diff --git a/repertory/librepertory/include/comm/curl/curl_comm.hpp b/repertory/librepertory/include/comm/curl/curl_comm.hpp
index d7fa784b..7875b1f8 100644
--- a/repertory/librepertory/include/comm/curl/curl_comm.hpp
+++ b/repertory/librepertory/include/comm/curl/curl_comm.hpp
@@ -61,13 +61,14 @@ public:
   [[nodiscard]] static auto reset_curl(CURL *curl_handle) -> CURL *;
 
 public:
-  [[nodiscard]] static auto
-  construct_url(CURL *curl, const std::string &relative_path,
-                const host_config &cfg) -> std::string;
+  [[nodiscard]] static auto construct_url(CURL *curl,
+                                          const std::string &relative_path,
+                                          const host_config &cfg)
+      -> std::string;
 
-  [[nodiscard]] static auto
-  create_host_config(const s3_config &cfg,
-                     bool use_s3_path_style) -> host_config;
+  [[nodiscard]] static auto create_host_config(const s3_config &cfg,
+                                               bool use_s3_path_style)
+      -> host_config;
 
   [[nodiscard]] static auto url_encode(CURL *curl, const std::string &data,
                                        bool allow_slash) -> std::string;
@@ -75,8 +76,8 @@ public:
   template <typename request_type>
   [[nodiscard]] static auto
   make_encrypted_request(const host_config &cfg, const request_type &request,
-                         long &response_code,
-                         stop_type &stop_requested) -> bool {
+                         long &response_code, stop_type &stop_requested)
+      -> bool {
     response_code = 0;
 
     if (not request.decryption_token.has_value() ||
@@ -193,6 +194,16 @@ public:
                        request.aws_service.value().c_str());
     }
 
+    curl_slist *header_list{nullptr};
+    if (not request.headers.empty()) {
+      for (const auto &&header : request.headers) {
+        header_list = curl_slist_append(
+            header_list,
+            fmt::format("{}: {}", header.first, header.second).c_str());
+      }
+      curl_easy_setopt(curl, CURLOPT_HTTPHEADER, header_list);
+    }
+
     auto url = construct_url(curl, request.get_path(), cfg) + parameters;
     curl_easy_setopt(curl, CURLOPT_URL, url.c_str());
 
@@ -200,6 +211,11 @@ public:
 
     CURLcode curl_code{};
     curl_request.get_result(curl_code, response_code);
+
+    if (header_list != nullptr) {
+      curl_slist_free_all(header_list);
+    }
+
     if (curl_code != CURLE_OK) {
       event_system::instance().raise<curl_error>(url, curl_code);
       return false;
@@ -215,26 +231,30 @@ public:
 public:
   void enable_s3_path_style(bool enable) override;
 
-  [[nodiscard]] auto
-  make_request(const curl::requests::http_delete &del, long &response_code,
-               stop_type &stop_requested) const -> bool override;
+  [[nodiscard]] auto make_request(const curl::requests::http_delete &del,
+                                  long &response_code,
+                                  stop_type &stop_requested) const
+      -> bool override;
 
-  [[nodiscard]] auto
-  make_request(const curl::requests::http_get &get, long &response_code,
-               stop_type &stop_requested) const -> bool override;
+  [[nodiscard]] auto make_request(const curl::requests::http_get &get,
+                                  long &response_code,
+                                  stop_type &stop_requested) const
+      -> bool override;
 
-  [[nodiscard]] auto
-  make_request(const curl::requests::http_head &head, long &response_code,
-               stop_type &stop_requested) const -> bool override;
+  [[nodiscard]] auto make_request(const curl::requests::http_head &head,
+                                  long &response_code,
+                                  stop_type &stop_requested) const
+      -> bool override;
 
-  [[nodiscard]] auto
-  make_request(const curl::requests::http_post &post_file, long &response_code,
-               stop_type &stop_requested) const -> bool override;
+  [[nodiscard]] auto make_request(const curl::requests::http_post &post_file,
+                                  long &response_code,
+                                  stop_type &stop_requested) const
+      -> bool override;
 
-  [[nodiscard]] auto
-  make_request(const curl::requests::http_put_file &put_file,
-               long &response_code,
-               stop_type &stop_requested) const -> bool override;
+  [[nodiscard]] auto make_request(const curl::requests::http_put_file &put_file,
+                                  long &response_code,
+                                  stop_type &stop_requested) const
+      -> bool override;
 };
 } // namespace repertory
 
diff --git a/repertory/librepertory/include/comm/curl/requests/http_post.hpp b/repertory/librepertory/include/comm/curl/requests/http_post.hpp
index 225d5c3d..c5425e12 100644
--- a/repertory/librepertory/include/comm/curl/requests/http_post.hpp
+++ b/repertory/librepertory/include/comm/curl/requests/http_post.hpp
@@ -32,15 +32,15 @@ struct http_post final : http_request_base {
   auto operator=(const http_post &) -> http_post & = default;
   auto operator=(http_post &&) -> http_post & = default;
 
-  ~http_post() override;
+  ~http_post() override = default;
 
   std::optional<nlohmann::json> json;
 
-  [[nodiscard]] auto
-  set_method(CURL *curl, stop_type & /*stop_requested*/) const -> bool override;
+  [[nodiscard]] auto set_method(CURL *curl,
+                                stop_type & /*stop_requested*/) const
+      -> bool override;
 
 private:
-  mutable curl_slist *headers{nullptr};
   mutable std::optional<std::string> json_str;
 };
 } // namespace repertory::curl::requests
diff --git a/repertory/librepertory/include/comm/curl/requests/http_request_base.hpp b/repertory/librepertory/include/comm/curl/requests/http_request_base.hpp
index 4a14cb53..a99d88da 100644
--- a/repertory/librepertory/include/comm/curl/requests/http_request_base.hpp
+++ b/repertory/librepertory/include/comm/curl/requests/http_request_base.hpp
@@ -51,7 +51,7 @@ struct http_request_base {
   bool allow_timeout{};
   std::optional<std::string> aws_service;
   std::optional<std::string> decryption_token{};
-  http_headers headers{};
+  mutable http_headers headers{};
   std::string path{};
   http_query_parameters query{};
   std::optional<http_range> range{};
diff --git a/repertory/librepertory/src/comm/curl/requests/http_post.cpp b/repertory/librepertory/src/comm/curl/requests/http_post.cpp
index e7a41b98..ca052a0a 100644
--- a/repertory/librepertory/src/comm/curl/requests/http_post.cpp
+++ b/repertory/librepertory/src/comm/curl/requests/http_post.cpp
@@ -22,18 +22,11 @@
 #include "comm/curl/requests/http_post.hpp"
 
 namespace repertory::curl::requests {
-http_post::~http_post() {
-  if (headers != nullptr) {
-    curl_slist_free_all(headers);
-  }
-}
-
 auto http_post::set_method(CURL *curl, stop_type & /*stop_requested*/) const
     -> bool {
   curl_easy_setopt(curl, CURLOPT_CUSTOMREQUEST, "POST");
   if (json.has_value()) {
-    headers = curl_slist_append(headers, "content-type: application/json");
-    curl_easy_setopt(curl, CURLOPT_HTTPHEADER, headers);
+    headers["content-type"] = "application/json";
 
     json_str = json->dump();
     curl_easy_setopt(curl, CURLOPT_POSTFIELDS, json_str->c_str());
diff --git a/support/include/utils/config.hpp b/support/include/utils/config.hpp
index 719a6ca0..e995f7f0 100644
--- a/support/include/utils/config.hpp
+++ b/support/include/utils/config.hpp
@@ -468,7 +468,7 @@ struct http_range final {
   std::uint64_t end{};
 };
 
-using http_headers = std::unordered_map<std::string, std::string>;
+using http_headers = std::map<std::string, std::string>;
 using http_query_parameters = std::map<std::string, std::string>;
 using http_ranges = std::vector<http_range>;
 #endif // defined(PROJECT_ENABLE_CURL)