diff --git a/src/NzbDrone.Common/Sonarr.Common.csproj b/src/NzbDrone.Common/Sonarr.Common.csproj
index 6778f7fb5..4994793cf 100644
--- a/src/NzbDrone.Common/Sonarr.Common.csproj
+++ b/src/NzbDrone.Common/Sonarr.Common.csproj
@@ -5,6 +5,7 @@
   </PropertyGroup>
   <ItemGroup>
     <PackageReference Include="DryIoc.dll" Version="5.4.3" />
+    <PackageReference Include="IPAddressRange" Version="6.0.0" />
     <PackageReference Include="Microsoft.Extensions.DependencyInjection" Version="6.0.1" />
     <PackageReference Include="Microsoft.Extensions.Hosting.WindowsServices" Version="6.0.2" />
     <PackageReference Include="Newtonsoft.Json" Version="13.0.3" />
diff --git a/src/NzbDrone.Core.Test/Http/HttpProxySettingsProviderFixture.cs b/src/NzbDrone.Core.Test/Http/HttpProxySettingsProviderFixture.cs
index 067149904..2beeb16f9 100644
--- a/src/NzbDrone.Core.Test/Http/HttpProxySettingsProviderFixture.cs
+++ b/src/NzbDrone.Core.Test/Http/HttpProxySettingsProviderFixture.cs
@@ -12,7 +12,7 @@ public class HttpProxySettingsProviderFixture : TestBase<HttpProxySettingsProvid
     {
         private HttpProxySettings GetProxySettings()
         {
-            return new HttpProxySettings(ProxyType.Socks5, "localhost", 8080, "*.httpbin.org,google.com", true, null, null);
+            return new HttpProxySettings(ProxyType.Socks5, "localhost", 8080, "*.httpbin.org,google.com,172.16.0.0/12", true, null, null);
         }
 
         [Test]
@@ -23,6 +23,7 @@ public void should_bypass_proxy()
             Subject.ShouldProxyBeBypassed(settings, new HttpUri("http://eu.httpbin.org/get")).Should().BeTrue();
             Subject.ShouldProxyBeBypassed(settings, new HttpUri("http://google.com/get")).Should().BeTrue();
             Subject.ShouldProxyBeBypassed(settings, new HttpUri("http://localhost:8654/get")).Should().BeTrue();
+            Subject.ShouldProxyBeBypassed(settings, new HttpUri("http://172.21.0.1:8989/api/v3/indexer/schema")).Should().BeTrue();
         }
 
         [Test]
@@ -31,6 +32,7 @@ public void should_not_bypass_proxy()
             var settings = GetProxySettings();
 
             Subject.ShouldProxyBeBypassed(settings, new HttpUri("http://bing.com/get")).Should().BeFalse();
+            Subject.ShouldProxyBeBypassed(settings, new HttpUri("http://172.3.0.1:8989/api/v3/indexer/schema")).Should().BeFalse();
         }
     }
 }
diff --git a/src/NzbDrone.Core/Http/HttpProxySettingsProvider.cs b/src/NzbDrone.Core/Http/HttpProxySettingsProvider.cs
index edf77b31f..1c69bbec5 100644
--- a/src/NzbDrone.Core/Http/HttpProxySettingsProvider.cs
+++ b/src/NzbDrone.Core/Http/HttpProxySettingsProvider.cs
@@ -1,5 +1,7 @@
 using System;
+using System.Linq;
 using System.Net;
+using NetTools;
 using NzbDrone.Common.Http;
 using NzbDrone.Common.Http.Proxy;
 using NzbDrone.Core.Configuration;
@@ -52,7 +54,15 @@ 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
             var proxy = new WebProxy(proxySettings.Host + ":" + proxySettings.Port, proxySettings.BypassLocalAddress, proxySettings.BypassListAsArray);
 
-            return proxy.IsBypassed((Uri)url);
+            return proxy.IsBypassed((Uri)url) || IsBypassedByIpAddressRange(proxySettings.BypassListAsArray, url.Host);
+        }
+
+        private static bool IsBypassedByIpAddressRange(string[] bypassList, string host)
+        {
+            return bypassList.Any(bypass =>
+                IPAddressRange.TryParse(bypass, out var ipAddressRange) &&
+                IPAddress.TryParse(host, out var ipAddress) &&
+                ipAddressRange.Contains(ipAddress));
         }
     }
 }