diff --git a/src/BirdsiteLive.Common/Regexes/UrlRegexes.cs b/src/BirdsiteLive.Common/Regexes/UrlRegexes.cs
index ea3e5c2..1f2b279 100644
--- a/src/BirdsiteLive.Common/Regexes/UrlRegexes.cs
+++ b/src/BirdsiteLive.Common/Regexes/UrlRegexes.cs
@@ -4,6 +4,6 @@ namespace BirdsiteLive.Common.Regexes
 {
     public class UrlRegexes
     {
-        public static readonly Regex Url = new Regex(@"((http|ftp|https):\/\/[\w\-_]+(\.[\w\-_]+)+([\w\-\.,@?^=%&:/~\+#]*[\w\-\@?^=%&/~\+#])?)");
+        public static readonly Regex Url = new Regex(@"(.?)(((http|ftp|https):\/\/)[\w\-_]+(\.[\w\-_]+)+([\w\-\.,@?^=%&:/~\+#]*[\w\-\@?^=%&/~\+#])?)");
     }
 }
\ No newline at end of file
diff --git a/src/BirdsiteLive.Domain/Tools/StatusExtractor.cs b/src/BirdsiteLive.Domain/Tools/StatusExtractor.cs
index a43ccb0..7df4c0e 100644
--- a/src/BirdsiteLive.Domain/Tools/StatusExtractor.cs
+++ b/src/BirdsiteLive.Domain/Tools/StatusExtractor.cs
@@ -44,11 +44,8 @@ namespace BirdsiteLive.Domain.Tools
             var urlMatch = UrlRegexes.Url.Matches(messageContent);
             foreach (Match m in urlMatch)
             {
-                var url = m.ToString().Replace("\n", string.Empty).Trim();
-
-                var protocol = "https://";
-                if (url.StartsWith("http://")) protocol = "http://";
-                else if (url.StartsWith("ftp://")) protocol = "ftp://";
+                var url = m.Groups[2].ToString();
+                var protocol = m.Groups[3].ToString();
 
                 var truncatedUrl = url.Replace(protocol, string.Empty);
 
@@ -68,7 +65,7 @@ namespace BirdsiteLive.Domain.Tools
                 }
 
                 messageContent = Regex.Replace(messageContent, m.ToString(),
-                    $@" <a href=""{url}"" rel=""nofollow noopener noreferrer"" target=""_blank""><span class=""invisible"">{protocol}</span><span class=""ellipsis"">{firstPart}</span><span class=""invisible"">{secondPart}</span></a>");
+                    $@"{m.Groups[1]}<a href=""{url}"" rel=""nofollow noopener noreferrer"" target=""_blank""><span class=""invisible"">{protocol}</span><span class=""ellipsis"">{firstPart}</span><span class=""invisible"">{secondPart}</span></a>");
             }
 
             // Extract Hashtags
diff --git a/src/Tests/BirdsiteLive.Domain.Tests/Tools/StatusExtractorTests.cs b/src/Tests/BirdsiteLive.Domain.Tests/Tools/StatusExtractorTests.cs
index 924461f..06d8f9a 100644
--- a/src/Tests/BirdsiteLive.Domain.Tests/Tools/StatusExtractorTests.cs
+++ b/src/Tests/BirdsiteLive.Domain.Tests/Tools/StatusExtractorTests.cs
@@ -136,7 +136,7 @@ namespace BirdsiteLive.Domain.Tests.Tools
         }
 
         [TestMethod]
-        public void Extract_MultiUrls__Test()
+        public void Extract_MultiUrls_Test()
         {
             #region Stubs
             var message = $"https://t.co/L8BpyHgg25 Bla!{Environment.NewLine}https://www.eff.org/deeplinks/2020/07/pact-act-not-solution-problem-harmful-online-content";
@@ -160,6 +160,63 @@ namespace BirdsiteLive.Domain.Tests.Tools
             #endregion
         }
 
+        [TestMethod]
+        public void Extract_SmallUrl_Test()
+        {
+            #region Stubs
+            var message = @"🚀 test http://GOV.UK date 🎉 data http://GOV.UK woopsi.";
+            #endregion
+
+            #region Mocks
+            var logger = new Mock<ILogger<StatusExtractor>>();
+            #endregion
+
+            var service = new StatusExtractor(_settings, logger.Object);
+            var result = service.Extract(message);
+
+            #region Validations
+            Assert.AreEqual(@"🚀 test <a href=""http://GOV.UK"" rel=""nofollow noopener noreferrer"" target=""_blank""><span class=""invisible"">http://</span><span class=""ellipsis"">GOV.UK</span><span class=""invisible""></span></a> date 🎉 data <a href=""http://GOV.UK"" rel=""nofollow noopener noreferrer"" target=""_blank""><span class=""invisible"">http://</span><span class=""ellipsis"">GOV.UK</span><span class=""invisible""></span></a> woopsi.", result.content);
+            #endregion
+        }
+
+        [TestMethod]
+        public void Extract_SmallUrl_2_Test()
+        {
+            #region Stubs
+            var message = @"🚀http://GOV.UK";
+            #endregion
+
+            #region Mocks
+            var logger = new Mock<ILogger<StatusExtractor>>();
+            #endregion
+
+            var service = new StatusExtractor(_settings, logger.Object);
+            var result = service.Extract(message);
+
+            #region Validations
+            Assert.AreEqual(@"🚀<a href=""http://GOV.UK"" rel=""nofollow noopener noreferrer"" target=""_blank""><span class=""invisible"">http://</span><span class=""ellipsis"">GOV.UK</span><span class=""invisible""></span></a>", result.content);
+            #endregion
+        }
+
+        [TestMethod]
+        public void Extract_SmallUrl_3_Test()
+        {
+            #region Stubs
+            var message = @"🚀http://GOV.UK.";
+            #endregion
+
+            #region Mocks
+            var logger = new Mock<ILogger<StatusExtractor>>();
+            #endregion
+
+            var service = new StatusExtractor(_settings, logger.Object);
+            var result = service.Extract(message);
+
+            #region Validations
+            Assert.AreEqual(@"🚀<a href=""http://GOV.UK"" rel=""nofollow noopener noreferrer"" target=""_blank""><span class=""invisible"">http://</span><span class=""ellipsis"">GOV.UK</span><span class=""invisible""></span></a>.", result.content);
+            #endregion
+        }
+
         [TestMethod]
         public void Extract_SingleHashTag_Test()
         {