diff --git a/src/WireMock.Net.Abstractions/Models/IDigitalSignature.cs b/src/WireMock.Net.Abstractions/Models/IDigitalSignature.cs
new file mode 100644
index 00000000..843b0018
--- /dev/null
+++ b/src/WireMock.Net.Abstractions/Models/IDigitalSignature.cs
@@ -0,0 +1,41 @@
+// Copyright © WireMock.Net
+
+using System.Threading.Tasks;
+using WireMock.Util;
+
+namespace WireMock.Models;
+
+/// <summary>
+/// A delegate encapsulating logic for fetching or generating a private key.
+/// </summary>
+/// <returns>An async task containing the value of the private key.</returns>
+public delegate Task<string> PrivateKeyCallback();
+
+/// <summary>
+/// A delegate encapsulating logic for fetching or generating a digital signature.
+/// </summary>
+/// <param name="privateKey">The value of the private key returned by <see cref="PrivateKeyCallback"/>.</param>
+/// <param name="bodyData">The body data associated with the request.</param>
+/// <returns>An async task containing the value of the digital signature.</returns>
+public delegate Task<string> DigitalSignatureCallback(string privateKey, IBodyData? bodyData);
+
+/// <summary>
+/// An interface encapsulating logic for generating a digital signature.
+/// </summary>
+public interface IDigitalSignature
+{
+    /// <summary>
+    /// The header name to use for the digital signature.
+    /// </summary>
+    string HeaderName { get; set; }
+
+    /// <summary>
+    /// The callback used to fetch or generate the private key.
+    /// </summary>
+    PrivateKeyCallback PrivateKeyCallback { get; set; }
+
+    /// <summary>
+    /// The callback used to fetch or generate the digital signature.
+    /// </summary>
+    DigitalSignatureCallback DigitalSignatureCallback { get; set; }
+}
\ No newline at end of file
diff --git a/src/WireMock.Net.Abstractions/Models/IWebhookRequest.cs b/src/WireMock.Net.Abstractions/Models/IWebhookRequest.cs
index 5acee5e0..54380e1d 100644
--- a/src/WireMock.Net.Abstractions/Models/IWebhookRequest.cs
+++ b/src/WireMock.Net.Abstractions/Models/IWebhookRequest.cs
@@ -60,4 +60,14 @@ public interface IWebhookRequest
     /// Gets or sets the maximum random delay in milliseconds.
     /// </summary>
     int? MaximumRandomDelay { get; set; }
+
+    /// <summary>
+    /// Gets or sets the value used to determine if digital signatures are generated.
+    /// </summary>
+    bool? UseDigitalSignatures { get; set; }
+
+    /// <summary>
+    /// Gets or sets the values used generate digital signatures.
+    /// </summary>
+    IDigitalSignature[]? DigitalSignatures { get; set; }
 }
\ No newline at end of file
diff --git a/src/WireMock.Net/Http/WebhookSender.cs b/src/WireMock.Net/Http/WebhookSender.cs
index 95947e45..fe7e0288 100644
--- a/src/WireMock.Net/Http/WebhookSender.cs
+++ b/src/WireMock.Net/Http/WebhookSender.cs
@@ -78,6 +78,31 @@ IResponseMessage originalResponseMessage
             webhookRequestUrl = webhookRequest.Url;
         }
 
+        // Add digital signatures to header (if required)
+        if (webhookRequest.UseDigitalSignatures == true)
+        {
+            if (webhookRequest.DigitalSignatures is not null)
+            {
+                foreach (var digitalSignature in webhookRequest.DigitalSignatures)
+                {
+                    var privateKey = await digitalSignature.PrivateKeyCallback();
+                    var signature = await digitalSignature.DigitalSignatureCallback(privateKey, bodyData);
+
+                    // headers may be null here
+                    headers ??= new Dictionary<string, WireMockList<string>>();
+
+                    if (headers.ContainsKey(digitalSignature.HeaderName))
+                    {
+                        headers[digitalSignature.HeaderName].Add(signature);
+                    }
+                    else
+                    {
+                        headers[digitalSignature.HeaderName] = new WireMockList<string>(signature);
+                    }
+                }
+            }
+        }
+
         // Create RequestMessage
         var requestMessage = new RequestMessage(
             new UrlDetails(webhookRequestUrl),
diff --git a/src/WireMock.Net/Models/DigitalSignature.cs b/src/WireMock.Net/Models/DigitalSignature.cs
new file mode 100644
index 00000000..5bec6880
--- /dev/null
+++ b/src/WireMock.Net/Models/DigitalSignature.cs
@@ -0,0 +1,20 @@
+// Copyright © WireMock.Net
+
+using System.Threading.Tasks;
+
+namespace WireMock.Models;
+
+/// <summary>
+/// A class encapsulating logic for generating a digital signature.
+/// </summary>
+public class DigitalSignature : IDigitalSignature
+{
+    /// <inheritdoc/>
+    public string HeaderName { get; set; } = "";
+
+    /// <inheritdoc/>
+    public PrivateKeyCallback PrivateKeyCallback { get; set; } = async () => await Task.FromResult("");
+
+    /// <inheritdoc/>
+    public DigitalSignatureCallback DigitalSignatureCallback { get; set; } = async (privateKey, bodyData) => await Task.FromResult("");
+}
diff --git a/src/WireMock.Net/Models/WebhookRequest.cs b/src/WireMock.Net/Models/WebhookRequest.cs
index 9c6e0978..062618f5 100644
--- a/src/WireMock.Net/Models/WebhookRequest.cs
+++ b/src/WireMock.Net/Models/WebhookRequest.cs
@@ -40,4 +40,10 @@ public class WebhookRequest : IWebhookRequest
 
     /// <inheritdoc />
     public int? MaximumRandomDelay { get; set; }
+
+    /// <inheritdoc />
+    public bool? UseDigitalSignatures { get; set; }
+
+    /// <inheritdoc />
+    public IDigitalSignature[]? DigitalSignatures { get; set; }
 }
\ No newline at end of file