diff --git a/src/libraries/System.Net.Security/src/System/Net/Security/SslStreamPal.Windows.cs b/src/libraries/System.Net.Security/src/System/Net/Security/SslStreamPal.Windows.cs
index aecaa2feca9e07..77d4de1bec6c4c 100644
--- a/src/libraries/System.Net.Security/src/System/Net/Security/SslStreamPal.Windows.cs
+++ b/src/libraries/System.Net.Security/src/System/Net/Security/SslStreamPal.Windows.cs
@@ -26,6 +26,15 @@ internal static class SslStreamPal
             // API is supported since Windows 10 1809 (17763) but there is no reason to use at the moment.
             Environment.OSVersion.Version.Major >= 10 && Environment.OSVersion.Version.Build >= 18836;
 
+        // On Windows Server 2022 (build 20348) and older, Schannel has a race condition where
+        // ApplyControlToken(SSL_SESSION_DISABLE_RECONNECTS) doesn't reliably prevent the session
+        // cache from being repopulated. The workaround is to delete the context and retry
+        // InitializeSecurityContext after ApplyControlToken. This follows the same pattern used by
+        // Schannel's own webcli.c test and http.sys. The issue was fixed in newer Schannel builds
+        // shipping with Windows 11+ (build 22000+).
+        private static readonly bool NeedsDisableTlsResumeWorkaround =
+            Environment.OSVersion.Version.Build < 22000;
+
         private const string SecurityPackage = "Microsoft Unified Security Protocol Provider";
 
         private const Interop.SspiCli.ContextFlags RequiredFlags =
@@ -188,13 +197,6 @@ public static ProtocolToken InitializeSecurityContext(
 
             token.Status = SecurityStatusAdapterPal.GetSecurityStatusPalFromNativeInt(errorCode);
 
-            consumed = inputBuffer.Length;
-            if (inputBuffers._item1.Type == SecurityBufferType.SECBUFFER_EXTRA)
-            {
-                // not all data were consumed
-                consumed -= inputBuffers._item1.Token.Length;
-            }
-
             bool allowTlsResume = sslAuthenticationOptions.AllowTlsResume && !LocalAppContextSwitches.DisableTlsResume;
 
             if (!allowTlsResume && newContext && context != null)
@@ -206,11 +208,44 @@ public static ProtocolToken InitializeSecurityContext(
                     ref context,
                     in securityBuffer));
 
-
                 if (result.ErrorCode != SecurityStatusPalErrorCode.OK)
                 {
                     token.Status = result;
                 }
+                else if (NeedsDisableTlsResumeWorkaround)
+                {
+                    // On affected builds, Schannel's internal LookupCacheByName finds a fresh
+                    // resumable entry and embeds the session ID in the ClientHello before
+                    // ApplyControlToken can expire it. Deleting the context and retrying ISC
+                    // ensures the new ClientHello is generated without a stale session ID.
+                    // We can reuse inputBuffers since this only runs on the very first ISC call
+                    // (newContext == true) where the input is empty.
+                    context?.Dispose();
+                    context = null;
+                    token.ReleasePayload();
+                    token = default;
+                    token.RentBuffer = true;
+
+                    errorCode = SSPIWrapper.InitializeSecurityContext(
+                                    GlobalSSPI.SSPISecureChannel,
+                                    ref credentialsHandle,
+                                    ref context,
+                                    targetName,
+                                    RequiredFlags | Interop.SspiCli.ContextFlags.InitManualCredValidation,
+                                    Interop.SspiCli.Endianness.SECURITY_NATIVE_DREP,
+                                    ref inputBuffers,
+                                    ref token,
+                                    ref unusedAttributes);
+
+                    token.Status = SecurityStatusAdapterPal.GetSecurityStatusPalFromNativeInt(errorCode);
+                }
+            }
+
+            consumed = inputBuffer.Length;
+            if (inputBuffers._item1.Type == SecurityBufferType.SECBUFFER_EXTRA)
+            {
+                // not all data were consumed
+                consumed -= inputBuffers._item1.Token.Length;
             }
 
             return token;
diff --git a/src/libraries/System.Net.Security/tests/FunctionalTests/SslStreamAllowTlsResumeTests.cs b/src/libraries/System.Net.Security/tests/FunctionalTests/SslStreamAllowTlsResumeTests.cs
index 54031f0224d717..34cb3b50901d12 100644
--- a/src/libraries/System.Net.Security/tests/FunctionalTests/SslStreamAllowTlsResumeTests.cs
+++ b/src/libraries/System.Net.Security/tests/FunctionalTests/SslStreamAllowTlsResumeTests.cs
@@ -34,7 +34,6 @@ private bool CheckResumeFlag(SslStream ssl)
         [ConditionalTheory]
         [InlineData(true)]
         [InlineData(false)]
-        [ActiveIssue("https://github.com/dotnet/runtime/issues/103449", TestPlatforms.Windows)]
         public async Task ClientDisableTlsResume_Succeeds(bool testClient)
         {
             SslServerAuthenticationOptions serverOptions = new SslServerAuthenticationOptions