diff --git a/src/libraries/System.ComponentModel.Annotations/src/System/ComponentModel/DataAnnotations/EmailAddressAttribute.cs b/src/libraries/System.ComponentModel.Annotations/src/System/ComponentModel/DataAnnotations/EmailAddressAttribute.cs
index 2e28b0cb6ac3d..c7743f0144baa 100644
--- a/src/libraries/System.ComponentModel.Annotations/src/System/ComponentModel/DataAnnotations/EmailAddressAttribute.cs
+++ b/src/libraries/System.ComponentModel.Annotations/src/System/ComponentModel/DataAnnotations/EmailAddressAttribute.cs
@@ -27,6 +27,11 @@ public override bool IsValid(object? value)
                 return false;
             }
 
+            if (valueAsString.AsSpan().ContainsAny('\r', '\n'))
+            {
+                return false;
+            }
+
             // only return true if there is only 1 '@' character
             // and it is neither the first nor the last character
             int index = valueAsString.IndexOf('@');
diff --git a/src/libraries/System.ComponentModel.Annotations/tests/System/ComponentModel/DataAnnotations/EmailAddressAttributeTests.cs b/src/libraries/System.ComponentModel.Annotations/tests/System/ComponentModel/DataAnnotations/EmailAddressAttributeTests.cs
index a0c67ed7d2b92..da80016608e40 100644
--- a/src/libraries/System.ComponentModel.Annotations/tests/System/ComponentModel/DataAnnotations/EmailAddressAttributeTests.cs
+++ b/src/libraries/System.ComponentModel.Annotations/tests/System/ComponentModel/DataAnnotations/EmailAddressAttributeTests.cs
@@ -29,6 +29,7 @@ protected override IEnumerable<TestCase> InvalidValues()
             yield return new TestCase(new EmailAddressAttribute(), 0);
             yield return new TestCase(new EmailAddressAttribute(), "");
             yield return new TestCase(new EmailAddressAttribute(), " \r \t \n" );
+            yield return new TestCase(new EmailAddressAttribute(), "someName@[\r\n\tsomeDomain]");
             yield return new TestCase(new EmailAddressAttribute(), "@someDomain.com");
             yield return new TestCase(new EmailAddressAttribute(), "@someDomain@abc.com");
             yield return new TestCase(new EmailAddressAttribute(), "someName");
diff --git a/src/libraries/System.Net.Mail/src/System/Net/Mail/MailAddress.cs b/src/libraries/System.Net.Mail/src/System/Net/Mail/MailAddress.cs
index 47ac65dbf9b5d..a4cc338453b8e 100644
--- a/src/libraries/System.Net.Mail/src/System/Net/Mail/MailAddress.cs
+++ b/src/libraries/System.Net.Mail/src/System/Net/Mail/MailAddress.cs
@@ -216,6 +216,12 @@ private string GetHost(bool allowUnicode)
                     throw new SmtpException(SR.Format(SR.SmtpInvalidHostName, Address), argEx);
                 }
             }
+
+            if (domain.AsSpan().ContainsAny('\r', '\n'))
+            {
+                throw new SmtpException(SR.Format(SR.SmtpInvalidHostName, Address));
+            }
+
             return domain;
         }
 
diff --git a/src/libraries/System.Net.Mail/tests/Functional/SmtpClientTest.cs b/src/libraries/System.Net.Mail/tests/Functional/SmtpClientTest.cs
index 306368df20218..c8c5734b04cf4 100644
--- a/src/libraries/System.Net.Mail/tests/Functional/SmtpClientTest.cs
+++ b/src/libraries/System.Net.Mail/tests/Functional/SmtpClientTest.cs
@@ -9,11 +9,15 @@
 // (C) 2006 John Luke
 //
 
+using System.Collections.Generic;
+using System.Globalization;
 using System.IO;
 using System.Net.NetworkInformation;
 using System.Net.Sockets;
+using System.Reflection;
 using System.Threading;
 using System.Threading.Tasks;
+using Microsoft.DotNet.RemoteExecutor;
 using Systen.Net.Mail.Tests;
 using System.Net.Test.Common;
 using Xunit;
@@ -573,5 +577,41 @@ public void TestGssapiAuthentication()
 
             Assert.Equal("GSSAPI", server.AuthMethodUsed, StringComparer.OrdinalIgnoreCase);
         }
+
+        [Theory]
+        [MemberData(nameof(SendMail_MultiLineDomainLiterals_Data))]
+        public async Task SendMail_MultiLineDomainLiterals_Disabled_Throws(string from, string to, bool asyncSend)
+        {
+            using var server = new LoopbackSmtpServer();
+
+            using SmtpClient client = server.CreateClient();
+            client.Credentials = new NetworkCredential("Foo", "Bar");
+
+            using var msg = new MailMessage(@from, @to, "subject", "body");
+
+            await Assert.ThrowsAsync<SmtpException>(async () =>
+            {
+                if (asyncSend)
+                {
+                    await client.SendMailAsync(msg).WaitAsync(TimeSpan.FromSeconds(30));
+                }
+                else
+                {
+                    client.Send(msg);
+                }
+            });
+        }
+
+        public static IEnumerable<object[]> SendMail_MultiLineDomainLiterals_Data()
+        {
+            foreach (bool async in new[] { true, false })
+            {
+                foreach (string address in new[] { "foo@[\r\n bar]", "foo@[bar\r\n ]", "foo@[bar\r\n baz]" })
+                {
+                    yield return new object[] { address, "foo@example.com", async };
+                    yield return new object[] { "foo@example.com", address, async };
+                }
+            }
+        }
     }
 }