diff --git a/src/Cli.Tests/VersionCheckTests.cs b/src/Cli.Tests/VersionCheckTests.cs
new file mode 100644
index 0000000000..2d14fe36c2
--- /dev/null
+++ b/src/Cli.Tests/VersionCheckTests.cs
@@ -0,0 +1,31 @@
+// Copyright (c) Microsoft Corporation.
+// Licensed under the MIT License.
+
+using Azure.DataApiBuilder.Core;
+
+namespace Cli.Tests;
+
+[TestClass]
+public class VersionCheckTests
+{
+    [TestMethod]
+    public void GetVersions_LatestVersionNotNull()
+    {
+        VersionChecker.IsCurrentVersion(out string? nugetVersion, out string? _);
+        Assert.IsNotNull(nugetVersion, "Nuget version should not be null.");
+    }
+
+    [TestMethod]
+    public void GetVersions_CurrentVersionNotNull()
+    {
+        VersionChecker.IsCurrentVersion(out string? _, out string? localVersion);
+        Assert.IsNotNull(localVersion, "Local version should not be null.");
+    }
+
+    [TestMethod]
+    public void GetVersions_IsNotInNuGet()
+    {
+        bool result = VersionChecker.IsCurrentVersion(out string? nugetVersion, out string? localVersion);
+        Assert.IsFalse(result, $"Should not be in NuGet. {localVersion} -> {nugetVersion}");
+    }
+}
diff --git a/src/Core/Configurations/RuntimeConfigValidator.cs b/src/Core/Configurations/RuntimeConfigValidator.cs
index 5620ed352e..ddf8ef6340 100644
--- a/src/Core/Configurations/RuntimeConfigValidator.cs
+++ b/src/Core/Configurations/RuntimeConfigValidator.cs
@@ -141,6 +141,11 @@ public async Task<bool> TryValidateConfig(
         string configFilePath,
         ILoggerFactory loggerFactory)
     {
+        if (!VersionChecker.IsCurrentVersion(out string? nugetVersion, out string? localVersion))
+        {
+            _logger.LogWarning("A newer version of Data API builder is available. Update {LocalVersion} -> {NugetVersion}.", localVersion, nugetVersion);
+        }
+
         RuntimeConfig? runtimeConfig;
 
         if (!_runtimeConfigProvider.TryGetConfig(out runtimeConfig))
diff --git a/src/Core/VersionChecker.cs b/src/Core/VersionChecker.cs
new file mode 100644
index 0000000000..28d25b513a
--- /dev/null
+++ b/src/Core/VersionChecker.cs
@@ -0,0 +1,63 @@
+using System.Net.Http.Json;
+using System.Text.Json.Serialization;
+using Azure.DataApiBuilder.Product;
+
+namespace Azure.DataApiBuilder.Core;
+
+/// <summary>
+/// A class to test the local version of the engine against the NuGet version.
+/// </summary>
+/// <remarks>
+/// This is used in startup to suggest upgrading the engine.
+/// </remarks>
+public static class VersionChecker
+{
+    private const string NUGETURL = "https://api.nuget.org/v3-flatcontainer/microsoft.dataapibuilder/index.json";
+
+    /// <summary>
+    /// Checks if the current local version of the product matches the latest version available on NuGet.
+    /// </summary>
+    /// <param name="nugetVersion">Outputs the latest version available on NuGet.</param>
+    /// <param name="localVersion">Outputs the current local version of the product.</param>
+    /// <returns>
+    /// Returns <c>true</c> if the local version matches the latest NuGet version or if the NuGet version is not available;
+    /// otherwise, returns <c>false</c>.
+    /// </returns>
+    /// <remarks>
+    //  If the internet is unavailable or NuGet is down or the HTTP request fails for any reason
+    /// (there is a 2 second Timeout on the request), then the NuGet version will be <c>null</c> and
+    //  this method will return <c>true</c>. This is mostly because this check is a user courtesy.
+    // </remarks>
+    public static bool IsCurrentVersion(out string? nugetVersion, out string? localVersion)
+    {
+        nugetVersion = FetchLatestNuGetVersion();
+        localVersion = ProductInfo.GetProductVersion(false);
+        return string.IsNullOrEmpty(nugetVersion) || nugetVersion == localVersion;
+    }
+
+    private static string? FetchLatestNuGetVersion()
+    {
+        try
+        {
+            using HttpClient httpClient = new() { Timeout = TimeSpan.FromSeconds(2) };
+            NuGetVersionResponse? versionData = httpClient
+                .GetFromJsonAsync<NuGetVersionResponse>(new Uri(NUGETURL).ToString())
+                .GetAwaiter().GetResult();
+
+            return versionData?.Versions
+                ?.Where(version => !version.Contains("-rc")) // Filter out pre-release versions
+                .Select(version => new Version(version))     // Convert to Version objects
+                .Max()?.ToString();                          // Get the latest 
+        }
+        catch (Exception)
+        {
+            return null; // Assume no update available on failure
+        }
+    }
+
+    private class NuGetVersionResponse
+    {
+        [JsonPropertyName("versions")]
+        public string[]? Versions { get; set; }
+    }
+}