diff --git a/src/common/util/src/file_util.cpp b/src/common/util/src/file_util.cpp
index 89569a8bb95f2e..5436f26f03014a 100644
--- a/src/common/util/src/file_util.cpp
+++ b/src/common/util/src/file_util.cpp
@@ -294,12 +294,17 @@ void ov::util::create_directory_recursive(const std::wstring& path) {
 void ov::util::create_directory_recursive(const std::filesystem::path& path) {
     namespace fs = std::filesystem;
     auto dir_path = fs::weakly_canonical(path);
-    if (!dir_path.has_filename() || dir_path.has_extension()) {
-        dir_path = get_directory(dir_path);
-    }
 
     if (!dir_path.empty() && !directory_exists(dir_path)) {
-        if (std::error_code ec; !fs::create_directories(dir_path, ec)) {
+        // NOTE: Some standard library implementations (MSVC STL, libc++) may return `false`
+        // from create_directories(path, ec) (with ec == 0) when the path ends with a
+        // trailing separator (e.g. "a/b/c/"). Internally they create "a", "a/b", "a/b/c"
+        // and then the extra mkdir on "a/b/c/" yields an "already exists" condition,
+        // leading to a final `false` even though the directory tree was actually created.
+        // libstdc++ (GCC) returns `true` in that situation. The extra exists() check
+        // lets us treat "false + exists()" as success while still detecting a real failure
+        // ("false + !exists()"), keeping behavior consistent across platforms.
+        if (std::error_code ec; !fs::create_directories(dir_path, ec) && !std::filesystem::exists(dir_path)) {
             std::stringstream ss;
             ss << "Couldn't create directory [" << dir_path << "], err=" << ec.message() << ")";
             throw std::runtime_error(ss.str());
diff --git a/src/core/src/pass/serialize.cpp b/src/core/src/pass/serialize.cpp
index 4de66749b4fdff..e8ca7cc5526e2e 100644
--- a/src/core/src/pass/serialize.cpp
+++ b/src/core/src/pass/serialize.cpp
@@ -110,7 +110,7 @@ bool pass::Serialize::run_on_model(const std::shared_ptr<ov::Model>& model) {
     if (m_xmlFile && m_binFile) {
         serialize_func(*m_xmlFile, *m_binFile, model, m_version);
     } else {
-        ov::util::create_directory_recursive(m_xmlPath);
+        ov::util::create_directory_recursive(m_xmlPath.parent_path());
 
         std::ofstream bin_file(m_binPath, std::ios::binary);
         OPENVINO_ASSERT(bin_file, "Can't open bin file: \"", m_binPath, "\"");
diff --git a/src/plugins/intel_gpu/tests/functional/subgraph_tests/serialize.cpp b/src/plugins/intel_gpu/tests/functional/subgraph_tests/serialize.cpp
index 2eb46c8e4c3b01..09b5052df9dc07 100644
--- a/src/plugins/intel_gpu/tests/functional/subgraph_tests/serialize.cpp
+++ b/src/plugins/intel_gpu/tests/functional/subgraph_tests/serialize.cpp
@@ -4,6 +4,7 @@
 
 #include "shared_test_classes/base/ov_subgraph.hpp"
 #include "subgraphs_builders.hpp"
+#include "openvino/op/relu.hpp"
 
 namespace {
 
@@ -65,4 +66,44 @@ TEST_F(LSTMSequenceTest, smoke_serialize) {
 TEST_F(GRUSequenceTest, smoke_serialize) {
     run();
 }
+
+class GpuCacheDirWithDotsParamTest : public ::testing::TestWithParam<std::string> {
+protected:
+    ov::Core core;
+    std::string cacheDir;
+
+    void SetUp() override {
+        std::stringstream ss;
+        ss << std::hex << std::hash<std::string>{}(std::string(::testing::UnitTest::GetInstance()->current_test_info()->name()));
+
+        // Base (no trailing slash first)
+        cacheDir = ss.str() + GetParam();
+
+        // Clean previous
+        ov::test::utils::removeFilesWithExt(cacheDir, "blob");
+        ov::test::utils::removeFilesWithExt(cacheDir, "cl_cache");
+        ov::test::utils::removeDir(cacheDir);
+
+        core.set_property(ov::cache_dir(cacheDir));
+    }
+
+    void TearDown() override {
+        ov::test::utils::removeFilesWithExt(cacheDir, "blob");
+        ov::test::utils::removeFilesWithExt(cacheDir, "cl_cache");
+        ov::test::utils::removeDir(cacheDir);
+    }
+};
+
+TEST_P(GpuCacheDirWithDotsParamTest, smoke_PopulateAndReuseCache) {
+    auto param = std::make_shared<ov::op::v0::Parameter>(ov::element::f32, ov::Shape{1, 3, 8, 8});
+    auto relu = std::make_shared<ov::op::v0::Relu>(param);
+    auto res = std::make_shared<ov::op::v0::Result>(relu);
+    auto model = std::make_shared<ov::Model>(ov::ResultVector{res}, ov::ParameterVector{param}, "CacheDotsModel");
+    core.compile_model(model, "GPU");
+}
+
+INSTANTIATE_TEST_SUITE_P(CacheDirDotVariants,
+                         GpuCacheDirWithDotsParamTest,
+                         ::testing::Values("/test_encoder/test_encoder.encrypted/", "/test_encoder/test_encoder.encrypted"));
+
 }  // namespace