diff --git a/src/CrestApps.Core.Docs/docs/changelog/2.0.0.md b/src/CrestApps.Core.Docs/docs/changelog/2.0.0.md
index 2b81ecbd..6ecd79ee 100644
--- a/src/CrestApps.Core.Docs/docs/changelog/2.0.0.md
+++ b/src/CrestApps.Core.Docs/docs/changelog/2.0.0.md
@@ -864,3 +864,19 @@ microphone, desk speakers):
   docs version from patch tags only when that major/minor docs version does not
   already exist, and skips prerelease tags successfully after logging why no docs
   version PR was needed
+- **Fixed: one of two AI provider connections whose names differ only by case disappeared without a
+  trace.** A connection's identifier hashes its lowercased client and connection name, so `Shared-Azure`
+  declared under `CrestApps:AI:Connections` and `shared-azure` declared under
+  `CrestApps:AI:Providers:Azure:Connections` resolved to the same identifier, and the second silently
+  replaced the first — taking its endpoint and its credentials with it. Every deployment naming that
+  connection then reached whichever resource happened to be read last, which surfaces as an unexplained
+  `DeploymentNotFound` when the model is deployed only on the other one. The first definition now wins,
+  matching how configured deployments are read, and the dropped entry is logged as a warning that names
+  the entry it collided with. A site that has such a pair today will switch to the earlier definition;
+  the warning names both, so the duplicate can be renamed.
+- **A failed Azure OpenAI completion now names the deployment and endpoint that served it.** The
+  provider's own exception names neither, so a misrouted request — a deployment bound to the wrong
+  connection, or a model name that does not exist on the resource that connection points at — read as a
+  bare HTTP error with nothing to say where the request went. Both the streaming and non-streaming paths
+  now log the deployment name, the model name that forms the request URL, the connection name, and the
+  endpoint host.
diff --git a/src/Primitives/CrestApps.Core.AI.OpenAI.Azure/Services/AzureOpenAICompletionClient.cs b/src/Primitives/CrestApps.Core.AI.OpenAI.Azure/Services/AzureOpenAICompletionClient.cs
index 3ffc0543..fc9df0eb 100644
--- a/src/Primitives/CrestApps.Core.AI.OpenAI.Azure/Services/AzureOpenAICompletionClient.cs
+++ b/src/Primitives/CrestApps.Core.AI.OpenAI.Azure/Services/AzureOpenAICompletionClient.cs
@@ -11,6 +11,7 @@
 using CrestApps.Core.AI.OpenAI.Azure.Models;
 using CrestApps.Core.AI.Services;
 using CrestApps.Core.Extensions;
+using CrestApps.Core.Infrastructure;
 using CrestApps.Core.Templates.Services;
 using Microsoft.AspNetCore.DataProtection;
 using Microsoft.Extensions.DependencyInjection;
@@ -177,7 +178,7 @@ public string ClientName
         }
         catch (Exception ex)
         {
-            _logger.LogError(ex, "Unable to get chat completion result from Azure OpenAI.");
+            LogCompletionFailure(ex, deployment, connectionProperties);
         }
 
         return null;
@@ -251,8 +252,36 @@ public string ClientName
         while (iterations <= _defaultOptions.MaximumIterationsPerRequest)
         {
             var hasToolCalls = false;
-            await foreach (var update in chatClient.CompleteChatStreamingAsync(prompts, chatOptions, cancellationToken))
+
+            // Enumerated by hand rather than with `await foreach` so the call into the provider sits in a
+            // try block: a yield cannot appear inside one, and without it a failed request leaves no record
+            // of which deployment and endpoint produced it.
+            await using var updates = chatClient
+                .CompleteChatStreamingAsync(prompts, chatOptions, cancellationToken)
+                .GetAsyncEnumerator(cancellationToken);
+
+            while (true)
             {
+                try
+                {
+                    if (!await updates.MoveNextAsync())
+                    {
+                        break;
+                    }
+                }
+                catch (OperationCanceledException)
+                {
+                    throw;
+                }
+                catch (Exception ex)
+                {
+                    LogCompletionFailure(ex, deployment, connection);
+
+                    throw;
+                }
+
+                var update = updates.Current;
+
                 // Accumulate tool call updates as they arrive.
                 foreach (var toolCallUpdate in update.ToolCallUpdates)
                 {
@@ -474,6 +503,30 @@ private AzureOpenAIClient GetChatClient(AIProviderConnectionEntry connection)
         return AzureOpenAIClientFactory.Create(connection, _loggerFactory, _azureClientOptions);
     }
 
+    /// <summary>
+    /// Logs a failed completion together with the deployment and endpoint that served it.
+    /// </summary>
+    /// <remarks>
+    /// The provider's own exception names neither. A misrouted request -- a deployment bound to the wrong
+    /// connection, or a model name that does not exist on the resource that connection points at -- reads
+    /// as a bare <c>DeploymentNotFound</c> without them, which says nothing about where the request went.
+    /// The model name is the one that forms the request URL, so it is reported even when it matches the
+    /// deployment name.
+    /// </remarks>
+    /// <param name="exception">The exception the request failed with.</param>
+    /// <param name="deployment">The deployment that served the request.</param>
+    /// <param name="connection">The connection that served the request.</param>
+    private void LogCompletionFailure(Exception exception, AIDeployment deployment, AIProviderConnectionEntry connection)
+    {
+        _logger.LogError(
+            exception,
+            "Unable to get chat completion result from Azure OpenAI using deployment '{DeploymentName}' (model '{ModelName}') on connection '{ConnectionName}' at '{Endpoint}'.",
+            deployment.Name,
+            deployment.ModelName,
+            deployment.ConnectionName,
+            connection.GetEndpoint(throwException: false)?.Host);
+    }
+
     private static async ValueTask<IReadOnlyList<Microsoft.Extensions.AI.AIFunction>> ConfigureOptionsAsync(ChatCompletionOptions chatOptions, AICompletionContext context, List<ChatMessage> prompts)
     {
         var optionsContext = new AzureOpenAIChatOptionsContext(chatOptions, context, prompts);
diff --git a/src/Primitives/CrestApps.Core.AI/Services/ConfigurationAIProviderConnectionSource.cs b/src/Primitives/CrestApps.Core.AI/Services/ConfigurationAIProviderConnectionSource.cs
index 41e15eed..bc6340e1 100644
--- a/src/Primitives/CrestApps.Core.AI/Services/ConfigurationAIProviderConnectionSource.cs
+++ b/src/Primitives/CrestApps.Core.AI/Services/ConfigurationAIProviderConnectionSource.cs
@@ -194,6 +194,21 @@ private void AddConfiguredConnection(
             return;
         }
 
+        // The identifier hashes the lowercased provider and connection name, so two entries whose names
+        // differ only by case land on the same one. The first definition wins, matching how configured
+        // deployments are read; without this the later entry replaced the earlier one in silence and an
+        // entire connection -- its endpoint and its credentials -- disappeared with no diagnostic.
+        if (connections.TryGetValue(connection.ItemId, out var existingConnection))
+        {
+            _logger.LogWarning(
+                "Skipping AI connection '{ConnectionName}' from '{SourceDescription}' because '{ExistingConnectionName}' resolves to the same identifier. Connection names are case-insensitive; rename one of them so both are read.",
+                connection.Name,
+                sourceDescription,
+                existingConnection.Name);
+
+            return;
+        }
+
         if (_logger.IsEnabled(LogLevel.Debug))
         {
             _logger.LogDebug("Adding AI connection '{ConnectionName}' (ClientName: '{ClientName}', ItemId: '{ItemId}') from '{SourceDescription}'.",
diff --git a/tests/CrestApps.Core.Tests/Framework/Mvc/AIProviderConnectionOptionsTests.cs b/tests/CrestApps.Core.Tests/Framework/Mvc/AIProviderConnectionOptionsTests.cs
index 568681a3..2c39d4f4 100644
--- a/tests/CrestApps.Core.Tests/Framework/Mvc/AIProviderConnectionOptionsTests.cs
+++ b/tests/CrestApps.Core.Tests/Framework/Mvc/AIProviderConnectionOptionsTests.cs
@@ -609,6 +609,30 @@ public async Task ConfigurationAIProviderConnectionStore_ShouldSkipConfiguredCon
         Assert.Equal("ui-connection", connections.Single().ItemId);
     }
 
+    [Fact]
+    public async Task ConfigurationAIProviderConnectionStore_WhenTwoConfiguredNamesDifferOnlyByCase_ShouldKeepTheFirstOne()
+    {
+        var configuration = new ConfigurationBuilder()
+            .AddInMemoryCollection(new Dictionary<string, string>
+            {
+                ["CrestApps:AI:Connections:0:Name"] = "Shared-Azure",
+                ["CrestApps:AI:Connections:0:ClientName"] = "Azure",
+                ["CrestApps:AI:Connections:0:Endpoint"] = "https://first.openai.azure.com/",
+                ["CrestApps:AI:Providers:Azure:Connections:shared-azure:Endpoint"] = "https://second.openai.azure.com/",
+            })
+            .Build();
+
+        var store = CreateConnectionStore(configuration);
+
+        var connections = await store.GetAllAsync(TestContext.Current.CancellationToken);
+
+        // Both entries hash to the same identifier, so only one survives. The later one used to replace
+        // the earlier in silence, taking its endpoint and its credentials with it.
+        var connection = Assert.Single(connections);
+        Assert.Equal("Shared-Azure", connection.Name);
+        Assert.Equal("https://first.openai.azure.com/", connection.Properties["Endpoint"]?.ToString());
+    }
+
     private static DefaultAIDeploymentCapabilityService CreateCapabilityService()
     {
         return new DefaultAIDeploymentCapabilityService(Options.Create(new AIDeploymentCapabilityOptions()), Mock.Of<IAIDeploymentStore>());