diff --git a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/Send-MailMessage.cs b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/Send-MailMessage.cs
index 96689806b..5e91d0fdc 100644
--- a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/Send-MailMessage.cs
+++ b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/Send-MailMessage.cs
@@ -14,6 +14,7 @@ namespace Microsoft.PowerShell.Commands
     /// <summary>
     /// Implementation for the Send-MailMessage command.
     /// </summary>
+    [Obsolete("This cmdlet does not guarantee secure connections to SMTP servers. While there is no immediate replacement available in PowerShell, we recommend you do not use Send-MailMessage at this time. See https://aka.ms/SendMailMessage for more information.")]
     [Cmdlet(VerbsCommunications.Send, "MailMessage", HelpUri = "https://go.microsoft.com/fwlink/?LinkID=135256")]
     public sealed class SendMailMessage : PSCmdlet
     {
diff --git a/test/powershell/Modules/Microsoft.PowerShell.Utility/Send-MailMessage.Tests.ps1 b/test/powershell/Modules/Microsoft.PowerShell.Utility/Send-MailMessage.Tests.ps1
index ef851fab5..9b003a208 100644
--- a/test/powershell/Modules/Microsoft.PowerShell.Utility/Send-MailMessage.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.PowerShell.Utility/Send-MailMessage.Tests.ps1
@@ -78,7 +78,16 @@ Describe "Send-MailMessage" -Tags CI, RequireSudoOnUnix {
 
         $server | Should -Not -Be $null
 
-        Send-MailMessage @InputObject -ErrorAction SilentlyContinue
+        $powershell = [PowerShell]::Create()
+
+        $null = $powershell.AddCommand("Send-MailMessage").AddParameters($InputObject).AddParameter("ErrorAction","SilentlyContinue")
+
+        $powershell.Invoke()
+
+        $warnings = $powershell.Streams.Warning
+
+        $warnings.count | Should -BeGreaterThan 0
+        $warnings[0].ToString() | Should  -BeLike  "The command 'Send-MailMessage' is obsolete. *"
 
         $mail = Read-Mail