diff --git a/common/chat.cpp b/common/chat.cpp
index f4ac9fd2d..8d4331cb1 100644
--- a/common/chat.cpp
+++ b/common/chat.cpp
@@ -606,8 +606,8 @@ static common_chat_params common_chat_params_init_deepseek_r1(const common_chat_
         // Fix up tool call delta example added by Minja
         prompt = std::regex_replace(
             prompt,
-            std::regex("<｜tool▁call▁end｜>[\\s\\r\\n]*<｜User｜>"),
-            "<｜tool▁call▁end｜><｜tool▁calls▁end｜><｜User｜>");
+            std::regex("(<｜tool▁call▁end｜>)[\\s\\r\\n]*(<｜tool▁outputs▁begin｜>|<｜User｜>)"),
+            "$1<｜tool▁calls▁end｜><｜end▁of▁sentence｜>$2");
     }
     data.prompt = prompt;
     data.format = COMMON_CHAT_FORMAT_DEEPSEEK_R1;
@@ -617,7 +617,7 @@ static common_chat_msg common_chat_parse_deepseek_r1(const std::string & input)
     static std::regex trigger_regex("(<｜tool▁calls▁begin｜>|<｜tool_calls_begin｜>|<｜tool calls begin｜>|<｜tool\\\\_calls\\\\_begin｜>)?");
     static std::regex function_regex("<｜tool▁call▁begin｜>function<｜tool▁sep｜>([^\n]+)\n```json\n");
     static std::regex close_regex("```[\\s\\r\\n]*<｜tool▁call▁end｜>");
-    static std::regex think_regex(R"(<think>([\s\S\n]*)(</think>)?([\s\S\r\n]*))");
+    static std::regex think_regex("<think>([\\s\\S\\n]*?)</think>([\\s\\S\\r\\n]*)");
     auto msg = parse_json_tool_calls(input, trigger_regex, function_regex, close_regex);
     std::smatch match;
     if (std::regex_match(msg.content, match, think_regex)) {
diff --git a/tests/test-chat.cpp b/tests/test-chat.cpp
index a130d6c6c..b0eee0a0a 100644
--- a/tests/test-chat.cpp
+++ b/tests/test-chat.cpp
@@ -108,6 +108,8 @@ static std::string dump(const json & j) {
 static void assert_msg_equals(const common_chat_msg & expected, const common_chat_msg & actual) {
     assert_equals(expected.role, actual.role);
     assert_equals(expected.content, actual.content);
+    assert_equals(expected.thoughts, actual.thoughts);
+    assert_equals(expected.tool_plan, actual.tool_plan);
     assert_equals(expected.tool_calls.size(), actual.tool_calls.size());
     for (size_t i = 0; i < expected.tool_calls.size(); i++) {
         const auto & expected_tool_call = expected.tool_calls[i];
@@ -226,7 +228,8 @@ static delta_data init_delta(const common_chat_template & tmpl, const std::vecto
 */
 static void test_template(const common_chat_template & tmpl, const std::vector<std::string> & end_tokens,
                           const json & test_message, const json & tools = {}, const std::string & expected_delta = "",
-                          bool expect_grammar_triggered = true) {
+                          bool expect_grammar_triggered = true,
+                          bool test_grammar_if_triggered = true) {
     common_chat_msg expected_msg = msg_from_json(test_message);
 
     auto user_message = json{
@@ -277,7 +280,7 @@ static void test_template(const common_chat_template & tmpl, const std::vector<s
                 assert_equals(expect_grammar_triggered, grammar_triggered);
             }
 
-            if (grammar_triggered && !match_string(constrained, grammar.get())) {
+            if (grammar_triggered && test_grammar_if_triggered && !match_string(constrained, grammar.get())) {
                 throw std::runtime_error("Failed to match delta against grammar:\n\n" + data.delta +
                                             "\n\nGrammar: " + data.params.grammar);
             }
@@ -290,6 +293,11 @@ static void test_template_output_parsers() {
         { "role",    "assistant"     },
         { "content", "Hello, world!" },
     };
+    json text_thoughts_message {
+        { "role",    "assistant"     },
+        { "content", "Hello, world!" },
+        { "thoughts", "I'm thinking" },
+    };
     json tool_calls = json::array({{
         { "type", "function" },
         { "function", { { "name", "special_function" }, { "arguments", "{\"arg1\": 1}" } } },
@@ -389,6 +397,26 @@ static void test_template_output_parsers() {
     inputs_tools_builtin.tools              = json::array();
     inputs_tools_builtin.tools.push_back(python_tool);
 
+    {
+        // Original DeepSeek R1 template. Leaves <｜tool▁calls▁begin｜> and others unclosed. Our logic fixes the prompt.
+        const common_chat_template tmpl(read_file("models/templates/deepseek-ai-DeepSeek-R1-Distill-Llama-8B.jinja"),
+                                        "<s>", "</s>");
+        std::vector<std::string>   end_tokens{ "<｜end▁of▁sentence｜>" };
+
+        assert_equals(COMMON_CHAT_FORMAT_DEEPSEEK_R1, common_chat_params_init(tmpl, inputs_tools).format);
+
+        test_template(tmpl, end_tokens, text_message, tools, "Hello, world!", /* expect_grammar_triggered= */ false);
+        test_template(tmpl, end_tokens, text_thoughts_message, tools, "Hello, world!", /* expect_grammar_triggered= */ false);
+        assert_msg_equals(msg_from_json(text_thoughts_message), common_chat_parse("<think>I'm thinking</think>Hello, world!", COMMON_CHAT_FORMAT_DEEPSEEK_R1));
+        test_template(tmpl, end_tokens, tool_call_message, tools,
+                      "<｜tool▁calls▁begin｜><｜tool▁call▁begin｜>function<｜tool▁sep｜>special_function\n"
+                      "```json\n"
+                      "{\"arg1\": 1}\n"
+                      // Look what's not here: <｜tool▁calls▁end｜> (also missing the <｜end▁of▁sentence｜>, but that is removed lazily by the test's delta logic)
+                      "```<｜tool▁call▁end｜>",
+                      /* expect_grammar_triggered= */ true,
+                      /* test_grammar_if_triggered= */ false); 
+    }
     {
         // Not supported yet
         const common_chat_template tmpl(read_file("models/templates/CohereForAI-c4ai-command-r-plus-tool_use.jinja"), "<s>", "</s>");
@@ -558,20 +586,6 @@ static void test_template_output_parsers() {
         test_template(tmpl, end_tokens, tool_call_message, tools,
                       " functools[{\"name\": \"special_function\", \"arguments\": {\"arg1\": 1}}]");
     }
-    {
-        const common_chat_template tmpl(read_file("models/templates/deepseek-ai-DeepSeek-R1-Distill-Llama-8B.jinja"),
-                                        "<s>", "</s>");
-        std::vector<std::string>   end_tokens{ "<｜end▁of▁sentence｜>" };
-
-        assert_equals(COMMON_CHAT_FORMAT_DEEPSEEK_R1, common_chat_params_init(tmpl, inputs_tools).format);
-
-        test_template(tmpl, end_tokens, text_message, tools, "Hello, world!", /* expect_grammar_triggered= */ false);
-        test_template(tmpl, end_tokens, tool_call_message, tools,
-                      "<｜tool▁calls▁begin｜><｜tool▁call▁begin｜>function<｜tool▁sep｜>special_function\n"
-                      "```json\n"
-                      "{\"arg1\": 1}\n"
-                      "```<｜tool▁call▁end｜>");
-    }
 }
 
 int main(int argc, char ** argv) {