diff --git a/src/Billing/Billing.csproj b/src/Billing/Billing.csproj
index 18c627c5de..d6eb2b4411 100644
--- a/src/Billing/Billing.csproj
+++ b/src/Billing/Billing.csproj
@@ -11,6 +11,7 @@
     <ProjectReference Include="..\Core\Core.csproj" />
   </ItemGroup>
   <ItemGroup>
+    <PackageReference Include="MarkDig" Version="0.41.3" />
     <PackageReference Include="Swashbuckle.AspNetCore" Version="9.0.2" />
   </ItemGroup>
 
diff --git a/src/Billing/BillingSettings.cs b/src/Billing/BillingSettings.cs
index 5609879eeb..32630e4a4a 100644
--- a/src/Billing/BillingSettings.cs
+++ b/src/Billing/BillingSettings.cs
@@ -34,6 +34,10 @@ public class BillingSettings
         public virtual string Region { get; set; }
         public virtual string UserFieldName { get; set; }
         public virtual string OrgFieldName { get; set; }
+
+        public virtual bool RemoveNewlinesInReplies { get; set; } = false;
+        public virtual string AutoReplyGreeting { get; set; } = string.Empty;
+        public virtual string AutoReplySalutation { get; set; } = string.Empty;
     }
 
     public class OnyxSettings
diff --git a/src/Billing/Controllers/FreshdeskController.cs b/src/Billing/Controllers/FreshdeskController.cs
index a854d2d49f..66d4f47d92 100644
--- a/src/Billing/Controllers/FreshdeskController.cs
+++ b/src/Billing/Controllers/FreshdeskController.cs
@@ -11,6 +11,7 @@ using Bit.Billing.Models;
 using Bit.Core.Repositories;
 using Bit.Core.Settings;
 using Bit.Core.Utilities;
+using Markdig;
 using Microsoft.AspNetCore.Mvc;
 using Microsoft.Extensions.Options;
 
@@ -184,6 +185,52 @@ public class FreshdeskController : Controller
         return Ok();
     }
 
+    [HttpPost("webhook-onyx-ai-reply")]
+    public async Task<IActionResult> PostWebhookOnyxAiReply([FromQuery, Required] string key,
+        [FromBody, Required] FreshdeskOnyxAiWebhookModel model)
+    {
+        // NOTE:
+        // at this time, this endpoint is a duplicate of `webhook-onyx-ai`
+        // eventually, we will merge both endpoints into one webhook for Freshdesk
+
+        // ensure that the key is from Freshdesk
+        if (!IsValidRequestFromFreshdesk(key) || !ModelState.IsValid)
+        {
+            return new BadRequestResult();
+        }
+
+        // if there is no description, then we don't send anything to onyx
+        if (string.IsNullOrEmpty(model.TicketDescriptionText.Trim()))
+        {
+            return Ok();
+        }
+
+        // create the onyx `answer-with-citation` request
+        var onyxRequestModel = new OnyxAnswerWithCitationRequestModel(model.TicketDescriptionText, _billingSettings.Onyx.PersonaId);
+        var onyxRequest = new HttpRequestMessage(HttpMethod.Post,
+                            string.Format("{0}/query/answer-with-citation", _billingSettings.Onyx.BaseUrl))
+        {
+            Content = JsonContent.Create(onyxRequestModel, mediaType: new MediaTypeHeaderValue("application/json")),
+        };
+        var (_, onyxJsonResponse) = await CallOnyxApi<OnyxAnswerWithCitationResponseModel>(onyxRequest);
+
+        // the CallOnyxApi will return a null if we have an error response
+        if (onyxJsonResponse?.Answer == null || !string.IsNullOrEmpty(onyxJsonResponse?.ErrorMsg))
+        {
+            _logger.LogWarning("Error getting answer from Onyx AI. Freshdesk model: {model}\r\n Onyx query {query}\r\nresponse: {response}. ",
+                    JsonSerializer.Serialize(model),
+                    JsonSerializer.Serialize(onyxRequestModel),
+                    JsonSerializer.Serialize(onyxJsonResponse));
+
+            return Ok(); // return ok so we don't retry
+        }
+
+        // add the reply to the ticket
+        await AddReplyToTicketAsync(onyxJsonResponse.Answer, model.TicketId);
+
+        return Ok();
+    }
+
     private bool IsValidRequestFromFreshdesk(string key)
     {
         if (string.IsNullOrWhiteSpace(key)
@@ -238,6 +285,53 @@ public class FreshdeskController : Controller
         }
     }
 
+    private async Task AddReplyToTicketAsync(string note, string ticketId)
+    {
+        // if there is no content, then we don't need to add a note
+        if (string.IsNullOrWhiteSpace(note))
+        {
+            return;
+        }
+
+        // convert note from markdown to html
+        var htmlNote = note;
+        try
+        {
+            var pipeline = new MarkdownPipelineBuilder().UseAdvancedExtensions().Build();
+            htmlNote = Markdig.Markdown.ToHtml(note, pipeline);
+        }
+        catch (Exception ex)
+        {
+            _logger.LogError(ex, "Error converting markdown to HTML for Freshdesk reply. Ticket Id: {0}. Note: {1}",
+                            ticketId, note);
+            htmlNote = note; // fallback to the original note
+        }
+
+        // clear out any new lines that Freshdesk doesn't like
+        if (_billingSettings.FreshDesk.RemoveNewlinesInReplies)
+        {
+            htmlNote = htmlNote.Replace(Environment.NewLine, string.Empty);
+        }
+
+        var replyBody = new FreshdeskReplyRequestModel
+        {
+            Body = $"{_billingSettings.FreshDesk.AutoReplyGreeting}{htmlNote}{_billingSettings.FreshDesk.AutoReplySalutation}",
+        };
+
+        var replyRequest = new HttpRequestMessage(HttpMethod.Post,
+                    string.Format("https://bitwarden.freshdesk.com/api/v2/tickets/{0}/reply", ticketId))
+        {
+            Content = JsonContent.Create(replyBody),
+        };
+
+        var addReplyResponse = await CallFreshdeskApiAsync(replyRequest);
+        if (addReplyResponse.StatusCode != System.Net.HttpStatusCode.Created)
+        {
+            _logger.LogError("Error adding reply to Freshdesk ticket. Ticket Id: {0}. Status: {1}",
+                            ticketId, addReplyResponse.ToString());
+        }
+    }
+
     private async Task<HttpResponseMessage> CallFreshdeskApiAsync(HttpRequestMessage request, int retriedCount = 0)
     {
         try
diff --git a/src/Billing/Models/FreshdeskReplyRequestModel.cs b/src/Billing/Models/FreshdeskReplyRequestModel.cs
new file mode 100644
index 0000000000..3927039769
--- /dev/null
+++ b/src/Billing/Models/FreshdeskReplyRequestModel.cs
@@ -0,0 +1,9 @@
+using System.Text.Json.Serialization;
+
+namespace Bit.Billing.Models;
+
+public class FreshdeskReplyRequestModel
+{
+    [JsonPropertyName("body")]
+    public required string Body { get; set; }
+}
diff --git a/src/Billing/appsettings.json b/src/Billing/appsettings.json
index aae25dde0b..0074b5aafe 100644
--- a/src/Billing/appsettings.json
+++ b/src/Billing/appsettings.json
@@ -72,7 +72,10 @@
       "webhookKey": "SECRET",
       "region": "US",
       "userFieldName": "cf_user",
-      "orgFieldName": "cf_org"
+      "orgFieldName": "cf_org",
+      "removeNewlinesInReplies": true,
+      "autoReplyGreeting": "<b>Greetings,</b><br /><br />Thank you for contacting Bitwarden. The reply below was generated by our AI agent based on your message:<br /><br />",
+      "autoReplySalutation": "<br /><br />If this response doesn’t fully address your question, simply reply to this email and a member of our Customer Success team will be happy to assist you further.<br /><p><b>Best Regards,</b><br />The Bitwarden Customer Success Team</p>"
     },
     "onyx": {
       "apiKey": "SECRET",