diff --git a/src/NzbDrone.Common/Http/BasicNetworkCredential.cs b/src/NzbDrone.Common/Http/BasicNetworkCredential.cs
new file mode 100644
index 000000000..26710f766
--- /dev/null
+++ b/src/NzbDrone.Common/Http/BasicNetworkCredential.cs
@@ -0,0 +1,12 @@
+using System.Net;
+
+namespace NzbDrone.Common.Http
+{
+    public class BasicNetworkCredential : NetworkCredential
+    {
+        public BasicNetworkCredential(string user, string pass)
+        : base(user, pass)
+        {
+        }
+    }
+}
diff --git a/src/NzbDrone.Common/Http/Dispatchers/ManagedHttpDispatcher.cs b/src/NzbDrone.Common/Http/Dispatchers/ManagedHttpDispatcher.cs
index 1eb490ad6..a539b3b3e 100644
--- a/src/NzbDrone.Common/Http/Dispatchers/ManagedHttpDispatcher.cs
+++ b/src/NzbDrone.Common/Http/Dispatchers/ManagedHttpDispatcher.cs
@@ -2,6 +2,7 @@ using System;
 using System.IO;
 using System.Net;
 using System.Reflection;
+using System.Text;
 using NLog;
 using NLog.Fluent;
 using NzbDrone.Common.EnvironmentInfo;
@@ -52,6 +53,22 @@ namespace NzbDrone.Common.Http.Dispatchers
             webRequest.AllowAutoRedirect = false;
             webRequest.CookieContainer = cookies;
 
+            if (request.Credentials != null)
+            {
+                if (request.Credentials is BasicNetworkCredential nc)
+                {
+                    // Manually set header to avoid initial challenge response
+                    var authInfo = nc.UserName + ":" + nc.Password;
+                    authInfo = Convert.ToBase64String(Encoding.GetEncoding("ISO-8859-1").GetBytes(authInfo));
+                    webRequest.Headers.Add("Authorization", "Basic " + authInfo);
+                }
+                else
+                {
+                    webRequest.PreAuthenticate = true;
+                    webRequest.Credentials = request.Credentials;
+                }
+            }
+
             if (request.RequestTimeout != TimeSpan.Zero)
             {
                 webRequest.Timeout = (int)Math.Ceiling(request.RequestTimeout.TotalMilliseconds);
diff --git a/src/NzbDrone.Common/Http/HttpRequest.cs b/src/NzbDrone.Common/Http/HttpRequest.cs
index 840f4b614..ecb5784af 100644
--- a/src/NzbDrone.Common/Http/HttpRequest.cs
+++ b/src/NzbDrone.Common/Http/HttpRequest.cs
@@ -1,6 +1,7 @@
 using System;
 using System.Collections.Generic;
 using System.IO;
+using System.Net;
 using System.Text;
 using NzbDrone.Common.EnvironmentInfo;
 using NzbDrone.Common.Extensions;
@@ -33,6 +34,7 @@ namespace NzbDrone.Common.Http
         public HttpHeader Headers { get; set; }
         public byte[] ContentData { get; set; }
         public string ContentSummary { get; set; }
+        public ICredentials Credentials { get; set; }
         public bool SuppressHttpError { get; set; }
         public bool UseSimplifiedUserAgent { get; set; }
         public bool AllowAutoRedirect { get; set; }
@@ -80,12 +82,5 @@ namespace NzbDrone.Common.Http
             var encoding = HttpHeader.GetEncodingFromContentType(Headers.ContentType);
             ContentData = encoding.GetBytes(data);
         }
-
-        public void AddBasicAuthentication(string username, string password)
-        {
-            var authInfo = Convert.ToBase64String(Encoding.GetEncoding("ISO-8859-1").GetBytes($"{username}:{password}"));
-
-            Headers.Set("Authorization", "Basic " + authInfo);
-        }
     }
 }
diff --git a/src/NzbDrone.Common/Http/HttpRequestBuilder.cs b/src/NzbDrone.Common/Http/HttpRequestBuilder.cs
index 2e9bf1a5b..ccc3567c6 100644
--- a/src/NzbDrone.Common/Http/HttpRequestBuilder.cs
+++ b/src/NzbDrone.Common/Http/HttpRequestBuilder.cs
@@ -24,10 +24,9 @@ namespace NzbDrone.Common.Http
         public bool ConnectionKeepAlive { get; set; }
         public TimeSpan RateLimit { get; set; }
         public bool LogResponseContent { get; set; }
-        public NetworkCredential NetworkCredential { get; set; }
+        public ICredentials NetworkCredential { get; set; }
         public Dictionary<string, string> Cookies { get; private set; }
         public List<HttpFormData> FormData { get; private set; }
-
         public Action<HttpRequest> PostProcess { get; set; }
 
         public HttpRequestBuilder(string baseUrl)
@@ -105,13 +104,7 @@ namespace NzbDrone.Common.Http
             request.ConnectionKeepAlive = ConnectionKeepAlive;
             request.RateLimit = RateLimit;
             request.LogResponseContent = LogResponseContent;
-
-            if (NetworkCredential != null)
-            {
-                var authInfo = NetworkCredential.UserName + ":" + NetworkCredential.Password;
-                authInfo = Convert.ToBase64String(Encoding.GetEncoding("ISO-8859-1").GetBytes(authInfo));
-                request.Headers.Set("Authorization", "Basic " + authInfo);
-            }
+            request.Credentials = NetworkCredential;
 
             foreach (var header in Headers)
             {
diff --git a/src/NzbDrone.Common/Http/Proxy/ManagedWebProxyFactory.cs b/src/NzbDrone.Common/Http/Proxy/ManagedWebProxyFactory.cs
index ca58fedee..ef3c5950c 100644
--- a/src/NzbDrone.Common/Http/Proxy/ManagedWebProxyFactory.cs
+++ b/src/NzbDrone.Common/Http/Proxy/ManagedWebProxyFactory.cs
@@ -39,7 +39,7 @@ namespace NzbDrone.Common.Http.Proxy
                 case ProxyType.Http:
                     if (proxySettings.Username.IsNotNullOrWhiteSpace() && proxySettings.Password.IsNotNullOrWhiteSpace())
                     {
-                        return new WebProxy(proxySettings.Host + ":" + proxySettings.Port, proxySettings.BypassLocalAddress, proxySettings.BypassListAsArray, new NetworkCredential(proxySettings.Username, proxySettings.Password));
+                        return new WebProxy(proxySettings.Host + ":" + proxySettings.Port, proxySettings.BypassLocalAddress, proxySettings.BypassListAsArray, new BasicNetworkCredential(proxySettings.Username, proxySettings.Password));
                     }
                     else
                     {
diff --git a/src/NzbDrone.Core/Download/Clients/Hadouken/HadoukenProxy.cs b/src/NzbDrone.Core/Download/Clients/Hadouken/HadoukenProxy.cs
index 75917c8d9..fc9a57cd9 100644
--- a/src/NzbDrone.Core/Download/Clients/Hadouken/HadoukenProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/Hadouken/HadoukenProxy.cs
@@ -74,7 +74,7 @@ namespace NzbDrone.Core.Download.Clients.Hadouken
 
             var requestBuilder = new JsonRpcRequestBuilder(baseUrl, method, parameters);
             requestBuilder.LogResponseContent = true;
-            requestBuilder.NetworkCredential = new NetworkCredential(settings.Username, settings.Password);
+            requestBuilder.NetworkCredential = new BasicNetworkCredential(settings.Username, settings.Password);
             requestBuilder.Headers.Add("Accept-Encoding", "gzip,deflate");
 
             var httpRequest = requestBuilder.Build();
diff --git a/src/NzbDrone.Core/Download/Clients/Nzbget/NzbgetProxy.cs b/src/NzbDrone.Core/Download/Clients/Nzbget/NzbgetProxy.cs
index 698e620cc..9e81eeaba 100644
--- a/src/NzbDrone.Core/Download/Clients/Nzbget/NzbgetProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/Nzbget/NzbgetProxy.cs
@@ -229,7 +229,7 @@ namespace NzbDrone.Core.Download.Clients.Nzbget
 
             var requestBuilder = new JsonRpcRequestBuilder(baseUrl, method, parameters);
             requestBuilder.LogResponseContent = true;
-            requestBuilder.NetworkCredential = new NetworkCredential(settings.Username, settings.Password);
+            requestBuilder.NetworkCredential = new BasicNetworkCredential(settings.Username, settings.Password);
 
             var httpRequest = requestBuilder.Build();
 
diff --git a/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrentProxyV1.cs b/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrentProxyV1.cs
index f095f32ee..f225a327d 100644
--- a/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrentProxyV1.cs
+++ b/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrentProxyV1.cs
@@ -261,7 +261,7 @@ namespace NzbDrone.Core.Download.Clients.QBittorrent
             var requestBuilder = new HttpRequestBuilder(settings.UseSsl, settings.Host, settings.Port, settings.UrlBase)
             {
                 LogResponseContent = true,
-                NetworkCredential = new NetworkCredential(settings.Username, settings.Password)
+                NetworkCredential = new BasicNetworkCredential(settings.Username, settings.Password)
             };
             return requestBuilder;
         }
diff --git a/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrentProxyV2.cs b/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrentProxyV2.cs
index d20d15126..a2a3092b3 100644
--- a/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrentProxyV2.cs
+++ b/src/NzbDrone.Core/Download/Clients/QBittorrent/QBittorrentProxyV2.cs
@@ -270,7 +270,7 @@ namespace NzbDrone.Core.Download.Clients.QBittorrent
             var requestBuilder = new HttpRequestBuilder(settings.UseSsl, settings.Host, settings.Port, settings.UrlBase)
             {
                 LogResponseContent = true,
-                NetworkCredential = new NetworkCredential(settings.Username, settings.Password)
+                NetworkCredential = new BasicNetworkCredential(settings.Username, settings.Password)
             };
             return requestBuilder;
         }
diff --git a/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionProxy.cs b/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionProxy.cs
index 945894c6c..bf4c2cfdd 100644
--- a/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/Transmission/TransmissionProxy.cs
@@ -200,7 +200,7 @@ namespace NzbDrone.Core.Download.Clients.Transmission
                 .Accept(HttpAccept.Json);
 
             requestBuilder.LogResponseContent = true;
-            requestBuilder.NetworkCredential = new NetworkCredential(settings.Username, settings.Password);
+            requestBuilder.NetworkCredential = new BasicNetworkCredential(settings.Username, settings.Password);
             requestBuilder.AllowAutoRedirect = false;
 
             return requestBuilder;
diff --git a/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrentProxy.cs b/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrentProxy.cs
index 39f4d2cc2..aa8b40a8f 100644
--- a/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrentProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/rTorrent/RTorrentProxy.cs
@@ -4,6 +4,7 @@ using System.Net;
 using CookComputing.XmlRpc;
 using NLog;
 using NzbDrone.Common.Extensions;
+using NzbDrone.Common.Http;
 
 namespace NzbDrone.Core.Download.Clients.RTorrent
 {
@@ -246,7 +247,7 @@ namespace NzbDrone.Core.Download.Clients.RTorrent
 
             if (!settings.Username.IsNullOrWhiteSpace())
             {
-                client.Credentials = new NetworkCredential(settings.Username, settings.Password);
+                client.Credentials = new BasicNetworkCredential(settings.Username, settings.Password);
             }
 
             return client;
diff --git a/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrentProxy.cs b/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrentProxy.cs
index b50e9b121..f954af748 100644
--- a/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrentProxy.cs
+++ b/src/NzbDrone.Core/Download/Clients/uTorrent/UTorrentProxy.cs
@@ -196,7 +196,7 @@ namespace NzbDrone.Core.Download.Clients.UTorrent
                 .Accept(HttpAccept.Json);
 
             requestBuilder.LogResponseContent = true;
-            requestBuilder.NetworkCredential = new NetworkCredential(settings.Username, settings.Password);
+            requestBuilder.NetworkCredential = new BasicNetworkCredential(settings.Username, settings.Password);
 
             return requestBuilder;
         }
diff --git a/src/NzbDrone.Core/Notifications/Email/EmailService.cs b/src/NzbDrone.Core/Notifications/Email/EmailService.cs
index be1a8fe54..efe26cbbe 100644
--- a/src/NzbDrone.Core/Notifications/Email/EmailService.cs
+++ b/src/NzbDrone.Core/Notifications/Email/EmailService.cs
@@ -1,10 +1,10 @@
 using System;
 using System.Collections.Generic;
 using System.Linq;
-using System.Net;
 using System.Net.Mail;
 using FluentValidation.Results;
 using NLog;
+using NzbDrone.Common.Http;
 
 namespace NzbDrone.Core.Notifications.Email
 {
@@ -44,11 +44,11 @@ namespace NzbDrone.Core.Notifications.Email
                 }
             }
 
-            NetworkCredential credentials = null;
+            BasicNetworkCredential credentials = null;
 
             if (!string.IsNullOrWhiteSpace(settings.Username))
             {
-                credentials = new NetworkCredential(settings.Username, settings.Password);
+                credentials = new BasicNetworkCredential(settings.Username, settings.Password);
             }
 
             try
@@ -63,7 +63,7 @@ namespace NzbDrone.Core.Notifications.Email
             }
         }
 
-        private void Send(MailMessage email, string server, int port, bool ssl, NetworkCredential credentials)
+        private void Send(MailMessage email, string server, int port, bool ssl, BasicNetworkCredential credentials)
         {
             var smtp = new SmtpClient(server, port);
             smtp.EnableSsl = ssl;
diff --git a/src/NzbDrone.Core/Notifications/Webhook/WebhookProxy.cs b/src/NzbDrone.Core/Notifications/Webhook/WebhookProxy.cs
index f7eedec69..6ff768fc2 100644
--- a/src/NzbDrone.Core/Notifications/Webhook/WebhookProxy.cs
+++ b/src/NzbDrone.Core/Notifications/Webhook/WebhookProxy.cs
@@ -1,3 +1,4 @@
+using System.Net;
 using NzbDrone.Common.Extensions;
 using NzbDrone.Common.Http;
 using NzbDrone.Common.Serializer;
@@ -33,7 +34,7 @@ namespace NzbDrone.Core.Notifications.Webhook
 
                 if (settings.Username.IsNotNullOrWhiteSpace() || settings.Password.IsNotNullOrWhiteSpace())
                 {
-                    request.AddBasicAuthentication(settings.Username, settings.Password);
+                    request.Credentials = new BasicNetworkCredential(settings.Username, settings.Password);
                 }
 
                 _httpClient.Execute(request);