diff --git a/tools/server/server.cpp b/tools/server/server.cpp
index 41ecb279feb89..5c477c8897b47 100644
--- a/tools/server/server.cpp
+++ b/tools/server/server.cpp
@@ -3727,7 +3727,7 @@ struct server_context {
                             }
                         } else {
                             if (slot.n_prompt_tokens() >= slot.n_ctx) {
-                                send_error(slot, "the request exceeds the available context size. try increasing the context size or enable context shift", ERROR_TYPE_EXCEED_CONTEXT_SIZE);
+                                send_error(slot, "the request exceeds the available context size, try increasing it", ERROR_TYPE_EXCEED_CONTEXT_SIZE);
                                 slot.release();
                                 continue;
                             }
@@ -4955,9 +4955,17 @@ int main(int argc, char ** argv) {
                 // Everything else, including multimodal completions.
                 inputs = tokenize_input_prompts(ctx_server.vocab, ctx_server.mctx, prompt, true, true);
             }
-
+            const size_t n_ctx_slot = ctx_server.n_ctx / ctx_server.params_base.n_parallel;
             tasks.reserve(inputs.size());
             for (size_t i = 0; i < inputs.size(); i++) {
+                auto n_prompt_tokens = inputs[i].size();
+                if (n_prompt_tokens >= n_ctx_slot) {
+                    json error_data = format_error_response("the request exceeds the available context size, try increasing it", ERROR_TYPE_EXCEED_CONTEXT_SIZE);
+                    error_data["n_prompt_tokens"] = n_prompt_tokens;
+                    error_data["n_ctx"] = n_ctx_slot;
+                    res_error(res, error_data);
+                    return;
+                }
                 server_task task = server_task(type);
 
                 task.id    = ctx_server.queue_tasks.get_new_id();
diff --git a/tools/server/tests/unit/test_chat_completion.py b/tools/server/tests/unit/test_chat_completion.py
index 6e5a3488e789b..d56d3d5f178b8 100644
--- a/tools/server/tests/unit/test_chat_completion.py
+++ b/tools/server/tests/unit/test_chat_completion.py
@@ -408,6 +408,28 @@ def test_context_size_exceeded():
     assert res.body["error"]["n_ctx"] == server.n_ctx // server.n_slots
 
 
+def test_context_size_exceeded_stream():
+    global server
+    server.start()
+    try:
+        for _ in server.make_stream_request("POST", "/chat/completions", data={
+            "messages": [
+                {"role": "system", "content": "Book"},
+                {"role": "user", "content": "What is the best book"},
+            ] * 100, # make the prompt too long
+            "stream": True}):
+                pass
+        assert False, "Should have failed"
+    except ServerError as e:
+        assert e.code == 400
+        assert "error" in e.body
+        assert e.body["error"]["type"] == "exceed_context_size_error"
+        assert e.body["error"]["n_prompt_tokens"] > 0
+        assert server.n_ctx is not None
+        assert server.n_slots is not None
+        assert e.body["error"]["n_ctx"] == server.n_ctx // server.n_slots
+
+
 @pytest.mark.parametrize(
     "n_batch,batch_count,reuse_cache",
     [
diff --git a/tools/server/tests/utils.py b/tools/server/tests/utils.py
index abd6fff10d0d1..4ba3d43c33044 100644
--- a/tools/server/tests/utils.py
+++ b/tools/server/tests/utils.py
@@ -35,6 +35,12 @@ class ServerResponse:
     body: dict | Any
 
 
+class ServerError(Exception):
+    def __init__(self, code, body):
+        self.code = code
+        self.body = body
+
+
 class ServerProcess:
     # default options
     debug: bool = False
@@ -297,6 +303,8 @@ def make_stream_request(
             response = requests.post(url, headers=headers, json=data, stream=True)
         else:
             raise ValueError(f"Unimplemented method: {method}")
+        if response.status_code != 200:
+            raise ServerError(response.status_code, response.json())
         for line_bytes in response.iter_lines():
             line = line_bytes.decode("utf-8")
             if '[DONE]' in line: