diff --git a/src/NzbDrone.Common/Http/Proxy/IHttpProxySettingsProvider.cs b/src/NzbDrone.Common/Http/Proxy/IHttpProxySettingsProvider.cs
index a288a46c4..bb5909395 100644
--- a/src/NzbDrone.Common/Http/Proxy/IHttpProxySettingsProvider.cs
+++ b/src/NzbDrone.Common/Http/Proxy/IHttpProxySettingsProvider.cs
@@ -3,5 +3,6 @@ namespace NzbDrone.Common.Http.Proxy
     public interface IHttpProxySettingsProvider
     {
         HttpProxySettings GetProxySettings(HttpRequest request);
+        HttpProxySettings GetProxySettings();
     }
 }
diff --git a/src/NzbDrone.Core/Http/HttpProxySettingsProvider.cs b/src/NzbDrone.Core/Http/HttpProxySettingsProvider.cs
index 6e5a23e07..6c335abae 100644
--- a/src/NzbDrone.Core/Http/HttpProxySettingsProvider.cs
+++ b/src/NzbDrone.Core/Http/HttpProxySettingsProvider.cs
@@ -17,18 +17,9 @@ namespace NzbDrone.Core.Http
 
         public HttpProxySettings GetProxySettings(HttpRequest request)
         {
-            if (!_configService.ProxyEnabled)
-            {
+            var proxySettings = GetProxySettings();
+            if (proxySettings == null)
                 return null;
-            }
-            
-            var proxySettings = new HttpProxySettings(_configService.ProxyType,
-                                _configService.ProxyHostname,
-                                _configService.ProxyPort,
-                                _configService.ProxyBypassFilter,
-                                _configService.ProxyBypassLocalAddresses,
-                                _configService.ProxyUsername,
-                                _configService.ProxyPassword);
 
             if (ShouldProxyBeBypassed(proxySettings, request.Url))
             {
@@ -38,6 +29,22 @@ namespace NzbDrone.Core.Http
             return proxySettings;
         }
 
+        public HttpProxySettings GetProxySettings()
+        {
+            if (!_configService.ProxyEnabled)
+            {
+                return null;
+            }
+
+            return new HttpProxySettings(_configService.ProxyType,
+                                _configService.ProxyHostname,
+                                _configService.ProxyPort,
+                                _configService.ProxyBypassFilter,
+                                _configService.ProxyBypassLocalAddresses,
+                                _configService.ProxyUsername,
+                                _configService.ProxyPassword);
+        }
+
         public bool ShouldProxyBeBypassed(HttpProxySettings proxySettings, HttpUri url)
         {
             //We are utilising the WebProxy implementation here to save us having to reimplement it. This way we use Microsofts implementation
diff --git a/src/NzbDrone.Core/Notifications/Boxcar/BoxcarProxy.cs b/src/NzbDrone.Core/Notifications/Boxcar/BoxcarProxy.cs
index d4028d595..2d61b7467 100644
--- a/src/NzbDrone.Core/Notifications/Boxcar/BoxcarProxy.cs
+++ b/src/NzbDrone.Core/Notifications/Boxcar/BoxcarProxy.cs
@@ -16,11 +16,13 @@ namespace NzbDrone.Core.Notifications.Boxcar
 
     public class BoxcarProxy : IBoxcarProxy
     {
+        private readonly IRestClientFactory _restClientFactory;
         private readonly Logger _logger;
         private const string URL = "https://new.boxcar.io/api/notifications";
 
-        public BoxcarProxy(Logger logger)
+        public BoxcarProxy(IRestClientFactory restClientFactory, Logger logger)
         {
+            _restClientFactory = restClientFactory;
             _logger = logger;
         }
 
@@ -71,7 +73,7 @@ namespace NzbDrone.Core.Notifications.Boxcar
         {
             try
             {
-                var client = RestClientFactory.BuildClient(URL);
+                var client = _restClientFactory.BuildClient(URL);
 
                 request.AddParameter("user_credentials", settings.Token);
                 request.AddParameter("notification[title]", title);
diff --git a/src/NzbDrone.Core/Notifications/Gotify/GotifyProxy.cs b/src/NzbDrone.Core/Notifications/Gotify/GotifyProxy.cs
index b14b530d3..3aed74304 100644
--- a/src/NzbDrone.Core/Notifications/Gotify/GotifyProxy.cs
+++ b/src/NzbDrone.Core/Notifications/Gotify/GotifyProxy.cs
@@ -10,9 +10,16 @@ namespace NzbDrone.Core.Notifications.Gotify
 
     public class GotifyProxy : IGotifyProxy
     {
+        private readonly IRestClientFactory _restClientFactory;
+
+        public GotifyProxy(IRestClientFactory restClientFactory)
+        {
+            _restClientFactory = restClientFactory;
+        }
+
         public void SendNotification(string title, string message, GotifySettings settings)
         {
-            var client = RestClientFactory.BuildClient(settings.Server);
+            var client = _restClientFactory.BuildClient(settings.Server);
             var request = new RestRequest("message", Method.POST);
 
             request.AddQueryParameter("token", settings.AppToken);
diff --git a/src/NzbDrone.Core/Notifications/Join/JoinProxy.cs b/src/NzbDrone.Core/Notifications/Join/JoinProxy.cs
index c8d8bed6c..37da514be 100644
--- a/src/NzbDrone.Core/Notifications/Join/JoinProxy.cs
+++ b/src/NzbDrone.Core/Notifications/Join/JoinProxy.cs
@@ -16,11 +16,13 @@ namespace NzbDrone.Core.Notifications.Join
 
     public class JoinProxy : IJoinProxy
     {
+        private readonly IRestClientFactory _restClientFactory;
         private readonly Logger _logger;
         private const string URL = "https://joinjoaomgcd.appspot.com/_ah/api/messaging/v1/sendPush?";
 
-        public JoinProxy(Logger logger)
+        public JoinProxy(IRestClientFactory restClientFactory, Logger logger)
         {
+            _restClientFactory = restClientFactory;
             _logger = logger;
         }
 
@@ -49,7 +51,7 @@ namespace NzbDrone.Core.Notifications.Join
                 SendNotification(title, body, settings);
                 return null;
             }
-            catch(JoinInvalidDeviceException ex)
+            catch (JoinInvalidDeviceException ex)
             {
                 _logger.Error(ex, "Unable to send test Join message. Invalid Device IDs supplied.");
                 return new ValidationFailure("DeviceIds", "Device IDs appear invalid.");
@@ -59,7 +61,7 @@ namespace NzbDrone.Core.Notifications.Join
                 _logger.Error(ex, "Unable to send test Join message.");
                 return new ValidationFailure("ApiKey", ex.Message);
             }
-            catch(RestException ex)
+            catch (RestException ex)
             {
                 _logger.Error(ex, "Unable to send test Join message. Server connection failed.");
                 return new ValidationFailure("ApiKey", "Unable to connect to Join API. Please try again later.");
@@ -74,7 +76,7 @@ namespace NzbDrone.Core.Notifications.Join
         private void SendNotification(string title, string message, RestRequest request, JoinSettings settings)
         {
 
-            var client = RestClientFactory.BuildClient(URL);
+            var client = _restClientFactory.BuildClient(URL);
 
             if (settings.DeviceNames.IsNotNullOrWhiteSpace())
             {
@@ -88,7 +90,7 @@ namespace NzbDrone.Core.Notifications.Join
             {
                 request.AddParameter("deviceId", "group.all");
             }
-                
+
             request.AddParameter("apikey", settings.ApiKey);
             request.AddParameter("title", title);
             request.AddParameter("text", message);
diff --git a/src/NzbDrone.Core/Notifications/PushBullet/PushBulletProxy.cs b/src/NzbDrone.Core/Notifications/PushBullet/PushBulletProxy.cs
index dcc94a116..d916225e0 100644
--- a/src/NzbDrone.Core/Notifications/PushBullet/PushBulletProxy.cs
+++ b/src/NzbDrone.Core/Notifications/PushBullet/PushBulletProxy.cs
@@ -21,12 +21,14 @@ namespace NzbDrone.Core.Notifications.PushBullet
 
     public class PushBulletProxy : IPushBulletProxy
     {
+        private readonly IRestClientFactory _restClientFactory;
         private readonly Logger _logger;
         private const string PUSH_URL = "https://api.pushbullet.com/v2/pushes";
         private const string DEVICE_URL = "https://api.pushbullet.com/v2/devices";
 
-        public PushBulletProxy(Logger logger)
+        public PushBulletProxy(IRestClientFactory restClientFactory, Logger logger)
         {
+            _restClientFactory = restClientFactory;
             _logger = logger;
         }
 
@@ -96,7 +98,7 @@ namespace NzbDrone.Core.Notifications.PushBullet
         {
             try
             {
-                var client = RestClientFactory.BuildClient(DEVICE_URL);
+                var client = _restClientFactory.BuildClient(DEVICE_URL);
                 var request = new RestRequest(Method.GET);
 
                 client.Authenticator = new HttpBasicAuthenticator(settings.ApiKey, string.Empty);
@@ -175,7 +177,7 @@ namespace NzbDrone.Core.Notifications.PushBullet
         {
             try
             {
-                var client = RestClientFactory.BuildClient(PUSH_URL);
+                var client = _restClientFactory.BuildClient(PUSH_URL);
 
                 request.AddParameter("type", "note");
                 request.AddParameter("title", title);
diff --git a/src/NzbDrone.Core/Notifications/Pushover/PushoverProxy.cs b/src/NzbDrone.Core/Notifications/Pushover/PushoverProxy.cs
index d032220eb..81139377a 100644
--- a/src/NzbDrone.Core/Notifications/Pushover/PushoverProxy.cs
+++ b/src/NzbDrone.Core/Notifications/Pushover/PushoverProxy.cs
@@ -15,17 +15,19 @@ namespace NzbDrone.Core.Notifications.Pushover
 
     public class PushoverProxy : IPushoverProxy
     {
+        private readonly IRestClientFactory _restClientFactory;
         private readonly Logger _logger;
         private const string URL = "https://api.pushover.net/1/messages.json";
 
-        public PushoverProxy(Logger logger)
+        public PushoverProxy(IRestClientFactory restClientFactory, Logger logger)
         {
+            _restClientFactory = restClientFactory;
             _logger = logger;
         }
 
         public void SendNotification(string title, string message, PushoverSettings settings)
         {
-            var client = RestClientFactory.BuildClient(URL);
+            var client = _restClientFactory.BuildClient(URL);
             var request = new RestRequest(Method.POST);
             request.AddParameter("token", settings.ApiKey);
             request.AddParameter("user", settings.UserKey);
diff --git a/src/NzbDrone.Core/Notifications/Telegram/TelegramService.cs b/src/NzbDrone.Core/Notifications/Telegram/TelegramService.cs
index 35f2193d5..4aaaee99c 100644
--- a/src/NzbDrone.Core/Notifications/Telegram/TelegramService.cs
+++ b/src/NzbDrone.Core/Notifications/Telegram/TelegramService.cs
@@ -4,6 +4,7 @@ using FluentValidation.Results;
 using NLog;
 using NzbDrone.Common.Extensions;
 using NzbDrone.Common.Serializer;
+using NzbDrone.Common.Http.Proxy;
 using RestSharp;
 using NzbDrone.Core.Rest;
 using System.Web;
@@ -18,11 +19,13 @@ namespace NzbDrone.Core.Notifications.Telegram
 
     public class TelegramProxy : ITelegramProxy
     {
+        private readonly IRestClientFactory _restClientFactory;
         private readonly Logger _logger;
         private const string URL = "https://api.telegram.org";
 
-        public TelegramProxy(Logger logger)
+        public TelegramProxy(IRestClientFactory restClientFactory, Logger logger)
         {
+            _restClientFactory = restClientFactory;
             _logger = logger;
         }
 
@@ -30,7 +33,8 @@ namespace NzbDrone.Core.Notifications.Telegram
         {
             //Format text to add the title before and bold using markdown
             var text = $"<b>{HttpUtility.HtmlEncode(title)}</b>\n{HttpUtility.HtmlEncode(message)}";
-            var client = RestClientFactory.BuildClient(URL);
+            var client = _restClientFactory.BuildClient(URL);
+
             var request = new RestRequest("bot{token}/sendmessage", Method.POST);
 
             request.AddUrlSegment("token", settings.BotToken);
@@ -54,9 +58,11 @@ namespace NzbDrone.Core.Notifications.Telegram
             {
                 _logger.Error(ex, "Unable to send test message");
 
-                var restException = ex as RestException;
-
-                if (restException != null && restException.Response.StatusCode == HttpStatusCode.BadRequest)
+                if (ex is WebException webException)
+                {
+                    return new ValidationFailure("Connection", $"{webException.Status.ToString()}: {webException.Message}");
+                }
+                else if (ex is RestException restException && restException.Response.StatusCode == HttpStatusCode.BadRequest)
                 {
                     var error = Json.Deserialize<TelegramError>(restException.Response.Content);
                     var property = error.Description.ContainsIgnoreCase("chat not found") ? "ChatId" : "BotToken";
diff --git a/src/NzbDrone.Core/Notifications/Xbmc/XbmcJsonApiProxy.cs b/src/NzbDrone.Core/Notifications/Xbmc/XbmcJsonApiProxy.cs
index 37040ad1d..f3db41132 100644
--- a/src/NzbDrone.Core/Notifications/Xbmc/XbmcJsonApiProxy.cs
+++ b/src/NzbDrone.Core/Notifications/Xbmc/XbmcJsonApiProxy.cs
@@ -21,10 +21,12 @@ namespace NzbDrone.Core.Notifications.Xbmc
 
     public class XbmcJsonApiProxy : IXbmcJsonApiProxy
     {
+        private readonly IRestClientFactory _restClientFactory;
         private readonly Logger _logger;
 
-        public XbmcJsonApiProxy(Logger logger)
+        public XbmcJsonApiProxy(IRestClientFactory restClientFactory, Logger logger)
         {
+            _restClientFactory = restClientFactory;
             _logger = logger;
         }
 
@@ -110,7 +112,7 @@ namespace NzbDrone.Core.Notifications.Xbmc
         private IRestClient BuildClient(XbmcSettings settings)
         {
             var url = string.Format(@"http://{0}/jsonrpc", settings.Address);
-            var client = RestClientFactory.BuildClient(url);
+            var client = _restClientFactory.BuildClient(url);
 
             if (!settings.Username.IsNullOrWhiteSpace())
             {
diff --git a/src/NzbDrone.Core/Rest/IRestClientFactory.cs b/src/NzbDrone.Core/Rest/IRestClientFactory.cs
new file mode 100644
index 000000000..39754016d
--- /dev/null
+++ b/src/NzbDrone.Core/Rest/IRestClientFactory.cs
@@ -0,0 +1,9 @@
+using RestSharp;
+
+namespace NzbDrone.Core.Rest
+{
+    public interface IRestClientFactory
+    {
+        RestClient BuildClient(string baseUrl);
+    }
+}
diff --git a/src/NzbDrone.Core/Rest/RestClientFactory.cs b/src/NzbDrone.Core/Rest/RestClientFactory.cs
index cc657c4b6..6197f09ba 100644
--- a/src/NzbDrone.Core/Rest/RestClientFactory.cs
+++ b/src/NzbDrone.Core/Rest/RestClientFactory.cs
@@ -1,17 +1,32 @@
 using RestSharp;
 using NzbDrone.Common.EnvironmentInfo;
+using NzbDrone.Common.Http.Proxy;
 
 namespace NzbDrone.Core.Rest
 {
-    public static class RestClientFactory
+    public class RestClientFactory : IRestClientFactory
     {
-        public static RestClient BuildClient(string baseUrl)
+        private readonly IHttpProxySettingsProvider _httpProxySettingsProvider;
+        private readonly ICreateManagedWebProxy _createManagedWebProxy;
+
+        public RestClientFactory(IHttpProxySettingsProvider httpProxySettingsProvider, ICreateManagedWebProxy createManagedWebProxy)
+        {
+            _httpProxySettingsProvider = httpProxySettingsProvider;
+            _createManagedWebProxy = createManagedWebProxy;
+        }
+
+        public RestClient BuildClient(string baseUrl)
         {
             var restClient = new RestClient(baseUrl)
             {
                 UserAgent = $"{BuildInfo.AppName}/{BuildInfo.Version} ({OsInfo.Os})"
             };
 
+            var proxySettings = _httpProxySettingsProvider.GetProxySettings();
+            if (proxySettings != null)
+            {
+                restClient.Proxy = _createManagedWebProxy.GetWebProxy(proxySettings);
+            }
 
             return restClient;
         }