diff --git a/.azure-pipelines/build-job.yml b/.azure-pipelines/build-job.yml
index 8f560d4300..f82a0d4cc4 100644
--- a/.azure-pipelines/build-job.yml
+++ b/.azure-pipelines/build-job.yml
@@ -138,6 +138,7 @@ jobs:
     - script: ${{ variables.devCommand }} testl0 Debug ${{ parameters.os }}-${{ parameters.arch }}
       workingDirectory: src
       displayName: Unit tests
+      timeoutInMinutes: 5
 
   # Install nuget
   - ${{ if eq(parameters.os, 'win') }}:
diff --git a/src/Agent.Sdk/Knob/AgentKnobs.cs b/src/Agent.Sdk/Knob/AgentKnobs.cs
index 03d4be36da..b5b4ba3591 100644
--- a/src/Agent.Sdk/Knob/AgentKnobs.cs
+++ b/src/Agent.Sdk/Knob/AgentKnobs.cs
@@ -506,11 +506,17 @@ public class AgentKnobs
             new EnvironmentKnobSource("AGENT_DISABLE_CLEAN_REPO_DEFAULT_VALUE"),
             new BuiltInDefaultKnobSource("false"));
 
-          public static readonly Knob IgnoreVSTSTaskLib = new Knob(
+        public static readonly Knob IgnoreVSTSTaskLib = new Knob(
             nameof(IgnoreVSTSTaskLib),
             "Ignores the VSTSTaskLib folder when copying tasks.",
             new RuntimeKnobSource("AZP_AGENT_IGNORE_VSTSTASKLIB"),
             new EnvironmentKnobSource("AZP_AGENT_IGNORE_VSTSTASKLIB"),
             new BuiltInDefaultKnobSource("false"));
+
+        public static readonly Knob CheckForTaskDeprecation = new Knob(
+            nameof(CheckForTaskDeprecation),
+            "If true, the agent will check in the 'Initialize job' step each task used in the job for task deprecation.",
+            new EnvironmentKnobSource("AZP_AGENT_CHECK_FOR_TASK_DEPRECATION"),
+            new BuiltInDefaultKnobSource("false"));
     }
 }
diff --git a/src/Agent.Worker/TaskManager.cs b/src/Agent.Worker/TaskManager.cs
index 908b6752eb..3d944f1f3a 100644
--- a/src/Agent.Worker/TaskManager.cs
+++ b/src/Agent.Worker/TaskManager.cs
@@ -7,6 +7,7 @@
 using Pipelines = Microsoft.TeamFoundation.DistributedTask.Pipelines;
 using Microsoft.VisualStudio.Services.Agent.Util;
 using Newtonsoft.Json;
+using Newtonsoft.Json.Linq;
 using System;
 using System.Collections.Generic;
 using System.IO;
@@ -73,7 +74,13 @@ into taskGrouping
                     Trace.Info("Skip download checkout task.");
                     continue;
                 }
+
                 await DownloadAsync(executionContext, task);
+
+                if (AgentKnobs.CheckForTaskDeprecation.GetValue(UtilKnobValueContext.Instance()).AsBoolean())
+                {
+                    CheckForTaskDeprecation(executionContext, task);
+                }
             }
         }
 
@@ -308,6 +315,45 @@ private async Task DownloadAsync(IExecutionContext executionContext, Pipelines.T
             }
         }
 
+        private void CheckForTaskDeprecation(IExecutionContext executionContext, Pipelines.TaskStepDefinitionReference task)
+        {
+            string taskJsonPath = Path.Combine(GetDirectory(task), "task.json");
+            string taskJsonText = File.ReadAllText(taskJsonPath);
+            JObject taskJson = JObject.Parse(taskJsonText);
+            var deprecated = taskJson["deprecated"];
+
+            if (deprecated != null && deprecated.Value<bool>())
+            {
+                string friendlyName = taskJson["friendlyName"].Value<string>();
+                int majorVersion = new Version(task.Version).Major;
+                string deprecationMessage = StringUtil.Loc("DeprecationMessage", friendlyName, majorVersion, task.Name);
+                var removalDate = taskJson["removalDate"];
+
+                if (removalDate != null)
+                {
+                    string whitespace = " ";
+                    string removalDateString = removalDate.Value<DateTime>().ToString("MMMM d, yyyy");
+                    deprecationMessage += whitespace + StringUtil.Loc("DeprecationMessageRemovalDate", removalDateString);
+                    var helpUrl = taskJson["helpUrl"];
+
+                    if (helpUrl != null)
+                    {
+                        string helpUrlString = helpUrl.Value<string>();
+                        string category = taskJson["category"].Value<string>().ToLower();
+                        string urlPrefix = $"https://docs.microsoft.com/azure/devops/pipelines/tasks/{category}/";
+
+                        if (helpUrlString.StartsWith(urlPrefix))
+                        {
+                            string versionHelpUrl = $"{helpUrlString}-v{majorVersion}".Replace(urlPrefix, $"https://learn.microsoft.com/azure/devops/pipelines/tasks/reference/");
+                            deprecationMessage += whitespace + StringUtil.Loc("DeprecationMessageHelpUrl", versionHelpUrl);
+                        }
+                    }
+                }
+
+                executionContext.Warning(deprecationMessage);
+            }
+        }
+
         private void ExtractZip(String zipFile, String destinationDirectory)
         {
             ZipFile.ExtractToDirectory(zipFile, destinationDirectory);
diff --git a/src/Misc/layoutbin/en-US/strings.json b/src/Misc/layoutbin/en-US/strings.json
index 2250c75638..7f755a6a94 100644
--- a/src/Misc/layoutbin/en-US/strings.json
+++ b/src/Misc/layoutbin/en-US/strings.json
@@ -262,6 +262,9 @@
   "DeploymentPoolNotFound": "Deployment pool not found: '{0}'",
   "DeprecatedNode6": "This task uses Node 6 execution handler, which will be removed March 31st 2022. If you are the developer of the task - please consider the migration guideline to Node 10 handler - https://aka.ms/migrateTaskNode10 (check this page also if you would like to disable Node 6 deprecation warnings). If you are the user - feel free to reach out to the owners of this task to proceed on migration.",
   "DeprecatedRunner": "Task '{0}' is dependent on a task runner that is end-of-life and will be removed in the future. Authors should review Node upgrade guidance: https://aka.ms/node-runner-guidance.",
+  "DeprecationMessage": "Task '{0}' version {1} ({2}@{1}) is deprecated.",
+  "DeprecationMessageHelpUrl": "Please see {0} for more information about this task.",
+  "DeprecationMessageRemovalDate": "This task will be removed. From {0}, onwards it may no longer be available.",
   "DirectoryHierarchyUnauthorized": "Permission to read the directory contents is required for '{0}' and each directory up the hierarchy. {1}",
   "DirectoryIsEmptyForArtifact": "Directory '{0}' is empty. Nothing will be added to build artifact '{1}'.",
   "DirectoryNotFound": "Directory not found: '{0}'",