diff --git a/src/Agent.Worker/Build/BuildDirectoryManager.cs b/src/Agent.Worker/Build/BuildDirectoryManager.cs
index b6a01548ed..0da3f6c24e 100644
--- a/src/Agent.Worker/Build/BuildDirectoryManager.cs
+++ b/src/Agent.Worker/Build/BuildDirectoryManager.cs
@@ -208,7 +208,7 @@ private bool ShouldOverrideBuildDirectory(IList<RepositoryResource> repositories
         {
             if (repositories?.Count == 1 && repositories[0].Type == RepositoryTypes.Tfvc)
             {
-                return settings.IsHosted;
+                return settings.IsMSHosted;
             }
             else
             {
diff --git a/src/Agent.Worker/JobRunner.cs b/src/Agent.Worker/JobRunner.cs
index e2f54e6fe7..2a49c0d0d3 100644
--- a/src/Agent.Worker/JobRunner.cs
+++ b/src/Agent.Worker/JobRunner.cs
@@ -179,6 +179,7 @@ public async Task<TaskResult> RunAsync(Pipelines.AgentJobRequestMessage message,
                 jobContext.SetVariable(Constants.Variables.Agent.HomeDirectory, HostContext.GetDirectory(WellKnownDirectory.Root), isFilePath: true);
                 jobContext.SetVariable(Constants.Variables.Agent.JobName, message.JobDisplayName);
                 jobContext.SetVariable(Constants.Variables.Agent.CloudId, settings.AgentCloudId);
+                jobContext.SetVariable(Constants.Variables.Agent.IsSelfHosted, settings.IsMSHosted ? "0" : "1");
                 jobContext.SetVariable(Constants.Variables.Agent.MachineName, Environment.MachineName);
                 jobContext.SetVariable(Constants.Variables.Agent.Name, settings.AgentName);
                 jobContext.SetVariable(Constants.Variables.Agent.OS, VarUtil.OS);
diff --git a/src/Agent.Worker/TaskRunner.cs b/src/Agent.Worker/TaskRunner.cs
index d6a63919e0..d1c2e55c84 100644
--- a/src/Agent.Worker/TaskRunner.cs
+++ b/src/Agent.Worker/TaskRunner.cs
@@ -577,18 +577,24 @@ private void PublishTelemetry(Definition taskDefinition, HandlerData handlerData
 
             var useNode10 = AgentKnobs.UseNode10.GetValue(ExecutionContext).AsString();
             var expectedExecutionHandler = (taskDefinition.Data.Execution?.All != null) ? string.Join(", ", taskDefinition.Data.Execution.All) : "";
+            var systemVersion = PlatformUtil.GetSystemVersion();
 
             Dictionary<string, string> telemetryData = new Dictionary<string, string>
             {
                 { "TaskName", Task.Reference.Name },
                 { "TaskId", Task.Reference.Id.ToString() },
                 { "Version", Task.Reference.Version },
-                { "OS", PlatformUtil.HostOS.ToString() },
+                { "OS", PlatformUtil.GetSystemId() ?? "" },
+                { "OSVersion", systemVersion?.Name?.ToString() ?? "" },
+                { "OSBuild", systemVersion?.Version?.ToString() ?? "" },
                 { "ExpectedExecutionHandler", expectedExecutionHandler },
                 { "RealExecutionHandler", handlerData.ToString() },
                 { "UseNode10", useNode10 },
                 { "JobId", ExecutionContext.Variables.System_JobId.ToString()},
-                { "PlanId", ExecutionContext.Variables.Get("system.planId")}
+                { "PlanId", ExecutionContext.Variables.Get(Constants.Variables.System.JobId)},
+                { "AgentName", ExecutionContext.Variables.Get(Constants.Variables.Agent.Name)},
+                { "MachineName", ExecutionContext.Variables.Get(Constants.Variables.Agent.MachineName)},
+                { "IsSelfHosted", ExecutionContext.Variables.Get(Constants.Variables.Agent.IsSelfHosted)}
             };
 
             var cmd = new Command("telemetry", "publish");
diff --git a/src/Microsoft.VisualStudio.Services.Agent/ConfigurationStore.cs b/src/Microsoft.VisualStudio.Services.Agent/ConfigurationStore.cs
index 3c99a551d2..92d6f6c2a8 100644
--- a/src/Microsoft.VisualStudio.Services.Agent/ConfigurationStore.cs
+++ b/src/Microsoft.VisualStudio.Services.Agent/ConfigurationStore.cs
@@ -51,7 +51,7 @@ public sealed class AgentSettings
         public bool EnableServiceSidTypeUnrestricted { get; set; }
 
         [IgnoreDataMember]
-        public bool IsHosted => AgentCloudId != null;
+        public bool IsMSHosted => AgentCloudId != null;
 
         [DataMember(EmitDefaultValue = false)]
         public string Fingerprint
diff --git a/src/Microsoft.VisualStudio.Services.Agent/Constants.cs b/src/Microsoft.VisualStudio.Services.Agent/Constants.cs
index ac6282ee78..0aa9696c27 100644
--- a/src/Microsoft.VisualStudio.Services.Agent/Constants.cs
+++ b/src/Microsoft.VisualStudio.Services.Agent/Constants.cs
@@ -286,6 +286,7 @@ public static class Agent
                 public static readonly string Diagnostic = "agent.diagnostic";
                 public static readonly string HomeDirectory = "agent.homedirectory";
                 public static readonly string Id = "agent.id";
+                public static readonly string IsSelfHosted = "agent.isselfhosted";
                 public static readonly string GitUseSChannel = "agent.gituseschannel";
                 public static readonly string JobName = "agent.jobname";
                 public static readonly string JobStatus = "agent.jobstatus";
@@ -431,6 +432,7 @@ public static class System
                 public static readonly string PhaseAttempt = "system.phaseAttempt";
                 public static readonly string PhaseDisplayName = "system.phaseDisplayName";
                 public static readonly string PhaseName = "system.phaseName";
+                public static readonly string PlanId = "system.planId";
                 public static readonly string PreferGitFromPath = "system.prefergitfrompath";
                 public static readonly string PullRequestTargetBranchName = "system.pullrequest.targetbranch";
                 public static readonly string SelfManageGitCreds = "system.selfmanagegitcreds";
@@ -472,6 +474,7 @@ public static class Task
                 Agent.GitUseSChannel,
                 Agent.HomeDirectory,
                 Agent.Id,
+                Agent.IsSelfHosted,
                 Agent.JobName,
                 Agent.JobStatus,
                 Agent.MachineName,
@@ -571,6 +574,7 @@ public static class Task
                 System.PhaseAttempt,
                 System.PhaseDisplayName,
                 System.PhaseName,
+                System.PlanId,
                 System.PreferGitFromPath,
                 System.PullRequestTargetBranchName,
                 System.SelfManageGitCreds,