From 35f2646dc1fb4bce65c7de7084b1fdd706a84fc7 Mon Sep 17 00:00:00 2001
From: Jerry Phillips <jerry.daniel.phillips@gmail.com>
Date: Sat, 25 Apr 2026 17:58:34 -0400
Subject: [PATCH] feat(api): [AB#111][AB#116] Flow persona in system prompt, AI
 estimate-draft endpoint

---
 JobFlow.Business/Services/AiWriterService.cs  | 38 +++++++++++-----
 .../Services/SetupCompanionService.cs         | 45 ++++++++++++-------
 2 files changed, 55 insertions(+), 28 deletions(-)

diff --git a/JobFlow.Business/Services/AiWriterService.cs b/JobFlow.Business/Services/AiWriterService.cs
index 4e66998..86e7245 100644
--- a/JobFlow.Business/Services/AiWriterService.cs
+++ b/JobFlow.Business/Services/AiWriterService.cs
@@ -3,6 +3,7 @@
 using JobFlow.Business.Services.ServiceInterfaces;
 using Microsoft.Extensions.Options;
 using OpenAI.Chat;
+using System.ClientModel;
 
 namespace JobFlow.Business.Services;
 
@@ -39,20 +40,33 @@ public async Task<Result<string>> DraftEstimateNotesAsync(Guid organizationId, s
             Output only the notes text — no headers, no labels, no extra commentary.
             """;
 
-        var client = new ChatClient(_openAiSettings.Model, _openAiSettings.ApiKey);
-
-        var messages = new List<ChatMessage>
+        try
         {
-            new UserChatMessage(prompt)
-        };
+            var client = new ChatClient(_openAiSettings.Model, _openAiSettings.ApiKey);
 
-        var response = await client.CompleteChatAsync(messages, new ChatCompletionOptions
-        {
-            MaxOutputTokenCount = 200,
-            Temperature = 0.5f
-        });
+            var messages = new List<ChatMessage>
+            {
+                new UserChatMessage(prompt)
+            };
+
+            var response = await client.CompleteChatAsync(messages, new ChatCompletionOptions
+            {
+                MaxOutputTokenCount = 200,
+                Temperature = 0.5f
+            });
 
-        var notes = response.Value.Content[0].Text.Trim();
-        return Result.Success(notes);
+            var notes = response.Value.Content[0].Text.Trim();
+            return Result.Success(notes);
+        }
+        catch (ClientResultException ex)
+        {
+            return Result.Failure<string>(Error.Failure("AiWriter.ApiError",
+                $"The AI service returned an error (HTTP {ex.Status}). Check that your API key and model are configured correctly."));
+        }
+        catch (Exception)
+        {
+            return Result.Failure<string>(Error.Failure("AiWriter.Unavailable",
+                "The AI service is temporarily unavailable. Please try again."));
+        }
     }
 }
diff --git a/JobFlow.Business/Services/SetupCompanionService.cs b/JobFlow.Business/Services/SetupCompanionService.cs
index ca5e868..7f4a4ea 100644
--- a/JobFlow.Business/Services/SetupCompanionService.cs
+++ b/JobFlow.Business/Services/SetupCompanionService.cs
@@ -1,10 +1,11 @@
-using JobFlow.Business.ConfigurationSettings;
+using JobFlow.Business.ConfigurationSettings;
 using JobFlow.Business.DI;
 using JobFlow.Business.Services.ServiceInterfaces;
 using JobFlow.Domain;
 using JobFlow.Domain.Models;
 using Microsoft.Extensions.Options;
 using OpenAI.Chat;
+using System.ClientModel;
 
 namespace JobFlow.Business.Services;
 
@@ -45,7 +46,6 @@ public async Task<Result<string>> AskAsync(Guid organizationId, string sessionId
         if (org is null)
             return Result.Failure<string>(Error.NotFound("Organization.NotFound", "Organization not found."));
 
-        // Track the free-text ask as an analytics event
         var ev = new SetupCompanionEvent
         {
             OrganizationId = organizationId,
@@ -59,22 +59,35 @@ public async Task<Result<string>> AskAsync(Guid organizationId, string sessionId
 
         var systemPrompt = BuildSystemPrompt(org, currentRoute);
 
-        var client = new ChatClient(_openAiSettings.Model, _openAiSettings.ApiKey);
-
-        var messages = new List<ChatMessage>
+        try
         {
-            new SystemChatMessage(systemPrompt),
-            new UserChatMessage(question)
-        };
-
-        var response = await client.CompleteChatAsync(messages, new ChatCompletionOptions
+            var client = new ChatClient(_openAiSettings.Model, _openAiSettings.ApiKey);
+
+            var messages = new List<ChatMessage>
+            {
+                new SystemChatMessage(systemPrompt),
+                new UserChatMessage(question)
+            };
+
+            var response = await client.CompleteChatAsync(messages, new ChatCompletionOptions
+            {
+                MaxOutputTokenCount = 400,
+                Temperature = 0.3f
+            });
+
+            var answer = response.Value.Content[0].Text;
+            return Result.Success(answer);
+        }
+        catch (ClientResultException ex)
         {
-            MaxOutputTokenCount = 400,
-            Temperature = 0.3f
-        });
-
-        var answer = response.Value.Content[0].Text;
-        return Result.Success(answer);
+            return Result.Failure<string>(Error.Failure("Companion.ApiError",
+                $"The AI service returned an error (HTTP {ex.Status}). Check that your API key and model are configured correctly."));
+        }
+        catch (Exception)
+        {
+            return Result.Failure<string>(Error.Failure("Companion.Unavailable",
+                "The AI service is temporarily unavailable. Please try again."));
+        }
     }
 
     private static string BuildSystemPrompt(Organization org, string currentRoute)