diff --git a/src/libraries/Common/src/Interop/Unix/System.Security.Cryptography.Native/Interop.OpenSsl.cs b/src/libraries/Common/src/Interop/Unix/System.Security.Cryptography.Native/Interop.OpenSsl.cs
index f22665ebc260fc..21bf5905f45ec5 100644
--- a/src/libraries/Common/src/Interop/Unix/System.Security.Cryptography.Native/Interop.OpenSsl.cs
+++ b/src/libraries/Common/src/Interop/Unix/System.Security.Cryptography.Native/Interop.OpenSsl.cs
@@ -203,18 +203,20 @@ internal static unsafe SafeSslContextHandle AllocateSslContext(SslAuthentication
                 {
                     if (sslAuthenticationOptions.IsServer)
                     {
-                        Ssl.SslCtxSetCaching(sslCtx, 1, s_cacheSize, null, null);
+                        Span<byte> contextId = stackalloc byte[32];
+                        RandomNumberGenerator.Fill(contextId);
+                        Ssl.SslCtxSetCaching(sslCtx, 1, s_cacheSize, contextId.Length, contextId, null, null);
                     }
                     else
                     {
-                        int result = Ssl.SslCtxSetCaching(sslCtx, 1, s_cacheSize, &NewSessionCallback, &RemoveSessionCallback);
+                        int result = Ssl.SslCtxSetCaching(sslCtx, 1, s_cacheSize, 0, null, &NewSessionCallback, &RemoveSessionCallback);
                         Debug.Assert(result == 1);
                         sslCtx.EnableSessionCache();
                     }
                 }
                 else
                 {
-                    Ssl.SslCtxSetCaching(sslCtx, 0, -1, null, null);
+                    Ssl.SslCtxSetCaching(sslCtx, 0, -1, 0, null, null, null);
                 }
 
                 if (sslAuthenticationOptions.IsServer && sslAuthenticationOptions.ApplicationProtocols != null && sslAuthenticationOptions.ApplicationProtocols.Count != 0)
diff --git a/src/libraries/Common/src/Interop/Unix/System.Security.Cryptography.Native/Interop.SslCtx.cs b/src/libraries/Common/src/Interop/Unix/System.Security.Cryptography.Native/Interop.SslCtx.cs
index 18a6b27f825e12..4ed5c1881328eb 100644
--- a/src/libraries/Common/src/Interop/Unix/System.Security.Cryptography.Native/Interop.SslCtx.cs
+++ b/src/libraries/Common/src/Interop/Unix/System.Security.Cryptography.Native/Interop.SslCtx.cs
@@ -33,7 +33,7 @@ internal static partial class Ssl
         internal static unsafe partial void SslCtxSetAlpnSelectCb(SafeSslContextHandle ctx, delegate* unmanaged<IntPtr, byte**, byte*, byte*, uint, IntPtr, int> callback, IntPtr arg);
 
         [LibraryImport(Libraries.CryptoNative, EntryPoint = "CryptoNative_SslCtxSetCaching")]
-        internal static unsafe partial int SslCtxSetCaching(SafeSslContextHandle ctx, int mode, int cacheSize, delegate* unmanaged<IntPtr, IntPtr, int> neewSessionCallback, delegate* unmanaged<IntPtr, IntPtr, void> removeSessionCallback);
+        internal static unsafe partial int SslCtxSetCaching(SafeSslContextHandle ctx, int mode, int cacheSize, int contextIdLength, Span<byte> contextId, delegate* unmanaged<IntPtr, IntPtr, int> neewSessionCallback, delegate* unmanaged<IntPtr, IntPtr, void> removeSessionCallback);
 
         internal static bool AddExtraChainCertificates(SafeSslContextHandle ctx, X509Certificate2[] chain)
         {
diff --git a/src/native/libs/System.Security.Cryptography.Native/opensslshim.h b/src/native/libs/System.Security.Cryptography.Native/opensslshim.h
index 1fbf3ce6660422..efb0a9378ae77c 100644
--- a/src/native/libs/System.Security.Cryptography.Native/opensslshim.h
+++ b/src/native/libs/System.Security.Cryptography.Native/opensslshim.h
@@ -486,6 +486,7 @@ const EVP_CIPHER* EVP_chacha20_poly1305(void);
     REQUIRED_FUNCTION(SSL_CTX_set_quiet_shutdown) \
     FALLBACK_FUNCTION(SSL_CTX_set_options) \
     FALLBACK_FUNCTION(SSL_CTX_set_security_level) \
+    REQUIRED_FUNCTION(SSL_CTX_set_session_id_context) \
     REQUIRED_FUNCTION(SSL_CTX_set_verify) \
     REQUIRED_FUNCTION(SSL_CTX_use_certificate) \
     REQUIRED_FUNCTION(SSL_CTX_use_PrivateKey) \
@@ -965,6 +966,7 @@ FOR_ALL_OPENSSL_FUNCTIONS
 #define SSL_CTX_set_options SSL_CTX_set_options_ptr
 #define SSL_CTX_set_quiet_shutdown SSL_CTX_set_quiet_shutdown_ptr
 #define SSL_CTX_set_security_level SSL_CTX_set_security_level_ptr
+#define SSL_CTX_set_session_id_context SSL_CTX_set_session_id_context_ptr
 #define SSL_CTX_set_verify SSL_CTX_set_verify_ptr
 #define SSL_CTX_use_certificate SSL_CTX_use_certificate_ptr
 #define SSL_CTX_use_PrivateKey SSL_CTX_use_PrivateKey_ptr
diff --git a/src/native/libs/System.Security.Cryptography.Native/pal_ssl.c b/src/native/libs/System.Security.Cryptography.Native/pal_ssl.c
index 57f1b368b62abf..431c2b8ec06722 100644
--- a/src/native/libs/System.Security.Cryptography.Native/pal_ssl.c
+++ b/src/native/libs/System.Security.Cryptography.Native/pal_ssl.c
@@ -655,7 +655,7 @@ void CryptoNative_SslSetVerifyPeer(SSL* ssl)
     SSL_set_verify(ssl, SSL_VERIFY_PEER, verify_callback);
 }
 
-int CryptoNative_SslCtxSetCaching(SSL_CTX* ctx, int mode, int cacheSize, SslCtxNewSessionCallback newSessionCb, SslCtxRemoveSessionCallback removeSessionCb)
+int CryptoNative_SslCtxSetCaching(SSL_CTX* ctx, int mode, int cacheSize, int contextIdLength, uint8_t* contextId, SslCtxNewSessionCallback newSessionCb, SslCtxRemoveSessionCallback removeSessionCb)
 {
     int retValue = 1;
     if (mode && !API_EXISTS(SSL_SESSION_get0_hostname))
@@ -683,6 +683,11 @@ int CryptoNative_SslCtxSetCaching(SSL_CTX* ctx, int mode, int cacheSize, SslCtxN
         SSL_CTX_ctrl(ctx, SSL_CTRL_SET_SESS_CACHE_SIZE, (long)cacheSize, NULL);
     }
 
+    if (contextIdLength > 0 && contextId != NULL)
+    {
+        SSL_CTX_set_session_id_context(ctx, contextId, contextIdLength <= SSL_MAX_SID_CTX_LENGTH ? (unsigned int)contextIdLength : SSL_MAX_SID_CTX_LENGTH);
+    }
+
     if (newSessionCb != NULL)
     {
         SSL_CTX_sess_set_new_cb(ctx, newSessionCb);
diff --git a/src/native/libs/System.Security.Cryptography.Native/pal_ssl.h b/src/native/libs/System.Security.Cryptography.Native/pal_ssl.h
index 3b186a96cbb7d0..738511d31a1d96 100644
--- a/src/native/libs/System.Security.Cryptography.Native/pal_ssl.h
+++ b/src/native/libs/System.Security.Cryptography.Native/pal_ssl.h
@@ -162,7 +162,7 @@ PALEXPORT void CryptoNative_SslSetPostHandshakeAuth(SSL* ssl, int32_t val);
 /*
 Sets session caching. 0 is disabled.
 */
-PALEXPORT int CryptoNative_SslCtxSetCaching(SSL_CTX* ctx, int mode, int cacheSize, SslCtxNewSessionCallback newCb, SslCtxRemoveSessionCallback removeCb);
+PALEXPORT int CryptoNative_SslCtxSetCaching(SSL_CTX* ctx, int mode, int cacheSize, int contextIdLength, uint8_t* contextId, SslCtxNewSessionCallback newSessionCb, SslCtxRemoveSessionCallback removeSessionCb);
 
 /*
 Returns name associated with given ssl session.