diff --git a/eng/pipelines/templates/stages/platform-matrix.json b/eng/pipelines/templates/stages/platform-matrix.json
index 143149325..18f4db991 100644
--- a/eng/pipelines/templates/stages/platform-matrix.json
+++ b/eng/pipelines/templates/stages/platform-matrix.json
@@ -85,8 +85,13 @@
         }
       },
       "TargetPlatform": {
-        "Win32Api_debug_tests": {
-          "CmakeArgs": " -DBUILD_TESTING=ON -DBUILD_PERFORMANCE_TESTS=ON -DRUN_LONG_UNIT_TESTS=ON -DBUILD_TRANSPORT_CURL=ON -DBUILD_TRANSPORT_WINHTTP=ON -DMSVC_USE_STATIC_CRT=ON",
+        "Win32Api_debug_tests_curl": {
+          "CmakeArgs": " -DBUILD_TESTING=ON -DBUILD_PERFORMANCE_TESTS=ON -DRUN_LONG_UNIT_TESTS=ON -DBUILD_TRANSPORT_CURL=ON -DMSVC_USE_STATIC_CRT=ON",
+          "BuildArgs": "--parallel 8 --config Debug",
+          "PublishMapFiles": "true"
+        },
+        "Win32Api_debug_tests_winhttp": {
+          "CmakeArgs": " -DBUILD_TESTING=ON -DBUILD_PERFORMANCE_TESTS=ON -DRUN_LONG_UNIT_TESTS=ON -DMSVC_USE_STATIC_CRT=ON",
           "BuildArgs": "--parallel 8 --config Debug",
           "PublishMapFiles": "true"
         }
diff --git a/sdk/core/azure-core/inc/azure/core/http/http.hpp b/sdk/core/azure-core/inc/azure/core/http/http.hpp
index 0638a3f21..2f01b05df 100644
--- a/sdk/core/azure-core/inc/azure/core/http/http.hpp
+++ b/sdk/core/azure-core/inc/azure/core/http/http.hpp
@@ -311,6 +311,12 @@ namespace Azure { namespace Core { namespace Http {
      */
     Azure::Core::IO::BodyStream* GetBodyStream() { return this->m_bodyStream; }
 
+    /**
+     * @brief Get HTTP body as #Azure::Core::IO::BodyStream.
+     *
+     */
+    Azure::Core::IO::BodyStream const* GetBodyStream() const { return this->m_bodyStream; }
+
     /**
      * @brief A value indicating whether the returned raw response for this request will be buffered
      * within a memory buffer or if it will be returned as a body stream instead.
diff --git a/sdk/core/azure-core/src/http/winhttp/win_http_transport.cpp b/sdk/core/azure-core/src/http/winhttp/win_http_transport.cpp
index 199d741f8..d1d92ab09 100644
--- a/sdk/core/azure-core/src/http/winhttp/win_http_transport.cpp
+++ b/sdk/core/azure-core/src/http/winhttp/win_http_transport.cpp
@@ -202,13 +202,32 @@ std::string GetHeadersAsString(Azure::Core::Http::Request const& request)
 {
   std::string requestHeaderString;
 
-  for (auto const& header : request.GetHeaders())
+  // request.GetHeaders() aggregates the pre- and post-retry headers into a single map. Capture it
+  // so we don't recalculate the merge multiple times.
+  auto requestHeaders = request.GetHeaders();
+
+  for (auto const& header : requestHeaders)
   {
     requestHeaderString += header.first; // string (key)
     requestHeaderString += ": ";
     requestHeaderString += header.second; // string's value
     requestHeaderString += "\r\n";
   }
+
+  // The test recording infrastructure requires that a Patch verb have a Content-Length header,
+  // because it does not distinguish between requests with and without a body if there's no
+  // Content-Length header.
+  if (request.GetMethod() == HttpMethod::Patch)
+  {
+    if (requestHeaders.find("Content-Length") == requestHeaders.end())
+    {
+      if (request.GetBodyStream() == nullptr || request.GetBodyStream()->Length() == 0)
+      {
+        requestHeaderString += "Content-Length: 0\r\n";
+      }
+    }
+  }
+
   requestHeaderString += "\r\n";
 
   return requestHeaderString;