diff --git a/azure-pipelines.yml b/azure-pipelines.yml
index c519e153..d9e44872 100644
--- a/azure-pipelines.yml
+++ b/azure-pipelines.yml
@@ -57,10 +57,14 @@ jobs:
         Windows11:
           vmImage: "windows-2019"
           cli11.std: 11
-        WindowsLatest:
-          vmImage: "windows-2019"
+        Windows20:
+          vmImage: "windows-2022"
           cli11.std: 20
-          cli11.options: -DCMAKE_CXX_FLAGS="/std:c++latest /EHsc"
+          cli11.options: -DCMAKE_CXX_FLAGS="/EHsc"
+        WindowsLatest:
+          vmImage: "windows-2022"
+          cli11.std: 23
+          cli11.options: -DCMAKE_CXX_FLAGS="/EHsc"
         Linux17nortti:
           vmImage: "ubuntu-latest"
           cli11.std: 17
diff --git a/include/CLI/TypeTools.hpp b/include/CLI/TypeTools.hpp
index e3c97b17..2048a014 100644
--- a/include/CLI/TypeTools.hpp
+++ b/include/CLI/TypeTools.hpp
@@ -655,7 +655,8 @@ struct classify_object<
     typename std::enable_if<is_tuple_like<T>::value &&
                             ((type_count<T>::value >= 2 && !is_wrapper<T>::value) ||
                              (uncommon_type<T>::value && !is_direct_constructible<T, double>::value &&
-                              !is_direct_constructible<T, int>::value))>::type> {
+                              !is_direct_constructible<T, int>::value) ||
+                             (uncommon_type<T>::value && type_count<T>::value >= 2))>::type> {
     static constexpr object_category value{object_category::tuple_value};
     // the condition on this class requires it be like a tuple, but on some compilers (like Xcode) tuples can be
     // constructed from just the first element so tuples of <string, int,int> can be constructed from a string, which
diff --git a/tests/HelpersTest.cpp b/tests/HelpersTest.cpp
index 798a6d13..44e15520 100644
--- a/tests/HelpersTest.cpp
+++ b/tests/HelpersTest.cpp
@@ -1228,6 +1228,8 @@ TEST_CASE("Types: LexicalConversionTuple3", "[helpers]") {
 TEST_CASE("Types: LexicalConversionTuple4", "[helpers]") {
     CLI::results_t input = {"9.12", "19", "18.6", "5.87"};
     std::array<double, 4> x;
+    auto tsize = CLI::detail::type_count<decltype(x)>::value;
+    CHECK(tsize == 4);
     bool res = CLI::detail::lexical_conversion<decltype(x), decltype(x)>(input, x);
     CHECK(res);
     CHECK(19 == Approx(std::get<1>(x)));