diff --git a/src/Primitives/CrestApps.Core.AI.OpenAI.Azure/Handlers/AzureOpenAIConnectionHandler.cs b/src/Primitives/CrestApps.Core.AI.OpenAI.Azure/Handlers/AzureOpenAIConnectionHandler.cs
new file mode 100644
index 00000000..d1092982
--- /dev/null
+++ b/src/Primitives/CrestApps.Core.AI.OpenAI.Azure/Handlers/AzureOpenAIConnectionHandler.cs
@@ -0,0 +1,39 @@
+using CrestApps.Core.AI.Handlers;
+using CrestApps.Core.AI.Models;
+using CrestApps.Core.Azure.Models;
+using Microsoft.AspNetCore.DataProtection;
+
+namespace CrestApps.Core.AI.OpenAI.Azure.Handlers;
+
+internal sealed class AzureOpenAIConnectionHandler : AIProviderConnectionHandlerBase
+{
+    private const string ConnectionProtectorName = "AIProviderConnection";
+
+    private readonly IDataProtectionProvider _dataProtectionProvider;
+
+    public AzureOpenAIConnectionHandler(IDataProtectionProvider dataProtectionProvider)
+    {
+        _dataProtectionProvider = dataProtectionProvider;
+    }
+
+    public override void Initializing(InitializingAIProviderConnectionContext context)
+    {
+        if (!string.Equals(context.Connection.ClientName, AzureOpenAIConstants.ClientName, StringComparison.Ordinal))
+        {
+            return;
+        }
+
+        var metadata = context.Connection.GetOrCreate<AzureConnectionMetadata>();
+
+        context.Values["Endpoint"] = metadata.Endpoint?.ToString();
+        context.Values["AuthenticationType"] = metadata.AuthenticationType.ToString();
+        context.Values["IdentityId"] = metadata.IdentityId;
+
+        if (!string.IsNullOrEmpty(metadata.ApiKey))
+        {
+            var protector = _dataProtectionProvider.CreateProtector(ConnectionProtectorName);
+
+            context.Values["ApiKey"] = protector.Unprotect(metadata.ApiKey);
+        }
+    }
+}
diff --git a/src/Primitives/CrestApps.Core.AI.OpenAI.Azure/ServiceCollectionExtensions.cs b/src/Primitives/CrestApps.Core.AI.OpenAI.Azure/ServiceCollectionExtensions.cs
index f1e37ac8..e1018061 100644
--- a/src/Primitives/CrestApps.Core.AI.OpenAI.Azure/ServiceCollectionExtensions.cs
+++ b/src/Primitives/CrestApps.Core.AI.OpenAI.Azure/ServiceCollectionExtensions.cs
@@ -1,4 +1,6 @@
 using CrestApps.Core.AI.Clients;
+using CrestApps.Core.AI.Models;
+using CrestApps.Core.AI.OpenAI.Azure.Handlers;
 using CrestApps.Core.AI.OpenAI.Azure.Models;
 using CrestApps.Core.AI.OpenAI.Azure.Services;
 using CrestApps.Core.Builders;
@@ -22,6 +24,7 @@ public static IServiceCollection AddCoreAIAzureOpenAI(this IServiceCollection se
         services.TryAddEnumerable(ServiceDescriptor.Singleton<IConfigureOptions<AzureClientOptions>, AzureClientOptionsConfiguration>());
         services.TryAddEnumerable(ServiceDescriptor.Scoped<IAIClientProvider, AzureOpenAIClientProvider>());
         services.TryAddEnumerable(ServiceDescriptor.Scoped<IAIClientProvider, AzureSpeechClientProvider>());
+        services.TryAddEnumerable(ServiceDescriptor.Scoped<IAIProviderConnectionHandler, AzureOpenAIConnectionHandler>());
 
         services.AddCoreAIProfile<AzureOpenAICompletionClient>(AzureOpenAIConstants.ClientName, o =>
         {
diff --git a/src/Primitives/CrestApps.Core.AI.OpenAI/Handlers/OpenAIConnectionHandler.cs b/src/Primitives/CrestApps.Core.AI.OpenAI/Handlers/OpenAIConnectionHandler.cs
new file mode 100644
index 00000000..f2b79253
--- /dev/null
+++ b/src/Primitives/CrestApps.Core.AI.OpenAI/Handlers/OpenAIConnectionHandler.cs
@@ -0,0 +1,37 @@
+using CrestApps.Core.AI.Handlers;
+using CrestApps.Core.AI.Models;
+using CrestApps.Core.AI.OpenAI.Models;
+using Microsoft.AspNetCore.DataProtection;
+
+namespace CrestApps.Core.AI.OpenAI.Handlers;
+
+internal sealed class OpenAIConnectionHandler : AIProviderConnectionHandlerBase
+{
+    private const string ConnectionProtectorName = "AIProviderConnection";
+
+    private readonly IDataProtectionProvider _dataProtectionProvider;
+
+    public OpenAIConnectionHandler(IDataProtectionProvider dataProtectionProvider)
+    {
+        _dataProtectionProvider = dataProtectionProvider;
+    }
+
+    public override void Initializing(InitializingAIProviderConnectionContext context)
+    {
+        if (!string.Equals(context.Connection.ClientName, OpenAIConstants.ClientName, StringComparison.Ordinal))
+        {
+            return;
+        }
+
+        var metadata = context.Connection.GetOrCreate<OpenAIConnectionMetadata>();
+
+        if (!string.IsNullOrEmpty(metadata.ApiKey))
+        {
+            var protector = _dataProtectionProvider.CreateProtector(ConnectionProtectorName);
+
+            context.Values["ApiKey"] = protector.Unprotect(metadata.ApiKey);
+        }
+
+        context.Values["Endpoint"] = metadata.Endpoint?.ToString();
+    }
+}
diff --git a/src/Primitives/CrestApps.Core.AI.OpenAI/ServiceCollectionExtensions.cs b/src/Primitives/CrestApps.Core.AI.OpenAI/ServiceCollectionExtensions.cs
index 05c42b46..30e1b843 100644
--- a/src/Primitives/CrestApps.Core.AI.OpenAI/ServiceCollectionExtensions.cs
+++ b/src/Primitives/CrestApps.Core.AI.OpenAI/ServiceCollectionExtensions.cs
@@ -1,4 +1,6 @@
 using CrestApps.Core.AI.Clients;
+using CrestApps.Core.AI.Models;
+using CrestApps.Core.AI.OpenAI.Handlers;
 using CrestApps.Core.AI.OpenAI.Services;
 using CrestApps.Core.Builders;
 using Microsoft.Extensions.DependencyInjection;
@@ -17,6 +19,7 @@ public static IServiceCollection AddCoreAIOpenAI(this IServiceCollection service
         ArgumentNullException.ThrowIfNull(services);
 
         services.TryAddEnumerable(ServiceDescriptor.Scoped<IAIClientProvider, OpenAIClientProvider>());
+        services.TryAddEnumerable(ServiceDescriptor.Scoped<IAIProviderConnectionHandler, OpenAIConnectionHandler>());
 
         services.AddCoreAIProfile<OpenAICompletionClient>(OpenAIConstants.ClientName, o =>
         {
diff --git a/tests/CrestApps.Core.Tests/Framework/Mvc/AIProviderConnectionOptionsTests.cs b/tests/CrestApps.Core.Tests/Framework/Mvc/AIProviderConnectionOptionsTests.cs
index 2fb0a81b..afc8e9b7 100644
--- a/tests/CrestApps.Core.Tests/Framework/Mvc/AIProviderConnectionOptionsTests.cs
+++ b/tests/CrestApps.Core.Tests/Framework/Mvc/AIProviderConnectionOptionsTests.cs
@@ -1,6 +1,7 @@
 using CrestApps.Core.AI;
 using CrestApps.Core.AI.Deployments;
 using CrestApps.Core.AI.Models;
+using CrestApps.Core.AI.OpenAI;
 using CrestApps.Core.AI.OpenAI.Azure;
 using CrestApps.Core.AI.OpenAI.Azure.Models;
 using CrestApps.Core.AI.Services;
@@ -71,6 +72,36 @@ public void AddCoreAIAzureOpenAI_WhenAzureClientSettingsConfigured_ShouldBindAzu
         Assert.False(options.EnableMessageContentLogging);
     }
 
+    [Fact]
+    public void AddCoreAIAzureOpenAI_ShouldRegisterAzureConnectionHandler()
+    {
+        var services = new ServiceCollection();
+        services.AddLogging();
+        services.AddDataProtection();
+        services.AddCoreAIServices();
+        services.AddCoreAIAzureOpenAI();
+        using var serviceProvider = services.BuildServiceProvider();
+
+        var handlers = serviceProvider.GetServices<IAIProviderConnectionHandler>().ToArray();
+
+        Assert.Contains(handlers, handler => handler.GetType().FullName == "CrestApps.Core.AI.OpenAI.Azure.Handlers.AzureOpenAIConnectionHandler");
+    }
+
+    [Fact]
+    public void AddCoreAIOpenAI_ShouldRegisterOpenAIConnectionHandler()
+    {
+        var services = new ServiceCollection();
+        services.AddLogging();
+        services.AddDataProtection();
+        services.AddCoreAIServices();
+        services.AddCoreAIOpenAI();
+        using var serviceProvider = services.BuildServiceProvider();
+
+        var handlers = serviceProvider.GetServices<IAIProviderConnectionHandler>().ToArray();
+
+        Assert.Contains(handlers, handler => handler.GetType().FullName == "CrestApps.Core.AI.OpenAI.Handlers.OpenAIConnectionHandler");
+    }
+
     [Fact]
     public void AddCrestAppsAI_WhenClientNameIsMissing_ShouldIgnoreConnectionEntry()
     {