diff --git a/src/NzbDrone.Common.Test/Http/HttpClientFixture.cs b/src/NzbDrone.Common.Test/Http/HttpClientFixture.cs
index fa02134fd..756d4ce58 100644
--- a/src/NzbDrone.Common.Test/Http/HttpClientFixture.cs
+++ b/src/NzbDrone.Common.Test/Http/HttpClientFixture.cs
@@ -131,6 +131,18 @@ namespace NzbDrone.Common.Test.Http
             response.Content.Should().NotBeNullOrWhiteSpace();
         }
 
+        [Test]
+        public void should_throw_timeout_request()
+        {
+            var request = new HttpRequest($"https://{_httpBinHost}/delay/10");
+
+            request.RequestTimeout = new TimeSpan(0, 0, 5);
+
+            Assert.ThrowsAsync<WebException>(async () => await Subject.ExecuteAsync(request));
+
+            ExceptionVerification.ExpectedErrors(0);
+        }
+
         [Test]
         public async Task should_execute_https_get()
         {
diff --git a/src/NzbDrone.Common/Http/Dispatchers/ManagedHttpDispatcher.cs b/src/NzbDrone.Common/Http/Dispatchers/ManagedHttpDispatcher.cs
index 732c4fbe4..1d47c57a2 100644
--- a/src/NzbDrone.Common/Http/Dispatchers/ManagedHttpDispatcher.cs
+++ b/src/NzbDrone.Common/Http/Dispatchers/ManagedHttpDispatcher.cs
@@ -102,31 +102,38 @@ namespace NzbDrone.Common.Http.Dispatchers
 
             var httpClient = GetClient(request.Url);
 
-            using var responseMessage = await httpClient.SendAsync(requestMessage, HttpCompletionOption.ResponseHeadersRead, cts.Token);
+            try
             {
-                byte[] data = null;
-
-                try
+                using var responseMessage = await httpClient.SendAsync(requestMessage, HttpCompletionOption.ResponseHeadersRead, cts.Token);
                 {
-                    if (request.ResponseStream != null && responseMessage.StatusCode == HttpStatusCode.OK)
+                    byte[] data = null;
+
+                    try
                     {
-                        await responseMessage.Content.CopyToAsync(request.ResponseStream, null, cts.Token);
+                        if (request.ResponseStream != null && responseMessage.StatusCode == HttpStatusCode.OK)
+                        {
+                            await responseMessage.Content.CopyToAsync(request.ResponseStream, null, cts.Token);
+                        }
+                        else
+                        {
+                            data = responseMessage.Content.ReadAsByteArrayAsync(cts.Token).GetAwaiter().GetResult();
+                        }
                     }
-                    else
+                    catch (Exception ex)
                     {
-                        data = responseMessage.Content.ReadAsByteArrayAsync(cts.Token).GetAwaiter().GetResult();
+                        throw new WebException("Failed to read complete http response", ex, WebExceptionStatus.ReceiveFailure, null);
                     }
-                }
-                catch (Exception ex)
-                {
-                    throw new WebException("Failed to read complete http response", ex, WebExceptionStatus.ReceiveFailure, null);
-                }
 
-                var headers = responseMessage.Headers.ToNameValueCollection();
+                    var headers = responseMessage.Headers.ToNameValueCollection();
 
-                headers.Add(responseMessage.Content.Headers.ToNameValueCollection());
+                    headers.Add(responseMessage.Content.Headers.ToNameValueCollection());
 
-                return new HttpResponse(request, new HttpHeader(headers), data, responseMessage.StatusCode, responseMessage.Version);
+                    return new HttpResponse(request, new HttpHeader(headers), data, responseMessage.StatusCode, responseMessage.Version);
+                }
+            }
+            catch (OperationCanceledException ex) when (cts.IsCancellationRequested)
+            {
+                throw new WebException("Http request timed out", ex.InnerException, WebExceptionStatus.Timeout, null);
             }
         }