diff --git a/packages/generator/ni_measurement_plugin_sdk_generator/client/_support.py b/packages/generator/ni_measurement_plugin_sdk_generator/client/_support.py
index b9d99ff2e..79b327d2e 100644
--- a/packages/generator/ni_measurement_plugin_sdk_generator/client/_support.py
+++ b/packages/generator/ni_measurement_plugin_sdk_generator/client/_support.py
@@ -137,6 +137,11 @@ def get_configuration_and_output_metadata_by_index(
             annotations_dict["ni/enum.values"] = _validate_and_transform_enum_annotations(
                 configuration.annotations["ni/enum.values"]
             )
+
+        # In Python 3.13 and earlier, the ConfigurationParameter message sorted the annotation
+        # keys, but in Python 3.14, it started preserving order. Sort to keep tests passing.
+        annotations_dict = dict(sorted(annotations_dict.items()))
+
         configuration_parameter_list.append(
             ParameterMetadata.initialize(
                 display_name=configuration.name,
@@ -171,6 +176,11 @@ def get_configuration_and_output_metadata_by_index(
             annotations_dict["ni/enum.values"] = _validate_and_transform_enum_annotations(
                 output.annotations["ni/enum.values"]
             )
+
+        # In Python 3.13 and earlier, the ConfigurationParameter message sorted the annotation
+        # keys, but in Python 3.14, it started preserving order. Sort to keep tests passing.
+        annotations_dict = dict(sorted(annotations_dict.items()))
+
         output_parameter_list.append(
             ParameterMetadata.initialize(
                 display_name=output.name,
diff --git a/packages/generator/tox.ini b/packages/generator/tox.ini
index 6d445c3b0..ad01069cc 100644
--- a/packages/generator/tox.ini
+++ b/packages/generator/tox.ini
@@ -5,7 +5,7 @@
 
 [tox]
 isolated_build = true
-envlist = clean, py{39,310,311,312,313}, py39-{pb4,pb5,pb6}
+envlist = clean, py{39,310,311,312,313,314}, py39-{pb4,pb5,pb6}
 
 [testenv]
 skip_install = true
diff --git a/packages/service/tox.ini b/packages/service/tox.ini
index d25ec655e..60bdab4d4 100644
--- a/packages/service/tox.ini
+++ b/packages/service/tox.ini
@@ -5,7 +5,7 @@
 
 [tox]
 isolated_build = true
-envlist = clean, py{39,310,311,312,313}-all-extras, py39-{pb4,pb5,pb6}
+envlist = clean, py{39,310,311,312,313,314}-all-extras, py39-{pb4,pb5,pb6}
 
 [testenv]
 skip_install = true