: { 'Content-Type': 'application/json' },
+          credentials: 'include',
+          body: JSON.stringify(requestData),
+        });
+
+        const result = await response.json();
+
+        if (!response.ok) {
+          throw new Error(result.message || 'Failed to send invoice');
+        }
+
+        // Show success state
+        document.getElementById('invoiceDraftReviewSection').style.display = 'none';
+        document.getElementById('backToEditInvoiceBtn').style.display = 'none';
+        document.getElementById('sendInvoiceRequestBtn').style.display = 'none';
+
+        document.getElementById('invoiceSuccessSection').innerHTML = `
+          <div style="text-align: center; padding: 24px;">
+            <div style="font-size: 48px; margin-bottom: 16px;">✅</div>
+            <h3 style="color: var(--color-success-600); margin-bottom: 8px;">Invoice Sent!</h3>
+            <p style="color: var(--color-text-secondary); margin-bottom: 16px;">We've sent an invoice to <strong>${escapeHtml(requestData.contactEmail)}</strong>. Please check your email for payment instructions.</p>
+            <p style="font-size: 14px; color: var(--color-text-muted);">The invoice is due within 30 days. You can pay online via the link in the email.</p>
+          </div>
+        `;
+        document.getElementById('invoiceSuccessSection').style.display = 'block';
+
+      } catch (error) {
+        errorDiv.textContent = error.message || 'Something went wrong. Please try again or contact finance@agenticadvertising.org';
+        errorDiv.style.display = 'block';
+      } finally {
+        submitBtn.disabled = false;
+        submitBtn.textContent = 'Send Invoice';
+      }
+    }
   </script>
+
+  <!-- Invoice Request Modal (Two-Step Draft Process) -->
+  <div id="invoiceRequestModal" class="modal-overlay" style="display: none;">
+    <div style="background: var(--color-bg-card); border-radius: 12px; max-width: 520px; width: 100%; max-height: 90vh; overflow-y: auto; box-shadow: var(--shadow-xl);">
+      <div style="padding: 20px 24px; border-bottom: 1px solid var(--color-border); display: flex; justify-content: space-between; align-items: center;">
+        <h2 style="margin: 0; font-size: 18px; color: var(--color-text-heading);">Request an Invoice</h2>
+        <button onclick="closeInvoiceRequestModal()" style="background: none; border: none; font-size: 24px; color: var(--color-text-muted); cursor: pointer; padding: 0; line-height: 1;">&times;</button>
+      </div>
+      <form id="invoiceRequestForm" onsubmit="submitInvoiceRequest(event)">
+        <!-- Step 1: Form Section -->
+        <div id="invoiceFormSection" style="padding: 24px;">
+          <div style="margin-bottom: 16px;">
+            <label style="display: block; font-size: 14px; font-weight: 500; color: var(--color-text); margin-bottom: 4px;">Company Name *</label>
+            <input type="text" id="invoice-company" name="companyName" required placeholder="Acme Corporation" style="width: 100%; padding: 10px 12px; border: 1px solid var(--color-border); border-radius: 8px; font-size: 14px;">
+          </div>
+
+          <div style="display: grid; grid-template-columns: 1fr 1fr; gap: 12px; margin-bottom: 16px;">
+            <div>
+              <label style="display: block; font-size: 14px; font-weight: 500; color: var(--color-text); margin-bottom: 4px;">Contact Name *</label>
+              <input type="text" id="invoice-contact" name="contactName" required placeholder="John Smith" style="width: 100%; padding: 10px 12px; border: 1px solid var(--color-border); border-radius: 8px; font-size: 14px;">
+            </div>
+            <div>
+              <label style="display: block; font-size: 14px; font-weight: 500; color: var(--color-text); margin-bottom: 4px;">Billing Email *</label>
+              <input type="email" id="invoice-email" name="contactEmail" required placeholder="billing@acme.com" style="width: 100%; padding: 10px 12px; border: 1px solid var(--color-border); border-radius: 8px; font-size: 14px;">
+            </div>
+          </div>
+
+          <div style="margin-bottom: 16px;">
+            <label style="display: block; font-size: 14px; font-weight: 500; color: var(--color-text); margin-bottom: 4px;">Product *</label>
+            <select id="invoice-product" name="lookupKey" required style="width: 100%; padding: 10px 12px; border: 1px solid var(--color-border); border-radius: 8px; font-size: 14px; background: white;">
+              <option value="">Select a product...</option>
+            </select>
+          </div>
+
+          <div style="margin-bottom: 16px;">
+            <label style="display: block; font-size: 14px; font-weight: 500; color: var(--color-text); margin-bottom: 4px;">Billing Address Line 1 *</label>
+            <input type="text" id="invoice-address1" name="line1" required placeholder="123 Main Street" style="width: 100%; padding: 10px 12px; border: 1px solid var(--color-border); border-radius: 8px; font-size: 14px;">
+          </div>
+
+          <div style="margin-bottom: 16px;">
+            <label style="display: block; font-size: 14px; font-weight: 500; color: var(--color-text); margin-bottom: 4px;">Billing Address Line 2</label>
+            <input type="text" id="invoice-address2" name="line2" placeholder="Suite 100" style="width: 100%; padding: 10px 12px; border: 1px solid var(--color-border); border-radius: 8px; font-size: 14px;">
+          </div>
+
+          <div style="display: grid; grid-template-columns: 1fr 1fr; gap: 12px; margin-bottom: 16px;">
+            <div>
+              <label style="display: block; font-size: 14px; font-weight: 500; color: var(--color-text); margin-bottom: 4px;">City *</label>
+              <input type="text" id="invoice-city" name="city" required placeholder="San Francisco" style="width: 100%; padding: 10px 12px; border: 1px solid var(--color-border); border-radius: 8px; font-size: 14px;">
+            </div>
+            <div>
+              <label style="display: block; font-size: 14px; font-weight: 500; color: var(--color-text); margin-bottom: 4px;">State/Province *</label>
+              <input type="text" id="invoice-state" name="state" required placeholder="CA" style="width: 100%; padding: 10px 12px; border: 1px solid var(--color-border); border-radius: 8px; font-size: 14px;">
+            </div>
+          </div>
+
+          <div style="display: grid; grid-template-columns: 1fr 1fr; gap: 12px; margin-bottom: 16px;">
+            <div>
+              <label style="display: block; font-size: 14px; font-weight: 500; color: var(--color-text); margin-bottom: 4px;">Postal Code *</label>
+              <input type="text" id="invoice-postal" name="postal_code" required placeholder="94105" style="width: 100%; padding: 10px 12px; border: 1px solid var(--color-border); border-radius: 8px; font-size: 14px;">
+            </div>
+            <div>
+              <label style="display: block; font-size: 14px; font-weight: 500; color: var(--color-text); margin-bottom: 4px;">Country *</label>
+              <input type="text" id="invoice-country" name="country" required value="US" placeholder="US" style="width: 100%; padding: 10px 12px; border: 1px solid var(--color-border); border-radius: 8px; font-size: 14px;">
+            </div>
+          </div>
+
+          <div id="invoiceFormError" style="display: none; color: var(--color-error-600); font-size: 14px; padding: 12px; background: var(--color-error-50); border-radius: 8px;"></div>
+        </div>
+
+        <!-- Step 2: Draft Review Section -->
+        <div id="invoiceDraftReviewSection" style="display: none; padding: 24px;">
+          <div style="background: var(--color-info-50); border: 1px solid var(--color-info-200); border-radius: 8px; padding: 12px; margin-bottom: 16px;">
+            <strong style="color: var(--color-info-700);">Review Invoice Draft</strong>
+            <p style="margin: 4px 0 0; font-size: 13px; color: var(--color-text-secondary);">
+              Please review all details before sending. The invoice will be emailed to the billing contact.
+            </p>
+          </div>
+
+          <div id="invoiceDraftReviewContent" style="background: var(--color-bg-subtle); border-radius: 8px; padding: 16px; margin-bottom: 16px;">
+            <!-- Populated by JavaScript -->
+          </div>
+
+          <div id="invoiceMissingFields" style="display: none; background: var(--color-warning-50); border: 1px solid var(--color-warning-200); border-radius: 8px; padding: 12px; color: var(--color-warning-700);"></div>
+        </div>
+
+        <!-- Step 3: Success Section -->
+        <div id="invoiceSuccessSection" style="display: none;">
+          <!-- Populated by JavaScript -->
+        </div>
+
+        <div style="padding: 16px 24px; border-top: 1px solid var(--color-border); display: flex; gap: 12px; justify-content: flex-end;">
+          <button type="button" class="btn btn-secondary" onclick="closeInvoiceRequestModal()">Cancel</button>
+          <button type="button" class="btn btn-secondary" id="backToEditInvoiceBtn" style="display: none;" onclick="backToEditInvoiceRequest()">Edit Details</button>
+          <button type="button" class="btn btn-primary" id="prepareDraftInvoiceBtn" onclick="prepareDraftInvoice()">Prepare Draft</button>
+          <button type="submit" class="btn btn-primary" id="sendInvoiceRequestBtn" style="display: none;">Send Invoice</button>
+        </div>
+      </form>
+    </div>
+  </div>
 </body>
 </html>
diff --git a/server/src/addie/mcp/admin-tools.ts b/server/src/addie/mcp/admin-tools.ts
index 9590e1f78d..d9df7501ec 100644
--- a/server/src/addie/mcp/admin-tools.ts
+++ b/server/src/addie/mcp/admin-tools.ts
@@ -555,6 +555,7 @@ USE THIS when an admin says things like:
 - "Help [company] pay for membership"
 - "Give Acme a 20% discount and send them a payment link"
 - "Send a discounted link to the startup"
+- "Let's issue an invoice to Boltive" (use draft_invoice first, then send_invoice to confirm)
 
 This tool will:
 1. Find the company (or create it if it doesn't exist)
@@ -563,9 +564,13 @@ This tool will:
 4. Generate a direct Stripe payment link OR send an invoice
 
 For payment links: Returns a direct Stripe checkout URL you can share with the prospect.
-For invoices: Sends an email from Stripe with a payment link - good for companies that need NET30/PO.
-For discounts: Can create a new discount or auto-apply an existing org discount.`,
-    usage_hints: 'This is the primary tool for converting prospects to members. Use it whenever payment is discussed.',
+For invoices: Use action="draft_invoice" FIRST to prepare and review, then action="send_invoice" to send.
+For discounts: Can create a new discount or auto-apply an existing org discount.
+
+IMPORTANT: For invoices, ALWAYS use the two-step process:
+1. First call with action="draft_invoice" to prepare and show the draft for admin review
+2. Then call with action="send_invoice" after admin confirms (or makes changes)`,
+    usage_hints: 'This is the primary tool for converting prospects to members. Use it whenever payment is discussed. For invoices, use draft_invoice first.',
     input_schema: {
       type: 'object',
       properties: {
@@ -591,8 +596,8 @@ For discounts: Can create a new discount or auto-apply an existing org discount.
         },
         action: {
           type: 'string',
-          enum: ['payment_link', 'invoice', 'lookup_only'],
-          description: 'What to do: payment_link (default), invoice (sends email), or lookup_only (just show info)',
+          enum: ['payment_link', 'draft_invoice', 'send_invoice', 'lookup_only'],
+          description: 'What to do: payment_link (default), draft_invoice (prepare invoice for review), send_invoice (send after review), or lookup_only (just show info). For invoices, ALWAYS use draft_invoice first, then send_invoice to confirm.',
         },
         lookup_key: {
           type: 'string',
@@ -2897,8 +2902,120 @@ export function createAdminToolHandlers(
       }
     }
 
-    // Send invoice
-    if (action === 'invoice') {
+    // Draft invoice - prepare and show for review (TWO-STEP PROCESS: Step 1)
+    if (action === 'draft_invoice') {
+      if (!finalProduct) {
+        return response + `\n❌ No membership products available. Please check Stripe configuration.`;
+      }
+
+      // Determine what discount would be applied
+      let appliedDiscount: string | undefined;
+      let finalAmount = finalProduct.amount_cents || 0;
+
+      // Check if a new discount is being requested
+      if (discountPercent !== undefined || discountAmountDollars !== undefined) {
+        if (!discountReason) {
+          return response + `\n❌ Please provide a discount_reason when applying a discount.`;
+        }
+        appliedDiscount = discountPercent ? `${discountPercent}% off` : `$${discountAmountDollars} off`;
+        if (discountPercent) {
+          finalAmount = Math.round(finalAmount * (1 - discountPercent / 100));
+        } else if (discountAmountDollars) {
+          finalAmount = Math.max(0, finalAmount - (discountAmountDollars * 100));
+        }
+      } else if (useExistingDiscount && (org.discount_percent || org.discount_amount_cents)) {
+        // Use existing org discount
+        appliedDiscount = org.discount_percent
+          ? `${org.discount_percent}% off`
+          : `$${(org.discount_amount_cents || 0) / 100} off`;
+        if (org.discount_percent) {
+          finalAmount = Math.round(finalAmount * (1 - org.discount_percent / 100));
+        } else if (org.discount_amount_cents) {
+          finalAmount = Math.max(0, finalAmount - org.discount_amount_cents);
+        }
+      }
+
+      response += `### 📋 Draft Invoice for Review\n\n`;
+      response += `---\n\n`;
+
+      // Company info
+      response += `**Company:** ${org.name}\n`;
+      if (org.revenue_tier) {
+        const tierLabels: Record<string, string> = {
+          'under_1m': 'Under $1M',
+          '1m_5m': '$1M-$5M',
+          '5m_50m': '$5M-$50M',
+          '50m_250m': '$50M-$250M',
+          '250m_1b': '$250M-$1B',
+          '1b_plus': 'Over $1B'
+        };
+        response += `**Revenue Tier:** ${tierLabels[org.revenue_tier] || org.revenue_tier}\n`;
+      }
+
+      // Contact info
+      response += `\n**Contact:** ${org.prospect_contact_name || contactName || '_Not set_'}\n`;
+      response += `**Email:** ${emailToUse || '_Not set - required for invoice_'}\n`;
+
+      // Billing address
+      response += `\n**Billing Address:**\n`;
+      if (billingAddress?.line1) {
+        response += `${billingAddress.line1}\n`;
+        if (billingAddress.line2) response += `${billingAddress.line2}\n`;
+        response += `${billingAddress.city || ''}, ${billingAddress.state || ''} ${billingAddress.postal_code || ''}\n`;
+        response += `${billingAddress.country || 'US'}\n`;
+      } else {
+        response += `_Not provided - required for invoice_\n`;
+      }
+
+      // Product and pricing
+      response += `\n---\n\n`;
+      response += `**Product:** ${finalProduct.display_name}\n`;
+      if (finalProduct.amount_cents) {
+        const listPrice = finalProduct.amount_cents / 100;
+        const netPrice = finalAmount / 100;
+        if (appliedDiscount) {
+          response += `**List Price:** ~~$${listPrice.toLocaleString()}~~/year\n`;
+          response += `**Discount:** ${appliedDiscount}`;
+          if (org.discount_percent || org.discount_amount_cents) {
+            response += ` (existing org discount)`;
+          }
+          response += `\n`;
+          response += `**Invoice Amount:** **$${netPrice.toLocaleString()}**/year\n`;
+        } else {
+          response += `**Invoice Amount:** $${listPrice.toLocaleString()}/year\n`;
+        }
+      }
+      response += `**Payment Terms:** NET 30\n`;
+
+      // What's missing
+      const missingFields: string[] = [];
+      if (!emailToUse) missingFields.push('contact_email');
+      if (!billingAddress?.line1) missingFields.push('billing_address');
+
+      if (missingFields.length > 0) {
+        response += `\n---\n\n`;
+        response += `⚠️ **Missing required fields:** ${missingFields.join(', ')}\n`;
+        response += `\n_Please provide these fields to proceed._\n`;
+      } else {
+        response += `\n---\n\n`;
+        response += `✅ **Ready to send!**\n\n`;
+        response += `To send this invoice, confirm with the admin then call this tool again with:\n`;
+        response += `- \`action: "send_invoice"\`\n`;
+        response += `- Same company_name and all other parameters\n`;
+        response += `\nOr if changes are needed, ask the admin what to modify.\n`;
+      }
+
+      logger.info(
+        { orgId: org.workos_organization_id, orgName: org.name, product: finalProduct.lookup_key, discount: appliedDiscount },
+        'Addie prepared draft invoice'
+      );
+
+      return response;
+    }
+
+    // Send invoice - actually send after review (TWO-STEP PROCESS: Step 2)
+    // Also support legacy 'invoice' action for backward compatibility
+    if (action === 'send_invoice' || action === 'invoice') {
       if (!emailToUse) {
         return response + `\n❌ Cannot send invoice without an email address. Please provide contact_email.`;
       }
@@ -2998,6 +3115,10 @@ export function createAdminToolHandlers(
               discountedAmount = originalAmount * (1 - discountPercent / 100);
             } else if (discountAmountDollars) {
               discountedAmount = originalAmount - discountAmountDollars;
+            } else if (org.discount_percent) {
+              discountedAmount = originalAmount * (1 - org.discount_percent / 100);
+            } else if (org.discount_amount_cents) {
+              discountedAmount = originalAmount - (org.discount_amount_cents / 100);
             }
             response += ` → **$${discountedAmount.toLocaleString()}** (${appliedDiscount} applied)`;
           }
@@ -3022,7 +3143,7 @@ export function createAdminToolHandlers(
       }
     }
 
-    return response + `\n❌ Unknown action: ${action}. Use "payment_link", "invoice", or "lookup_only".`;
+    return response + `\n❌ Unknown action: ${action}. Use "payment_link", "draft_invoice", "send_invoice", or "lookup_only".`;
   });
 
   // Search Lusha for prospects
diff --git a/server/src/routes/admin.ts b/server/src/routes/admin.ts
index 5a2b3313c0..b19f7689c3 100644
--- a/server/src/routes/admin.ts
+++ b/server/src/routes/admin.ts
@@ -590,6 +590,7 @@ export function createAdminRouter(): { pageRouter: Router; apiRouter: Router } {
           contact_name,
           contact_email,
           billing_address,
+          coupon_id,
         } = req.body;
 
         if (!lookup_key || !company_name || !contact_name || !contact_email || !billing_address) {
@@ -609,7 +610,7 @@ export function createAdminRouter(): { pageRouter: Router; apiRouter: Router } {
 
         const pool = getPool();
         const orgResult = await pool.query(
-          `SELECT workos_organization_id, name FROM organizations WHERE workos_organization_id = $1`,
+          `SELECT workos_organization_id, name, stripe_coupon_id FROM organizations WHERE workos_organization_id = $1`,
           [orgId]
         );
 
@@ -619,6 +620,9 @@ export function createAdminRouter(): { pageRouter: Router; apiRouter: Router } {
 
         const org = orgResult.rows[0];
 
+        // Use explicit coupon_id from request, or fall back to org's saved coupon
+        const effectiveCouponId = coupon_id || org.stripe_coupon_id;
+
         const result = await createAndSendInvoice({
           lookupKey: lookup_key,
           companyName: company_name,
@@ -633,6 +637,7 @@ export function createAdminRouter(): { pageRouter: Router; apiRouter: Router } {
             country: billing_address.country,
           },
           workosOrganizationId: orgId,
+          couponId: effectiveCouponId,
         });
 
         if (!result) {
diff --git a/server/src/routes/billing-public.ts b/server/src/routes/billing-public.ts
index d7b96b00b6..713f7e5c4d 100644
--- a/server/src/routes/billing-public.ts
+++ b/server/src/routes/billing-public.ts
@@ -375,6 +375,10 @@ export function createPublicBillingRouter(): Router {
           workosOrganizationId: orgId,
           workosUserId: user.id,
           isPersonalWorkspace: org.is_personal || false,
+          // Apply org's stored coupon if available
+          couponId: org.stripe_coupon_id || undefined,
+          // Only use promotion code if no coupon ID (coupon takes precedence)
+          promotionCode: !org.stripe_coupon_id ? (org.stripe_promotion_code || undefined) : undefined,
         };
 
         const result = await createCheckoutSession(checkoutData);
@@ -607,6 +611,10 @@ export function createPublicBillingRouter(): Router {
           // Enrichment-based suggestions for prefilling the profile modal
           suggested_company_type: suggestedCompanyType,
           suggested_revenue_tier: suggestedRevenueTier,
+          // Discount info for display (if any)
+          discount_percent: org.discount_percent || null,
+          discount_amount_cents: org.discount_amount_cents || null,
+          stripe_promotion_code: org.stripe_promotion_code || null,
         });
       } catch (error) {
         logger.error({ err: error }, "Get billing info error:");