diff --git a/api/test/singleton/CMakeLists.txt b/api/test/singleton/CMakeLists.txt
index 450308cd82..7c30d6e571 100644
--- a/api/test/singleton/CMakeLists.txt
+++ b/api/test/singleton/CMakeLists.txt
@@ -3,59 +3,53 @@
 
 include(GoogleTest)
 
-# Header only singletons are not available in windows yet.
-
-if(NOT WIN32)
-
-  add_library(component_a STATIC component_a.cc)
-  target_link_libraries(component_a opentelemetry_api)
-
-  add_library(component_b STATIC component_b.cc)
-  target_link_libraries(component_b opentelemetry_api)
-
-  add_library(component_c SHARED component_c.cc)
-  set_target_properties(component_c PROPERTIES CXX_VISIBILITY_PRESET default)
-  target_link_libraries(component_c opentelemetry_api)
-
-  add_library(component_d SHARED component_d.cc)
-  set_target_properties(component_d PROPERTIES CXX_VISIBILITY_PRESET hidden)
-  target_link_libraries(component_d opentelemetry_api)
-
-  add_library(component_e SHARED component_e.cc)
-  set_target_properties(component_e PROPERTIES CXX_VISIBILITY_PRESET default)
-  target_link_libraries(component_e opentelemetry_api)
-
-  add_library(component_f SHARED component_f.cc)
-  set_target_properties(component_f PROPERTIES CXX_VISIBILITY_PRESET hidden)
-  target_link_libraries(component_f opentelemetry_api)
-
-  add_library(component_g SHARED component_g.cc)
-  set_target_properties(component_g PROPERTIES CXX_VISIBILITY_PRESET default)
-  target_link_libraries(component_g opentelemetry_api)
-
-  add_library(component_h SHARED component_h.cc)
-  set_target_properties(component_h PROPERTIES CXX_VISIBILITY_PRESET hidden)
-  target_link_libraries(component_h opentelemetry_api)
-
-  add_executable(singleton_test singleton_test.cc)
-
-  # Not linking with component_g and component_h on purpose
-  target_link_libraries(
-    singleton_test
-    component_a
-    component_b
-    component_c
-    component_d
-    component_e
-    component_f
-    ${GTEST_BOTH_LIBRARIES}
-    ${CMAKE_THREAD_LIBS_INIT}
-    ${CMAKE_DL_LIBS}
-    opentelemetry_api)
-
-  gtest_add_tests(
-    TARGET singleton_test
-    TEST_PREFIX singleton.
-    TEST_LIST singleton_test)
-
-endif()
+add_library(component_a STATIC component_a.cc)
+target_link_libraries(component_a opentelemetry_api)
+
+add_library(component_b STATIC component_b.cc)
+target_link_libraries(component_b opentelemetry_api)
+
+add_library(component_c SHARED component_c.cc)
+set_target_properties(component_c PROPERTIES CXX_VISIBILITY_PRESET default)
+target_link_libraries(component_c opentelemetry_api)
+
+add_library(component_d SHARED component_d.cc)
+set_target_properties(component_d PROPERTIES CXX_VISIBILITY_PRESET hidden)
+target_link_libraries(component_d opentelemetry_api)
+
+add_library(component_e SHARED component_e.cc)
+set_target_properties(component_e PROPERTIES CXX_VISIBILITY_PRESET default)
+target_link_libraries(component_e opentelemetry_api)
+
+add_library(component_f SHARED component_f.cc)
+set_target_properties(component_f PROPERTIES CXX_VISIBILITY_PRESET hidden)
+target_link_libraries(component_f opentelemetry_api)
+
+add_library(component_g SHARED component_g.cc)
+set_target_properties(component_g PROPERTIES CXX_VISIBILITY_PRESET default)
+target_link_libraries(component_g opentelemetry_api)
+
+add_library(component_h SHARED component_h.cc)
+set_target_properties(component_h PROPERTIES CXX_VISIBILITY_PRESET hidden)
+target_link_libraries(component_h opentelemetry_api)
+
+add_executable(singleton_test singleton_test.cc)
+
+# Not linking with component_g and component_h on purpose
+target_link_libraries(
+  singleton_test
+  component_a
+  component_b
+  component_c
+  component_d
+  component_e
+  component_f
+  ${GTEST_BOTH_LIBRARIES}
+  ${CMAKE_THREAD_LIBS_INIT}
+  ${CMAKE_DL_LIBS}
+  opentelemetry_api)
+
+gtest_add_tests(
+  TARGET singleton_test
+  TEST_PREFIX singleton.
+  TEST_LIST singleton_test)
diff --git a/api/test/singleton/singleton_test.cc b/api/test/singleton/singleton_test.cc
index d212221118..8b8cb1587d 100644
--- a/api/test/singleton/singleton_test.cc
+++ b/api/test/singleton/singleton_test.cc
@@ -4,12 +4,9 @@
 #include <gtest/gtest.h>
 #include <stdint.h>
 
-/*
-  TODO:
-  Once singleton are supported for windows,
-  expand this test to use ::LoadLibrary, ::GetProcAddress, ::FreeLibrary
-*/
-#ifndef _WIN32
+#ifdef _WIN32
+#  include <windows.h>
+#else
 #  include <dlfcn.h>
 #endif
 
@@ -58,28 +55,57 @@ void do_something()
 #ifndef BAZEL_BUILD
   /* Call do_something_in_g() */
 
+#  ifdef _WIN32
+  HMODULE component_g = LoadLibraryA("component_g.dll");
+#  else
   void *component_g = dlopen("libcomponent_g.so", RTLD_NOW);
+#  endif
+
   EXPECT_NE(component_g, nullptr);
 
+#  ifdef _WIN32
+  auto *func_g = reinterpret_cast<void (*)()>(GetProcAddress(component_g, "do_something_in_g"));
+#  else
   auto *func_g = reinterpret_cast<void (*)()>(dlsym(component_g, "do_something_in_g"));
+#  endif
+
   EXPECT_NE(func_g, nullptr);
 
   (*func_g)();
 
+#  ifdef _WIN32
+  FreeLibrary(component_g);
+#  else
   dlclose(component_g);
+#  endif
 
   /* Call do_something_in_h() */
 
+#  ifdef _WIN32
+  HMODULE component_h = LoadLibraryA("component_h.dll");
+#  else
   void *component_h = dlopen("libcomponent_h.so", RTLD_NOW);
+#  endif
+
   EXPECT_NE(component_h, nullptr);
 
+#  ifdef _WIN32
+  auto *func_h = reinterpret_cast<void (*)()>(GetProcAddress(component_h, "do_something_in_h"));
+#  else
   auto *func_h = reinterpret_cast<void (*)()>(dlsym(component_h, "do_something_in_h"));
+#  endif
+
   EXPECT_NE(func_h, nullptr);
 
   (*func_h)();
 
+#  ifdef _WIN32
+  FreeLibrary(component_h);
+#  else
   dlclose(component_h);
-#endif
+#  endif
+
+#endif /* BAZEL_BUILD */
 }
 
 int span_a_lib_count   = 0;
@@ -316,6 +342,14 @@ void cleanup_otel()
   trace_api::Provider::SetTracerProvider(provider);
 }
 
+// TODO: Remove once windows api singletons are supported.
+// See https://github.com/open-telemetry/opentelemetry-cpp/issues/2534
+#ifdef _WIN32
+#  define RUN_FAILING_WINDOWS_TEST 0
+#else
+#  define RUN_FAILING_WINDOWS_TEST 1
+#endif
+
 TEST(SingletonTest, Uniqueness)
 {
   do_something();
@@ -357,26 +391,31 @@ TEST(SingletonTest, Uniqueness)
   EXPECT_EQ(span_b_lib_count, 1);
   EXPECT_EQ(span_b_f1_count, 2);
   EXPECT_EQ(span_b_f2_count, 1);
-  EXPECT_EQ(span_c_lib_count, 1);
-  EXPECT_EQ(span_c_f1_count, 2);
-  EXPECT_EQ(span_c_f2_count, 1);
-  EXPECT_EQ(span_d_lib_count, 1);
-  EXPECT_EQ(span_d_f1_count, 2);
-  EXPECT_EQ(span_d_f2_count, 1);
-  EXPECT_EQ(span_e_lib_count, 1);
-  EXPECT_EQ(span_e_f1_count, 2);
-  EXPECT_EQ(span_e_f2_count, 1);
-  EXPECT_EQ(span_f_lib_count, 1);
-  EXPECT_EQ(span_f_f1_count, 2);
-  EXPECT_EQ(span_f_f2_count, 1);
+
+#if RUN_FAILING_WINDOWS_TEST
+  EXPECT_EQ(span_c_lib_count, 1);  // Fails with shared libraries on Windows
+  EXPECT_EQ(span_c_f1_count, 2);   // Fails with shared libraries on Windows
+  EXPECT_EQ(span_c_f2_count, 1);   // Fails with shared libraries on Windows
+  EXPECT_EQ(span_d_lib_count, 1);  // Fails with shared libraries on Windows
+  EXPECT_EQ(span_d_f1_count, 2);   // Fails with shared libraries on Windows
+  EXPECT_EQ(span_d_f2_count, 1);   // Fails with shared libraries on Windows
+  EXPECT_EQ(span_e_lib_count, 1);  // Fails with shared libraries on Windows
+  EXPECT_EQ(span_e_f1_count, 2);   // Fails with shared libraries on Windows
+  EXPECT_EQ(span_e_f2_count, 1);   // Fails with shared libraries on Windows
+  EXPECT_EQ(span_f_lib_count, 1);  // Fails with shared libraries on Windows
+  EXPECT_EQ(span_f_f1_count, 2);   // Fails with shared libraries on Windows
+  EXPECT_EQ(span_f_f2_count, 1);   // Fails with shared libraries on Windows
+#endif
 
 #ifndef BAZEL_BUILD
-  EXPECT_EQ(span_g_lib_count, 1);
-  EXPECT_EQ(span_g_f1_count, 2);
-  EXPECT_EQ(span_g_f2_count, 1);
-  EXPECT_EQ(span_h_lib_count, 1);
-  EXPECT_EQ(span_h_f1_count, 2);
-  EXPECT_EQ(span_h_f2_count, 1);
+#  if RUN_FAILING_WINDOWS_TEST
+  EXPECT_EQ(span_g_lib_count, 1);  // Fails with shared libraries on Windows
+  EXPECT_EQ(span_g_f1_count, 2);   // Fails with shared libraries on Windows
+  EXPECT_EQ(span_g_f2_count, 1);   // Fails with shared libraries on Windows
+  EXPECT_EQ(span_h_lib_count, 1);  // Fails with shared libraries on Windows
+  EXPECT_EQ(span_h_f1_count, 2);   // Fails with shared libraries on Windows
+  EXPECT_EQ(span_h_f2_count, 1);   // Fails with shared libraries on Windows
+#  endif
 #endif
 
   EXPECT_EQ(unknown_span_count, 0);
diff --git a/ci/do_ci.ps1 b/ci/do_ci.ps1
index e9c1f64646..a04ec938f5 100644
--- a/ci/do_ci.ps1
+++ b/ci/do_ci.ps1
@@ -27,6 +27,8 @@ $PLUGIN_DIR = Join-Path "$SRC_DIR" "plugin"
 
 $VCPKG_DIR = Join-Path "$SRC_DIR" "tools" "vcpkg"
 
+$Env:CTEST_OUTPUT_ON_FAILURE = "1"
+
 switch ($action) {
   "bazel.build" {
     bazel $BAZEL_STARTUP_OPTIONS build $BAZEL_OPTIONS --action_env=VCPKG_DIR=$VCPKG_DIR --deleted_packages=opentracing-shim -- //...