diff --git a/examples/server/tests/features/steps/steps.py b/examples/server/tests/features/steps/steps.py
index f71e0d706..21b08ecd6 100644
--- a/examples/server/tests/features/steps/steps.py
+++ b/examples/server/tests/features/steps/steps.py
@@ -47,6 +47,8 @@ def step_server_config(context, server_fqdn, server_port):
     context.n_ga = None
     context.n_ga_w = None
     context.n_predict = None
+    context.n_keep = 0
+    context.n_truncate = 0
     context.n_prompts = 0
     context.n_server_predict = None
     context.slot_save_path = None
@@ -66,6 +68,7 @@ def step_server_config(context, server_fqdn, server_port):
     context.user_api_key = None
     context.response_format = None
 
+    context.stop_string = []
     context.tasks_result = []
     context.concurrent_tasks = []
     context.prompts = []
@@ -168,6 +171,7 @@ def step_start_server(context):
 
     addrs = socket.getaddrinfo(context.server_fqdn, context.server_port, type=socket.SOCK_STREAM)
     family, typ, proto, _, sockaddr = addrs[0]
+    print(sockaddr)
 
     while True:
         with closing(socket.socket(family, typ, proto)) as sock:
@@ -231,17 +235,33 @@ async def step_all_slots_status(context, expected_slot_status_string):
 @step('a completion request with {api_error} api error')
 @async_run_until_complete
 async def step_request_completion(context, api_error):
+   await make_completion_request(context, api_error)
+
+
+@step('an ongoing completion request')
+@async_run_until_complete
+async def step_request_ongoing_completion(context):
+   await make_completion_request(context, '', True)
+
+
+async def make_completion_request(context, api_error, ongoing=False):
     expect_api_error = api_error == 'raised'
-    completion = await request_completion(context.prompts.pop(),
+    prompt = context.prompts[-1] if ongoing else context.prompts.pop()
+    completion = await request_completion(prompt,
                                           context.base_url,
                                           debug=context.debug,
                                           n_predict=context.n_predict,
+                                          n_keep=context.n_keep,
+                                          n_truncate=context.n_truncate,
                                           cache_prompt=context.cache_prompt,
+                                          stop_string=context.stop_string,
                                           id_slot=context.id_slot,
                                           seed=await completions_seed(context),
                                           expect_api_error=expect_api_error,
                                           user_api_key=context.user_api_key)
     context.tasks_result.append(completion)
+    if ongoing and not expect_api_error:
+        context.prompts[-1] += completion['content']
     if context.debug:
         print(f"Completion response: {completion}")
     if expect_api_error:
@@ -306,6 +326,16 @@ def step_max_tokens(context, max_tokens):
     context.n_predict = max_tokens
 
 
+@step('{n_keep:d} tokens to keep')
+def step_keep_tokens(context, n_keep):
+    context.n_keep = n_keep
+
+
+@step('{n_truncate:d} tokens to truncate')
+def step_truncate_tokens(context, n_truncate):
+    context.n_truncate = n_truncate
+
+
 @step('a response format {response_format}')
 def step_response_format(context, response_format):
     context.response_format = json.loads(response_format)
@@ -355,6 +385,10 @@ def step_n_ubatch(context, n_ubatch):
 def step_seed(context, seed):
     context.seed = seed
 
+@step('a list of stop strings {stop_list}')
+def step_stop_string(context, stop_list):
+    context.stop_string = json.loads(stop_list)
+
 
 @step('a prefix prompt')
 def step_prompt_prefix(context):
@@ -457,6 +491,11 @@ def step_a_prompt_prompt(context, prompt):
     context.n_prompts = len(context.prompts)
 
 
+@step('an ongoing prompt')
+def step_a_ongoing_prompt(context):
+    context.prompts[-1] += context_text(context)
+
+
 @step('concurrent completion requests')
 @async_run_until_complete()
 async def step_concurrent_completion_requests(context):
@@ -786,7 +825,10 @@ async def request_completion(prompt,
                              prompt_prefix=None,
                              prompt_suffix=None,
                              n_predict=None,
+                             n_keep=0,
+                             n_truncate=0,
                              cache_prompt=False,
+                             stop_string=None,
                              id_slot=None,
                              seed=None,
                              expect_api_error=None,
@@ -809,7 +851,10 @@ async def request_completion(prompt,
                                     "prompt": prompt,
                                     "input_suffix": prompt_suffix,
                                     "n_predict": n_predict if n_predict is not None else -1,
+                                    "n_keep": n_keep,
+                                    "n_truncate": n_truncate,
                                     "cache_prompt": cache_prompt,
+                                    "stop": stop_string if stop_string is not None else [],
                                     "id_slot": id_slot,
                                     "seed": seed if seed is not None else 42
                                 },
diff --git a/examples/server/tests/features/truncation.feature b/examples/server/tests/features/truncation.feature
new file mode 100644
index 000000000..74ca992f7
--- /dev/null
+++ b/examples/server/tests/features/truncation.feature
@@ -0,0 +1,44 @@
+# run with: ./tests.sh --no-skipped --tags truncation
+@trucation
+@slow
+Feature: Chat truncation
+
+  Background: Server startup
+    Given a server listening on localhost:8080
+    And   a model file mistral-7b-v0.2-iq3_s-imat.gguf from HF repo ggml-org/models
+    And   prompt caching is enabled
+    And   a list of stop strings ["\n"]
+    And   82 tokens to keep
+    And   256 KV cache size
+    And   32 server max tokens to predict
+    Then  the server is starting
+    Then  the server is healthy
+
+  Scenario: Correctly truncate the prompt when the prompt exceeds the context size
+    Given a prompt:
+    """
+    Continue the chat below.
+    Me: Hey there, how's it going?
+    You: I'm doing well, thanks for asking! How are you?
+    Me: I'm doing good, just trying to get some work done. How's your day?
+    You: My day has been pretty productive so far. I've been working on a new project.
+    Me: That's great to hear! What's the new project you're working on?
+    You: It's a web application that's designed to help people manage their personal finances. I'm really excited about it.
+    Me: That sounds really useful, I'd be interested to hear more about it. Do you have a timeframe for when you expect to have it ready to launch?
+    You: I'm aiming to have the initial version ready within the next few months. I want to ensure it's robust before launching it.
+    Me: That's really nice, are you happy with the progress so far?
+
+    """
+    And   an ongoing completion request
+    Then  -1 tokens are predicted matching You:
+    Given an ongoing prompt:
+    """
+
+    Me: I have one more question for you my friend. What's the most value thing you learned during your development journey?
+
+    """
+    And   52 tokens to truncate
+    And   a completion request with no api error
+    Then  -1 tokens are predicted matching You:
+    # 28 because '\n' stop string is not pushed to the context
+    And   28 prompt tokens are processed
\ No newline at end of file
diff --git a/examples/server/tests/tests.sh b/examples/server/tests/tests.sh
index 72a0fbad8..56cfb3429 100755
--- a/examples/server/tests/tests.sh
+++ b/examples/server/tests/tests.sh
@@ -5,7 +5,7 @@ set -eu
 if [ $# -lt 1 ]
 then
     # Start @llama.cpp scenario
-    behave --summary --stop --no-capture --exclude 'issues|wrong_usages|passkey' --tags llama.cpp
+    behave --summary --stop --no-capture --exclude 'issues|wrong_usages|passkey|truncation' --tags llama.cpp
 else
     behave "$@"
 fi