diff --git a/sdk/core/azure-core/CHANGELOG.md b/sdk/core/azure-core/CHANGELOG.md
index b79b2cf6e..cf790f7ee 100644
--- a/sdk/core/azure-core/CHANGELOG.md
+++ b/sdk/core/azure-core/CHANGELOG.md
@@ -3,10 +3,13 @@
 ## 1.5.0-beta.1 (Unreleased)
 
 ### Features Added
+
 - When a `RequestFailedException` exception is thrown, the `what()` method now includes information about the HTTP request which failed.
 
 ### Other Changes
 
+- Improve output message for `Azure::Core::Http::TransportException`.
+
 ## 1.4.0 (2022-03-03)
 
 ### Features Added
diff --git a/sdk/core/azure-core/src/http/curl/curl.cpp b/sdk/core/azure-core/src/http/curl/curl.cpp
index e16c4b454..ade2629e5 100644
--- a/sdk/core/azure-core/src/http/curl/curl.cpp
+++ b/sdk/core/azure-core/src/http/curl/curl.cpp
@@ -1246,9 +1246,10 @@ std::unique_ptr<CurlNetworkConnection> CurlConnectionPool::ExtractOrCreateCurlCo
     bool resetPool)
 {
   uint16_t port = request.GetUrl().GetPort();
-  std::string const& host = request.GetUrl().GetScheme() + request.GetUrl().GetHost()
-      + (port != 0 ? std::to_string(port) : "");
-  std::string const connectionKey = GetConnectionKey(host, options);
+  // Generate a display name for the host being connected to
+  std::string const& hostDisplayName = request.GetUrl().GetScheme() + "://"
+      + request.GetUrl().GetHost() + (port != 0 ? ":" + std::to_string(port) : "");
+  std::string const connectionKey = GetConnectionKey(hostDisplayName, options);
 
   {
     decltype(CurlConnectionPool::g_curlConnectionPool
@@ -1303,7 +1304,7 @@ std::unique_ptr<CurlNetworkConnection> CurlConnectionPool::ExtractOrCreateCurlCo
   if (!newHandle)
   {
     throw Azure::Core::Http::TransportException(
-        _detail::DefaultFailedToGetNewConnectionTemplate + host + ". "
+        _detail::DefaultFailedToGetNewConnectionTemplate + hostDisplayName + ". "
         + std::string("curl_easy_init returned Null"));
   }
   CURLcode result;
@@ -1312,21 +1313,21 @@ std::unique_ptr<CurlNetworkConnection> CurlConnectionPool::ExtractOrCreateCurlCo
   if (!SetLibcurlOption(newHandle, CURLOPT_URL, request.GetUrl().GetAbsoluteUrl().data(), &result))
   {
     throw Azure::Core::Http::TransportException(
-        _detail::DefaultFailedToGetNewConnectionTemplate + host + ". "
+        _detail::DefaultFailedToGetNewConnectionTemplate + hostDisplayName + ". "
         + std::string(curl_easy_strerror(result)));
   }
 
   if (port != 0 && !SetLibcurlOption(newHandle, CURLOPT_PORT, port, &result))
   {
     throw Azure::Core::Http::TransportException(
-        _detail::DefaultFailedToGetNewConnectionTemplate + host + ". "
+        _detail::DefaultFailedToGetNewConnectionTemplate + hostDisplayName + ". "
         + std::string(curl_easy_strerror(result)));
   }
 
   if (!SetLibcurlOption(newHandle, CURLOPT_CONNECT_ONLY, 1L, &result))
   {
     throw Azure::Core::Http::TransportException(
-        _detail::DefaultFailedToGetNewConnectionTemplate + host + ". "
+        _detail::DefaultFailedToGetNewConnectionTemplate + hostDisplayName + ". "
         + std::string(curl_easy_strerror(result)));
   }
 
@@ -1336,7 +1337,7 @@ std::unique_ptr<CurlNetworkConnection> CurlConnectionPool::ExtractOrCreateCurlCo
   if (!SetLibcurlOption(newHandle, CURLOPT_TIMEOUT, 60L * 60L * 24L, &result))
   {
     throw Azure::Core::Http::TransportException(
-        _detail::DefaultFailedToGetNewConnectionTemplate + host + ". "
+        _detail::DefaultFailedToGetNewConnectionTemplate + hostDisplayName + ". "
         + std::string(curl_easy_strerror(result)));
   }
 
@@ -1345,7 +1346,7 @@ std::unique_ptr<CurlNetworkConnection> CurlConnectionPool::ExtractOrCreateCurlCo
     if (!SetLibcurlOption(newHandle, CURLOPT_CONNECTTIMEOUT_MS, options.ConnectionTimeout, &result))
     {
       throw Azure::Core::Http::TransportException(
-          _detail::DefaultFailedToGetNewConnectionTemplate + host
+          _detail::DefaultFailedToGetNewConnectionTemplate + hostDisplayName
           + ". Fail setting connect timeout to: "
           + std::to_string(options.ConnectionTimeout.count()) + " ms. "
           + std::string(curl_easy_strerror(result)));
@@ -1360,8 +1361,9 @@ std::unique_ptr<CurlNetworkConnection> CurlConnectionPool::ExtractOrCreateCurlCo
     if (!SetLibcurlOption(newHandle, CURLOPT_PROXY, options.Proxy.c_str(), &result))
     {
       throw Azure::Core::Http::TransportException(
-          _detail::DefaultFailedToGetNewConnectionTemplate + host + ". Failed to set proxy to:"
-          + options.Proxy + ". " + std::string(curl_easy_strerror(result)));
+          _detail::DefaultFailedToGetNewConnectionTemplate + hostDisplayName
+          + ". Failed to set proxy to:" + options.Proxy + ". "
+          + std::string(curl_easy_strerror(result)));
     }
   }
 
@@ -1370,8 +1372,9 @@ std::unique_ptr<CurlNetworkConnection> CurlConnectionPool::ExtractOrCreateCurlCo
     if (!SetLibcurlOption(newHandle, CURLOPT_CAINFO, options.CAInfo.c_str(), &result))
     {
       throw Azure::Core::Http::TransportException(
-          _detail::DefaultFailedToGetNewConnectionTemplate + host + ". Failed to set CA cert to:"
-          + options.CAInfo + ". " + std::string(curl_easy_strerror(result)));
+          _detail::DefaultFailedToGetNewConnectionTemplate + hostDisplayName
+          + ". Failed to set CA cert to:" + options.CAInfo + ". "
+          + std::string(curl_easy_strerror(result)));
     }
   }
 
@@ -1384,7 +1387,7 @@ std::unique_ptr<CurlNetworkConnection> CurlConnectionPool::ExtractOrCreateCurlCo
   if (!SetLibcurlOption(newHandle, CURLOPT_SSL_OPTIONS, sslOption, &result))
   {
     throw Azure::Core::Http::TransportException(
-        _detail::DefaultFailedToGetNewConnectionTemplate + host
+        _detail::DefaultFailedToGetNewConnectionTemplate + hostDisplayName
         + ". Failed to set ssl options to long bitmask:" + std::to_string(sslOption) + ". "
         + std::string(curl_easy_strerror(result)));
   }
@@ -1394,7 +1397,7 @@ std::unique_ptr<CurlNetworkConnection> CurlConnectionPool::ExtractOrCreateCurlCo
     if (!SetLibcurlOption(newHandle, CURLOPT_SSL_VERIFYPEER, 0L, &result))
     {
       throw Azure::Core::Http::TransportException(
-          _detail::DefaultFailedToGetNewConnectionTemplate + host
+          _detail::DefaultFailedToGetNewConnectionTemplate + hostDisplayName
           + ". Failed to disable ssl verify peer. " + std::string(curl_easy_strerror(result)));
     }
   }
@@ -1404,7 +1407,7 @@ std::unique_ptr<CurlNetworkConnection> CurlConnectionPool::ExtractOrCreateCurlCo
     if (!SetLibcurlOption(newHandle, CURLOPT_NOSIGNAL, 1L, &result))
     {
       throw Azure::Core::Http::TransportException(
-          _detail::DefaultFailedToGetNewConnectionTemplate + host
+          _detail::DefaultFailedToGetNewConnectionTemplate + hostDisplayName
           + ". Failed to set NOSIGNAL option for libcurl. "
           + std::string(curl_easy_strerror(result)));
     }
@@ -1416,15 +1419,15 @@ std::unique_ptr<CurlNetworkConnection> CurlConnectionPool::ExtractOrCreateCurlCo
   if (!SetLibcurlOption(newHandle, CURLOPT_HTTP_VERSION, CURL_HTTP_VERSION_1_1, &result))
   {
     throw Azure::Core::Http::TransportException(
-        _detail::DefaultFailedToGetNewConnectionTemplate + host + ". Failed to set libcurl HTTP/1.1"
-        + ". " + std::string(curl_easy_strerror(result)));
+        _detail::DefaultFailedToGetNewConnectionTemplate + hostDisplayName
+        + ". Failed to set libcurl HTTP/1.1" + ". " + std::string(curl_easy_strerror(result)));
   }
 
   auto performResult = curl_easy_perform(newHandle);
   if (performResult != CURLE_OK)
   {
     throw Http::TransportException(
-        _detail::DefaultFailedToGetNewConnectionTemplate + host + ". "
+        _detail::DefaultFailedToGetNewConnectionTemplate + hostDisplayName + ". "
         + std::string(curl_easy_strerror(performResult)));
   }
 
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 720a35740..50b4d10db 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
@@ -26,6 +26,16 @@ using testing::ValuesIn;
 using namespace Azure::Core::Http::_detail;
 using namespace std::chrono_literals;
 
+namespace {
+inline std::string CreateConnectionKey(
+    std::string const& schema,
+    std::string const& host,
+    std::string const& configurationKey)
+{
+  return schema + "://" + host + configurationKey;
+}
+} // namespace
+
 namespace Azure { namespace Core { namespace Test {
 
 /***********************  Unique Tests for Libcurl   ********************************/
@@ -44,8 +54,8 @@ namespace Azure { namespace Core { namespace Test {
       // Use the same request for all connections.
       Azure::Core::Http::Request req(
           Azure::Core::Http::HttpMethod::Get, Azure::Core::Url(AzureSdkHttpbinServer::Get()));
-      std::string const expectedConnectionKey
-          = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "001100";
+      std::string const expectedConnectionKey(CreateConnectionKey(
+          AzureSdkHttpbinServer::Schema(), AzureSdkHttpbinServer::Host(), "001100"));
 
       {
         // Creating a new connection with default options
@@ -114,7 +124,7 @@ 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() + "00100200000";
+          = AzureSdkHttpbinServer::Schema() + "://" + AzureSdkHttpbinServer::Host() + "00100200000";
       {
         // Creating a new connection with options
         Azure::Core::Http::CurlTransportOptions options;
@@ -404,8 +414,8 @@ namespace Azure { namespace Core { namespace Test {
         std::string const authority(AzureSdkHttpbinServer::Get());
         Azure::Core::Http::Request req(
             Azure::Core::Http::HttpMethod::Get, Azure::Core::Url(authority));
-        std::string const expectedConnectionKey
-            = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "001100";
+        std::string const expectedConnectionKey(CreateConnectionKey(
+            AzureSdkHttpbinServer::Schema(), AzureSdkHttpbinServer::Host(), "001100"));
 
         // Creating a new connection with default options
         auto connection = Azure::Core::Http::_detail::CurlConnectionPool::g_curlConnectionPool
@@ -440,8 +450,8 @@ namespace Azure { namespace Core { namespace Test {
         std::string const authority(AzureSdkHttpbinServer::WithPort());
         Azure::Core::Http::Request req(
             Azure::Core::Http::HttpMethod::Get, Azure::Core::Url(authority));
-        std::string const expectedConnectionKey
-            = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "443001100";
+        std::string const expectedConnectionKey(CreateConnectionKey(
+            AzureSdkHttpbinServer::Schema(), AzureSdkHttpbinServer::Host(), ":443001100"));
 
         // Creating a new connection with default options
         auto connection = Azure::Core::Http::_detail::CurlConnectionPool::g_curlConnectionPool
@@ -477,8 +487,8 @@ namespace Azure { namespace Core { namespace Test {
         std::string const authority(AzureSdkHttpbinServer::Get());
         Azure::Core::Http::Request req(
             Azure::Core::Http::HttpMethod::Get, Azure::Core::Url(authority));
-        std::string const expectedConnectionKey
-            = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "001100";
+        std::string const expectedConnectionKey(CreateConnectionKey(
+            AzureSdkHttpbinServer::Schema(), AzureSdkHttpbinServer::Host(), "001100"));
 
         // Creating a new connection with default options
         auto connection = Azure::Core::Http::_detail::CurlConnectionPool::g_curlConnectionPool
@@ -512,8 +522,8 @@ namespace Azure { namespace Core { namespace Test {
         std::string const authority(AzureSdkHttpbinServer::WithPort());
         Azure::Core::Http::Request req(
             Azure::Core::Http::HttpMethod::Get, Azure::Core::Url(authority));
-        std::string const expectedConnectionKey
-            = AzureSdkHttpbinServer::Schema() + AzureSdkHttpbinServer::Host() + "443001100";
+        std::string const expectedConnectionKey(CreateConnectionKey(
+            AzureSdkHttpbinServer::Schema(), AzureSdkHttpbinServer::Host(), ":443001100"));
 
         // Creating a new connection with default options
         auto connection = Azure::Core::Http::_detail::CurlConnectionPool::g_curlConnectionPool