diff --git a/common/chat.cpp b/common/chat.cpp
index eeb38ad06a0..e716ef9ad07 100644
--- a/common/chat.cpp
+++ b/common/chat.cpp
@@ -2877,7 +2877,19 @@ static common_chat_params common_chat_templates_apply_jinja(
         : *tmpls->template_default;
     const auto & src = tmpl.source();
     const auto & caps = tmpl.original_caps();
-    params.messages = common_chat_msgs_to_json_oaicompat(inputs.messages, /* concat_text= */ !tmpl.original_caps().requires_typed_content);
+    params.messages = common_chat_msgs_to_json_oaicompat(inputs.messages, /* concat_text= */ !caps.requires_typed_content);
+
+    // If template requires typed content, ensure all string contents are converted into json arrays
+    if (caps.requires_typed_content) {
+        for (auto & msg : params.messages) {
+            if (msg.contains("content") && msg.at("content").is_string()) {
+                const auto text = msg.at("content").get<std::string>();
+                json content_arr = json::array();
+                content_arr.push_back(json::object({ {"type", "text"}, {"text", text} }));
+                msg["content"] = std::move(content_arr);
+            }
+        }
+    }
     params.add_generation_prompt = inputs.add_generation_prompt;
     params.tool_choice = inputs.tool_choice;
     params.reasoning_format = inputs.reasoning_format;
diff --git a/common/jinja/caps.cpp b/common/jinja/caps.cpp
index f27490f1fb7..8623b7120c0 100644
--- a/common/jinja/caps.cpp
+++ b/common/jinja/caps.cpp
@@ -105,13 +105,19 @@ caps caps_get(jinja::program & prog) {
             // tools
             return json{nullptr};
         },
-        [&](bool, value & messages, value &) {
+        [&](bool success, value & messages, value &) {
             auto & content = messages->at(0)->at("content");
             caps_print_stats(content, "messages[0].content");
             if (has_op(content, "selectattr") || has_op(content, "array_access")) {
                 // accessed as an array
                 result.requires_typed_content = true;
             }
+
+            // If the template uses content and fails with a string, it likely expects an array
+            if (!success && content->stats.used) {
+                JJ_DEBUG("%s", "Template failed with string content, likely expects typed content array");
+                result.requires_typed_content = true;
+            }
         }
     );