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 a4cc338453b8ed..3c19b90c149e0d 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
@@ -264,10 +264,16 @@ public override string ToString()
             }
             else
             {
-                return "\"" + DisplayName.Replace("\"", "\\\"") + "\" " + SmtpAddress;
+                return "\"" + EscapeQuotedStringContent(DisplayName) + "\" " + SmtpAddress;
             }
         }
 
+        // Escapes backslashes and embedded quotes so the display name forms a
+        // valid RFC 5322 quoted-string. Order matters: escaping quotes first
+        // would also escape the backslashes introduced by it.
+        private static string EscapeQuotedStringContent(string displayName) =>
+            displayName.Replace("\\", "\\\\").Replace("\"", "\\\"");
+
         public override bool Equals([NotNullWhen(true)] object? value)
         {
             if (value == null)
@@ -299,7 +305,7 @@ internal string Encode(int charsConsumed, bool allowUnicode)
                 //be appended.
                 if (MimeBasePart.IsAscii(_displayName, false) || allowUnicode)
                 {
-                    encodedAddress = "\"" + _displayName + "\"";
+                    encodedAddress = "\"" + EscapeQuotedStringContent(_displayName) + "\"";
                 }
                 else
                 {
diff --git a/src/libraries/System.Net.Mail/tests/Unit/MailAddressTests/MailAddressDisplayNameTest.cs b/src/libraries/System.Net.Mail/tests/Unit/MailAddressTests/MailAddressDisplayNameTest.cs
index 198ff9c24aad8a..e08151c9195b44 100644
--- a/src/libraries/System.Net.Mail/tests/Unit/MailAddressTests/MailAddressDisplayNameTest.cs
+++ b/src/libraries/System.Net.Mail/tests/Unit/MailAddressTests/MailAddressDisplayNameTest.cs
@@ -28,11 +28,16 @@ public static IEnumerable<object[]> MailAddressTestDataQuotes()
                 "Display \"Test\" Name",
                 "Display \\\"Test\\\" Name",
                 "\"",
+                "Display \\ Name",
+                "Display \\\\ Name",
+                "C:\\path\\to\\file",
+                "\\",
             };
             foreach (var displayName in displayNamesWithQuotes)
             {
-                yield return new object[]{ Address, displayName, null, $"\"{displayName.Replace("\"", "\\\"")}\" <{Address}>" };
-                yield return new object[]{ Address, $"\"{displayName}\"", displayName, $"\"{displayName.Replace("\"", "\\\"")}\" <{Address}>" };
+                string escaped = displayName.Replace("\\", "\\\\").Replace("\"", "\\\"");
+                yield return new object[]{ Address, displayName, null, $"\"{escaped}\" <{Address}>" };
+                yield return new object[]{ Address, $"\"{displayName}\"", displayName, $"\"{escaped}\" <{Address}>" };
             }
 
             yield return new object[]{ Address, null, "", Address };
diff --git a/src/libraries/System.Net.Mail/tests/Unit/MailAddressTests/MailAddressEncodeTest.cs b/src/libraries/System.Net.Mail/tests/Unit/MailAddressTests/MailAddressEncodeTest.cs
index d96fc787ccbd04..016e707be5023c 100644
--- a/src/libraries/System.Net.Mail/tests/Unit/MailAddressTests/MailAddressEncodeTest.cs
+++ b/src/libraries/System.Net.Mail/tests/Unit/MailAddressTests/MailAddressEncodeTest.cs
@@ -129,15 +129,15 @@ public void EncodeSingleMailAddress_WithAddressAndLongDisplayNameUnicode_ShouldQ
         public void EncodeSingleMailAddress_WithAddressAndNonAsciiAndRangeOfChars_ShouldQEncode(Func<string, string, MailAddress> factory)
         {
             MailAddress testAddress = factory("test@example.com",
-                "\u00AE !#$%&'()+,-./0123456789:;<=>?@ABCDEFGHIJKLMNOPQRSTUVWXYZ[\\]^_`abcdefghijklmnopqrstuvwxyz{|}~");
+                "\u00AE !\"#$%&'()+,-./0123456789:;<=>?@ABCDEFGHIJKLMNOPQRSTUVWXYZ[\\]^_`abcdefghijklmnopqrstuvwxyz{|}~");
             string result = testAddress.Encode(0, false);
-            Assert.Equal("=?utf-8?Q?=C2=AE_=21=23=24=25=26=27=28=29=2B=2C=2D=2E=2F0123456789=3A?="
-                + "\r\n =?utf-8?Q?=3B=3C=3D=3E=3F=40ABCDEFGHIJKLMNOPQRSTUVWXYZ=5B=5C=5D=5E=5F?="
-                + "\r\n =?utf-8?Q?=60abcdefghijklmnopqrstuvwxyz=7B=7C=7D=7E?= <test@example.com>", result);
+            Assert.Equal("=?utf-8?Q?=C2=AE_=21=22=23=24=25=26=27=28=29=2B=2C=2D=2E=2F012345678?="
+                + "\r\n =?utf-8?Q?9=3A=3B=3C=3D=3E=3F=40ABCDEFGHIJKLMNOPQRSTUVWXYZ=5B=5C=5D?="
+                + "\r\n =?utf-8?Q?=5E=5F=60abcdefghijklmnopqrstuvwxyz=7B=7C=7D=7E?= <test@example.com>", result);
 
             result = testAddress.Encode(0, true);
             Assert.Equal(
-                "\"\u00AE !#$%&'()+,-./0123456789:;<=>?@ABCDEFGHIJKLMNOPQRSTUVWXYZ[\\]^_`abcdefghijklmnopqrstuvwxyz{|}~\" "
+                "\"\u00AE !\\\"#$%&'()+,-./0123456789:;<=>?@ABCDEFGHIJKLMNOPQRSTUVWXYZ[\\\\]^_`abcdefghijklmnopqrstuvwxyz{|}~\" "
                 + "<test@example.com>", result);
         }
 
@@ -214,6 +214,50 @@ public void EncodeMultipleMailAddress_WithManyAddressesThatAreDifferentAndContai
                 + " \"test\u00DC\" <test2@example.com>", result);
         }
 
+        public static IEnumerable<object[]> DisplayNamesWithSpecialChars()
+        {
+            // displayName, expected encoded form (without the address suffix).
+            // Both '"' and '\' are RFC 5322 quoted-string specials and must be
+            // escaped as quoted-pairs ('\"' and '\\').
+            yield return new object[] { "Henry \"The Fonz\" Winkler", "\"Henry \\\"The Fonz\\\" Winkler\"" };
+            yield return new object[] { "with \" quote", "\"with \\\" quote\"" };
+            yield return new object[] { "with \\ backslash", "\"with \\\\ backslash\"" };
+            yield return new object[] { "with \\\" both", "\"with \\\\\\\" both\"" };
+            yield return new object[] { "C:\\path\\to\\file", "\"C:\\\\path\\\\to\\\\file\"" };
+            yield return new object[] { "\\", "\"\\\\\"" };
+            yield return new object[] { "\"", "\"\\\"\"" };
+        }
+
+        [Theory]
+        [MemberData(nameof(DisplayNamesWithSpecialChars))]
+        public void EncodeSingleMailAddress_WithDisplayNameContainingSpecials_ShouldEscapeAsQuotedPairs(string displayName, string expectedEncodedDisplayName)
+        {
+            string expected = $"{expectedEncodedDisplayName} <test@example.com>";
+
+            MailAddress ctorAddress = new MailAddress("test@example.com", displayName);
+            Assert.Equal(expected, ctorAddress.Encode(0, false));
+            Assert.Equal(expected, ctorAddress.Encode(0, true));
+            Assert.Equal(expected, ctorAddress.ToString());
+
+            Assert.True(MailAddress.TryCreate("test@example.com", displayName, out MailAddress tryCreateAddress));
+            Assert.Equal(expected, tryCreateAddress.Encode(0, false));
+            Assert.Equal(expected, tryCreateAddress.Encode(0, true));
+            Assert.Equal(expected, tryCreateAddress.ToString());
+        }
+
+        [Theory]
+        [MemberData(nameof(DisplayNamesWithSpecialChars))]
+        public void EncodeMultipleMailAddress_WithDisplayNameContainingSpecials_ShouldEscapeAsQuotedPairs(string displayName, string expectedEncodedDisplayName)
+        {
+            MailAddress testAddress = new MailAddress("test@example.com", displayName);
+            MailAddressCollection collection = new MailAddressCollection();
+            collection.Add(testAddress);
+
+            string expected = $"{expectedEncodedDisplayName} <test@example.com>";
+            Assert.Equal(expected, collection.Encode(0, false));
+            Assert.Equal(expected, collection.Encode(0, true));
+        }
+
         [Fact]
         public void CustomEncoding_Null()
         {