diff --git a/sdk/core/azure-core/src/http/curl/curl.cpp b/sdk/core/azure-core/src/http/curl/curl.cpp
index b97d898a7..2453398fe 100644
--- a/sdk/core/azure-core/src/http/curl/curl.cpp
+++ b/sdk/core/azure-core/src/http/curl/curl.cpp
@@ -1414,6 +1414,10 @@ inline std::string GetConnectionKey(std::string const& host, CurlTransportOption
   key.append(",");
   key.append(options.SslOptions.AllowFailedCrlRetrieval ? "FC" : "0");
   key.append(",");
+  key.append(options.EnableCurlTracing ? "1" : "0");
+  key.append(",");
+  key.append(options.EnableCurlSslCaching ? "1" : "0");
+  key.append(",");
 #if LIBCURL_VERSION_NUM >= 0x074D00 // 7.77.0
   key.append(
       !options.SslOptions.PemEncodedExpectedRootCertificates.empty() ? std::to_string(
diff --git a/sdk/core/azure-core/test/ut/curl_connection_pool_test.cpp b/sdk/core/azure-core/test/ut/curl_connection_pool_test.cpp
index 61ecc1004..8902a982f 100644
--- a/sdk/core/azure-core/test/ut/curl_connection_pool_test.cpp
+++ b/sdk/core/azure-core/test/ut/curl_connection_pool_test.cpp
@@ -58,7 +58,7 @@ namespace Azure { namespace Core { namespace Test {
       std::string const expectedConnectionKey(CreateConnectionKey(
           AzureSdkHttpbinServer::Schema(),
           AzureSdkHttpbinServer::Host(),
-          ",0,0,0,0,0,1,1,0,0,0,0"));
+          ",0,0,0,0,0,1,1,0,0,0,1,0,0"));
 
       {
         // Creating a new connection with default options
@@ -129,7 +129,7 @@ namespace Azure { namespace Core { namespace Test {
 
       // Now test that using a different connection config won't re-use the same connection
       std::string const secondExpectedKey = AzureSdkHttpbinServer::Schema() + "://"
-          + AzureSdkHttpbinServer::Host() + ",0,0,0,0,0,1,0,0,0,0,200000";
+          + AzureSdkHttpbinServer::Host() + ",0,0,0,0,0,1,0,0,0,0,1,0,200000";
       {
         // Creating a new connection with options
         Azure::Core::Http::CurlTransportOptions options;
@@ -441,7 +441,7 @@ namespace Azure { namespace Core { namespace Test {
         std::string const expectedConnectionKey(CreateConnectionKey(
             AzureSdkHttpbinServer::Schema(),
             AzureSdkHttpbinServer::Host(),
-            ",0,0,0,0,0,1,1,0,0,0,0"));
+            ",0,0,0,0,0,1,1,0,0,0,1,0,0"));
 
         // Creating a new connection with default options
         auto connection = Azure::Core::Http::_detail::CurlConnectionPool::g_curlConnectionPool
@@ -479,7 +479,7 @@ namespace Azure { namespace Core { namespace Test {
         std::string const expectedConnectionKey(CreateConnectionKey(
             AzureSdkHttpbinServer::Schema(),
             AzureSdkHttpbinServer::Host(),
-            ":443,0,0,0,0,0,1,1,0,0,0,0"));
+            ":443,0,0,0,0,0,1,1,0,0,0,1,0,0"));
 
         // Creating a new connection with default options
         auto connection = Azure::Core::Http::_detail::CurlConnectionPool::g_curlConnectionPool
@@ -518,7 +518,7 @@ namespace Azure { namespace Core { namespace Test {
         std::string const expectedConnectionKey(CreateConnectionKey(
             AzureSdkHttpbinServer::Schema(),
             AzureSdkHttpbinServer::Host(),
-            ",0,0,0,0,0,1,1,0,0,0,0"));
+            ",0,0,0,0,0,1,1,0,0,0,1,0,0"));
 
         // Creating a new connection with default options
         auto connection = Azure::Core::Http::_detail::CurlConnectionPool::g_curlConnectionPool
@@ -555,7 +555,7 @@ namespace Azure { namespace Core { namespace Test {
         std::string const expectedConnectionKey(CreateConnectionKey(
             AzureSdkHttpbinServer::Schema(),
             AzureSdkHttpbinServer::Host(),
-            ":443,0,0,0,0,0,1,1,0,0,0,0"));
+            ":443,0,0,0,0,0,1,1,0,0,0,1,0,0"));
 
         // Creating a new connection with default options
         auto connection = Azure::Core::Http::_detail::CurlConnectionPool::g_curlConnectionPool