diff --git a/src/AWS.Deploy.CLI/ServerMode/Controllers/DeploymentController.cs b/src/AWS.Deploy.CLI/ServerMode/Controllers/DeploymentController.cs
index da87716a..303524e9 100644
--- a/src/AWS.Deploy.CLI/ServerMode/Controllers/DeploymentController.cs
+++ b/src/AWS.Deploy.CLI/ServerMode/Controllers/DeploymentController.cs
@@ -699,6 +699,15 @@ private IServiceProvider CreateSessionServiceProvider(SessionState state)
                 services.AddSingleton<IAWSResourceQueryer>(state.AWSResourceQueryService);
             }
 
+            if (state.SystemCapabilityEvaluator == null)
+            {
+                services.AddSingleton<ISystemCapabilityEvaluator, SystemCapabilityEvaluator>();
+            }
+            else
+            {
+                services.AddSingleton<ISystemCapabilityEvaluator>(state.SystemCapabilityEvaluator);
+            }
+
             services.AddCustomServices();
             var serviceProvider = services.BuildServiceProvider();
 
@@ -710,9 +719,11 @@ private IServiceProvider CreateSessionServiceProvider(SessionState state)
                 awsOptions.Region = RegionEndpoint.GetBySystemName(state.AWSRegion);
             });
 
-            // Cache the SessionAWSResourceQuery with the session state so it can be reused in future
-            // ServerMode API calls with the same session id.
+            // Cache the SessionAWSResourceQuery and SystemCapabilityEvaluator with the session state
+            // so they can be reused in future ServerMode API calls with the same session id. This avoids reloading
+            // existing resources from AWS and running the Docker/Node checks when they're not expected to change.
             state.AWSResourceQueryService = serviceProvider.GetRequiredService<IAWSResourceQueryer>() as SessionAWSResourceQuery;
+            state.SystemCapabilityEvaluator = serviceProvider.GetRequiredService<ISystemCapabilityEvaluator>() as SystemCapabilityEvaluator;
 
             return serviceProvider;
         }
diff --git a/src/AWS.Deploy.CLI/ServerMode/SessionState.cs b/src/AWS.Deploy.CLI/ServerMode/SessionState.cs
index bbac2086..19d9a3d3 100644
--- a/src/AWS.Deploy.CLI/ServerMode/SessionState.cs
+++ b/src/AWS.Deploy.CLI/ServerMode/SessionState.cs
@@ -5,6 +5,7 @@
 using System.Threading.Tasks;
 using AWS.Deploy.CLI.ServerMode.Services;
 using AWS.Deploy.Common;
+using AWS.Deploy.Orchestration;
 
 namespace AWS.Deploy.CLI.ServerMode
 {
@@ -30,6 +31,8 @@ public class SessionState
 
         public SessionAWSResourceQuery? AWSResourceQueryService { get; set; }
 
+        public SystemCapabilityEvaluator? SystemCapabilityEvaluator { get; set; }
+
         public Task? DeploymentTask { get; set; }
 
         public SessionState(