diff --git a/src/Multifactor.Radius.Adapter.v2.Application/Features/PacketHandler/UseCases/SecondFactor/Multifactor/MultifactorApiService.cs b/src/Multifactor.Radius.Adapter.v2.Application/Features/PacketHandler/UseCases/SecondFactor/Multifactor/MultifactorApiService.cs
index 8f2f303..fb6d49e 100644
--- a/src/Multifactor.Radius.Adapter.v2.Application/Features/PacketHandler/UseCases/SecondFactor/Multifactor/MultifactorApiService.cs
+++ b/src/Multifactor.Radius.Adapter.v2.Application/Features/PacketHandler/UseCases/SecondFactor/Multifactor/MultifactorApiService.cs
@@ -292,6 +292,7 @@ private SecondFactorResponse ProcessMfException(
         
         if (IsUserPassThrow(context))
         {
+            LogApiUnreachableBypass(context, identity);
             var code = ConvertToAuthCode(AccessRequestResponse.Bypass);
             return new SecondFactorResponse(code);
         }
@@ -299,6 +300,23 @@ private SecondFactorResponse ProcessMfException(
         return new SecondFactorResponse(radCode);
     }
 
+    private void LogApiUnreachableBypass(RadiusPipelineContext context, string identity)
+    {
+        var callingStationIdAttributeName = context.ClientConfiguration.CallingStationIdAttribute;
+        var callingStationIdAttr = context.RequestPacket.GetCallingStationIdAttribute(callingStationIdAttributeName);
+        var callingStationId = RequestDataExtractor.GetCallingStationId(
+            callingStationIdAttr,
+            context.RequestPacket.RemoteEndpoint,
+            context.ClientConfiguration.IsIpFromUdp);
+
+        _logger.LogInformation(
+            "Bypass second factor for user '{user:l}' with calling-station-id {csi:l} from {host:l}:{port} because Multifactor API is unreachable",
+            identity,
+            callingStationId,
+            context.RequestPacket.RemoteEndpoint.Address,
+            context.RequestPacket.RemoteEndpoint.Port);
+    }
+
     private bool IsUserPassThrow(RadiusPipelineContext context)
     {
         if (!context.ClientConfiguration.BypassSecondFactorWhenApiUnreachable)
@@ -343,4 +361,4 @@ private SecondFactorResponse ProcessException(Exception ex, string identity, IPE
 
     private static bool ShouldCacheResponse(bool apiResponseCacheEnabled, AuthenticationStatus responseCode, AccessRequestResponse? response) 
         => apiResponseCacheEnabled && responseCode == AuthenticationStatus.Accept && !(response?.Bypassed ?? false);
-}
\ No newline at end of file
+}
diff --git a/src/Multifactor.Radius.Adapter.v2.Infrastructure/Features/PacketHandler/UseCases/SecondFactor/CreateAccessRequest.cs b/src/Multifactor.Radius.Adapter.v2.Infrastructure/Features/PacketHandler/UseCases/SecondFactor/CreateAccessRequest.cs
index 3754557..ea15f8b 100644
--- a/src/Multifactor.Radius.Adapter.v2.Infrastructure/Features/PacketHandler/UseCases/SecondFactor/CreateAccessRequest.cs
+++ b/src/Multifactor.Radius.Adapter.v2.Infrastructure/Features/PacketHandler/UseCases/SecondFactor/CreateAccessRequest.cs
@@ -51,7 +51,9 @@ public async Task<AccessRequestResponse> Execute(AccessRequestDto dto, Multifact
         catch (TaskCanceledException) when (!cancellationToken.IsCancellationRequested)
         {
             _logger.LogWarning("Multifactor API timeout expired for endpoint: {Url}", Url);
-            return CreateDeniedResponse("Request timeout");
+            throw new MultifactorApiUnreachableException(
+                $"Multifactor API timeout expired for endpoint: {Url}. " +
+                $"Host: {client.BaseAddress?.OriginalString}. Reason: Request timeout");
         }
         catch (OperationCanceledException)
         {
@@ -144,4 +146,4 @@ private HttpClient CreateClient(MultifactorAuthData authData)
         
         return client;
     }
-}
\ No newline at end of file
+}
diff --git a/src/Multifactor.Radius.Adapter.v2.Infrastructure/Features/PacketHandler/UseCases/SecondFactor/SendChallengeAsync.cs b/src/Multifactor.Radius.Adapter.v2.Infrastructure/Features/PacketHandler/UseCases/SecondFactor/SendChallengeAsync.cs
index 6563859..1ba67ce 100644
--- a/src/Multifactor.Radius.Adapter.v2.Infrastructure/Features/PacketHandler/UseCases/SecondFactor/SendChallengeAsync.cs
+++ b/src/Multifactor.Radius.Adapter.v2.Infrastructure/Features/PacketHandler/UseCases/SecondFactor/SendChallengeAsync.cs
@@ -49,7 +49,9 @@ public async Task<AccessRequestResponse> Execute(ChallengeRequestDto dto, Multif
         catch (TaskCanceledException) when (!cancellationToken.IsCancellationRequested)
         {
             _logger.LogWarning("Multifactor API timeout expired for endpoint: {Url}", Url);
-            return CreateDeniedResponse("Request timeout");
+            throw new MultifactorApiUnreachableException(
+                $"Multifactor API timeout expired for endpoint: {Url}. " +
+                $"Host: {client.BaseAddress?.OriginalString}. Reason: Request timeout");
         }
         catch (OperationCanceledException)
         {
@@ -142,4 +144,4 @@ private HttpClient CreateClient(MultifactorAuthData authData)
         
         return client;
     }
-}
\ No newline at end of file
+}