[PM-23717] premium renewal email (#6672)

* [PM-23717] premium renewal email

* pr feedback

* pr feedback

src/Billing/Services/Implementations/UpcomingInvoiceHandler.cs

@@ -11,6 +11,7 @@ using Bit.Core.Billing.Pricing;
 using Bit.Core.Entities;
 using Bit.Core.Models.Mail.Billing.Renewal.Families2019Renewal;
 using Bit.Core.Models.Mail.Billing.Renewal.Families2020Renewal;
+using Bit.Core.Models.Mail.Billing.Renewal.Premium;
 using Bit.Core.OrganizationFeatures.OrganizationSponsorships.FamiliesForEnterprise.Interfaces;
 using Bit.Core.Platform.Mail.Mailer;
 using Bit.Core.Repositories;
@@ -606,14 +607,27 @@ public class UpcomingInvoiceHandler(
         User user,
         PremiumPlan premiumPlan)
     {
-        /* TODO: Replace with proper premium renewal email template once finalized.
+        var coupon = await stripeFacade.GetCoupon(CouponIDs.Milestone2SubscriptionDiscount);
-           Using Families2020RenewalMail as a temporary stop-gap. */
+        if (coupon == null)
-        var email = new Families2020RenewalMail
+        {
+            throw new InvalidOperationException($"Coupon for sending premium renewal email id:{CouponIDs.Milestone2SubscriptionDiscount} not found");
+        }
+
+        if (coupon.PercentOff == null)
+        {
+            throw new InvalidOperationException($"coupon.PercentOff for sending premium renewal email id:{CouponIDs.Milestone2SubscriptionDiscount} is null");
+        }
+
+        var discountedAnnualRenewalPrice = premiumPlan.Seat.Price * (100 - coupon.PercentOff.Value) / 100;
+
+        var email = new PremiumRenewalMail
         {
             ToEmails = [user.Email],
-            View = new Families2020RenewalMailView
+            View = new PremiumRenewalMailView
             {
-                MonthlyRenewalPrice = (premiumPlan.Seat.Price / 12).ToString("C", new CultureInfo("en-US"))
+                BaseMonthlyRenewalPrice = (premiumPlan.Seat.Price / 12).ToString("C", new CultureInfo("en-US")),
+                DiscountAmount = $"{coupon.PercentOff}%",
+                DiscountedMonthlyRenewalPrice = (discountedAnnualRenewalPrice / 12).ToString("C", new CultureInfo("en-US"))
             }
         };
 

src/Core/MailTemplates/Mjml/emails/Billing/Renewals/premium-renewal.mjml

@@ -0,0 +1,41 @@
+<mjml>
+    <mj-head>
+        <mj-include path="../../../components/head.mjml"/>
+    </mj-head>
+
+    <!-- Blue Header Section-->
+    <mj-body css-class="border-fix">
+        <mj-wrapper css-class="border-fix" padding="20px 20px 0px 20px">
+            <mj-bw-simple-hero />
+        </mj-wrapper>
+
+        <!-- Main Content Section -->
+        <mj-wrapper padding="0px 20px 0px 20px">
+            <mj-section background-color="#fff" padding="15px 10px 10px 10px">
+                <mj-column>
+                    <mj-text font-size="16px" line-height="24px" padding="10px 15px 15px 15px">
+                        Your Bitwarden Premium subscription renews in 15 days. The price is updating to {{BaseMonthlyRenewalPrice}}/month, billed annually.
+                    </mj-text>
+                    <mj-text font-size="16px" line-height="24px" padding="10px 15px 15px 15px">
+                        As an existing Bitwarden customer, you will receive a one-time {{DiscountAmount}} loyalty discount for this renewal.
+                        This renewal now will be {{DiscountedMonthlyRenewalPrice}}/month, billed annually.
+                    </mj-text>
+                    <mj-text font-size="16px" line-height="24px" padding="10px 15px">
+                        Questions? Contact
+                        <a href="mailto:support@bitwarden.com" class="link">support@bitwarden.com</a>
+                    </mj-text>
+                </mj-column>
+            </mj-section>
+            <mj-section background-color="#fff" padding="0 20px 20px 20px">
+            </mj-section>
+        </mj-wrapper>
+
+        <!-- Learn More Section -->
+        <mj-wrapper padding="0px 20px 10px 20px">
+            <mj-bw-learn-more-footer/>
+        </mj-wrapper>
+
+        <!-- Footer -->
+        <mj-include path="../../../components/footer.mjml"/>
+    </mj-body>
+</mjml>

src/Core/Models/Mail/Billing/Renewal/Premium/PremiumRenewalMailView.cs

@@ -0,0 +1,15 @@
+using Bit.Core.Platform.Mail.Mailer;
+
+namespace Bit.Core.Models.Mail.Billing.Renewal.Premium;
+
+public class PremiumRenewalMailView : BaseMailView
+{
+    public required string BaseMonthlyRenewalPrice { get; set; }
+    public required string DiscountedMonthlyRenewalPrice { get; set; }
+    public required string DiscountAmount { get; set; }
+}
+
+public class PremiumRenewalMail : BaseMail<PremiumRenewalMailView>
+{
+    public override string Subject { get => "Your Bitwarden Premium renewal is updating"; }
+}

src/Core/Models/Mail/Billing/Renewal/Premium/PremiumRenewalMailView.html.hbs

@@ -0,0 +1,583 @@
+<!doctype html>
+<html lang="und" dir="auto" xmlns="http://www.w3.org/1999/xhtml" xmlns:v="urn:schemas-microsoft-com:vml" xmlns:o="urn:schemas-microsoft-com:office:office">
+  <head>
+    <title></title>
+    <!--[if !mso]><!-->
+    <meta http-equiv="X-UA-Compatible" content="IE=edge">
+    <!--<![endif]-->
+    <meta http-equiv="Content-Type" content="text/html; charset=UTF-8">
+    <meta name="viewport" content="width=device-width, initial-scale=1">
+    <style type="text/css">
+      #outlook a { padding:0; }
+      body { margin:0;padding:0;-webkit-text-size-adjust:100%;-ms-text-size-adjust:100%; }
+      table, td { border-collapse:collapse;mso-table-lspace:0pt;mso-table-rspace:0pt; }
+      img { border:0;height:auto;line-height:100%; outline:none;text-decoration:none;-ms-interpolation-mode:bicubic; }
+      p { display:block;margin:13px 0; }
+    </style>
+    <!--[if mso]>
+    <noscript>
+    <xml>
+    <o:OfficeDocumentSettings>
+      <o:AllowPNG/>
+      <o:PixelsPerInch>96</o:PixelsPerInch>
+    </o:OfficeDocumentSettings>
+    </xml>
+    </noscript>
+    <![endif]-->
+    <!--[if lte mso 11]>
+    <style type="text/css">
+      .mj-outlook-group-fix { width:100% !important; }
+    </style>
+    <![endif]-->
+    
+    
+    <style type="text/css">
+      @media only screen and (min-width:480px) {
+        .mj-column-per-100 { width:100% !important; max-width: 100%; }
+.mj-column-per-70 { width:70% !important; max-width: 70%; }
+.mj-column-per-30 { width:30% !important; max-width: 30%; }
+      }
+    </style>
+    <style media="screen and (min-width:480px)">
+      .moz-text-html .mj-column-per-100 { width:100% !important; max-width: 100%; }
+.moz-text-html .mj-column-per-70 { width:70% !important; max-width: 70%; }
+.moz-text-html .mj-column-per-30 { width:30% !important; max-width: 30%; }
+    </style>
+    
+    
+  
+    
+    <style type="text/css">
+
+      @media only screen and (max-width:480px) {
+        .mj-bw-learn-more-footer-responsive-img {
+          display: none !important;
+        }
+      }
+    
+
+    @media only screen and (max-width:479px) {
+      table.mj-full-width-mobile { width: 100% !important; }
+      td.mj-full-width-mobile { width: auto !important; }
+    }
+  
+    </style>
+     
+    <style type="text/css">
+.border-fix > table {
+    border-collapse: separate !important;
+  }
+  .border-fix > table > tbody > tr > td {
+    border-radius: 3px;
+  }
+    </style>
+    
+  </head>
+  <body style="word-spacing:normal;background-color:#e6e9ef;">
+    
+    
+      <div class="border-fix" style="background-color:#e6e9ef;" lang="und" dir="auto">
+        
+      
+      <!--[if mso | IE]><table align="center" border="0" cellpadding="0" cellspacing="0" class="border-fix-outlook" role="presentation" style="width:660px;" width="660" ><tr><td style="line-height:0px;font-size:0px;mso-line-height-rule:exactly;"><![endif]-->
+    
+      
+      <div class="border-fix" style="margin:0px auto;max-width:660px;">
+        
+        <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="width:100%;">
+          <tbody>
+            <tr>
+              <td style="direction:ltr;font-size:0px;padding:20px 20px 0px 20px;text-align:center;">
+                <!--[if mso | IE]><table role="presentation" border="0" cellpadding="0" cellspacing="0"><tr><td class="" width="660px" ><![endif]-->
+            
+      <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="background:#175ddc;background-color:#175ddc;width:100%;border-radius:4px 4px 0px 0px;">
+        <tbody>
+          <tr>
+            <td>
+              
+        
+      <!--[if mso | IE]><table align="center" border="0" cellpadding="0" cellspacing="0" class="" role="presentation" style="width:620px;" width="620" bgcolor="#175ddc" ><tr><td style="line-height:0px;font-size:0px;mso-line-height-rule:exactly;"><![endif]-->
+    
+        
+      <div style="margin:0px auto;border-radius:4px 4px 0px 0px;max-width:620px;">
+        
+        <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="width:100%;border-radius:4px 4px 0px 0px;">
+          <tbody>
+            <tr>
+              <td style="direction:ltr;font-size:0px;padding:20px 20px;text-align:center;">
+                <!--[if mso | IE]><table role="presentation" border="0" cellpadding="0" cellspacing="0"><tr><td class="" style="vertical-align:top;width:580px;" ><![endif]-->
+            
+      <div class="mj-column-per-100 mj-outlook-group-fix" style="font-size:0px;text-align:left;direction:ltr;display:inline-block;vertical-align:top;width:100%;">
+        
+      <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="vertical-align:top;" width="100%">
+        <tbody>
+          
+              <tr>
+                <td align="left" style="font-size:0px;padding:10px 5px;word-break:break-word;">
+                  
+      <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="border-collapse:collapse;border-spacing:0px;">
+        <tbody>
+          <tr>
+            <td style="width:150px;">
+              
+      <img alt src="https://bitwarden.com/images/logo-horizontal-white.png" style="border:0;display:block;outline:none;text-decoration:none;height:30px;width:100%;font-size:16px;" width="150" height="30">
+    
+            </td>
+          </tr>
+        </tbody>
+      </table>
+    
+                </td>
+              </tr>
+            
+        </tbody>
+      </table>
+    
+      </div>
+    
+          <!--[if mso | IE]></td></tr></table><![endif]-->
+              </td>
+            </tr>
+          </tbody>
+        </table>
+        
+      </div>
+    
+        
+      <!--[if mso | IE]></td></tr></table><![endif]-->
+    
+      
+            </td>
+          </tr>
+        </tbody>
+      </table>
+    
+          <!--[if mso | IE]></td></tr></table><![endif]-->
+              </td>
+            </tr>
+          </tbody>
+        </table>
+        
+      </div>
+    
+      
+      <!--[if mso | IE]></td></tr></table><![endif]-->
+    
+    <!-- Main Content Section -->
+      
+      <!--[if mso | IE]><table align="center" border="0" cellpadding="0" cellspacing="0" class="" role="presentation" style="width:660px;" width="660" ><tr><td style="line-height:0px;font-size:0px;mso-line-height-rule:exactly;"><![endif]-->
+    
+      
+      <div style="margin:0px auto;max-width:660px;">
+        
+        <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="width:100%;">
+          <tbody>
+            <tr>
+              <td style="direction:ltr;font-size:0px;padding:0px 20px 0px 20px;text-align:center;">
+                <!--[if mso | IE]><table role="presentation" border="0" cellpadding="0" cellspacing="0"><tr><td class="" width="660px" ><table align="center" border="0" cellpadding="0" cellspacing="0" class="" role="presentation" style="width:620px;" width="620" bgcolor="#ffffff" ><tr><td style="line-height:0px;font-size:0px;mso-line-height-rule:exactly;"><![endif]-->
+    
+      
+      <div style="background:#ffffff;background-color:#ffffff;margin:0px auto;max-width:620px;">
+        
+        <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="background:#ffffff;background-color:#ffffff;width:100%;">
+          <tbody>
+            <tr>
+              <td style="direction:ltr;font-size:0px;padding:15px 10px 10px 10px;text-align:center;">
+                <!--[if mso | IE]><table role="presentation" border="0" cellpadding="0" cellspacing="0"><tr><td class="" style="vertical-align:top;width:600px;" ><![endif]-->
+            
+      <div class="mj-column-per-100 mj-outlook-group-fix" style="font-size:0px;text-align:left;direction:ltr;display:inline-block;vertical-align:top;width:100%;">
+        
+      <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="vertical-align:top;" width="100%">
+        <tbody>
+          
+              <tr>
+                <td align="left" style="font-size:0px;padding:10px 15px 15px 15px;word-break:break-word;">
+                  
+      <div style="font-family:'Helvetica Neue', Helvetica, Arial, sans-serif;font-size:16px;line-height:24px;text-align:left;color:#1B2029;">Your Bitwarden Premium subscription renews in 15 days. The price is updating to {{BaseMonthlyRenewalPrice}}/month, billed annually.</div>
+    
+                </td>
+              </tr>
+            
+              <tr>
+                <td align="left" style="font-size:0px;padding:10px 15px 15px 15px;word-break:break-word;">
+                  
+      <div style="font-family:'Helvetica Neue', Helvetica, Arial, sans-serif;font-size:16px;line-height:24px;text-align:left;color:#1B2029;">As an existing Bitwarden customer, you will receive a one-time {{DiscountAmount}} loyalty discount for this renewal.
+                        This renewal now will be {{DiscountedMonthlyRenewalPrice}}/month, billed annually.</div>
+    
+                </td>
+              </tr>
+            
+              <tr>
+                <td align="left" style="font-size:0px;padding:10px 15px;word-break:break-word;">
+                  
+      <div style="font-family:'Helvetica Neue', Helvetica, Arial, sans-serif;font-size:16px;line-height:24px;text-align:left;color:#1B2029;">Questions? Contact
+                        <a href="mailto:support@bitwarden.com" class="link" style="text-decoration: none; color: #175ddc; font-weight: 600;">support@bitwarden.com</a></div>
+    
+                </td>
+              </tr>
+            
+        </tbody>
+      </table>
+    
+      </div>
+    
+          <!--[if mso | IE]></td></tr></table><![endif]-->
+              </td>
+            </tr>
+          </tbody>
+        </table>
+        
+      </div>
+    
+      
+      <!--[if mso | IE]></td></tr></table></td></tr><tr><td class="" width="660px" ><table align="center" border="0" cellpadding="0" cellspacing="0" class="" role="presentation" style="width:620px;" width="620" bgcolor="#ffffff" ><tr><td style="line-height:0px;font-size:0px;mso-line-height-rule:exactly;"><![endif]-->
+    
+      
+      <div style="background:#ffffff;background-color:#ffffff;margin:0px auto;max-width:620px;">
+        
+        <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="background:#ffffff;background-color:#ffffff;width:100%;">
+          <tbody>
+            <tr>
+              <td style="direction:ltr;font-size:0px;padding:0 20px 20px 20px;text-align:center;">
+                <!--[if mso | IE]><table role="presentation" border="0" cellpadding="0" cellspacing="0"><tr></tr></table><![endif]-->
+              </td>
+            </tr>
+          </tbody>
+        </table>
+        
+      </div>
+    
+      
+      <!--[if mso | IE]></td></tr></table></td></tr></table><![endif]-->
+              </td>
+            </tr>
+          </tbody>
+        </table>
+        
+      </div>
+    
+      
+      <!--[if mso | IE]></td></tr></table><![endif]-->
+    
+    <!-- Learn More Section -->
+      
+      <!--[if mso | IE]><table align="center" border="0" cellpadding="0" cellspacing="0" class="" role="presentation" style="width:660px;" width="660" ><tr><td style="line-height:0px;font-size:0px;mso-line-height-rule:exactly;"><![endif]-->
+    
+      
+      <div style="margin:0px auto;max-width:660px;">
+        
+        <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="width:100%;">
+          <tbody>
+            <tr>
+              <td style="direction:ltr;font-size:0px;padding:0px 20px 10px 20px;text-align:center;">
+                <!--[if mso | IE]><table role="presentation" border="0" cellpadding="0" cellspacing="0"><tr><td class="" width="660px" ><table align="center" border="0" cellpadding="0" cellspacing="0" class="" role="presentation" style="width:620px;" width="620" bgcolor="#f6f6f6" ><tr><td style="line-height:0px;font-size:0px;mso-line-height-rule:exactly;"><![endif]-->
+    
+      
+      <div style="background:#f6f6f6;background-color:#f6f6f6;margin:0px auto;border-radius:0px 0px 4px 4px;max-width:620px;">
+        
+        <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="background:#f6f6f6;background-color:#f6f6f6;width:100%;border-radius:0px 0px 4px 4px;">
+          <tbody>
+            <tr>
+              <td style="direction:ltr;font-size:0px;padding:5px 10px 10px 10px;text-align:center;">
+                <!--[if mso | IE]><table role="presentation" border="0" cellpadding="0" cellspacing="0"><tr><td class="" style="vertical-align:top;width:420px;" ><![endif]-->
+            
+      <div class="mj-column-per-70 mj-outlook-group-fix" style="font-size:0px;text-align:left;direction:ltr;display:inline-block;vertical-align:top;width:100%;">
+        
+      <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="vertical-align:top;" width="100%">
+        <tbody>
+          
+              <tr>
+                <td align="left" style="font-size:0px;padding:10px 25px;word-break:break-word;">
+                  
+      <div style="font-family:'Helvetica Neue', Helvetica, Arial, sans-serif;font-size:16px;line-height:24px;text-align:left;color:#1B2029;"><p style="font-size: 18px; line-height: 28px; font-weight: bold;">
+              Learn more about Bitwarden
+            </p>
+            Find user guides, product documentation, and videos on the
+            <a href="https://bitwarden.com/help/" class="link" style="text-decoration: none; color: #175ddc; font-weight: 600;"> Bitwarden Help Center</a>.</div>
+    
+                </td>
+              </tr>
+            
+        </tbody>
+      </table>
+    
+      </div>
+    
+          <!--[if mso | IE]></td><td class="" style="vertical-align:top;width:180px;" ><![endif]-->
+            
+      <div class="mj-column-per-30 mj-outlook-group-fix" style="font-size:0px;text-align:left;direction:ltr;display:inline-block;vertical-align:top;width:100%;">
+        
+      <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="vertical-align:top;" width="100%">
+        <tbody>
+          
+              <tr>
+                <td align="center" class="mj-bw-learn-more-footer-responsive-img" style="font-size:0px;padding:10px 25px;word-break:break-word;">
+                  
+      <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="border-collapse:collapse;border-spacing:0px;">
+        <tbody>
+          <tr>
+            <td style="width:94px;">
+              
+      <img alt src="https://assets.bitwarden.com/email/v1/spot-community.png" style="border:0;display:block;outline:none;text-decoration:none;height:auto;width:100%;font-size:16px;" width="94" height="auto">
+    
+            </td>
+          </tr>
+        </tbody>
+      </table>
+    
+                </td>
+              </tr>
+            
+        </tbody>
+      </table>
+    
+      </div>
+    
+          <!--[if mso | IE]></td></tr></table><![endif]-->
+              </td>
+            </tr>
+          </tbody>
+        </table>
+        
+      </div>
+    
+      
+      <!--[if mso | IE]></td></tr></table></td></tr></table><![endif]-->
+              </td>
+            </tr>
+          </tbody>
+        </table>
+        
+      </div>
+    
+      
+      <!--[if mso | IE]></td></tr></table><![endif]-->
+    
+    <!-- Footer -->
+      
+      <!--[if mso | IE]><table align="center" border="0" cellpadding="0" cellspacing="0" class="" role="presentation" style="width:660px;" width="660" ><tr><td style="line-height:0px;font-size:0px;mso-line-height-rule:exactly;"><![endif]-->
+    
+      
+      <div style="margin:0px auto;max-width:660px;">
+        
+        <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="width:100%;">
+          <tbody>
+            <tr>
+              <td style="direction:ltr;font-size:0px;padding:20px 0;text-align:center;">
+                <!--[if mso | IE]><table role="presentation" border="0" cellpadding="0" cellspacing="0"><tr><td class="" style="vertical-align:top;width:660px;" ><![endif]-->
+            
+      <div class="mj-column-per-100 mj-outlook-group-fix" style="font-size:0px;text-align:left;direction:ltr;display:inline-block;vertical-align:top;width:100%;">
+        
+      <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="vertical-align:top;" width="100%">
+        <tbody>
+          
+              <tr>
+                <td align="center" style="font-size:0px;padding:0;word-break:break-word;">
+                  
+      
+     <!--[if mso | IE]><table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" ><tr><td><![endif]-->
+              <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="float:none;display:inline-table;">
+                <tbody>
+                  
+      <tr>
+        <td style="padding:10px;vertical-align:middle;">
+          <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="border-radius:3px;width:30px;">
+            <tbody>
+              <tr>
+                <td style="font-size:0;height:30px;vertical-align:middle;width:30px;">
+                  <a href="https://x.com/bitwarden" target="_blank">
+                    <img alt height="30" src="https://assets.bitwarden.com/email/v1/mail-x.png" style="border-radius:3px;display:block;" width="30">
+                  </a>
+                </td>
+              </tr>
+            </tbody>
+          </table>
+        </td>
+        
+      </tr>
+    
+                </tbody>
+              </table>
+            <!--[if mso | IE]></td><td><![endif]-->
+              <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="float:none;display:inline-table;">
+                <tbody>
+                  
+      <tr>
+        <td style="padding:10px;vertical-align:middle;">
+          <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="border-radius:3px;width:30px;">
+            <tbody>
+              <tr>
+                <td style="font-size:0;height:30px;vertical-align:middle;width:30px;">
+                  <a href="https://www.reddit.com/r/Bitwarden/" target="_blank">
+                    <img alt height="30" src="https://assets.bitwarden.com/email/v1/mail-reddit.png" style="border-radius:3px;display:block;" width="30">
+                  </a>
+                </td>
+              </tr>
+            </tbody>
+          </table>
+        </td>
+        
+      </tr>
+    
+                </tbody>
+              </table>
+            <!--[if mso | IE]></td><td><![endif]-->
+              <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="float:none;display:inline-table;">
+                <tbody>
+                  
+      <tr>
+        <td style="padding:10px;vertical-align:middle;">
+          <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="border-radius:3px;width:30px;">
+            <tbody>
+              <tr>
+                <td style="font-size:0;height:30px;vertical-align:middle;width:30px;">
+                  <a href="https://community.bitwarden.com/" target="_blank">
+                    <img alt height="30" src="https://assets.bitwarden.com/email/v1/mail-discourse.png" style="border-radius:3px;display:block;" width="30">
+                  </a>
+                </td>
+              </tr>
+            </tbody>
+          </table>
+        </td>
+        
+      </tr>
+    
+                </tbody>
+              </table>
+            <!--[if mso | IE]></td><td><![endif]-->
+              <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="float:none;display:inline-table;">
+                <tbody>
+                  
+      <tr>
+        <td style="padding:10px;vertical-align:middle;">
+          <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="border-radius:3px;width:30px;">
+            <tbody>
+              <tr>
+                <td style="font-size:0;height:30px;vertical-align:middle;width:30px;">
+                  <a href="https://github.com/bitwarden" target="_blank">
+                    <img alt height="30" src="https://assets.bitwarden.com/email/v1/mail-github.png" style="border-radius:3px;display:block;" width="30">
+                  </a>
+                </td>
+              </tr>
+            </tbody>
+          </table>
+        </td>
+        
+      </tr>
+    
+                </tbody>
+              </table>
+            <!--[if mso | IE]></td><td><![endif]-->
+              <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="float:none;display:inline-table;">
+                <tbody>
+                  
+      <tr>
+        <td style="padding:10px;vertical-align:middle;">
+          <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="border-radius:3px;width:30px;">
+            <tbody>
+              <tr>
+                <td style="font-size:0;height:30px;vertical-align:middle;width:30px;">
+                  <a href="https://www.youtube.com/channel/UCId9a_jQqvJre0_dE2lE_Rw" target="_blank">
+                    <img alt height="30" src="https://assets.bitwarden.com/email/v1/mail-youtube.png" style="border-radius:3px;display:block;" width="30">
+                  </a>
+                </td>
+              </tr>
+            </tbody>
+          </table>
+        </td>
+        
+      </tr>
+    
+                </tbody>
+              </table>
+            <!--[if mso | IE]></td><td><![endif]-->
+              <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="float:none;display:inline-table;">
+                <tbody>
+                  
+      <tr>
+        <td style="padding:10px;vertical-align:middle;">
+          <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="border-radius:3px;width:30px;">
+            <tbody>
+              <tr>
+                <td style="font-size:0;height:30px;vertical-align:middle;width:30px;">
+                  <a href="https://www.linkedin.com/company/bitwarden1/" target="_blank">
+                    <img alt height="30" src="https://assets.bitwarden.com/email/v1/mail-linkedin.png" style="border-radius:3px;display:block;" width="30">
+                  </a>
+                </td>
+              </tr>
+            </tbody>
+          </table>
+        </td>
+        
+      </tr>
+    
+                </tbody>
+              </table>
+            <!--[if mso | IE]></td><td><![endif]-->
+              <table align="center" border="0" cellpadding="0" cellspacing="0" role="presentation" style="float:none;display:inline-table;">
+                <tbody>
+                  
+      <tr>
+        <td style="padding:10px;vertical-align:middle;">
+          <table border="0" cellpadding="0" cellspacing="0" role="presentation" style="border-radius:3px;width:30px;">
+            <tbody>
+              <tr>
+                <td style="font-size:0;height:30px;vertical-align:middle;width:30px;">
+                  <a href="https://www.facebook.com/bitwarden/" target="_blank">
+                    <img alt height="30" src="https://assets.bitwarden.com/email/v1/mail-facebook.png" style="border-radius:3px;display:block;" width="30">
+                  </a>
+                </td>
+              </tr>
+            </tbody>
+          </table>
+        </td>
+        
+      </tr>
+    
+                </tbody>
+              </table>
+            <!--[if mso | IE]></td></tr></table><![endif]-->
+    
+    
+                </td>
+              </tr>
+            
+              <tr>
+                <td align="center" style="font-size:0px;padding:10px 25px;word-break:break-word;">
+                  
+      <div style="font-family:'Helvetica Neue', Helvetica, Arial, sans-serif;font-size:12px;line-height:16px;text-align:center;color:#5A6D91;"><p style="margin-bottom: 5px">
+        © 2025 Bitwarden Inc. 1 N. Calle Cesar Chavez, Suite 102, Santa
+        Barbara, CA, USA
+      </p>
+      <p style="margin-top: 5px">
+        Always confirm you are on a trusted Bitwarden domain before logging
+        in:<br>
+        <a href="https://bitwarden.com/">bitwarden.com</a> |
+        <a href="https://bitwarden.com/help/emails-from-bitwarden/">Learn why we include this</a>
+      </p></div>
+    
+                </td>
+              </tr>
+            
+        </tbody>
+      </table>
+    
+      </div>
+    
+          <!--[if mso | IE]></td></tr></table><![endif]-->
+              </td>
+            </tr>
+          </tbody>
+        </table>
+        
+      </div>
+    
+      
+      <!--[if mso | IE]></td></tr></table><![endif]-->
+    
+    
+      </div>
+    
+  </body>
+</html>
+  

src/Core/Models/Mail/Billing/Renewal/Premium/PremiumRenewalMailView.text.hbs

@@ -0,0 +1,6 @@
+Your Bitwarden Premium subscription renews in 15 days. The price is updating to {{BaseMonthlyRenewalPrice}}/month, billed annually.
+
+As an existing Bitwarden customer, you will receive a one-time {{DiscountAmount}} loyalty discount for this renewal.
+This renewal now will be {{DiscountedMonthlyRenewalPrice}}/month, billed annually.
+
+Questions? Contact support@bitwarden.com

test/Billing.Test/Services/UpcomingInvoiceHandlerTests.cs

@@ -13,6 +13,7 @@ using Bit.Core.Billing.Pricing.Premium;
 using Bit.Core.Entities;
 using Bit.Core.Models.Mail.Billing.Renewal.Families2019Renewal;
 using Bit.Core.Models.Mail.Billing.Renewal.Families2020Renewal;
+using Bit.Core.Models.Mail.Billing.Renewal.Premium;
 using Bit.Core.OrganizationFeatures.OrganizationSponsorships.FamiliesForEnterprise.Interfaces;
 using Bit.Core.Platform.Mail.Mailer;
 using Bit.Core.Repositories;
@@ -253,6 +254,9 @@ public class UpcomingInvoiceHandlerTests
             .IsEnabled(FeatureFlagKeys.PM23341_Milestone_2)
             .Returns(true);
 
+        var coupon = new Coupon { PercentOff = 20, Id = CouponIDs.Milestone2SubscriptionDiscount };
+
+        _stripeFacade.GetCoupon(CouponIDs.Milestone2SubscriptionDiscount).Returns(coupon);
 
         // Act
         await _sut.HandleAsync(parsedEvent);
@@ -260,6 +264,7 @@ public class UpcomingInvoiceHandlerTests
         // Assert
         await _userRepository.Received(1).GetByIdAsync(_userId);
         await _pricingClient.Received(1).GetAvailablePremiumPlan();
+        await _stripeFacade.Received(1).GetCoupon(CouponIDs.Milestone2SubscriptionDiscount);
         await _stripeFacade.Received(1).UpdateSubscription(
             Arg.Is("sub_123"),
             Arg.Is<SubscriptionUpdateOptions>(o =>
@@ -269,11 +274,15 @@ public class UpcomingInvoiceHandlerTests
                 o.ProrationBehavior == "none"));
 
         // Verify the updated invoice email was sent with correct price
+        var discountedPrice = plan.Seat.Price * (100 - coupon.PercentOff.Value) / 100;
         await _mailer.Received(1).SendEmail(
-            Arg.Is<Families2020RenewalMail>(email =>
+            Arg.Is<PremiumRenewalMail>(email =>
                 email.ToEmails.Contains("user@example.com") &&
-                email.Subject == "Your Bitwarden Families renewal is updating" &&
+                email.Subject == "Your Bitwarden Premium renewal is updating" &&
-                email.View.MonthlyRenewalPrice == (plan.Seat.Price / 12).ToString("C", new CultureInfo("en-US"))));
+                email.View.BaseMonthlyRenewalPrice == (plan.Seat.Price / 12).ToString("C", new CultureInfo("en-US")) &&
+                email.View.DiscountedMonthlyRenewalPrice == (discountedPrice / 12).ToString("C", new CultureInfo("en-US")) &&
+                email.View.DiscountAmount == $"{coupon.PercentOff}%"
+            ));
     }
 
     [Fact]
@@ -1474,6 +1483,200 @@ public class UpcomingInvoiceHandlerTests
         await _mailer.DidNotReceive().SendEmail(Arg.Any<Families2020RenewalMail>());
     }
 
+    [Fact]
+    public async Task HandleAsync_WhenMilestone3Enabled_AndCouponNotFound_LogsErrorAndSendsTraditionalEmail()
+    {
+        // Arrange
+        var parsedEvent = new Event { Id = "evt_123", Type = "invoice.upcoming" };
+        var customerId = "cus_123";
+        var subscriptionId = "sub_123";
+        var passwordManagerItemId = "si_pm_123";
+
+        var invoice = new Invoice
+        {
+            CustomerId = customerId,
+            AmountDue = 40000,
+            NextPaymentAttempt = DateTime.UtcNow.AddDays(7),
+            Lines = new StripeList<InvoiceLineItem>
+            {
+                Data = [new() { Description = "Test Item" }]
+            }
+        };
+
+        var families2019Plan = new Families2019Plan();
+        var familiesPlan = new FamiliesPlan();
+
+        var subscription = new Subscription
+        {
+            Id = subscriptionId,
+            CustomerId = customerId,
+            Items = new StripeList<SubscriptionItem>
+            {
+                Data =
+                [
+                    new()
+                    {
+                        Id = passwordManagerItemId,
+                        Price = new Price { Id = families2019Plan.PasswordManager.StripePlanId }
+                    }
+                ]
+            },
+            AutomaticTax = new SubscriptionAutomaticTax { Enabled = true },
+            Metadata = new Dictionary<string, string>()
+        };
+
+        var customer = new Customer
+        {
+            Id = customerId,
+            Subscriptions = new StripeList<Subscription> { Data = [subscription] },
+            Address = new Address { Country = "US" }
+        };
+
+        var organization = new Organization
+        {
+            Id = _organizationId,
+            BillingEmail = "org@example.com",
+            PlanType = PlanType.FamiliesAnnually2019
+        };
+
+        _stripeEventService.GetInvoice(parsedEvent).Returns(invoice);
+        _stripeFacade.GetCustomer(customerId, Arg.Any<CustomerGetOptions>()).Returns(customer);
+        _stripeEventUtilityService
+            .GetIdsFromMetadata(subscription.Metadata)
+            .Returns(new Tuple<Guid?, Guid?, Guid?>(_organizationId, null, null));
+        _organizationRepository.GetByIdAsync(_organizationId).Returns(organization);
+        _pricingClient.GetPlanOrThrow(PlanType.FamiliesAnnually2019).Returns(families2019Plan);
+        _pricingClient.GetPlanOrThrow(PlanType.FamiliesAnnually).Returns(familiesPlan);
+        _featureService.IsEnabled(FeatureFlagKeys.PM26462_Milestone_3).Returns(true);
+        _stripeEventUtilityService.IsSponsoredSubscription(subscription).Returns(false);
+        _stripeFacade.GetCoupon(CouponIDs.Milestone3SubscriptionDiscount).Returns((Coupon)null);
+        _stripeFacade.UpdateSubscription(Arg.Any<string>(), Arg.Any<SubscriptionUpdateOptions>())
+            .Returns(subscription);
+
+        // Act
+        await _sut.HandleAsync(parsedEvent);
+
+        // Assert - Exception is caught, error is logged, and traditional email is sent
+        _logger.Received(1).Log(
+            LogLevel.Error,
+            Arg.Any<EventId>(),
+            Arg.Is<object>(o =>
+                o.ToString().Contains($"Failed to align subscription concerns for Organization ({_organizationId})") &&
+                o.ToString().Contains(parsedEvent.Type) &&
+                o.ToString().Contains(parsedEvent.Id)),
+            Arg.Is<Exception>(e => e is InvalidOperationException && e.Message.Contains("Coupon for sending families 2019 email")),
+            Arg.Any<Func<object, Exception, string>>());
+
+        await _mailer.DidNotReceive().SendEmail(Arg.Any<Families2019RenewalMail>());
+
+        await _mailService.Received(1).SendInvoiceUpcoming(
+            Arg.Is<IEnumerable<string>>(emails => emails.Contains("org@example.com")),
+            Arg.Is<decimal>(amount => amount == invoice.AmountDue / 100M),
+            Arg.Is<DateTime>(dueDate => dueDate == invoice.NextPaymentAttempt.Value),
+            Arg.Is<List<string>>(items => items.Count == invoice.Lines.Data.Count),
+            Arg.Is<bool>(b => b == true));
+    }
+
+    [Fact]
+    public async Task HandleAsync_WhenMilestone3Enabled_AndCouponPercentOffIsNull_LogsErrorAndSendsTraditionalEmail()
+    {
+        // Arrange
+        var parsedEvent = new Event { Id = "evt_123", Type = "invoice.upcoming" };
+        var customerId = "cus_123";
+        var subscriptionId = "sub_123";
+        var passwordManagerItemId = "si_pm_123";
+
+        var invoice = new Invoice
+        {
+            CustomerId = customerId,
+            AmountDue = 40000,
+            NextPaymentAttempt = DateTime.UtcNow.AddDays(7),
+            Lines = new StripeList<InvoiceLineItem>
+            {
+                Data = [new() { Description = "Test Item" }]
+            }
+        };
+
+        var families2019Plan = new Families2019Plan();
+        var familiesPlan = new FamiliesPlan();
+
+        var subscription = new Subscription
+        {
+            Id = subscriptionId,
+            CustomerId = customerId,
+            Items = new StripeList<SubscriptionItem>
+            {
+                Data =
+                [
+                    new()
+                    {
+                        Id = passwordManagerItemId,
+                        Price = new Price { Id = families2019Plan.PasswordManager.StripePlanId }
+                    }
+                ]
+            },
+            AutomaticTax = new SubscriptionAutomaticTax { Enabled = true },
+            Metadata = new Dictionary<string, string>()
+        };
+
+        var customer = new Customer
+        {
+            Id = customerId,
+            Subscriptions = new StripeList<Subscription> { Data = [subscription] },
+            Address = new Address { Country = "US" }
+        };
+
+        var organization = new Organization
+        {
+            Id = _organizationId,
+            BillingEmail = "org@example.com",
+            PlanType = PlanType.FamiliesAnnually2019
+        };
+
+        var coupon = new Coupon
+        {
+            Id = CouponIDs.Milestone3SubscriptionDiscount,
+            PercentOff = null
+        };
+
+        _stripeEventService.GetInvoice(parsedEvent).Returns(invoice);
+        _stripeFacade.GetCustomer(customerId, Arg.Any<CustomerGetOptions>()).Returns(customer);
+        _stripeEventUtilityService
+            .GetIdsFromMetadata(subscription.Metadata)
+            .Returns(new Tuple<Guid?, Guid?, Guid?>(_organizationId, null, null));
+        _organizationRepository.GetByIdAsync(_organizationId).Returns(organization);
+        _pricingClient.GetPlanOrThrow(PlanType.FamiliesAnnually2019).Returns(families2019Plan);
+        _pricingClient.GetPlanOrThrow(PlanType.FamiliesAnnually).Returns(familiesPlan);
+        _featureService.IsEnabled(FeatureFlagKeys.PM26462_Milestone_3).Returns(true);
+        _stripeEventUtilityService.IsSponsoredSubscription(subscription).Returns(false);
+        _stripeFacade.GetCoupon(CouponIDs.Milestone3SubscriptionDiscount).Returns(coupon);
+        _stripeFacade.UpdateSubscription(Arg.Any<string>(), Arg.Any<SubscriptionUpdateOptions>())
+            .Returns(subscription);
+
+        // Act
+        await _sut.HandleAsync(parsedEvent);
+
+        // Assert - Exception is caught, error is logged, and traditional email is sent
+        _logger.Received(1).Log(
+            LogLevel.Error,
+            Arg.Any<EventId>(),
+            Arg.Is<object>(o =>
+                o.ToString().Contains($"Failed to align subscription concerns for Organization ({_organizationId})") &&
+                o.ToString().Contains(parsedEvent.Type) &&
+                o.ToString().Contains(parsedEvent.Id)),
+            Arg.Is<Exception>(e => e is InvalidOperationException && e.Message.Contains("coupon.PercentOff")),
+            Arg.Any<Func<object, Exception, string>>());
+
+        await _mailer.DidNotReceive().SendEmail(Arg.Any<Families2019RenewalMail>());
+
+        await _mailService.Received(1).SendInvoiceUpcoming(
+            Arg.Is<IEnumerable<string>>(emails => emails.Contains("org@example.com")),
+            Arg.Is<decimal>(amount => amount == invoice.AmountDue / 100M),
+            Arg.Is<DateTime>(dueDate => dueDate == invoice.NextPaymentAttempt.Value),
+            Arg.Is<List<string>>(items => items.Count == invoice.Lines.Data.Count),
+            Arg.Is<bool>(b => b == true));
+    }
+
     [Fact]
     public async Task HandleAsync_WhenMilestone3Enabled_AndSeatAddOnExists_DeletesItem()
     {
@@ -1996,4 +2199,332 @@ public class UpcomingInvoiceHandlerTests
         await _organizationRepository.DidNotReceive().ReplaceAsync(
             Arg.Is<Organization>(org => org.PlanType == PlanType.FamiliesAnnually));
     }
+
+    #region Premium Renewal Email Tests
+
+    [Fact]
+    public async Task HandleAsync_WhenMilestone2Enabled_AndCouponNotFound_LogsErrorAndSendsTraditionalEmail()
+    {
+        // Arrange
+        var parsedEvent = new Event { Id = "evt_123" };
+        var customerId = "cus_123";
+        var invoice = new Invoice
+        {
+            CustomerId = customerId,
+            AmountDue = 10000,
+            NextPaymentAttempt = DateTime.UtcNow.AddDays(7),
+            Lines = new StripeList<InvoiceLineItem>
+            {
+                Data = [new() { Description = "Test Item" }]
+            }
+        };
+        var subscription = new Subscription
+        {
+            Id = "sub_123",
+            CustomerId = customerId,
+            Items = new StripeList<SubscriptionItem>
+            {
+                Data = [new() { Id = "si_123", Price = new Price { Id = Prices.PremiumAnnually } }]
+            },
+            AutomaticTax = new SubscriptionAutomaticTax { Enabled = false },
+            Customer = new Customer { Id = customerId },
+            Metadata = new Dictionary<string, string>()
+        };
+        var user = new User { Id = _userId, Email = "user@example.com", Premium = true };
+        var plan = new PremiumPlan
+        {
+            Name = "Premium",
+            Available = true,
+            LegacyYear = null,
+            Seat = new Purchasable { Price = 10M, StripePriceId = Prices.PremiumAnnually },
+            Storage = new Purchasable { Price = 4M, StripePriceId = Prices.StoragePlanPersonal }
+        };
+        var customer = new Customer
+        {
+            Id = customerId,
+            Tax = new CustomerTax { AutomaticTax = AutomaticTaxStatus.Supported },
+            Subscriptions = new StripeList<Subscription> { Data = [subscription] }
+        };
+
+        _stripeEventService.GetInvoice(parsedEvent).Returns(invoice);
+        _stripeFacade.GetCustomer(customerId, Arg.Any<CustomerGetOptions>()).Returns(customer);
+        _stripeEventUtilityService.GetIdsFromMetadata(subscription.Metadata)
+            .Returns(new Tuple<Guid?, Guid?, Guid?>(null, _userId, null));
+        _userRepository.GetByIdAsync(_userId).Returns(user);
+        _pricingClient.GetAvailablePremiumPlan().Returns(plan);
+        _featureService.IsEnabled(FeatureFlagKeys.PM23341_Milestone_2).Returns(true);
+        _stripeFacade.GetCoupon(CouponIDs.Milestone2SubscriptionDiscount).Returns((Coupon)null);
+        _stripeFacade.UpdateSubscription(Arg.Any<string>(), Arg.Any<SubscriptionUpdateOptions>())
+            .Returns(subscription);
+
+        // Act
+        await _sut.HandleAsync(parsedEvent);
+
+        // Assert - Exception is caught, error is logged, and traditional email is sent
+        _logger.Received(1).Log(
+            LogLevel.Error,
+            Arg.Any<EventId>(),
+            Arg.Is<object>(o =>
+                o.ToString().Contains($"Failed to update user's ({user.Id}) subscription price id") &&
+                o.ToString().Contains(parsedEvent.Id)),
+            Arg.Is<Exception>(e => e is InvalidOperationException
+                                   && e.Message == $"Coupon for sending premium renewal email id:{CouponIDs.Milestone2SubscriptionDiscount} not found"),
+            Arg.Any<Func<object, Exception, string>>());
+
+        await _mailer.DidNotReceive().SendEmail(Arg.Any<PremiumRenewalMail>());
+
+        await _mailService.Received(1).SendInvoiceUpcoming(
+            Arg.Is<IEnumerable<string>>(emails => emails.Contains("user@example.com")),
+            Arg.Is<decimal>(amount => amount == invoice.AmountDue / 100M),
+            Arg.Is<DateTime>(dueDate => dueDate == invoice.NextPaymentAttempt.Value),
+            Arg.Is<List<string>>(items => items.Count == invoice.Lines.Data.Count),
+            Arg.Is<bool>(b => b == true));
+    }
+
+    [Fact]
+    public async Task HandleAsync_WhenMilestone2Enabled_AndCouponPercentOffIsNull_LogsErrorAndSendsTraditionalEmail()
+    {
+        // Arrange
+        var parsedEvent = new Event { Id = "evt_123" };
+        var customerId = "cus_123";
+        var invoice = new Invoice
+        {
+            CustomerId = customerId,
+            AmountDue = 10000,
+            NextPaymentAttempt = DateTime.UtcNow.AddDays(7),
+            Lines = new StripeList<InvoiceLineItem>
+            {
+                Data = [new() { Description = "Test Item" }]
+            }
+        };
+        var subscription = new Subscription
+        {
+            Id = "sub_123",
+            CustomerId = customerId,
+            Items = new StripeList<SubscriptionItem>
+            {
+                Data = [new() { Id = "si_123", Price = new Price { Id = Prices.PremiumAnnually } }]
+            },
+            AutomaticTax = new SubscriptionAutomaticTax { Enabled = false },
+            Customer = new Customer { Id = customerId },
+            Metadata = new Dictionary<string, string>()
+        };
+        var user = new User { Id = _userId, Email = "user@example.com", Premium = true };
+        var plan = new PremiumPlan
+        {
+            Name = "Premium",
+            Available = true,
+            LegacyYear = null,
+            Seat = new Purchasable { Price = 10M, StripePriceId = Prices.PremiumAnnually },
+            Storage = new Purchasable { Price = 4M, StripePriceId = Prices.StoragePlanPersonal }
+        };
+        var customer = new Customer
+        {
+            Id = customerId,
+            Tax = new CustomerTax { AutomaticTax = AutomaticTaxStatus.Supported },
+            Subscriptions = new StripeList<Subscription> { Data = [subscription] }
+        };
+        var coupon = new Coupon
+        {
+            Id = CouponIDs.Milestone2SubscriptionDiscount,
+            PercentOff = null
+        };
+
+        _stripeEventService.GetInvoice(parsedEvent).Returns(invoice);
+        _stripeFacade.GetCustomer(customerId, Arg.Any<CustomerGetOptions>()).Returns(customer);
+        _stripeEventUtilityService.GetIdsFromMetadata(subscription.Metadata)
+            .Returns(new Tuple<Guid?, Guid?, Guid?>(null, _userId, null));
+        _userRepository.GetByIdAsync(_userId).Returns(user);
+        _pricingClient.GetAvailablePremiumPlan().Returns(plan);
+        _featureService.IsEnabled(FeatureFlagKeys.PM23341_Milestone_2).Returns(true);
+        _stripeFacade.GetCoupon(CouponIDs.Milestone2SubscriptionDiscount).Returns(coupon);
+        _stripeFacade.UpdateSubscription(Arg.Any<string>(), Arg.Any<SubscriptionUpdateOptions>())
+            .Returns(subscription);
+
+        // Act
+        await _sut.HandleAsync(parsedEvent);
+
+        // Assert - Exception is caught, error is logged, and traditional email is sent
+        _logger.Received(1).Log(
+            LogLevel.Error,
+            Arg.Any<EventId>(),
+            Arg.Is<object>(o =>
+                o.ToString().Contains($"Failed to update user's ({user.Id}) subscription price id") &&
+                o.ToString().Contains(parsedEvent.Id)),
+            Arg.Is<Exception>(e => e is InvalidOperationException
+                                   && e.Message == $"coupon.PercentOff for sending premium renewal email id:{CouponIDs.Milestone2SubscriptionDiscount} is null"),
+            Arg.Any<Func<object, Exception, string>>());
+
+        await _mailer.DidNotReceive().SendEmail(Arg.Any<PremiumRenewalMail>());
+
+        await _mailService.Received(1).SendInvoiceUpcoming(
+            Arg.Is<IEnumerable<string>>(emails => emails.Contains("user@example.com")),
+            Arg.Is<decimal>(amount => amount == invoice.AmountDue / 100M),
+            Arg.Is<DateTime>(dueDate => dueDate == invoice.NextPaymentAttempt.Value),
+            Arg.Is<List<string>>(items => items.Count == invoice.Lines.Data.Count),
+            Arg.Is<bool>(b => b == true));
+    }
+
+    [Fact]
+    public async Task HandleAsync_WhenMilestone2Enabled_AndValidCoupon_SendsPremiumRenewalEmail()
+    {
+        // Arrange
+        var parsedEvent = new Event { Id = "evt_123" };
+        var customerId = "cus_123";
+        var invoice = new Invoice
+        {
+            CustomerId = customerId,
+            AmountDue = 10000,
+            NextPaymentAttempt = DateTime.UtcNow.AddDays(7),
+            Lines = new StripeList<InvoiceLineItem>
+            {
+                Data = [new() { Description = "Test Item" }]
+            }
+        };
+        var subscription = new Subscription
+        {
+            Id = "sub_123",
+            CustomerId = customerId,
+            Items = new StripeList<SubscriptionItem>
+            {
+                Data = [new() { Id = "si_123", Price = new Price { Id = Prices.PremiumAnnually } }]
+            },
+            AutomaticTax = new SubscriptionAutomaticTax { Enabled = false },
+            Customer = new Customer { Id = customerId },
+            Metadata = new Dictionary<string, string>()
+        };
+        var user = new User { Id = _userId, Email = "user@example.com", Premium = true };
+        var plan = new PremiumPlan
+        {
+            Name = "Premium",
+            Available = true,
+            LegacyYear = null,
+            Seat = new Purchasable { Price = 10M, StripePriceId = Prices.PremiumAnnually },
+            Storage = new Purchasable { Price = 4M, StripePriceId = Prices.StoragePlanPersonal }
+        };
+        var customer = new Customer
+        {
+            Id = customerId,
+            Tax = new CustomerTax { AutomaticTax = AutomaticTaxStatus.Supported },
+            Subscriptions = new StripeList<Subscription> { Data = [subscription] }
+        };
+        var coupon = new Coupon
+        {
+            Id = CouponIDs.Milestone2SubscriptionDiscount,
+            PercentOff = 30
+        };
+
+        _stripeEventService.GetInvoice(parsedEvent).Returns(invoice);
+        _stripeFacade.GetCustomer(customerId, Arg.Any<CustomerGetOptions>()).Returns(customer);
+        _stripeEventUtilityService.GetIdsFromMetadata(subscription.Metadata)
+            .Returns(new Tuple<Guid?, Guid?, Guid?>(null, _userId, null));
+        _userRepository.GetByIdAsync(_userId).Returns(user);
+        _pricingClient.GetAvailablePremiumPlan().Returns(plan);
+        _featureService.IsEnabled(FeatureFlagKeys.PM23341_Milestone_2).Returns(true);
+        _stripeFacade.GetCoupon(CouponIDs.Milestone2SubscriptionDiscount).Returns(coupon);
+        _stripeFacade.UpdateSubscription(Arg.Any<string>(), Arg.Any<SubscriptionUpdateOptions>())
+            .Returns(subscription);
+
+        // Act
+        await _sut.HandleAsync(parsedEvent);
+
+        // Assert
+        var expectedDiscountedPrice = plan.Seat.Price * (100 - coupon.PercentOff.Value) / 100;
+        await _mailer.Received(1).SendEmail(
+            Arg.Is<PremiumRenewalMail>(email =>
+                email.ToEmails.Contains("user@example.com") &&
+                email.Subject == "Your Bitwarden Premium renewal is updating" &&
+                email.View.BaseMonthlyRenewalPrice == (plan.Seat.Price / 12).ToString("C", new CultureInfo("en-US")) &&
+                email.View.DiscountAmount == "30%" &&
+                email.View.DiscountedMonthlyRenewalPrice == (expectedDiscountedPrice / 12).ToString("C", new CultureInfo("en-US"))
+            ));
+
+        await _mailService.DidNotReceive().SendInvoiceUpcoming(
+            Arg.Any<IEnumerable<string>>(),
+            Arg.Any<decimal>(),
+            Arg.Any<DateTime>(),
+            Arg.Any<List<string>>(),
+            Arg.Any<bool>());
+    }
+
+    [Fact]
+    public async Task HandleAsync_WhenMilestone2Enabled_AndGetCouponThrowsException_LogsErrorAndSendsTraditionalEmail()
+    {
+        // Arrange
+        var parsedEvent = new Event { Id = "evt_123" };
+        var customerId = "cus_123";
+        var invoice = new Invoice
+        {
+            CustomerId = customerId,
+            AmountDue = 10000,
+            NextPaymentAttempt = DateTime.UtcNow.AddDays(7),
+            Lines = new StripeList<InvoiceLineItem>
+            {
+                Data = [new() { Description = "Test Item" }]
+            }
+        };
+        var subscription = new Subscription
+        {
+            Id = "sub_123",
+            CustomerId = customerId,
+            Items = new StripeList<SubscriptionItem>
+            {
+                Data = [new() { Id = "si_123", Price = new Price { Id = Prices.PremiumAnnually } }]
+            },
+            AutomaticTax = new SubscriptionAutomaticTax { Enabled = false },
+            Customer = new Customer { Id = customerId },
+            Metadata = new Dictionary<string, string>()
+        };
+        var user = new User { Id = _userId, Email = "user@example.com", Premium = true };
+        var plan = new PremiumPlan
+        {
+            Name = "Premium",
+            Available = true,
+            LegacyYear = null,
+            Seat = new Purchasable { Price = 10M, StripePriceId = Prices.PremiumAnnually },
+            Storage = new Purchasable { Price = 4M, StripePriceId = Prices.StoragePlanPersonal }
+        };
+        var customer = new Customer
+        {
+            Id = customerId,
+            Tax = new CustomerTax { AutomaticTax = AutomaticTaxStatus.Supported },
+            Subscriptions = new StripeList<Subscription> { Data = [subscription] }
+        };
+
+        _stripeEventService.GetInvoice(parsedEvent).Returns(invoice);
+        _stripeFacade.GetCustomer(customerId, Arg.Any<CustomerGetOptions>()).Returns(customer);
+        _stripeEventUtilityService.GetIdsFromMetadata(subscription.Metadata)
+            .Returns(new Tuple<Guid?, Guid?, Guid?>(null, _userId, null));
+        _userRepository.GetByIdAsync(_userId).Returns(user);
+        _pricingClient.GetAvailablePremiumPlan().Returns(plan);
+        _featureService.IsEnabled(FeatureFlagKeys.PM23341_Milestone_2).Returns(true);
+        _stripeFacade.GetCoupon(CouponIDs.Milestone2SubscriptionDiscount)
+            .ThrowsAsync(new StripeException("Stripe API error"));
+        _stripeFacade.UpdateSubscription(Arg.Any<string>(), Arg.Any<SubscriptionUpdateOptions>())
+            .Returns(subscription);
+
+        // Act
+        await _sut.HandleAsync(parsedEvent);
+
+        // Assert - Exception is caught, error is logged, and traditional email is sent
+        _logger.Received(1).Log(
+            LogLevel.Error,
+            Arg.Any<EventId>(),
+            Arg.Is<object>(o =>
+                o.ToString().Contains($"Failed to update user's ({user.Id}) subscription price id") &&
+                o.ToString().Contains(parsedEvent.Id)),
+            Arg.Is<Exception>(e => e is StripeException),
+            Arg.Any<Func<object, Exception, string>>());
+
+        await _mailer.DidNotReceive().SendEmail(Arg.Any<PremiumRenewalMail>());
+
+        await _mailService.Received(1).SendInvoiceUpcoming(
+            Arg.Is<IEnumerable<string>>(emails => emails.Contains("user@example.com")),
+            Arg.Is<decimal>(amount => amount == invoice.AmountDue / 100M),
+            Arg.Is<DateTime>(dueDate => dueDate == invoice.NextPaymentAttempt.Value),
+            Arg.Is<List<string>>(items => items.Count == invoice.Lines.Data.Count),
+            Arg.Is<bool>(b => b == true));
+    }
+
+    #endregion
 }