diff --git a/blotztask-api/Modules/BreakDown/Commands/BreakdownTask.cs b/blotztask-api/Modules/BreakDown/Commands/BreakdownTask.cs
index 8e20db6ae..35fdc45fa 100644
--- a/blotztask-api/Modules/BreakDown/Commands/BreakdownTask.cs
+++ b/blotztask-api/Modules/BreakDown/Commands/BreakdownTask.cs
@@ -1,5 +1,6 @@
 using System.ComponentModel;
 using System.ComponentModel.DataAnnotations;
+using System.ClientModel;
 using Azure.AI.Projects;
 using BlotzTask.Extension;
 using BlotzTask.Modules.AiUsage.Services;
@@ -110,15 +111,13 @@ await recordAiUsageService.RecordAiUsageAsync(new RecordAiUsageRequest
             logger.LogWarning(oce, "Task breakdown was canceled");
             throw new AiTaskGenerationException(AiErrorCode.Canceled, "The request was canceled.", oce);
         }
-        catch (Exception ex) when (
-            ex.Message.Contains("429", StringComparison.OrdinalIgnoreCase) ||
-            ex.Message.Contains("quota", StringComparison.OrdinalIgnoreCase) ||
-            ex.Message.Contains("token", StringComparison.OrdinalIgnoreCase))
+        catch (ClientResultException ex) when (ex.Status == 429)
         {
-            logger.LogWarning(ex, "Token limit exceeded during task breakdown.");
+            logger.LogError(ex, "Azure AI rate limit hit during task breakdown.");
             throw new AzureAiException();
         }
-        catch (Exception ex) when (
+        catch (ClientResultException ex) when (
+            ex.Status == 400 &&
             ex.Message.Contains("content_filter", StringComparison.OrdinalIgnoreCase))
         {
             logger.LogWarning(ex, "Request blocked by content filter during task breakdown.");
diff --git a/blotztask-api/Modules/ChatTaskGenerator/Services/AiChatService.cs b/blotztask-api/Modules/ChatTaskGenerator/Services/AiChatService.cs
index 8b2ef12a3..664206106 100644
--- a/blotztask-api/Modules/ChatTaskGenerator/Services/AiChatService.cs
+++ b/blotztask-api/Modules/ChatTaskGenerator/Services/AiChatService.cs
@@ -1,4 +1,5 @@
 using System.Diagnostics;
+using System.ClientModel;
 using Azure.AI.Projects;
 using BlotzTask.Extension;
 using BlotzTask.Modules.AiUsage.Services;
@@ -117,15 +118,13 @@ await recordAiUsageService.RecordAiUsageAsync(new RecordAiUsageRequest
             logger.LogInformation(oce, "AI task generation cancelled.");
             throw new AiTaskGenerationException(AiErrorCode.Canceled, "The request was canceled.", oce);
         }
-        catch (Exception ex) when (
-            ex.Message.Contains("429", StringComparison.OrdinalIgnoreCase) ||
-            ex.Message.Contains("quota", StringComparison.OrdinalIgnoreCase) ||
-            ex.Message.Contains("token", StringComparison.OrdinalIgnoreCase))
+        catch (ClientResultException ex) when (ex.Status == 429)
         {
-            logger.LogWarning(ex, "Token limit exceeded during AI task generation.");
+            logger.LogError(ex, "Azure AI rate limit hit during AI task generation.");
             throw new AzureAiException();
         }
-        catch (Exception ex) when (
+        catch (ClientResultException ex) when (
+            ex.Status == 400 &&
             ex.Message.Contains("content_filter", StringComparison.OrdinalIgnoreCase))
         {
             logger.LogWarning(ex, "Request blocked by content filter.");
@@ -138,4 +137,4 @@ await recordAiUsageService.RecordAiUsageAsync(new RecordAiUsageRequest
                 "An unhandled exception occurred during AI task generation.", ex);
         }
     }
-}
\ No newline at end of file
+}