diff --git a/src/gui/render.cpp b/src/gui/render.cpp
index 4bcf822..a429131 100644
--- a/src/gui/render.cpp
+++ b/src/gui/render.cpp
@@ -1719,26 +1719,6 @@ int Render::DrawServerWindow() {
 }
 
 int Render::Run() {
-  latest_version_info_ = CheckUpdate();
-  if (!latest_version_info_.empty() &&
-      latest_version_info_.contains("version") &&
-      latest_version_info_["version"].is_string()) {
-    latest_version_ = 'v' + latest_version_info_["version"].get<std::string>();
-    if (latest_version_info_.contains("releaseNotes") &&
-        latest_version_info_["releaseNotes"].is_string()) {
-      release_notes_ = latest_version_info_["releaseNotes"].get<std::string>();
-    } else {
-      release_notes_ = "";
-    }
-    update_available_ = IsNewerVersion(CROSSDESK_VERSION, latest_version_);
-    if (update_available_) {
-      show_update_notification_window_ = true;
-    }
-  } else {
-    latest_version_ = "";
-    update_available_ = false;
-  }
-
   path_manager_ = std::make_unique<PathManager>("CrossDesk");
   if (path_manager_) {
     exec_log_path_ = path_manager_->GetLogPath().string();
@@ -1767,6 +1747,29 @@ int Render::Run() {
   InitializeLogger();
   LOG_INFO("CrossDesk version: {}", CROSSDESK_VERSION);
 
+  latest_version_info_ = CheckUpdate();
+  if (!latest_version_info_.empty() &&
+      latest_version_info_.contains("version") &&
+      latest_version_info_["version"].is_string()) {
+    latest_version_ = 'v' + latest_version_info_["version"].get<std::string>();
+    if (latest_version_info_.contains("releaseNotes") &&
+        latest_version_info_["releaseNotes"].is_string()) {
+      release_notes_ = latest_version_info_["releaseNotes"].get<std::string>();
+    } else {
+      release_notes_ = "";
+    }
+    update_available_ = IsNewerVersion(CROSSDESK_VERSION, latest_version_);
+    LOG_INFO("Update check: current={}, latest={}, available={}",
+             CROSSDESK_VERSION, latest_version_, update_available_);
+    if (update_available_) {
+      show_update_notification_window_ = true;
+    }
+  } else {
+    latest_version_ = "";
+    update_available_ = false;
+    LOG_WARN("Update check skipped: version.json is empty or missing version");
+  }
+
   InitializeSettings();
   InitializeSDL();
   InitializeModules();
diff --git a/src/version_checker/version_checker.cpp b/src/version_checker/version_checker.cpp
index 196692c..7907800 100644
--- a/src/version_checker/version_checker.cpp
+++ b/src/version_checker/version_checker.cpp
@@ -8,6 +8,8 @@
 
 #include <httplib.h>
 
+#include "rd_log.h"
+
 #include <algorithm>
 #include <cctype>
 #include <iostream>
@@ -225,6 +227,15 @@ bool ReadPatchField(const nlohmann::json& json, int* patch) {
   return false;
 }
 
+void LogHttpError(const httplib::Result& result) {
+  LOG_WARN("Failed to fetch version.json: error={}, message={}",
+           static_cast<int>(result.error()), httplib::to_string(result.error()));
+#ifdef CPPHTTPLIB_OPENSSL_SUPPORT
+  LOG_WARN("version.json SSL error={}, OpenSSL error={}", result.ssl_error(),
+           result.ssl_openssl_error());
+#endif
+}
+
 }  // namespace
 
 std::string ExtractNumericPart(const std::string& ver) {
@@ -312,8 +323,10 @@ nlohmann::json CheckUpdate() {
 
   cli.set_connection_timeout(5);
   cli.set_read_timeout(5);
+  cli.set_follow_location(true);
 
-  if (auto res = cli.Get("/version.json")) {
+  auto res = cli.Get("/version.json");
+  if (res) {
     if (res->status == 200) {
       try {
         auto j = nlohmann::json::parse(res->body);
@@ -324,16 +337,22 @@ nlohmann::json CheckUpdate() {
         }
         latest_patch_ = 0;
         latest_patch_available_ = ReadPatchField(j, &latest_patch_);
+        LOG_INFO("Fetched version.json: version={}, releaseDate={}, patch={}",
+                 j.value("version", ""), j.value("releaseDate", ""),
+                 latest_patch_available_ ? latest_patch_ : -1);
         return j;
-      } catch (std::exception&) {
+      } catch (const std::exception& e) {
+        LOG_WARN("Failed to parse version.json: {}", e.what());
         ResetLatestMetadata();
         return nlohmann::json{};
       }
     } else {
+      LOG_WARN("Failed to fetch version.json: HTTP status={}", res->status);
       ResetLatestMetadata();
       return nlohmann::json{};
     }
   } else {
+    LogHttpError(res);
     ResetLatestMetadata();
     return nlohmann::json{};
   }
diff --git a/xmake/targets.lua b/xmake/targets.lua
index f7a86ab..6b8d0ed 100644
--- a/xmake/targets.lua
+++ b/xmake/targets.lua
@@ -74,9 +74,14 @@ function setup_targets()
         set_kind("binary")
         set_default(false)
         add_packages("cpp-httplib")
+        add_deps("rd_log")
         add_includedirs("src/version_checker")
         add_files("tests/version_checker_test.cpp",
             "src/version_checker/version_checker.cpp")
+        if is_os("macosx") then
+            add_defines("CPPHTTPLIB_USE_CERTS_FROM_MACOSX_KEYCHAIN")
+            add_frameworks("Security", "CoreFoundation")
+        end
 
     target("screen_capturer")
         set_kind("object")
@@ -177,6 +182,10 @@ function setup_targets()
         add_deps("rd_log")
         add_files("src/version_checker/*.cpp")
         add_includedirs("src/version_checker", {public = true})
+        if is_os("macosx") then
+            add_defines("CPPHTTPLIB_USE_CERTS_FROM_MACOSX_KEYCHAIN")
+            add_frameworks("Security", "CoreFoundation")
+        end
 
     target("tools")
         set_kind("object")