diff --git a/src/Core/Billing/Models/Mail/TrialInititaionVerifyEmail.cs b/src/Core/Billing/Models/Mail/TrialInititaionVerifyEmail.cs
index df08296083..33b9578d0e 100644
--- a/src/Core/Billing/Models/Mail/TrialInititaionVerifyEmail.cs
+++ b/src/Core/Billing/Models/Mail/TrialInititaionVerifyEmail.cs
@@ -5,6 +5,7 @@ namespace Bit.Core.Billing.Models.Mail;
 
 public class TrialInitiationVerifyEmail : RegisterVerifyEmail
 {
+    public bool IsExistingUser { get; set; }
     /// <summary>
     /// See comment on <see cref="RegisterVerifyEmail"/>.<see cref="RegisterVerifyEmail.Url"/>
     /// </summary>
@@ -26,8 +27,18 @@ public class TrialInitiationVerifyEmail : RegisterVerifyEmail
     /// Currently we only support one product type at a time, despite Product being a collection.
     /// If we receive both PasswordManager and SecretsManager, we'll send the user to the PM trial route
     /// </summary>
-    private string Route =>
-        Product.Any(p => p == ProductType.PasswordManager)
-            ? "trial-initiation"
-            : "secrets-manager-trial-initiation";
+    private string Route
+    {
+        get
+        {
+            if (IsExistingUser)
+            {
+                return "create-organization";
+            }
+
+            return Product.Any(p => p == ProductType.PasswordManager)
+                ? "trial-initiation"
+                : "secrets-manager-trial-initiation";
+        }
+    }
 }
diff --git a/src/Core/Billing/TrialInitiation/Registration/Implementations/SendTrialInitiationEmailForRegistrationCommand.cs b/src/Core/Billing/TrialInitiation/Registration/Implementations/SendTrialInitiationEmailForRegistrationCommand.cs
index 6657be085e..385d7ebbd6 100644
--- a/src/Core/Billing/TrialInitiation/Registration/Implementations/SendTrialInitiationEmailForRegistrationCommand.cs
+++ b/src/Core/Billing/TrialInitiation/Registration/Implementations/SendTrialInitiationEmailForRegistrationCommand.cs
@@ -43,10 +43,7 @@ public class SendTrialInitiationEmailForRegistrationCommand(
 
         await PerformConstantTimeOperationsAsync();
 
-        if (!userExists)
-        {
-            await mailService.SendTrialInitiationSignupEmailAsync(email, token, productTier, products);
-        }
+        await mailService.SendTrialInitiationSignupEmailAsync(userExists, email, token, productTier, products);
 
         return null;
     }
diff --git a/src/Core/Services/IMailService.cs b/src/Core/Services/IMailService.cs
index 77914c0188..92d05ddb7d 100644
--- a/src/Core/Services/IMailService.cs
+++ b/src/Core/Services/IMailService.cs
@@ -14,6 +14,7 @@ public interface IMailService
     Task SendVerifyEmailEmailAsync(string email, Guid userId, string token);
     Task SendRegistrationVerificationEmailAsync(string email, string token);
     Task SendTrialInitiationSignupEmailAsync(
+        bool isExistingUser,
         string email,
         string token,
         ProductTierType productTier,
diff --git a/src/Core/Services/Implementations/HandlebarsMailService.cs b/src/Core/Services/Implementations/HandlebarsMailService.cs
index 630c5b0bf0..d18a29b13a 100644
--- a/src/Core/Services/Implementations/HandlebarsMailService.cs
+++ b/src/Core/Services/Implementations/HandlebarsMailService.cs
@@ -74,6 +74,7 @@ public class HandlebarsMailService : IMailService
     }
 
     public async Task SendTrialInitiationSignupEmailAsync(
+        bool isExistingUser,
         string email,
         string token,
         ProductTierType productTier,
@@ -82,6 +83,7 @@ public class HandlebarsMailService : IMailService
         var message = CreateDefaultMessage("Verify your email", email);
         var model = new TrialInitiationVerifyEmail
         {
+            IsExistingUser = isExistingUser,
             Token = WebUtility.UrlEncode(token),
             Email = WebUtility.UrlEncode(email),
             WebVaultUrl = _globalSettings.BaseServiceUri.VaultWithHash,
diff --git a/src/Core/Services/NoopImplementations/NoopMailService.cs b/src/Core/Services/NoopImplementations/NoopMailService.cs
index 13914ddd86..d6b330294d 100644
--- a/src/Core/Services/NoopImplementations/NoopMailService.cs
+++ b/src/Core/Services/NoopImplementations/NoopMailService.cs
@@ -26,6 +26,7 @@ public class NoopMailService : IMailService
     }
 
     public Task SendTrialInitiationSignupEmailAsync(
+        bool isExistingUser,
         string email,
         string token,
         ProductTierType productTier,