diff --git a/common/chat.cpp b/common/chat.cpp
index 0a426f4478..be44c8abb0 100644
--- a/common/chat.cpp
+++ b/common/chat.cpp
@@ -319,7 +319,7 @@ json common_chat_msgs_to_json_oaicompat(const std::vector<common_chat_msg> & msg
                 }
             }
         } else {
-            jmsg["content"] = json(); // null
+            jmsg["content"] = "";
         }
         if (!msg.reasoning_content.empty()) {
             jmsg["reasoning_content"] = msg.reasoning_content;
diff --git a/models/templates/llama-cpp-deepseek-r1.jinja b/models/templates/llama-cpp-deepseek-r1.jinja
index fcb1732eb8..0d18870870 100644
--- a/models/templates/llama-cpp-deepseek-r1.jinja
+++ b/models/templates/llama-cpp-deepseek-r1.jinja
@@ -38,7 +38,7 @@ Example function tool call syntax:
     {%- if message['role'] == 'user' -%}
         {{- '<｜User｜>' + message['content'] + '<｜end▁of▁sentence｜>' -}}
     {%- endif -%}
-    {%- if message['role'] == 'assistant' and message['content'] is none -%}
+    {%- if message['role'] == 'assistant' and not message['content'] -%}
         {{- '<｜Assistant｜><｜tool▁calls▁begin｜>' -}}
         {%- set ns.is_first = true -%}
         {%- for tc in message['tool_calls'] -%}
@@ -53,7 +53,7 @@ Example function tool call syntax:
         {%- endfor -%}
         {{- '<｜tool▁calls▁end｜><｜end▁of▁sentence｜>' -}}
     {%- endif -%}
-    {%- if message['role'] == 'assistant' and message['content'] is  not none -%}
+    {%- if message['role'] == 'assistant' and message['content'] -%}
         {{- flush_tool_outputs() -}}
         {%- set content = message['content'] -%}
         {%- if '</think>' in content -%}
@@ -73,4 +73,4 @@ Example function tool call syntax:
 {{- flush_tool_outputs() -}}
 {%- if add_generation_prompt and not ns.is_tool_outputs -%}
     {{- '<｜Assistant｜><think>\n' -}}
-{%- endif -%}
\ No newline at end of file
+{%- endif -%}
diff --git a/tests/test-chat.cpp b/tests/test-chat.cpp
index 02af5251cc..a78627604e 100644
--- a/tests/test-chat.cpp
+++ b/tests/test-chat.cpp
@@ -650,7 +650,7 @@ static void test_msgs_oaicompat_json_conversion() {
             "[\n"
             "  {\n"
             "    \"role\": \"assistant\",\n"
-            "    \"content\": null,\n"
+            "    \"content\": \"\",\n"
             "    \"tool_calls\": [\n"
             "      {\n"
             "        \"type\": \"function\",\n"
@@ -906,7 +906,8 @@ static void test_template_output_parsers() {
                       "      },\n"
                       "      \"id\": \"123456789\"\n"
                       "    }\n"
-                      "  ]\n"
+                      "  ],\n"
+                      "  \"content\": \"\"\n"
                       "}");
     }
     {
@@ -1713,7 +1714,8 @@ static void test_template_output_parsers() {
                       "      },\n"
                       "      \"id\": \"123456789\"\n"
                       "    }\n"
-                      "  ]\n"
+                      "  ],\n"
+                      "  \"content\": \"\"\n"
                       "}",
                       /* expect_grammar_triggered= */ false
         );