diff --git a/src/libraries/Common/src/Interop/Windows/SspiCli/SecuritySafeHandles.cs b/src/libraries/Common/src/Interop/Windows/SspiCli/SecuritySafeHandles.cs
index e0128ab0b994a..3c5bbe532161e 100644
--- a/src/libraries/Common/src/Interop/Windows/SspiCli/SecuritySafeHandles.cs
+++ b/src/libraries/Common/src/Interop/Windows/SspiCli/SecuritySafeHandles.cs
@@ -171,11 +171,13 @@ internal abstract class SafeFreeCredentials : SafeHandle
     {
 #endif
 
+        internal DateTime _expiry;
         internal Interop.SspiCli.CredHandle _handle;    //should be always used as by ref in PInvokes parameters
 
         protected SafeFreeCredentials() : base(IntPtr.Zero, true)
         {
             _handle = default;
+            _expiry = DateTime.MaxValue;
         }
 
         public override bool IsInvalid
@@ -183,6 +185,8 @@ public override bool IsInvalid
             get { return IsClosed || _handle.IsZero; }
         }
 
+        public DateTime Expiry => _expiry;
+
 #if DEBUG
         public new IntPtr DangerousGetHandle()
         {
diff --git a/src/libraries/Common/src/System/Net/Security/Unix/SafeFreeCredentials.cs b/src/libraries/Common/src/System/Net/Security/Unix/SafeFreeCredentials.cs
index 7d26be95ab96b..c2e0e0226eace 100644
--- a/src/libraries/Common/src/System/Net/Security/Unix/SafeFreeCredentials.cs
+++ b/src/libraries/Common/src/System/Net/Security/Unix/SafeFreeCredentials.cs
@@ -1,6 +1,7 @@
 // Licensed to the .NET Foundation under one or more agreements.
 // The .NET Foundation licenses this file to you under the MIT license.
 
+using System;
 using System.Diagnostics;
 using System.Runtime.ConstrainedExecution;
 using System.Runtime.InteropServices;
@@ -18,8 +19,13 @@ internal abstract class SafeFreeCredentials : DebugSafeHandle
     internal abstract class SafeFreeCredentials : SafeHandle
     {
 #endif
+        internal DateTime _expiry;
+
+        public DateTime Expiry => _expiry;
+
         protected SafeFreeCredentials(IntPtr handle, bool ownsHandle) : base(handle, ownsHandle)
         {
+            _expiry = DateTime.MaxValue;
         }
     }
 
diff --git a/src/libraries/System.Net.Security/src/System/Net/Security/SecureChannel.cs b/src/libraries/System.Net.Security/src/System/Net/Security/SecureChannel.cs
index c9b67dda132ca..fbf29e0364cb0 100644
--- a/src/libraries/System.Net.Security/src/System/Net/Security/SecureChannel.cs
+++ b/src/libraries/System.Net.Security/src/System/Net/Security/SecureChannel.cs
@@ -171,8 +171,8 @@ internal void Close()
         {
             if (!_remoteCertificateExposed)
             {
-                  _remoteCertificate?.Dispose();
-                  _remoteCertificate = null;
+                _remoteCertificate?.Dispose();
+                _remoteCertificate = null;
             }
 
             _securityContext?.Dispose();
@@ -607,9 +607,7 @@ private bool AcquireClientCredentials(ref byte[]? thumbPrint)
                         _sslAuthenticationOptions.CertificateContext = SslStreamCertificateContext.Create(selectedCert!);
                     }
 
-                    _credentialsHandle = SslStreamPal.AcquireCredentialsHandle(_sslAuthenticationOptions.CertificateContext,
-                            _sslAuthenticationOptions.EnabledSslProtocols, _sslAuthenticationOptions.EncryptionPolicy, _sslAuthenticationOptions.IsServer);
-
+                    _credentialsHandle = AcquireCredentialsHandle(_sslAuthenticationOptions);
                     thumbPrint = guessedThumbPrint; // Delay until here in case something above threw.
                 }
             }
@@ -713,14 +711,65 @@ private bool AcquireServerCredentials(ref byte[]? thumbPrint)
             }
             else
             {
-                _credentialsHandle = SslStreamPal.AcquireCredentialsHandle(_sslAuthenticationOptions.CertificateContext, _sslAuthenticationOptions.EnabledSslProtocols,
-                        _sslAuthenticationOptions.EncryptionPolicy, _sslAuthenticationOptions.IsServer);
+                _credentialsHandle = AcquireCredentialsHandle(_sslAuthenticationOptions);
                 thumbPrint = guessedThumbPrint;
             }
 
             return cachedCred;
         }
 
+        private static SafeFreeCredentials AcquireCredentialsHandle(SslAuthenticationOptions sslAuthenticationOptions)
+        {
+            SafeFreeCredentials cred = SslStreamPal.AcquireCredentialsHandle(sslAuthenticationOptions.CertificateContext, sslAuthenticationOptions.EnabledSslProtocols,
+                sslAuthenticationOptions.EncryptionPolicy, sslAuthenticationOptions.IsServer);
+
+            if (sslAuthenticationOptions.CertificateContext != null)
+            {
+                //
+                // Since the SafeFreeCredentials can be cached and reused, it may happen on long running processes that some cert on
+                // the chain expires and all subsequent connections would send expired intermediate certificates. Find the earliest
+                // NotAfter timestamp on the chain and use it as expiration timestamp for the credentials.
+                // This provides an opportunity to recreate the credentials with an alternative (and still valid)
+                // certificate chain.
+                //
+                SslStreamCertificateContext certificateContext = sslAuthenticationOptions.CertificateContext;
+                cred._expiry = GetExpiryTimestamp(certificateContext);
+
+                if (cred._expiry < DateTime.UtcNow)
+                {
+                    //
+                    // The CertificateContext from auth options is recreated just before creating the SafeFreeCredentials. However, in case when
+                    // it was provided by the user code, it may still contain the (now expired) certificate chain. Such expiration timestamp would
+                    // effectively disable caching as it would lead to creating new credentials for each connection. We attempt to recover by creating
+                    // a temporary certificate context (which builds a new chain with hopefully more recent chain).
+                    //
+                    certificateContext = SslStreamCertificateContext.Create(
+                        certificateContext.Certificate,
+                        new X509Certificate2Collection(certificateContext.IntermediateCertificates),
+                        trust: certificateContext.Trust);
+
+                    cred._expiry = GetExpiryTimestamp(certificateContext);
+                }
+
+                static DateTime GetExpiryTimestamp(SslStreamCertificateContext certificateContext)
+                {
+                    DateTime expiry = certificateContext.Certificate.NotAfter;
+
+                    foreach (X509Certificate2 cert in certificateContext.IntermediateCertificates)
+                    {
+                        if (cert.NotAfter < expiry)
+                        {
+                            expiry = cert.NotAfter;
+                        }
+                    }
+
+                    return expiry.ToUniversalTime();
+                }
+            }
+
+            return cred;
+        }
+
         //
         internal ProtocolToken NextMessage(ReadOnlySpan<byte> incomingBuffer)
         {
diff --git a/src/libraries/System.Net.Security/src/System/Net/Security/SslSessionsCache.cs b/src/libraries/System.Net.Security/src/System/Net/Security/SslSessionsCache.cs
index f7b730c102c93..59009e72b4cfa 100644
--- a/src/libraries/System.Net.Security/src/System/Net/Security/SslSessionsCache.cs
+++ b/src/libraries/System.Net.Security/src/System/Net/Security/SslSessionsCache.cs
@@ -134,9 +134,9 @@ public bool Equals(SslCredKey other)
 
             //SafeCredentialReference? cached;
             SafeFreeCredentials? credentials = GetCachedCredential(key);
-            if (credentials == null || credentials.IsClosed || credentials.IsInvalid)
+            if (credentials == null || credentials.IsClosed || credentials.IsInvalid || credentials.Expiry < DateTime.UtcNow)
             {
-                if (NetEventSource.Log.IsEnabled()) NetEventSource.Info(null, $"Not found or invalid, Current Cache Coun = {s_cachedCreds.Count}");
+                if (NetEventSource.Log.IsEnabled()) NetEventSource.Info(null, $"Not found or invalid, Current Cache Count = {s_cachedCreds.Count}");
                 return null;
             }
 
@@ -169,12 +169,13 @@ internal static void CacheCredential(SafeFreeCredentials creds, byte[]? thumbPri
 
             SafeFreeCredentials? credentials = GetCachedCredential(key);
 
-            if (credentials == null || credentials.IsClosed || credentials.IsInvalid)
+            DateTime utcNow = DateTime.UtcNow;
+            if (credentials == null || credentials.IsClosed || credentials.IsInvalid || credentials.Expiry < utcNow)
             {
                 lock (s_cachedCreds)
                 {
                     credentials = GetCachedCredential(key);
-                    if (credentials == null || credentials.IsClosed || credentials.IsInvalid)
+                    if (credentials == null || credentials.IsClosed || credentials.IsInvalid || credentials.Expiry < utcNow)
                     {
                         SafeCredentialReference? cached = SafeCredentialReference.CreateReference(creds);