diff --git a/changelog/v1.17.0-rc2/passthrough-json-to-proto.yaml b/changelog/v1.17.0-rc2/passthrough-json-to-proto.yaml
new file mode 100644
index 00000000000..8d7460cdadd
--- /dev/null
+++ b/changelog/v1.17.0-rc2/passthrough-json-to-proto.yaml
@@ -0,0 +1,7 @@
+changelog:
+  - type: FIX
+    issueLink: https://github.com/solo-io/solo-projects/issues/5890
+    resolvesIssue: false
+    description: >-
+      Properly pass through the `json_to_proto` value from the gloo API to the envoy API for 
+      dynamic metadata transformations.
diff --git a/projects/gloo/pkg/plugins/transformation/plugin.go b/projects/gloo/pkg/plugins/transformation/plugin.go
index b1d981380c7..daf62264673 100644
--- a/projects/gloo/pkg/plugins/transformation/plugin.go
+++ b/projects/gloo/pkg/plugins/transformation/plugin.go
@@ -492,6 +492,7 @@ func translateTransformationTemplate(in *transformation.Transformation_Transform
 			outTemplate.GetDynamicMetadataValues()[i] = &envoytransformation.TransformationTemplate_DynamicMetadataValue{
 				MetadataNamespace: values[i].GetMetadataNamespace(),
 				Key:               values[i].GetKey(),
+				JsonToProto:       values[i].GetJsonToProto(),
 				Value: &envoytransformation.InjaTemplate{
 					Text: values[i].GetValue().GetText(),
 				},
diff --git a/projects/gloo/pkg/plugins/transformation/plugin_test.go b/projects/gloo/pkg/plugins/transformation/plugin_test.go
index 29355bd65ed..ababf0c271e 100644
--- a/projects/gloo/pkg/plugins/transformation/plugin_test.go
+++ b/projects/gloo/pkg/plugins/transformation/plugin_test.go
@@ -855,6 +855,14 @@ var _ = Describe("Plugin", func() {
 				TransformationType: &transformation.Transformation_TransformationTemplate{
 					TransformationTemplate: &transformation.TransformationTemplate{
 						AdvancedTemplates: true,
+						DynamicMetadataValues: []*transformation.TransformationTemplate_DynamicMetadataValue{
+							{
+								MetadataNamespace: "namespace",
+								Key:               "key",
+								Value:             &transformation.InjaTemplate{Text: "hello"},
+								JsonToProto:       true,
+							},
+						},
 						BodyTransformation: &transformation.TransformationTemplate_Body{
 							Body: &transformation.InjaTemplate{Text: "13"},
 						},
@@ -865,6 +873,14 @@ var _ = Describe("Plugin", func() {
 				TransformationType: &envoytransformation.Transformation_TransformationTemplate{
 					TransformationTemplate: &envoytransformation.TransformationTemplate{
 						AdvancedTemplates: true,
+						DynamicMetadataValues: []*envoytransformation.TransformationTemplate_DynamicMetadataValue{
+							{
+								MetadataNamespace: "namespace",
+								Key:               "key",
+								Value:             &envoytransformation.InjaTemplate{Text: "hello"},
+								JsonToProto:       true,
+							},
+						},
 						BodyTransformation: &envoytransformation.TransformationTemplate_Body{
 							Body: &envoytransformation.InjaTemplate{Text: "13"},
 						},
@@ -1160,7 +1176,7 @@ var _ = Describe("Plugin", func() {
 			value = filters[1].Filter.GetTypedConfig()
 			Expect(value.GetValue()).To(BeEmpty())
 		})
-		It("should upstream_http_filters when the postRouting transformation exists", func() {
+		It("should add upstream_http_filters when the postRouting transformation exists", func() {
 			out := &envoy_config_route_v3.Route{}
 			err := p.(plugins.RoutePlugin).ProcessRoute(plugins.RouteParams{VirtualHostParams: plugins.VirtualHostParams{
 				Params: plugins.Params{