diff --git a/libs/internal/include/launchdarkly/serialization/json_flag.hpp b/libs/internal/include/launchdarkly/serialization/json_flag.hpp
index ec5a5604c..49b4f8cf0 100644
--- a/libs/internal/include/launchdarkly/serialization/json_flag.hpp
+++ b/libs/internal/include/launchdarkly/serialization/json_flag.hpp
@@ -7,6 +7,9 @@
 
 namespace launchdarkly {
 
+struct VariationOrRolloutContext {};
+
+
 tl::expected<std::optional<data_model::Flag::Rollout>, JsonError> tag_invoke(
     boost::json::value_to_tag<
         tl::expected<std::optional<data_model::Flag::Rollout>,
@@ -69,6 +72,11 @@ void tag_invoke(boost::json::value_from_tag const& unused,
                 boost::json::value& json_value,
                 data_model::Flag::Rollout const& rollout);
 
+void tag_invoke(
+    boost::json::value_from_tag const& unused,
+    boost::json::value& json_value,
+    data_model::Flag::VariationOrRollout const& variation_or_rollout, const VariationOrRolloutContext&);
+
 void tag_invoke(
     boost::json::value_from_tag const& unused,
     boost::json::value& json_value,
diff --git a/libs/internal/include/launchdarkly/serialization/value_mapping.hpp b/libs/internal/include/launchdarkly/serialization/value_mapping.hpp
index 69ad964fe..2758de0f8 100644
--- a/libs/internal/include/launchdarkly/serialization/value_mapping.hpp
+++ b/libs/internal/include/launchdarkly/serialization/value_mapping.hpp
@@ -5,6 +5,7 @@
 #include <boost/core/ignore_unused.hpp>
 #include <boost/json.hpp>
 #include <tl/expected.hpp>
+#include <boost/version.hpp>
 
 #include <optional>
 #include <type_traits>
@@ -189,6 +190,25 @@ void WriteMinimal(boost::json::object& obj,
     }
 }
 
+template <typename T, typename C>
+void WriteMinimal(boost::json::object& obj,
+                  std::string const& key,
+                  T const& val,
+                  std::function<bool()> const& predicate, const C &c) {
+    if (predicate()) {
+        // In Boost 1.83 the ability to have a conversion context was added.
+        // It also introduces the potential for the wrong conversion to be used,
+        // so for boost 1.83 and greater we use a conversion context to ensure
+        // the correct serialization is used.
+#if BOOST_VERSION >= 108300
+        obj.emplace(key, boost::json::value_from(val, c));
+#else
+        boost::ignore_unused(c);
+        obj.emplace(key, boost::json::value_from(val));
+#endif
+    }
+}
+
 void WriteMinimal(boost::json::object& obj,
                   std::string const& key,  // No copy when not used.
                   bool val);
diff --git a/libs/internal/src/serialization/json_flag.cpp b/libs/internal/src/serialization/json_flag.cpp
index 404ee1def..2331af82b 100644
--- a/libs/internal/src/serialization/json_flag.cpp
+++ b/libs/internal/src/serialization/json_flag.cpp
@@ -255,7 +255,7 @@ void tag_invoke(boost::json::value_from_tag const& unused,
 void tag_invoke(
     boost::json::value_from_tag const& unused,
     boost::json::value& json_value,
-    data_model::Flag::VariationOrRollout const& variation_or_rollout) {
+    data_model::Flag::VariationOrRollout const& variation_or_rollout, const VariationOrRolloutContext&) {
     auto& obj = json_value.emplace_object();
     std::visit(
         [&obj](auto&& arg) {
@@ -273,6 +273,13 @@ void tag_invoke(
         variation_or_rollout);
 }
 
+void tag_invoke(
+    boost::json::value_from_tag const& unused,
+    boost::json::value& json_value,
+    data_model::Flag::VariationOrRollout const& variation_or_rollout) {
+    tag_invoke(unused, json_value, variation_or_rollout, VariationOrRolloutContext());
+}
+
 void tag_invoke(boost::json::value_from_tag const& unused,
                 boost::json::value& json_value,
                 data_model::Flag::Prerequisite const& prerequisite) {
@@ -364,7 +371,7 @@ void tag_invoke(boost::json::value_from_tag const& unused,
                 }
             },
             flag.fallthrough);
-    });
+    }, VariationOrRolloutContext());
     WriteMinimal(obj, "clientSideAvailability", flag.clientSideAvailability,
                  [&]() {
                      return flag.clientSideAvailability.usingEnvironmentId ||
diff --git a/libs/internal/tests/data_model_serialization_test.cpp b/libs/internal/tests/data_model_serialization_test.cpp
index 709af98f6..563d2e5f9 100644
--- a/libs/internal/tests/data_model_serialization_test.cpp
+++ b/libs/internal/tests/data_model_serialization_test.cpp
@@ -423,8 +423,13 @@ TEST(RolloutTests, SerializeAllFields) {
 TEST(VariationOrRolloutTests, SerializeVariation) {
     data_model::Flag::VariationOrRollout variation = 5;
 
-    auto json = boost::json::value_from(variation);
 
+    //Explanation in value_mapping.hpp.
+#if BOOST_VERSION >= 108300
+    auto json = boost::json::value_from(variation, VariationOrRolloutContext());
+#else
+    auto json = boost::json::value_from(variation);
+#endif
     auto expected = boost::json::parse(R"({"variation":5})");
     EXPECT_EQ(expected, json);
 }
@@ -438,8 +443,15 @@ TEST(VariationOrRolloutTests, SerializeRollout) {
     rollout.seed = 42;
     rollout.variations = {
         data_model::Flag::Rollout::WeightedVariation::Untracked(1, 2), {3, 4}};
-    data_model::Flag::VariationOrRollout var_or_roll = rollout;
+    data_model::Flag::VariationOrRollout var_or_roll;
+    var_or_roll.emplace<Rollout>(rollout);
+    //Explanation in value_mapping.hpp.
+#if BOOST_VERSION >= 108300
+    auto json = boost::json::value_from(var_or_roll, VariationOrRolloutContext());
+#else
     auto json = boost::json::value_from(var_or_roll);
+#endif
+
 
     auto expected = boost::json::parse(R"({
     "rollout":{