diff --git a/CHANGELOG.md b/CHANGELOG.md
index 951213f2..e6bbdb98 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -14,6 +14,11 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
   instead of `~/.config/recyclarr`. Recyclarr will attempt to move this directory when run. If it
   can't, then manual intervention is needed by users (e.g. `recyclarr migrate`).
 
+### Fixed
+
+- Print more useful diagnostics when there's a connectivity problem to a service (e.g. incorrect
+  `base_url`).
+
 ## [6.0.2] - 2023-10-20
 
 ### Fixed
diff --git a/src/Recyclarr.Cli/Processors/ErrorHandling/FlurlHttpExceptionHandler.cs b/src/Recyclarr.Cli/Processors/ErrorHandling/FlurlHttpExceptionHandler.cs
index 2775edc7..5e60e046 100644
--- a/src/Recyclarr.Cli/Processors/ErrorHandling/FlurlHttpExceptionHandler.cs
+++ b/src/Recyclarr.Cli/Processors/ErrorHandling/FlurlHttpExceptionHandler.cs
@@ -8,14 +8,16 @@ public class FlurlHttpExceptionHandler(ILogger log) : IFlurlHttpExceptionHandler
     [SuppressMessage("Design", "CA1031:Do not catch general exception types")]
     public async Task ProcessServiceErrorMessages(IServiceErrorMessageExtractor extractor)
     {
-        var statusCode = extractor.GetHttpStatusCode();
-
-        switch (statusCode)
+        switch (extractor)
         {
-            case 401:
+            case {HttpStatusCode: 401}:
                 log.Error("Reason: Recyclarr is unauthorized to talk to the service. Is your `api_key` correct?");
                 break;
 
+            case {HttpStatusCode: null}:
+                log.Error("Reason: Problem connecting to service. Is your `base_url` correct?");
+                break;
+
             default:
                 ProcessBody(await extractor.GetErrorMessage());
                 break;
@@ -47,6 +49,7 @@ public class FlurlHttpExceptionHandler(ILogger log) : IFlurlHttpExceptionHandler
         }
 
         // Last resort
-        log.Error("Reason: Unable to determine. Please report this as a bug and attach your `verbose.log` file.");
+        log.Error(
+            "Reason: Unable to determine. Please report this as a bug and attach your `debug.log` and `verbose.log` files.");
     }
 }
diff --git a/src/Recyclarr.Cli/Processors/ErrorHandling/IServiceErrorMessageExtractor.cs b/src/Recyclarr.Cli/Processors/ErrorHandling/IServiceErrorMessageExtractor.cs
index ff865e95..1248ddaa 100644
--- a/src/Recyclarr.Cli/Processors/ErrorHandling/IServiceErrorMessageExtractor.cs
+++ b/src/Recyclarr.Cli/Processors/ErrorHandling/IServiceErrorMessageExtractor.cs
@@ -3,5 +3,6 @@ namespace Recyclarr.Cli.Processors.ErrorHandling;
 public interface IServiceErrorMessageExtractor
 {
     Task<string> GetErrorMessage();
-    int? GetHttpStatusCode();
+    int? HttpStatusCode { get; }
+    HttpRequestError? HttpError { get; }
 }
diff --git a/src/Recyclarr.Cli/Processors/ErrorHandling/ServiceErrorMessageExtractor.cs b/src/Recyclarr.Cli/Processors/ErrorHandling/ServiceErrorMessageExtractor.cs
index 46d848b2..febb9c8a 100644
--- a/src/Recyclarr.Cli/Processors/ErrorHandling/ServiceErrorMessageExtractor.cs
+++ b/src/Recyclarr.Cli/Processors/ErrorHandling/ServiceErrorMessageExtractor.cs
@@ -4,13 +4,23 @@ namespace Recyclarr.Cli.Processors.ErrorHandling;
 
 public class ServiceErrorMessageExtractor(FlurlHttpException e) : IServiceErrorMessageExtractor
 {
-    public async Task<string> GetErrorMessage()
+    public HttpRequestError? HttpError
     {
-        return await e.GetResponseStringAsync();
+        get
+        {
+            if (e.InnerException is not HttpRequestException http)
+            {
+                return null;
+            }
+
+            return http.HttpRequestError;
+        }
     }
 
-    public int? GetHttpStatusCode()
+    public async Task<string> GetErrorMessage()
     {
-        return e.StatusCode;
+        return await e.GetResponseStringAsync();
     }
+
+    public int? HttpStatusCode => e.StatusCode;
 }