diff --git a/sdk/core/azure-core/CHANGELOG.md b/sdk/core/azure-core/CHANGELOG.md
index a1091caf0..6c080f72b 100644
--- a/sdk/core/azure-core/CHANGELOG.md
+++ b/sdk/core/azure-core/CHANGELOG.md
@@ -5,7 +5,8 @@
 ### Features Added
 
 - Add the static libcurl transport adapter.
-- Add `NoSignal` option to the `curlTransportAdapter`.
+- Add `NoSignal` option to the `CurlTransportAdapter`.
+- Add `ConnectionTimeout` option to the `CurlTransportAdapter`.
 
 ### Breaking Changes
 
diff --git a/sdk/core/azure-core/inc/azure/core/http/curl_transport.hpp b/sdk/core/azure-core/inc/azure/core/http/curl_transport.hpp
index ff8db0aa4..ec526e4a2 100644
--- a/sdk/core/azure-core/inc/azure/core/http/curl_transport.hpp
+++ b/sdk/core/azure-core/inc/azure/core/http/curl_transport.hpp
@@ -39,6 +39,13 @@ namespace Azure { namespace Core { namespace Http {
    */
   struct CurlTransportOptions final
   {
+    /**
+     * @brief Default Maximum time in seconds that you allow the connection phase to the server to
+     * take.
+     *
+     */
+    AZ_CORE_DLLEXPORT static const long DefaultConnectionTimeout = 300;
+
     /**
      * @brief The string for the proxy is passed directly to the libcurl handle without any parsing
      *
@@ -98,6 +105,15 @@ namespace Azure { namespace Core { namespace Http {
      *
      */
     bool NoSignal = false;
+
+    /**
+     * @brief Contain the maximum time in seconds that you allow the connection phase to the server
+     * to take.
+     *
+     * @details This only limits the connection phase, it has no impact once it has connected.
+     *
+     */
+    long ConnectionTimeout = DefaultConnectionTimeout;
   };
 
   /**
diff --git a/sdk/core/azure-core/inc/azure/core/http/static_curl_transport.hpp b/sdk/core/azure-core/inc/azure/core/http/static_curl_transport.hpp
index 9f7f89436..fedb70b91 100644
--- a/sdk/core/azure-core/inc/azure/core/http/static_curl_transport.hpp
+++ b/sdk/core/azure-core/inc/azure/core/http/static_curl_transport.hpp
@@ -44,6 +44,14 @@ namespace Azure { namespace Core { namespace Http {
    */
   struct StaticCurlTransportOptions final
   {
+
+    /**
+     * @brief Default Maximum time in seconds that you allow the connection phase to the server to
+     * take.
+     *
+     */
+    AZ_CORE_DLLEXPORT static const long DefaultConnectionTimeout = 300;
+
     /**
      * @brief The string for the proxy is passed directly to the libcurl handle without any parsing
      *
@@ -103,6 +111,15 @@ namespace Azure { namespace Core { namespace Http {
      *
      */
     bool NoSignal = false;
+
+    /**
+     * @brief Contain the maximum time in seconds that you allow the connection phase to the server
+     * to take.
+     *
+     * @details This only limits the connection phase, it has no impact once it has connected.
+     *
+     */
+    long ConnectionTimeout = DefaultConnectionTimeout;
   };
 
   /**
diff --git a/sdk/core/azure-core/src/http/curl/curl.cpp b/sdk/core/azure-core/src/http/curl/curl.cpp
index 4397e3742..0f76e65a9 100644
--- a/sdk/core/azure-core/src/http/curl/curl.cpp
+++ b/sdk/core/azure-core/src/http/curl/curl.cpp
@@ -1231,6 +1231,8 @@ inline std::string GetConnectionKey(std::string const& host, CurlTransportOption
   key.append(!options.SslOptions.EnableCertificateRevocationListCheck ? "1" : "0");
   key.append(options.SslVerifyPeer ? "1" : "0");
   key.append(options.NoSignal ? "1" : "0");
+  key.append(
+      options.ConnectionTimeout == CurlTransportOptions::DefaultConnectionTimeout ? "0" : "1");
 
   return key;
 }
@@ -1267,6 +1269,7 @@ std::unique_ptr<CurlNetworkConnection> CurlConnectionPool::ExtractOrCreateCurlCo
         // created and to discard all current connections in the pool for the host-index. A caller
         // might request this after getting broken/closed connections multiple-times.
         hostPoolIndex->second.clear();
+        Log::Write(Logger::Level::Verbose, LogMsgPrefix + "Reset connection pool requested.");
       }
       else
       {
@@ -1283,6 +1286,7 @@ std::unique_ptr<CurlNetworkConnection> CurlConnectionPool::ExtractOrCreateCurlCo
           g_curlConnectionPool.ConnectionPoolIndex.erase(hostPoolIndex);
         }
 
+        Log::Write(Logger::Level::Verbose, LogMsgPrefix + "Re-using connection from the pool.");
         // return connection ref
         return connection;
       }
@@ -1292,6 +1296,7 @@ std::unique_ptr<CurlNetworkConnection> CurlConnectionPool::ExtractOrCreateCurlCo
 
   // Creating a new connection is thread safe. No need to lock mutex here.
   // No available connection for the pool for the required host. Create one
+  Log::Write(Logger::Level::Verbose, LogMsgPrefix + "Spawn new connection.");
   CURL* newHandle = curl_easy_init();
   if (!newHandle)
   {
@@ -1333,6 +1338,17 @@ std::unique_ptr<CurlNetworkConnection> CurlConnectionPool::ExtractOrCreateCurlCo
         + std::string(curl_easy_strerror(result)));
   }
 
+  if (options.ConnectionTimeout != CurlTransportOptions::DefaultConnectionTimeout)
+  {
+    if (!SetLibcurlOption(newHandle, CURLOPT_CONNECTTIMEOUT, options.ConnectionTimeout, &result))
+    {
+      throw Azure::Core::Http::TransportException(
+          _detail::DefaultFailedToGetNewConnectionTemplate + host
+          + ". Fail setting connect timeout to: " + std::to_string(options.ConnectionTimeout) + ". "
+          + std::string(curl_easy_strerror(result)));
+    }
+  }
+
   /******************** Curl handle options apply to all connections created
    * The keepAlive option is managed by the session directly.
    */
diff --git a/sdk/core/azure-core/src/http/curl/static_curl.cpp b/sdk/core/azure-core/src/http/curl/static_curl.cpp
index 37d8c2a04..40c722147 100644
--- a/sdk/core/azure-core/src/http/curl/static_curl.cpp
+++ b/sdk/core/azure-core/src/http/curl/static_curl.cpp
@@ -300,6 +300,19 @@ public:
       }
     }
 
+    if (m_options.ConnectionTimeout
+        != Azure::Core::Http::StaticCurlTransportOptions::DefaultConnectionTimeout)
+    {
+      if (!SetStaticLibcurlOption(
+              m_libcurlHandle, CURLOPT_CONNECTTIMEOUT, m_options.ConnectionTimeout, &result))
+      {
+        throw Azure::Core::Http::TransportException(
+            FailedToGetNewConnectionTemplate + host
+            + ". Fail setting connect timeout to: " + std::to_string(m_options.ConnectionTimeout)
+            + ". " + std::string(curl_easy_strerror(result)));
+      }
+    }
+
     // headers sep-up
     auto const& headers = request.GetHeaders();
     if (headers.size() > 0)
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 e04f35cdf..444d9be5a 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
@@ -45,7 +45,7 @@ namespace Azure { namespace Core { namespace Test {
       Azure::Core::Http::Request req(
           Azure::Core::Http::HttpMethod::Get, Azure::Core::Url(AzureSdkHttpbinServer::Get()));
       std::string const expectedConnectionKey
-          = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "00110";
+          = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "001100";
 
       {
         // Creating a new connection with default options
@@ -114,7 +114,7 @@ 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() + "00100";
+          = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "001000";
       {
         // Creating a new connection with options
         Azure::Core::Http::CurlTransportOptions options;
@@ -394,7 +394,7 @@ namespace Azure { namespace Core { namespace Test {
         Azure::Core::Http::Request req(
             Azure::Core::Http::HttpMethod::Get, Azure::Core::Url(authority));
         std::string const expectedConnectionKey
-            = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "00110";
+            = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "001100";
 
         // Creating a new connection with default options
         auto connection = Azure::Core::Http::_detail::CurlConnectionPool::g_curlConnectionPool
@@ -430,7 +430,7 @@ namespace Azure { namespace Core { namespace Test {
         Azure::Core::Http::Request req(
             Azure::Core::Http::HttpMethod::Get, Azure::Core::Url(authority));
         std::string const expectedConnectionKey
-            = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "44300110";
+            = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "443001100";
 
         // Creating a new connection with default options
         auto connection = Azure::Core::Http::_detail::CurlConnectionPool::g_curlConnectionPool
@@ -467,7 +467,7 @@ namespace Azure { namespace Core { namespace Test {
         Azure::Core::Http::Request req(
             Azure::Core::Http::HttpMethod::Get, Azure::Core::Url(authority));
         std::string const expectedConnectionKey
-            = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "00110";
+            = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "001100";
 
         // Creating a new connection with default options
         auto connection = Azure::Core::Http::_detail::CurlConnectionPool::g_curlConnectionPool
@@ -502,7 +502,7 @@ namespace Azure { namespace Core { namespace Test {
         Azure::Core::Http::Request req(
             Azure::Core::Http::HttpMethod::Get, Azure::Core::Url(authority));
         std::string const expectedConnectionKey
-            = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "44300110";
+            = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "443001100";
 
         // Creating a new connection with default options
         auto connection = Azure::Core::Http::_detail::CurlConnectionPool::g_curlConnectionPool