diff --git a/src/Sonarr.RuntimePatches/Mono/BoringTLSVerifyFlagsPatch.cs b/src/Sonarr.RuntimePatches/Mono/BoringTLSVerifyFlagsPatch.cs
new file mode 100644
index 000000000..a7eec5b0f
--- /dev/null
+++ b/src/Sonarr.RuntimePatches/Mono/BoringTLSVerifyFlagsPatch.cs
@@ -0,0 +1,81 @@
+using System;
+using System.Collections.Generic;
+using System.IO.Compression;
+using System.Linq;
+using System.Reflection;
+using System.Reflection.Emit;
+using HarmonyLib;
+
+namespace NzbDrone.RuntimePatches.Mono
+{
+    // Mono 5.x - 6.x bug 19886
+    // The BoringTLS provider does not enable the trust-first option that's default on in openssl 1.1.0 and up. 
+    // This prevents it from building the short trusted chain and errors out on old (expired) chains included in the certificate.
+    // This is a problem with Cross-Signed certificates that have an expired legacy root signing the new root.
+    // The Flags default is 0, while X509_V_FLAG_TRUSTED_FIRST is 0x8000.
+    // There's no way to override the default flags via an option in mono so we have to hook in.
+    public class BoringTLSVerifyFlagsPatch : MonoRuntimePatchBase
+    {
+        private static BoringTLSVerifyFlagsPatch Instance;
+
+        public override Version MonoMinVersion => new Version(5, 0);
+        public override Version MonoMaxVersion => new Version(6, 10);
+
+        protected override void Patch()
+        {
+            Instance = this;
+
+            TryPatchMethod("Mono.Btls.MonoBtlsX509VerifyParam, System", "GetSslServer");
+        }
+
+        // We need a Transpiler coz MonoBtlsX509VerifyParam is non-public
+        // Note that MonoBtlsProvider.GetVerifyParam would be a more 'correct' patch location
+
+        // public static MonoBtlsX509VerifyParam GetSslServer ()
+        // {
+        // - return Lookup("ssl_server", true);
+        // + var orig = Lookup("ssl_server", true);
+        // + var copy = orig.Copy();
+        // + orig.Dispose();
+        // + copy.SetFlags(0x8000);
+        // + return copy;
+        // }
+        static IEnumerable<CodeInstruction> Transpiler_GetSslServer(IEnumerable<CodeInstruction> instructions, MethodBase method, ILGenerator generator)
+        {
+            var codes = instructions.ToList();
+
+            var patchable = codes.Matches(OpCodes.Ldstr, OpCodes.Ldc_I4_1, OpCodes.Call, OpCodes.Ret);
+
+            var targetType = method.DeclaringType;
+            var copyMethod = targetType.GetMethod("Copy");
+            var disposeMethod = targetType.GetMethod("Dispose");
+            var setFlagsMethod = targetType.GetMethod("SetFlags");
+
+            if (patchable && copyMethod != null && disposeMethod != null && setFlagsMethod != null)
+            {
+                var copy = generator.DeclareLocal(targetType);
+
+                // Remove Ret
+                codes.RemoveAt(codes.Count - 1);
+
+                codes.Add(new CodeInstruction(OpCodes.Dup));
+                codes.Add(new CodeInstruction(OpCodes.Call, copyMethod));           // Copy the readonly original
+                codes.Add(new CodeInstruction(OpCodes.Stloc, copy));
+                codes.Add(new CodeInstruction(OpCodes.Callvirt, disposeMethod));    // Dispose the original
+                codes.Add(new CodeInstruction(OpCodes.Ldloc, copy));
+                codes.Add(new CodeInstruction(OpCodes.Dup));
+                codes.Add(new CodeInstruction(OpCodes.Ldc_I4, 0x8000));             // X509_V_FLAG_TRUSTED_FIRST
+                codes.Add(new CodeInstruction(OpCodes.Call, setFlagsMethod));       // SetFlags is an or-operation
+                codes.Add(new CodeInstruction(OpCodes.Ret));
+
+                Instance.Debug($"Patch applied to method {method.GetSimplifiedName()}");
+            }
+            else
+            {
+                Instance.Error($"Skipped patching method {method.GetSimplifiedName()}: Method construct different than expected");
+            }
+
+            return codes;
+        }
+    }
+}