diff --git a/WireMock.Net Solution.sln b/WireMock.Net Solution.sln
index a1000602..0438f830 100644
--- a/WireMock.Net Solution.sln	
+++ b/WireMock.Net Solution.sln	
@@ -128,6 +128,8 @@ Project("{9A19103F-16F7-4668-BE54-9A1E7A4F7556}") = "WireMock.Net.TestWebApplica
 EndProject
 Project("{9A19103F-16F7-4668-BE54-9A1E7A4F7556}") = "WireMock.Net.Middleware.Tests", "test\WireMock.Net.Middleware.Tests\WireMock.Net.Middleware.Tests.csproj", "{A5FEF4F7-7DA2-4962-89A8-16BA942886E5}"
 EndProject
+Project("{FAE04EC0-301F-11D3-BF4B-00C04F79EFBC}") = "WireMock.Net.AwesomeAssertions", "src\WireMock.Net.AwesomeAssertions\WireMock.Net.AwesomeAssertions.csproj", "{7753670F-7C7F-44BF-8BC7-08325588E60C}"
+EndProject
 Global
 	GlobalSection(SolutionConfigurationPlatforms) = preSolution
 		Debug|Any CPU = Debug|Any CPU
@@ -302,6 +304,10 @@ Global
 		{A5FEF4F7-7DA2-4962-89A8-16BA942886E5}.Debug|Any CPU.Build.0 = Debug|Any CPU
 		{A5FEF4F7-7DA2-4962-89A8-16BA942886E5}.Release|Any CPU.ActiveCfg = Release|Any CPU
 		{A5FEF4F7-7DA2-4962-89A8-16BA942886E5}.Release|Any CPU.Build.0 = Release|Any CPU
+		{7753670F-7C7F-44BF-8BC7-08325588E60C}.Debug|Any CPU.ActiveCfg = Debug|Any CPU
+		{7753670F-7C7F-44BF-8BC7-08325588E60C}.Debug|Any CPU.Build.0 = Debug|Any CPU
+		{7753670F-7C7F-44BF-8BC7-08325588E60C}.Release|Any CPU.ActiveCfg = Release|Any CPU
+		{7753670F-7C7F-44BF-8BC7-08325588E60C}.Release|Any CPU.Build.0 = Release|Any CPU
 	EndGlobalSection
 	GlobalSection(SolutionProperties) = preSolution
 		HideSolutionNode = FALSE
@@ -351,6 +357,7 @@ Global
 		{B6269AAC-170A-4346-8B9A-579DED3D9A13} = {8F890C6F-9ACC-438D-928A-AD61CDA862F2}
 		{6B30AA9F-DA04-4EB5-B03C-45A8EF272ECE} = {0BB8B634-407A-4610-A91F-11586990767A}
 		{A5FEF4F7-7DA2-4962-89A8-16BA942886E5} = {0BB8B634-407A-4610-A91F-11586990767A}
+		{7753670F-7C7F-44BF-8BC7-08325588E60C} = {8F890C6F-9ACC-438D-928A-AD61CDA862F2}
 	EndGlobalSection
 	GlobalSection(ExtensibilityGlobals) = postSolution
 		SolutionGuid = {DC539027-9852-430C-B19F-FD035D018458}
diff --git a/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockANumberOfCallsAssertions.cs b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockANumberOfCallsAssertions.cs
new file mode 100644
index 00000000..65dc2713
--- /dev/null
+++ b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockANumberOfCallsAssertions.cs
@@ -0,0 +1,40 @@
+// Copyright © WireMock.Net
+
+using Stef.Validation;
+using WireMock.Server;
+
+// ReSharper disable once CheckNamespace
+namespace WireMock.FluentAssertions;
+
+/// <summary>
+/// Provides assertion methods to verify the number of calls made to a WireMock server.
+/// This class is used in the context of FluentAssertions.
+/// </summary>
+public class WireMockANumberOfCallsAssertions
+{
+    private readonly IWireMockServer _server;
+    private readonly int _callsCount;
+    private readonly AssertionChain _chain;
+
+    /// <summary>
+    /// Initializes a new instance of the <see cref="WireMockANumberOfCallsAssertions"/> class.
+    /// </summary>
+    /// <param name="server">The WireMock server to assert against.</param>
+    /// <param name="callsCount">The expected number of calls to assert.</param>
+    /// <param name="chain">The assertion chain</param>
+    public WireMockANumberOfCallsAssertions(IWireMockServer server, int callsCount, AssertionChain chain)
+    {
+        _server = Guard.NotNull(server);
+        _callsCount = callsCount;
+        _chain = chain;
+    }
+
+    /// <summary>
+    /// Returns an instance of <see cref="WireMockAssertions"/> which can be used to assert the expected number of calls.
+    /// </summary>
+    /// <returns>A <see cref="WireMockAssertions"/> instance for asserting the number of calls to the server.</returns>
+    public WireMockAssertions Calls()
+    {
+        return new WireMockAssertions(_server, _callsCount, _chain);
+    }
+}
\ No newline at end of file
diff --git a/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.AtUrl.cs b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.AtUrl.cs
new file mode 100644
index 00000000..87d8fb0f
--- /dev/null
+++ b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.AtUrl.cs
@@ -0,0 +1,83 @@
+// Copyright © WireMock.Net
+
+using WireMock.Extensions;
+using WireMock.Matchers;
+
+// ReSharper disable once CheckNamespace
+namespace WireMock.FluentAssertions;
+
+#pragma warning disable CS1591
+public partial class WireMockAssertions
+{
+    [CustomAssertion]
+    public AndWhichConstraint<WireMockAssertions, string> AtAbsoluteUrl(string absoluteUrl, string because = "", params object[] becauseArgs)
+    {
+        _ = AtAbsoluteUrl(new ExactMatcher(true, absoluteUrl), because, becauseArgs);
+
+        return new AndWhichConstraint<WireMockAssertions, string>(this, absoluteUrl);
+    }
+
+    [CustomAssertion]
+    public AndWhichConstraint<WireMockAssertions, IStringMatcher> AtAbsoluteUrl(IStringMatcher absoluteUrlMatcher, string because = "", params object[] becauseArgs)
+    {
+        var (filter, condition) = BuildFilterAndCondition(request => absoluteUrlMatcher.IsPerfectMatch(request.AbsoluteUrl));
+
+        var absoluteUrl = absoluteUrlMatcher.GetPatterns().FirstOrDefault().GetPattern();
+
+        _chain
+            .BecauseOf(because, becauseArgs)
+            .Given(() => RequestMessages)
+            .ForCondition(requests => CallsCount == 0 || requests.Any())
+            .FailWith(
+                "Expected {context:wiremockserver} to have been called at address matching the absolute url {0}{reason}, but no calls were made.",
+                absoluteUrl
+            )
+            .Then
+            .ForCondition(condition)
+            .FailWith(
+                "Expected {context:wiremockserver} to have been called at address matching the absolute url {0}{reason}, but didn't find it among the calls to {1}.",
+                _ => absoluteUrl,
+                requests => requests.Select(request => request.AbsoluteUrl)
+            );
+
+        FilterRequestMessages(filter);
+
+        return new AndWhichConstraint<WireMockAssertions, IStringMatcher>(this, absoluteUrlMatcher);
+    }
+
+    [CustomAssertion]
+    public AndWhichConstraint<WireMockAssertions, string> AtUrl(string url, string because = "", params object[] becauseArgs)
+    {
+        _ = AtUrl(new ExactMatcher(true, url), because, becauseArgs);
+
+        return new AndWhichConstraint<WireMockAssertions, string>(this, url);
+    }
+
+    [CustomAssertion]
+    public AndWhichConstraint<WireMockAssertions, IStringMatcher> AtUrl(IStringMatcher urlMatcher, string because = "", params object[] becauseArgs)
+    {
+        var (filter, condition) = BuildFilterAndCondition(request => urlMatcher.IsPerfectMatch(request.Url));
+
+        var url = urlMatcher.GetPatterns().FirstOrDefault().GetPattern();
+
+        _chain
+            .BecauseOf(because, becauseArgs)
+            .Given(() => RequestMessages)
+            .ForCondition(requests => CallsCount == 0 || requests.Any())
+            .FailWith(
+                "Expected {context:wiremockserver} to have been called at address matching the url {0}{reason}, but no calls were made.",
+                url
+            )
+            .Then
+            .ForCondition(condition)
+            .FailWith(
+                "Expected {context:wiremockserver} to have been called at address matching the url {0}{reason}, but didn't find it among the calls to {1}.",
+                _ => url,
+                requests => requests.Select(request => request.Url)
+            );
+
+        FilterRequestMessages(filter);
+
+        return new AndWhichConstraint<WireMockAssertions, IStringMatcher>(this, urlMatcher);
+    }
+}
\ No newline at end of file
diff --git a/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.FromClientIP.cs b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.FromClientIP.cs
new file mode 100644
index 00000000..9c0977ed
--- /dev/null
+++ b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.FromClientIP.cs
@@ -0,0 +1,35 @@
+// Copyright © WireMock.Net
+
+#pragma warning disable CS1591
+using System;
+
+// ReSharper disable once CheckNamespace
+namespace WireMock.FluentAssertions;
+
+public partial class WireMockAssertions
+{
+    [CustomAssertion]
+    public AndWhichConstraint<WireMockAssertions, string> FromClientIP(string clientIP, string because = "", params object[] becauseArgs)
+    {
+        var (filter, condition) = BuildFilterAndCondition(request => string.Equals(request.ClientIP, clientIP, StringComparison.OrdinalIgnoreCase));
+
+        _chain
+            .BecauseOf(because, becauseArgs)
+            .Given(() => RequestMessages)
+            .ForCondition(requests => CallsCount == 0 || requests.Any())
+            .FailWith(
+                "Expected {context:wiremockserver} to have been called from client IP {0}{reason}, but no calls were made.",
+                clientIP
+            )
+            .Then
+            .ForCondition(condition)
+            .FailWith(
+                "Expected {context:wiremockserver} to have been called from client IP {0}{reason}, but didn't find it among the calls from IP(s) {1}.",
+                _ => clientIP, requests => requests.Select(request => request.ClientIP)
+            );
+
+        FilterRequestMessages(filter);
+
+        return new AndWhichConstraint<WireMockAssertions, string>(this, clientIP);
+    }
+}
\ No newline at end of file
diff --git a/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.UsingMethod.cs b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.UsingMethod.cs
new file mode 100644
index 00000000..62301d31
--- /dev/null
+++ b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.UsingMethod.cs
@@ -0,0 +1,81 @@
+// Copyright © WireMock.Net
+
+#pragma warning disable CS1591
+using System;
+using WireMock.Constants;
+
+// ReSharper disable once CheckNamespace
+namespace WireMock.FluentAssertions;
+
+public partial class WireMockAssertions
+{
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> UsingConnect(string because = "", params object[] becauseArgs)
+        => UsingMethod(HttpRequestMethod.CONNECT, because, becauseArgs);
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> UsingDelete(string because = "", params object[] becauseArgs)
+        => UsingMethod(HttpRequestMethod.DELETE, because, becauseArgs);
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> UsingGet(string because = "", params object[] becauseArgs)
+        => UsingMethod(HttpRequestMethod.GET, because, becauseArgs);
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> UsingHead(string because = "", params object[] becauseArgs)
+        => UsingMethod(HttpRequestMethod.HEAD, because, becauseArgs);
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> UsingOptions(string because = "", params object[] becauseArgs)
+        => UsingMethod(HttpRequestMethod.OPTIONS, because, becauseArgs);
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> UsingPost(string because = "", params object[] becauseArgs)
+        => UsingMethod(HttpRequestMethod.POST, because, becauseArgs);
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> UsingPatch(string because = "", params object[] becauseArgs)
+        => UsingMethod(HttpRequestMethod.PATCH, because, becauseArgs);
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> UsingPut(string because = "", params object[] becauseArgs)
+        => UsingMethod(HttpRequestMethod.PUT, because, becauseArgs);
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> UsingTrace(string because = "", params object[] becauseArgs)
+        => UsingMethod(HttpRequestMethod.TRACE, because, becauseArgs);
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> UsingAnyMethod(string because = "", params object[] becauseArgs)
+        => UsingMethod(Any, because, becauseArgs);
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> UsingMethod(string method, string because = "", params object[] becauseArgs)
+    {
+        var any = method == Any;
+        Func<IRequestMessage, bool> predicate = request => (any && !string.IsNullOrEmpty(request.Method)) ||
+                                                           string.Equals(request.Method, method, StringComparison.OrdinalIgnoreCase);
+
+        var (filter, condition) = BuildFilterAndCondition(predicate);
+
+        _chain
+            .BecauseOf(because, becauseArgs)
+            .Given(() => RequestMessages)
+            .ForCondition(requests => CallsCount == 0 || requests.Any())
+            .FailWith(
+                "Expected {context:wiremockserver} to have been called using method {0}{reason}, but no calls were made.",
+                method
+            )
+            .Then
+            .ForCondition(condition)
+            .FailWith(
+                "Expected {context:wiremockserver} to have been called using method {0}{reason}, but didn't find it among the methods {1}.",
+                _ => method,
+                requests => requests.Select(request => request.Method)
+            );
+
+        FilterRequestMessages(filter);
+
+        return new AndConstraint<WireMockAssertions>(this);
+    }
+}
\ No newline at end of file
diff --git a/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.WithBody.cs b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.WithBody.cs
new file mode 100644
index 00000000..bdd04a42
--- /dev/null
+++ b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.WithBody.cs
@@ -0,0 +1,147 @@
+// Copyright © WireMock.Net
+
+#pragma warning disable CS1591
+using System;
+using System.Collections.Generic;
+using AnyOfTypes;
+using Newtonsoft.Json;
+using Newtonsoft.Json.Linq;
+using WireMock.Extensions;
+using WireMock.Matchers;
+using WireMock.Models;
+
+// ReSharper disable once CheckNamespace
+namespace WireMock.FluentAssertions;
+
+public partial class WireMockAssertions
+{
+    private const string MessageFormatNoCalls = "Expected {context:wiremockserver} to have been called using body {0}{reason}, but no calls were made.";
+    private const string MessageFormat = "Expected {context:wiremockserver} to have been called using body {0}{reason}, but didn't find it among the body/bodies {1}.";
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> WithBody(string body, string because = "", params object[] becauseArgs)
+    {
+        return WithBody(new WildcardMatcher(body), because, becauseArgs);
+    }
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> WithBody(IStringMatcher matcher, string because = "", params object[] becauseArgs)
+    {
+        var (filter, condition) = BuildFilterAndCondition(r => r.Body, matcher);
+
+        return ExecuteAssertionWithBodyStringMatcher(matcher, because, becauseArgs, condition, filter, r => r.Body);
+    }
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> WithBodyAsJson(object body, string because = "", params object[] becauseArgs)
+    {
+        return WithBodyAsJson(new JsonMatcher(body), because, becauseArgs);
+    }
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> WithBodyAsJson(string body, string because = "", params object[] becauseArgs)
+    {
+        return WithBodyAsJson(new JsonMatcher(body), because, becauseArgs);
+    }
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> WithBodyAsJson(IObjectMatcher matcher, string because = "", params object[] becauseArgs)
+    {
+        var (filter, condition) = BuildFilterAndCondition(r => r.BodyAsJson, matcher);
+
+        return ExecuteAssertionWithBodyAsIObjectMatcher(matcher, because, becauseArgs, condition, filter, r => r.BodyAsJson);
+    }
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> WithBodyAsBytes(byte[] body, string because = "", params object[] becauseArgs)
+    {
+        return WithBodyAsBytes(new ExactObjectMatcher(body), because, becauseArgs);
+    }
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> WithBodyAsBytes(ExactObjectMatcher matcher, string because = "", params object[] becauseArgs)
+    {
+        var (filter, condition) = BuildFilterAndCondition(r => r.BodyAsBytes, matcher);
+
+        return ExecuteAssertionWithBodyAsIObjectMatcher(matcher, because, becauseArgs, condition, filter, r => r.BodyAsBytes);
+    }
+
+    private AndConstraint<WireMockAssertions> ExecuteAssertionWithBodyStringMatcher(
+        IStringMatcher matcher,
+        string because,
+        object[] becauseArgs,
+        Func<IReadOnlyList<IRequestMessage>, bool> condition,
+        Func<IReadOnlyList<IRequestMessage>, IReadOnlyList<IRequestMessage>> filter,
+        Func<IRequestMessage, object?> expression
+    )
+    {
+        _chain
+            .BecauseOf(because, becauseArgs)
+            .Given(() => RequestMessages)
+            .ForCondition(requests => CallsCount == 0 || requests.Any())
+            .FailWith(
+                MessageFormatNoCalls,
+                FormatBody(matcher.GetPatterns())
+            )
+            .Then
+            .ForCondition(condition)
+            .FailWith(
+                MessageFormat,
+                _ => FormatBody(matcher.GetPatterns()),
+                requests => FormatBodies(requests.Select(expression))
+            );
+
+        FilterRequestMessages(filter);
+
+        return new AndConstraint<WireMockAssertions>(this);
+    }
+
+    private AndConstraint<WireMockAssertions> ExecuteAssertionWithBodyAsIObjectMatcher(
+        IObjectMatcher matcher,
+        string because,
+        object[] becauseArgs,
+        Func<IReadOnlyList<IRequestMessage>, bool> condition,
+        Func<IReadOnlyList<IRequestMessage>, IReadOnlyList<IRequestMessage>> filter,
+        Func<IRequestMessage, object?> expression
+    )
+    {
+        _chain
+            .BecauseOf(because, becauseArgs)
+            .Given(() => RequestMessages)
+            .ForCondition(requests => CallsCount == 0 || requests.Any())
+            .FailWith(
+                MessageFormatNoCalls,
+                FormatBody(matcher.Value)
+            )
+            .Then
+            .ForCondition(condition)
+            .FailWith(
+                MessageFormat,
+                _ => FormatBody(matcher.Value),
+                requests => FormatBodies(requests.Select(expression))
+            );
+
+        FilterRequestMessages(filter);
+
+        return new AndConstraint<WireMockAssertions>(this);
+    }
+
+    private static string? FormatBody(object? body)
+    {
+        return body switch
+        {
+            null => null,
+            string str => str,
+            AnyOf<string, StringPattern>[] stringPatterns => FormatBodies(stringPatterns.Select(p => p.GetPattern())),
+            byte[] bytes => $"byte[{bytes.Length}] {{...}}",
+            JToken jToken => jToken.ToString(Formatting.None),
+            _ => JToken.FromObject(body).ToString(Formatting.None)
+        };
+    }
+
+    private static string? FormatBodies(IEnumerable<object?> bodies)
+    {
+        var valueAsArray = bodies as object[] ?? bodies.ToArray();
+        return valueAsArray.Length == 1 ? FormatBody(valueAsArray[0]) : $"[ {string.Join(", ", valueAsArray.Select(FormatBody))} ]";
+    }
+}
\ No newline at end of file
diff --git a/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.WithHeader.cs b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.WithHeader.cs
new file mode 100644
index 00000000..d5642759
--- /dev/null
+++ b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.WithHeader.cs
@@ -0,0 +1,157 @@
+// Copyright © WireMock.Net
+
+#pragma warning disable CS1591
+
+// ReSharper disable once CheckNamespace
+namespace WireMock.FluentAssertions;
+
+public partial class WireMockAssertions
+{
+    [CustomAssertion]
+    public AndWhichConstraint<WireMockAssertions, string> WitHeaderKey(string expectedKey, string because = "", params object[] becauseArgs)
+    {
+        var (filter, condition) = BuildFilterAndCondition(request =>
+        {
+            return request.Headers?.Any(h => h.Key == expectedKey) == true;
+        });
+
+        _chain
+            .BecauseOf(because, becauseArgs)
+            .Given(() => RequestMessages)
+            .ForCondition(requests => CallsCount == 0 || requests.Any())
+            .FailWith(
+                "Expected {context:wiremockserver} to have been called with Header {0}{reason}.",
+                expectedKey
+            )
+            .Then
+            .ForCondition(condition)
+            .FailWith(
+                "Expected {context:wiremockserver} to have been called with Header {0}{reason}, but didn't find it among the calls with Header(s) {1}.",
+                _ => expectedKey,
+                requests => requests.Select(request => request.Headers)
+            );
+
+        FilterRequestMessages(filter);
+
+        return new AndWhichConstraint<WireMockAssertions, string>(this, expectedKey);
+    }
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> WithHeader(string expectedKey, string value, string because = "", params object[] becauseArgs)
+        => WithHeader(expectedKey, new[] { value }, because, becauseArgs);
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> WithHeader(string expectedKey, string[] expectedValues, string because = "", params object[] becauseArgs)
+    {
+        var (filter, condition) = BuildFilterAndCondition(request =>
+        {
+            var headers = request.Headers?.ToArray() ?? [];
+
+            var matchingHeaderValues = headers.Where(h => h.Key == expectedKey).SelectMany(h => h.Value.ToArray()).ToArray();
+
+            if (expectedValues.Length == 1 && matchingHeaderValues.Length == 1)
+            {
+                return matchingHeaderValues[0] == expectedValues[0];
+            }
+
+            var trimmedHeaderValues = string.Join(",", matchingHeaderValues.Select(x => x)).Split(',').Select(x => x.Trim()).ToArray();
+            return expectedValues.Any(trimmedHeaderValues.Contains);
+        });
+
+        _chain
+            .BecauseOf(because, becauseArgs)
+            .Given(() => RequestMessages)
+            .ForCondition(requests => CallsCount == 0 || requests.Any())
+            .FailWith(
+                "Expected {context:wiremockserver} to have been called with Header {0} and Values {1}{reason}.",
+                expectedKey,
+                expectedValues
+            )
+            .Then
+            .ForCondition(condition)
+            .FailWith(
+                "Expected {context:wiremockserver} to have been called with Header {0} and Values {1}{reason}, but didn't find it among the calls with Header(s) {2}.",
+                _ => expectedKey,
+                _ => expectedValues,
+                requests => requests.Select(request => request.Headers)
+            );
+
+        FilterRequestMessages(filter);
+
+        return new AndConstraint<WireMockAssertions>(this);
+    }
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> WithoutHeaderKey(string unexpectedKey, string because = "", params object[] becauseArgs)
+    {
+        var (filter, condition) = BuildFilterAndCondition(request =>
+        {
+            return request.Headers?.Any(h => h.Key == unexpectedKey) != true;
+        });
+
+        _chain
+            .BecauseOf(because, becauseArgs)
+            .Given(() => RequestMessages)
+            .ForCondition(requests => CallsCount == 0 || requests.Any())
+            .FailWith(
+                "Expected {context:wiremockserver} not to have been called with Header {0}{reason}.",
+                unexpectedKey
+            )
+            .Then
+            .ForCondition(condition)
+            .FailWith(
+                "Expected {context:wiremockserver} not to have been called with Header {0}{reason}, but found it among the calls with Header(s) {1}.",
+                _ => unexpectedKey,
+                requests => requests.Select(request => request.Headers)
+            );
+
+        FilterRequestMessages(filter);
+
+        return new AndConstraint<WireMockAssertions>(this);
+    }
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> WithoutHeader(string unexpectedKey, string value, string because = "", params object[] becauseArgs)
+        => WithoutHeader(unexpectedKey, new[] { value }, because, becauseArgs);
+
+    [CustomAssertion]
+    public AndConstraint<WireMockAssertions> WithoutHeader(string unexpectedKey, string[] expectedValues, string because = "", params object[] becauseArgs)
+    {
+        var (filter, condition) = BuildFilterAndCondition(request =>
+        {
+            var headers = request.Headers?.ToArray() ?? [];
+
+            var matchingHeaderValues = headers.Where(h => h.Key == unexpectedKey).SelectMany(h => h.Value.ToArray()).ToArray();
+
+            if (expectedValues.Length == 1 && matchingHeaderValues.Length == 1)
+            {
+                return matchingHeaderValues[0] != expectedValues[0];
+            }
+
+            var trimmedHeaderValues = string.Join(",", matchingHeaderValues.Select(x => x)).Split(',').Select(x => x.Trim()).ToArray();
+            return !expectedValues.Any(trimmedHeaderValues.Contains);
+        });
+
+        _chain
+            .BecauseOf(because, becauseArgs)
+            .Given(() => RequestMessages)
+            .ForCondition(requests => CallsCount == 0 || requests.Any())
+            .FailWith(
+                "Expected {context:wiremockserver} not to have been called with Header {0} and Values {1}{reason}.",
+                unexpectedKey,
+                expectedValues
+            )
+            .Then
+            .ForCondition(condition)
+            .FailWith(
+                "Expected {context:wiremockserver} not to have been called with Header {0} and Values {1}{reason}, but found it among the calls with Header(s) {2}.",
+                _ => unexpectedKey,
+                _ => expectedValues,
+                requests => requests.Select(request => request.Headers)
+            );
+
+        FilterRequestMessages(filter);
+
+        return new AndConstraint<WireMockAssertions>(this);
+    }
+}
\ No newline at end of file
diff --git a/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.WithProxy.cs b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.WithProxy.cs
new file mode 100644
index 00000000..6d51b3fd
--- /dev/null
+++ b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.WithProxy.cs
@@ -0,0 +1,36 @@
+// Copyright © WireMock.Net
+
+#pragma warning disable CS1591
+using System;
+
+// ReSharper disable once CheckNamespace
+namespace WireMock.FluentAssertions;
+
+public partial class WireMockAssertions
+{
+    [CustomAssertion]
+    public AndWhichConstraint<WireMockAssertions, string> WithProxyUrl(string proxyUrl, string because = "", params object[] becauseArgs)
+    {
+        var (filter, condition) = BuildFilterAndCondition(request => string.Equals(request.ProxyUrl, proxyUrl, StringComparison.OrdinalIgnoreCase));
+
+        _chain
+            .BecauseOf(because, becauseArgs)
+            .Given(() => RequestMessages)
+            .ForCondition(requests => CallsCount == 0 || requests.Any())
+            .FailWith(
+                "Expected {context:wiremockserver} to have been called with proxy url {0}{reason}, but no calls were made.",
+                proxyUrl
+            )
+            .Then
+            .ForCondition(condition)
+            .FailWith(
+                "Expected {context:wiremockserver} to have been called with proxy url {0}{reason}, but didn't find it among the calls with {1}.",
+                _ => proxyUrl,
+                requests => requests.Select(request => request.ProxyUrl)
+            );
+
+        FilterRequestMessages(filter);
+
+        return new AndWhichConstraint<WireMockAssertions, string>(this, proxyUrl);
+    }
+}
\ No newline at end of file
diff --git a/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.cs b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.cs
new file mode 100644
index 00000000..ca7a4194
--- /dev/null
+++ b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockAssertions.cs
@@ -0,0 +1,48 @@
+// Copyright © WireMock.Net
+
+#pragma warning disable CS1591
+using System;
+using System.Collections.Generic;
+using WireMock.Matchers;
+using WireMock.Server;
+
+// ReSharper disable once CheckNamespace
+namespace WireMock.FluentAssertions;
+
+public partial class WireMockAssertions
+{
+    public const string Any = "*";
+
+    public int? CallsCount { get; }
+    public IReadOnlyList<IRequestMessage> RequestMessages { get; private set; }
+    private readonly AssertionChain _chain;
+
+    public WireMockAssertions(IWireMockServer subject, int? callsCount, AssertionChain chain)
+    {
+        CallsCount = callsCount;
+        RequestMessages = subject.LogEntries.Select(logEntry => logEntry.RequestMessage).ToList();
+        _chain = chain;
+    }
+
+    public (Func<IReadOnlyList<IRequestMessage>, IReadOnlyList<IRequestMessage>> Filter, Func<IReadOnlyList<IRequestMessage>, bool> Condition) BuildFilterAndCondition(Func<IRequestMessage, bool> predicate)
+    {
+        Func<IReadOnlyList<IRequestMessage>, IReadOnlyList<IRequestMessage>> filter = requests => requests.Where(predicate).ToList();
+
+        return (filter, requests => (CallsCount is null && filter(requests).Any()) || CallsCount == filter(requests).Count);
+    }
+
+    public (Func<IReadOnlyList<IRequestMessage>, IReadOnlyList<IRequestMessage>> Filter, Func<IReadOnlyList<IRequestMessage>, bool> Condition) BuildFilterAndCondition(Func<IRequestMessage, string?> expression, IStringMatcher matcher)
+    {
+        return BuildFilterAndCondition(r => matcher.IsMatch(expression(r)).IsPerfect());
+    }
+
+    public (Func<IReadOnlyList<IRequestMessage>, IReadOnlyList<IRequestMessage>> Filter, Func<IReadOnlyList<IRequestMessage>, bool> Condition) BuildFilterAndCondition(Func<IRequestMessage, object?> expression, IObjectMatcher matcher)
+    {
+        return BuildFilterAndCondition(r => matcher.IsMatch(expression(r)).IsPerfect());
+    }
+
+    public void FilterRequestMessages(Func<IReadOnlyList<IRequestMessage>, IReadOnlyList<IRequestMessage>> filter)
+    {
+        RequestMessages = filter(RequestMessages).ToList();
+    }
+}
\ No newline at end of file
diff --git a/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockReceivedAssertions.cs b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockReceivedAssertions.cs
new file mode 100644
index 00000000..b2043fe4
--- /dev/null
+++ b/src/WireMock.Net.AwesomeAssertions/Assertions/WireMockReceivedAssertions.cs
@@ -0,0 +1,56 @@
+// Copyright © WireMock.Net
+
+using FluentAssertions.Primitives;
+using WireMock.Server;
+
+// ReSharper disable once CheckNamespace
+namespace WireMock.FluentAssertions;
+
+/// <summary>
+/// Contains a number of methods to assert that the <see cref="IWireMockServer"/> is in the expected state.
+/// </summary>
+public class WireMockReceivedAssertions : ReferenceTypeAssertions<IWireMockServer, WireMockReceivedAssertions>
+{
+    private readonly AssertionChain _chain;
+
+    /// <summary>
+    /// Create a WireMockReceivedAssertions.
+    /// </summary>
+    /// <param name="server">The <see cref="IWireMockServer"/>.</param>
+    /// <param name="chain">The assertion chain</param>
+    public WireMockReceivedAssertions(IWireMockServer server, AssertionChain chain) : base(server, chain)
+    {
+        _chain = chain;
+    }
+
+    /// <summary>
+    /// Asserts if <see cref="IWireMockServer"/> has received no calls.
+    /// </summary>
+    /// <returns><see cref="WireMockAssertions"/></returns>
+    public WireMockAssertions HaveReceivedNoCalls()
+    {
+        return new WireMockAssertions(Subject, 0, _chain);
+    }
+
+    /// <summary>
+    /// Asserts if <see cref="IWireMockServer"/> has received a call.
+    /// </summary>
+    /// <returns><see cref="WireMockAssertions"/></returns>
+    public WireMockAssertions HaveReceivedACall()
+    {
+        return new WireMockAssertions(Subject, null, _chain);
+    }
+
+    /// <summary>
+    /// Asserts if <see cref="IWireMockServer"/> has received n-calls.
+    /// </summary>
+    /// <param name="callsCount"></param>
+    /// <returns><see cref="WireMockANumberOfCallsAssertions"/></returns>
+    public WireMockANumberOfCallsAssertions HaveReceived(int callsCount)
+    {
+        return new WireMockANumberOfCallsAssertions(Subject, callsCount, _chain);
+    }
+
+    /// <inheritdoc />
+    protected override string Identifier => "wiremockserver";
+}
\ No newline at end of file
diff --git a/src/WireMock.Net.AwesomeAssertions/Extensions/WireMockExtensions.cs b/src/WireMock.Net.AwesomeAssertions/Extensions/WireMockExtensions.cs
new file mode 100644
index 00000000..73e2eac7
--- /dev/null
+++ b/src/WireMock.Net.AwesomeAssertions/Extensions/WireMockExtensions.cs
@@ -0,0 +1,23 @@
+// Copyright © WireMock.Net
+
+using WireMock.Server;
+
+// ReSharper disable once CheckNamespace
+namespace WireMock.FluentAssertions
+{
+    /// <summary>
+    /// Contains extension methods for custom assertions in unit tests.
+    /// </summary>
+    public static class WireMockExtensions
+    {
+        /// <summary>
+        /// Returns a <see cref="WireMockReceivedAssertions"/> object that can be used to assert the current <see cref="IWireMockServer"/>.
+        /// </summary>
+        /// <param name="instance">The WireMockServer</param>
+        /// <returns><see cref="WireMockReceivedAssertions"/></returns>
+        public static WireMockReceivedAssertions Should(this IWireMockServer instance)
+        {
+            return new WireMockReceivedAssertions(instance, AssertionChain.GetOrCreate());
+        }
+    }
+}
\ No newline at end of file
diff --git a/src/WireMock.Net.AwesomeAssertions/Usings.cs b/src/WireMock.Net.AwesomeAssertions/Usings.cs
new file mode 100644
index 00000000..82139e4f
--- /dev/null
+++ b/src/WireMock.Net.AwesomeAssertions/Usings.cs
@@ -0,0 +1,5 @@
+// Copyright © WireMock.Net
+
+global using System.Linq;
+global using FluentAssertions;
+global using FluentAssertions.Execution;
\ No newline at end of file
diff --git a/src/WireMock.Net.AwesomeAssertions/WireMock.Net.AwesomeAssertions.csproj b/src/WireMock.Net.AwesomeAssertions/WireMock.Net.AwesomeAssertions.csproj
new file mode 100644
index 00000000..5bebc1a1
--- /dev/null
+++ b/src/WireMock.Net.AwesomeAssertions/WireMock.Net.AwesomeAssertions.csproj
@@ -0,0 +1,39 @@
+<Project Sdk="Microsoft.NET.Sdk">
+
+    <PropertyGroup>
+        <Description>AwesomeAssertions extensions for WireMock.Net</Description>
+        <AssemblyTitle>WireMock.Net.AwesomeAssertions</AssemblyTitle>
+        <Authors>Francesco Venturoli;Mahmoud Ali;Stef Heyenrath</Authors>
+        <TargetFrameworks>net47;netstandard2.0;netstandard2.1</TargetFrameworks>
+        <GenerateDocumentationFile>true</GenerateDocumentationFile>
+        <AssemblyName>WireMock.Net.AwesomeAssertions</AssemblyName>
+        <PackageId>WireMock.Net.AwesomeAssertions</PackageId>
+        <PackageTags>wiremock;AwesomeAssertions;UnitTest;Assert;Assertions</PackageTags>
+        <RootNamespace>WireMock.AwesomeAssertions</RootNamespace>
+        <ProjectGuid>{9565C395-FC5D-4CB1-8381-EC3D9DA74779}</ProjectGuid>
+        <PublishRepositoryUrl>true</PublishRepositoryUrl>
+        <AllowedOutputExtensionsInPackageBuildOutputFolder>$(AllowedOutputExtensionsInPackageBuildOutputFolder);.pdb</AllowedOutputExtensionsInPackageBuildOutputFolder>
+        <EmbedUntrackedSources>true</EmbedUntrackedSources>
+        <AutoGenerateBindingRedirects>true</AutoGenerateBindingRedirects>
+        <GenerateBindingRedirectsOutputType>true</GenerateBindingRedirectsOutputType>
+        <CodeAnalysisRuleSet>../WireMock.Net/WireMock.Net.ruleset</CodeAnalysisRuleSet>
+        <SignAssembly>true</SignAssembly>
+        <AssemblyOriginatorKeyFile>../WireMock.Net/WireMock.Net.snk</AssemblyOriginatorKeyFile>
+        <!--<DelaySign>true</DelaySign>-->
+        <PublicSign Condition=" '$(OS)' != 'Windows_NT' ">true</PublicSign>
+        <PackageLicenseExpression>MIT</PackageLicenseExpression>
+    </PropertyGroup>
+
+    <PropertyGroup Condition=" '$(Configuration)' == 'Release' ">
+        <GeneratePackageOnBuild>true</GeneratePackageOnBuild>
+    </PropertyGroup>
+
+    <ItemGroup>
+        <PackageReference Include="AwesomeAssertions" Version="8.1.0" />
+    </ItemGroup>
+
+    <ItemGroup>
+        <ProjectReference Include="..\WireMock.Net\WireMock.Net.csproj" />
+    </ItemGroup>
+
+</Project>
\ No newline at end of file