diff --git a/source/Octopus.Client.Tests/PublicSurfaceAreaFixture.ThePublicSurfaceAreaShouldNotRegress..NETCore.approved.txt b/source/Octopus.Client.Tests/PublicSurfaceAreaFixture.ThePublicSurfaceAreaShouldNotRegress..NETCore.approved.txt
index e64a0bcb8..7a2476b13 100644
--- a/source/Octopus.Client.Tests/PublicSurfaceAreaFixture.ThePublicSurfaceAreaShouldNotRegress..NETCore.approved.txt
+++ b/source/Octopus.Client.Tests/PublicSurfaceAreaFixture.ThePublicSurfaceAreaShouldNotRegress..NETCore.approved.txt
@@ -3595,6 +3595,7 @@ Octopus.Client.Operations
     String[] EnvironmentNames { get; set; }
     String MachineName { get; set; }
     String MachinePolicy { get; set; }
+    String ProxyName { get; set; }
     String[] Roles { get; set; }
     Uri SubscriptionId { get; set; }
     String[] Tenants { get; set; }
@@ -3616,6 +3617,7 @@ Octopus.Client.Operations
     String[] EnvironmentNames { get; set; }
     String MachineName { get; set; }
     String MachinePolicy { get; set; }
+    String ProxyName { get; set; }
     String[] Roles { get; set; }
     Uri SubscriptionId { get; set; }
     String[] Tenants { get; set; }
diff --git a/source/Octopus.Client.Tests/PublicSurfaceAreaFixture.ThePublicSurfaceAreaShouldNotRegress..NETFramework.approved.txt b/source/Octopus.Client.Tests/PublicSurfaceAreaFixture.ThePublicSurfaceAreaShouldNotRegress..NETFramework.approved.txt
index a0faffa07..ea7b393c2 100644
--- a/source/Octopus.Client.Tests/PublicSurfaceAreaFixture.ThePublicSurfaceAreaShouldNotRegress..NETFramework.approved.txt
+++ b/source/Octopus.Client.Tests/PublicSurfaceAreaFixture.ThePublicSurfaceAreaShouldNotRegress..NETFramework.approved.txt
@@ -3998,6 +3998,7 @@ Octopus.Client.Operations
     String[] EnvironmentNames { get; set; }
     String MachineName { get; set; }
     String MachinePolicy { get; set; }
+    String ProxyName { get; set; }
     String[] Roles { get; set; }
     Uri SubscriptionId { get; set; }
     String[] Tenants { get; set; }
@@ -4022,6 +4023,7 @@ Octopus.Client.Operations
     String[] EnvironmentNames { get; set; }
     String MachineName { get; set; }
     String MachinePolicy { get; set; }
+    String ProxyName { get; set; }
     String[] Roles { get; set; }
     Uri SubscriptionId { get; set; }
     String[] Tenants { get; set; }
diff --git a/source/Octopus.Client/Operations/IRegisterMachineOperation.cs b/source/Octopus.Client/Operations/IRegisterMachineOperation.cs
index fd859b575..78f1d4abe 100644
--- a/source/Octopus.Client/Operations/IRegisterMachineOperation.cs
+++ b/source/Octopus.Client/Operations/IRegisterMachineOperation.cs
@@ -54,6 +54,11 @@ public interface IRegisterMachineOperation
         /// </summary>
         string TentacleThumbprint { get; set; }
 
+        /// <summary>
+        /// Gets or sets the name of the proxy that Octopus should use when communicating with the Tentacle.
+        /// </summary>
+        string ProxyName { get; set; }
+
         /// <summary>
         /// If a machine with the same name already exists, it won't be overwritten by default (instead, an
         /// <see cref="ArgumentException" /> will be thrown).
diff --git a/source/Octopus.Client/Operations/RegisterMachineOperation.cs b/source/Octopus.Client/Operations/RegisterMachineOperation.cs
index 4c0befb1f..93ba4bb34 100644
--- a/source/Octopus.Client/Operations/RegisterMachineOperation.cs
+++ b/source/Octopus.Client/Operations/RegisterMachineOperation.cs
@@ -77,6 +77,11 @@ public RegisterMachineOperation(IOctopusClientFactory clientFactory)
         /// </summary>
         public string TentacleThumbprint { get; set; }
 
+        /// <summary>
+        /// Gets or sets the name of the proxy that Octopus should use when communicating with the Tentacle.
+        /// </summary>
+        public string ProxyName { get; set; }
+
         /// <summary>
         /// If a machine with the same name already exists, it won't be overwritten by default (instead, an
         /// <see cref="ArgumentException" /> will be thrown).
@@ -135,8 +140,9 @@ public void Execute(IOctopusRepository repository)
             var machine = GetMachine(repository);
             var tenants = GetTenants(repository);
             ValidateTenantTags(repository);
+            var proxy = GetProxy(repository);
 
-            ApplyChanges(machine, selectedEnvironments, machinePolicy, tenants);
+            ApplyChanges(machine, selectedEnvironments, machinePolicy, tenants, proxy);
 
             if (machine.Id != null)
                 repository.Machines.Modify(machine);
@@ -199,6 +205,18 @@ MachinePolicyResource GetMachinePolicy(IOctopusRepository repository)
             return machinePolicy;
         }
 
+        ProxyResource GetProxy(IOctopusRepository repository)
+        {
+            var proxy = default(ProxyResource);
+            if (!string.IsNullOrEmpty(ProxyName))
+            {
+                proxy = repository.Proxies.FindByName(ProxyName);
+                if (proxy == null)
+                    throw new ArgumentException(CouldNotFindMessage("proxy name", ProxyName));
+            }
+            return proxy;
+        }
+
         MachineResource GetMachine(IOctopusRepository repository)
         {
             var existing = default(MachineResource);
@@ -255,9 +273,10 @@ public async Task ExecuteAsync(IOctopusAsyncRepository repository)
             var machineTask = GetMachine(repository).ConfigureAwait(false);
             var tenants = GetTenants(repository).ConfigureAwait(false);
             await ValidateTenantTags(repository).ConfigureAwait(false);
+            var proxy = GetProxy(repository).ConfigureAwait(false);
 
             var machine = await machineTask;
-            ApplyChanges(machine, await selectedEnvironments, await machinePolicy, await tenants);
+            ApplyChanges(machine, await selectedEnvironments, await machinePolicy, await tenants, await proxy);
 
             if (machine.Id != null)
                 await repository.Machines.Modify(machine).ConfigureAwait(false);
@@ -321,6 +340,18 @@ async Task<MachinePolicyResource> GetMachinePolicy(IOctopusAsyncRepository repos
             return machinePolicy;
         }
 
+        async Task<ProxyResource> GetProxy(IOctopusAsyncRepository repository)
+        {
+            var proxy = default(ProxyResource);
+            if (!string.IsNullOrEmpty(ProxyName))
+            {
+                proxy = await repository.Proxies.FindByName(ProxyName).ConfigureAwait(false);
+                if (proxy == null)
+                    throw new ArgumentException(CouldNotFindMessage("proxy name", ProxyName));
+            }
+            return proxy;
+        }
+
         async Task<MachineResource> GetMachine(IOctopusAsyncRepository repository)
         {
             var existing = default(MachineResource);
@@ -336,7 +367,7 @@ async Task<MachineResource> GetMachine(IOctopusAsyncRepository repository)
             return existing ?? new MachineResource();
         }
 
-        void ApplyChanges(MachineResource machine, IEnumerable<EnvironmentResource> environment, MachinePolicyResource machinePolicy, IEnumerable<TenantResource> tenants)
+        void ApplyChanges(MachineResource machine, IEnumerable<EnvironmentResource> environment, MachinePolicyResource machinePolicy, IEnumerable<TenantResource> tenants, ProxyResource proxy)
         {
             machine.EnvironmentIds = new ReferenceCollection(environment.Select(e => e.Id).ToArray());
             machine.TenantIds = new ReferenceCollection(tenants.Select(t => t.Id).ToArray());
@@ -351,6 +382,7 @@ void ApplyChanges(MachineResource machine, IEnumerable<EnvironmentResource> envi
                 var listening = new ListeningTentacleEndpointResource();
                 listening.Uri = new Uri("https://" + TentacleHostname.ToLowerInvariant() + ":" + TentaclePort.ToString(CultureInfo.InvariantCulture) + "/").ToString();
                 listening.Thumbprint = TentacleThumbprint;
+                listening.ProxyId = proxy?.Id;
                 machine.Endpoint = listening;
             }
             else if (CommunicationStyle == CommunicationStyle.TentacleActive)