diff --git a/API.Tests/Parser/ParserTest.cs b/API.Tests/Parser/ParserTest.cs
index ff1b4dc71..662e4c462 100644
--- a/API.Tests/Parser/ParserTest.cs
+++ b/API.Tests/Parser/ParserTest.cs
@@ -179,6 +179,7 @@ namespace API.Tests.Parser
         [InlineData(".test.jpg", false)]
         [InlineData("!test.jpg", true)]
         [InlineData("test.webp", true)]
+        [InlineData("test.gif", true)]
         public void IsImageTest(string filename, bool expected)
         {
             Assert.Equal(expected, IsImage(filename));
diff --git a/API.Tests/Services/Test Data/ArchiveService/Archives/macos_native.zip b/API.Tests/Services/Test Data/ArchiveService/Archives/macos_native.zip
index a84f32b35..c47021fd2 100644
Binary files a/API.Tests/Services/Test Data/ArchiveService/Archives/macos_native.zip and b/API.Tests/Services/Test Data/ArchiveService/Archives/macos_native.zip differ
diff --git a/API.Tests/Services/Test Data/ArchiveService/CoverImages/macos_native.zip b/API.Tests/Services/Test Data/ArchiveService/CoverImages/macos_native.zip
index a84f32b35..c47021fd2 100644
Binary files a/API.Tests/Services/Test Data/ArchiveService/CoverImages/macos_native.zip and b/API.Tests/Services/Test Data/ArchiveService/CoverImages/macos_native.zip differ
diff --git a/API/Parser/Parser.cs b/API/Parser/Parser.cs
index bc4fb2f8a..8d2dcf817 100644
--- a/API/Parser/Parser.cs
+++ b/API/Parser/Parser.cs
@@ -12,7 +12,7 @@ namespace API.Parser
         public const string DefaultVolume = "0";
         private static readonly TimeSpan RegexTimeout = TimeSpan.FromMilliseconds(500);
 
-        public const string ImageFileExtensions = @"^(\.png|\.jpeg|\.jpg|\.webp)";
+        public const string ImageFileExtensions = @"^(\.png|\.jpeg|\.jpg|\.webp|\.gif)";
         public const string ArchiveFileExtensions = @"\.cbz|\.zip|\.rar|\.cbr|\.tar.gz|\.7zip|\.7z|\.cb7|\.cbt";
         public const string BookFileExtensions = @"\.epub|\.pdf";
         public const string MacOsMetadataFileStartsWith = @"._";
diff --git a/UI/Web/src/app/events-widget/events-widget.component.scss b/UI/Web/src/app/events-widget/events-widget.component.scss
index 6a2070e78..7f9534400 100644
--- a/UI/Web/src/app/events-widget/events-widget.component.scss
+++ b/UI/Web/src/app/events-widget/events-widget.component.scss
@@ -21,6 +21,8 @@
         max-width: 250px;
         padding: 0px;
         box-shadow: 0px 0px 12px rgb(0 0 0 / 75%);
+        max-height: calc(100vh - 60px);
+        overflow-y: auto;
     }
 
     .popover {