diff --git a/README.md b/README.md
index dcd2509..0bfb158 100644
--- a/README.md
+++ b/README.md
@@ -1,5 +1,5 @@
 <h1 align="center" style="border-bottom: none">
-    Nameshield   Gateway AnyCA Gateway REST Plugin
+    Nameshield AnyCA Gateway REST Plugin
 </h1>
 
 <p align="center">
@@ -43,10 +43,10 @@ The Nameshield AnyCA Gateway REST plugin extends the capabilities of Nameshield
 
 ## Compatibility
 
-The Nameshield   Gateway AnyCA Gateway REST plugin is compatible with the Keyfactor AnyCA Gateway REST 24.2.0 and later.
+The Nameshield AnyCA Gateway REST plugin is compatible with the Keyfactor AnyCA Gateway REST 24.2.0 and later.
 
 ## Support
-The Nameshield   Gateway AnyCA Gateway REST plugin is open source and community supported, meaning that there is **no SLA** applicable. 
+The Nameshield AnyCA Gateway REST plugin is open source and community supported, meaning that there is **no SLA** applicable. 
 
 > To report a problem or suggest a new feature, use the **[Issues](../../issues)** tab. If you want to contribute actual bug fixes or proposed enhancements, use the **[Pull requests](../../pulls)** tab.
 
@@ -58,7 +58,7 @@ TODO Requirements is a required section
 
 1. Install the AnyCA Gateway REST per the [official Keyfactor documentation](https://software.keyfactor.com/Guides/AnyCAGatewayREST/Content/AnyCAGatewayREST/InstallIntroduction.htm).
 
-2. On the server hosting the AnyCA Gateway REST, download and unzip the latest [Nameshield   Gateway AnyCA Gateway REST plugin](https://github.com/Keyfactor/nameshield-caplugin/releases/latest) from GitHub.
+2. On the server hosting the AnyCA Gateway REST, download and unzip the latest [Nameshield AnyCA Gateway REST plugin](https://github.com/Keyfactor/nameshield-caplugin/releases/latest) from GitHub.
 
 3. Copy the unzipped directory (usually called `net6.0` or `net8.0`) to the Extensions directory:
 
@@ -69,11 +69,11 @@ TODO Requirements is a required section
     Program Files\Keyfactor\AnyCA Gateway\AnyGatewayREST\net8.0\Extensions
     ```
 
-    > The directory containing the Nameshield   Gateway AnyCA Gateway REST plugin DLLs (`net6.0` or `net8.0`) can be named anything, as long as it is unique within the `Extensions` directory.
+    > The directory containing the Nameshield AnyCA Gateway REST plugin DLLs (`net6.0` or `net8.0`) can be named anything, as long as it is unique within the `Extensions` directory.
 
 4. Restart the AnyCA Gateway REST service.
 
-5. Navigate to the AnyCA Gateway REST portal and verify that the Gateway recognizes the Nameshield   Gateway plugin by hovering over the ⓘ symbol to the right of the Gateway on the top left of the portal.
+5. Navigate to the AnyCA Gateway REST portal and verify that the Gateway recognizes the Nameshield plugin by hovering over the ⓘ symbol to the right of the Gateway on the top left of the portal.
 
 ## Configuration
 
diff --git a/nameshield-caplugin/Client/NameshieldClient.cs b/nameshield-caplugin/Client/NameshieldClient.cs
index e5de62e..ea34c2b 100644
--- a/nameshield-caplugin/Client/NameshieldClient.cs
+++ b/nameshield-caplugin/Client/NameshieldClient.cs
@@ -149,6 +149,23 @@ public async Task<RequestCertificateResponse> RequestCertificate(CertificateRequ
 			}
 		}
 
+		public async Task<RequestCertificateResponse> GetOrderDetails(string reqId)
+		{
+			var response = await RestClient.GetAsync($"ssl/v2/orders/{reqId}");
+			if (response.IsSuccessStatusCode)
+			{
+				string responseContent = await response.Content.ReadAsStringAsync();
+				Logger.LogTrace($"GET Order Details response: {responseContent}");
+				var responseObj = JsonConvert.DeserializeObject<OrderData>(responseContent);
+				return new RequestCertificateResponse { Order = responseObj.Order };
+			}
+			else
+			{
+				var errors = JsonConvert.DeserializeObject<ErrorData>(await response.Content.ReadAsStringAsync());
+				throw new Exception($"Error pulling order details: {errors.Errors[0].Title} | {errors.Errors[0].Detail}");
+			}
+		}
+
 		public async Task<bool> RevokeCertificate(string serialNum)
 		{
 			var response = await RestClient.PostAsync($"ssl/v2/certificates/{serialNum}/revoke", null);
diff --git a/nameshield-caplugin/NameshieldCAPlugin.cs b/nameshield-caplugin/NameshieldCAPlugin.cs
index 3aca18f..6469690 100644
--- a/nameshield-caplugin/NameshieldCAPlugin.cs
+++ b/nameshield-caplugin/NameshieldCAPlugin.cs
@@ -11,6 +11,7 @@
 using System;
 using System.Collections.Concurrent;
 using System.Collections.Generic;
+using System.Diagnostics.Metrics;
 using System.Linq;
 using System.Text;
 using System.Threading.Tasks;
@@ -37,14 +38,17 @@ public void Initialize(IAnyCAPluginConfigProvider configProvider, ICertificateDa
 
 		public async Task<EnrollmentResult> Enroll(string csr, string subject, Dictionary<string, string[]> san, EnrollmentProductInfo productInfo, RequestFormat requestFormat, EnrollmentType enrollmnentType)
 		{
+			_logger.MethodEntry(LogLevel.Debug);
 			NameshieldClient client = NameshieldClient.InitializeClient(_config);
 
 			var allProducts = Task.Run(async () => await client.ListProducts()).Result;
+			_logger.LogTrace($"Found {allProducts.Products.Count} products");
 			string productId = null;
 			foreach (var product in allProducts.Products)
 			{
 				if (string.Equals(product.Attributes.Name, productInfo.ProductID))
 				{
+					_logger.LogTrace($"Found {productInfo.ProductID} product, using ID {product.Id}");
 					productId = product.Id;
 					break;
 				}
@@ -58,6 +62,7 @@ public async Task<EnrollmentResult> Enroll(string csr, string subject, Dictionar
 			if (productInfo.ProductParameters.ContainsKey(Constants.Config.Template.ORGANIZATION_ID) && !string.IsNullOrEmpty(productInfo.ProductParameters[Constants.Config.Template.ORGANIZATION_ID]))
 			{
 				orgId = productInfo.ProductParameters[Constants.Config.Template.ORGANIZATION_ID];
+				_logger.LogTrace($"Using organization ID {orgId}");
 			}
 
 			if (string.IsNullOrEmpty(orgId))
@@ -72,10 +77,12 @@ public async Task<EnrollmentResult> Enroll(string csr, string subject, Dictionar
 					orgName = ParseSubject(subject, "O=");
 				}
 				var organizations = Task.Run(async () => await client.ListOrganizations()).Result;
+				_logger.LogTrace($"Found {organizations.Organizations.Count} organizations");
 				foreach (var organization in organizations.Organizations)
 				{
 					if (string.Equals(organization.Attributes.Name, orgName, StringComparison.OrdinalIgnoreCase))
 					{
+						_logger.LogTrace($"Found organization with name {orgName}, using ID {organization.Id}");
 						orgId = organization.Id;
 						break;
 					}
@@ -105,8 +112,20 @@ public async Task<EnrollmentResult> Enroll(string csr, string subject, Dictionar
 			{
 				throw new Exception($"Certificate request for subect {subject} was rejected");
 			}
-			else if (!string.Equals(status, "delivered", StringComparison.OrdinalIgnoreCase))
+			int time = 0;
+			while (string.Equals(status, "checked_out", StringComparison.OrdinalIgnoreCase) && time < 8)
+			{
+				_logger.LogTrace($"Cert retured CHECKED_OUT status, rechecking in 5 seconds. Pickup attempt {time} of 8");
+				// Sleep for 5 seconds then try again, up to a max of 8 tries
+				Thread.Sleep(5000);
+				time++;
+				response = Task.Run(async () => await client.GetOrderDetails(response.Order.Id)).Result;
+				status = response.Order.Attributes.Status;
+			}
+
+			if (!string.Equals(status, "delivered", StringComparison.OrdinalIgnoreCase))
 			{
+				_logger.LogTrace($"Cert request submitted successfully but not delivered, will be picked up by a fugure sync once it is issued.");
 				return new EnrollmentResult
 				{
 					CARequestID = response.Order.Id,