diff --git a/pyproject.toml b/pyproject.toml
index 505f3556..ad4149de 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -90,6 +90,9 @@ dev-dependencies = [
     "hatch>=1.14.1",
     "ruff>=0.12.1",
     "pyright>=1.1.403",
+    "pytest>=8.4.1",
+    "nbval>=0.11.0",
+    "pytest-xdist>=3.8.0",
 ]
 
 [tool.uv.sources]
diff --git a/scripts/run_checks.sh b/scripts/run_checks.sh
index ce2aebf0..79ff3671 100755
--- a/scripts/run_checks.sh
+++ b/scripts/run_checks.sh
@@ -27,6 +27,7 @@ fi
 # Track if any checks fail
 CHECKS_PASSED=true
 TYPECHECK_FAILED=false
+TESTS_FAILED=false
 
 # Run format check
 echo "📝 Checking code formatting..."
@@ -75,7 +76,7 @@ echo
 # Run type checking (Pyright)
 echo "🧠 Running type checking..."
 TMP_PYRIGHT_JSON=$(mktemp)
-echo "  Running: uv run pyright --outputjson src"
+echo "  Running: uv run pyright --outputjson src tests"
 # Capture JSON output quietly regardless of success/failure
 if uv run pyright --outputjson src > "$TMP_PYRIGHT_JSON" 2>/dev/null; then
     : # success, continue
@@ -125,6 +126,66 @@ fi
 rm -f "$TMP_PYRIGHT_JSON"
 echo
 
+# Run tests
+echo "🧪 Running unit tests..."
+echo "  Running: uv run pytest --nbval tests/unit"
+
+# Capture pytest output quietly to parse the summary
+PYTEST_OUTPUT=$(mktemp)
+if uv run pytest --nbval --tb=short tests/unit > "$PYTEST_OUTPUT" 2>&1; then
+    TEST_EXIT_CODE=0
+else
+    TEST_EXIT_CODE=$?
+fi
+
+# Extract the test summary line (e.g., "===== 5 passed, 2 failed, 1 skipped in 3.45s =====")
+# This regex captures various pytest summary formats
+TEST_SUMMARY=$(grep -E "^=+ .*(passed|failed|error|skipped|xfailed|xpassed|warning).*=+$" "$PYTEST_OUTPUT" | tail -1)
+
+if [[ -n "$TEST_SUMMARY" ]]; then
+    # Parse the summary to extract counts
+    PASSED=$(echo "$TEST_SUMMARY" | grep -oE "[0-9]+ passed" | grep -oE "[0-9]+" || echo "0")
+    FAILED=$(echo "$TEST_SUMMARY" | grep -oE "[0-9]+ failed" | grep -oE "[0-9]+" || echo "0")
+    ERRORS=$(echo "$TEST_SUMMARY" | grep -oE "[0-9]+ error" | grep -oE "[0-9]+" || echo "0")
+    SKIPPED=$(echo "$TEST_SUMMARY" | grep -oE "[0-9]+ skipped" | grep -oE "[0-9]+" || echo "0")
+    WARNINGS=$(echo "$TEST_SUMMARY" | grep -oE "[0-9]+ warning" | grep -oE "[0-9]+" || echo "0")
+    XFAILED=$(echo "$TEST_SUMMARY" | grep -oE "[0-9]+ xfailed" | grep -oE "[0-9]+" || echo "0")
+    XPASSED=$(echo "$TEST_SUMMARY" | grep -oE "[0-9]+ xpassed" | grep -oE "[0-9]+" || echo "0")
+    
+    # Build detailed summary
+    DETAILS=""
+    [[ "$PASSED" != "0" ]] && DETAILS="${DETAILS}Passed: $PASSED"
+    [[ "$FAILED" != "0" ]] && DETAILS="${DETAILS:+$DETAILS, }Failed: $FAILED"
+    [[ "$ERRORS" != "0" ]] && DETAILS="${DETAILS:+$DETAILS, }Errors: $ERRORS"
+    [[ "$SKIPPED" != "0" ]] && DETAILS="${DETAILS:+$DETAILS, }Skipped: $SKIPPED"
+    [[ "$XFAILED" != "0" ]] && DETAILS="${DETAILS:+$DETAILS, }XFailed: $XFAILED"
+    [[ "$XPASSED" != "0" ]] && DETAILS="${DETAILS:+$DETAILS, }XPassed: $XPASSED"
+    [[ "$WARNINGS" != "0" ]] && DETAILS="${DETAILS:+$DETAILS, }Warnings: $WARNINGS"
+    
+    # Check if there were any failures or errors
+    if [[ "$FAILED" == "0" && "$ERRORS" == "0" && $TEST_EXIT_CODE -eq 0 ]]; then
+        echo -e "${GREEN}✅ All tests passed${NC}"
+        [[ -n "$DETAILS" ]] && echo "  $DETAILS"
+    else
+        echo -e "${RED}❌ Tests failed${NC}"
+        [[ -n "$DETAILS" ]] && echo "  $DETAILS"
+        CHECKS_PASSED=false
+        TESTS_FAILED=true
+    fi
+else
+    # Fallback if we can't parse the summary
+    if [[ $TEST_EXIT_CODE -eq 0 ]]; then
+        echo -e "${GREEN}✅ All unit tests passed${NC}"
+    else
+        echo -e "${RED}❌ Some unit tests failed${NC}"
+        CHECKS_PASSED=false
+        TESTS_FAILED=true
+    fi
+fi
+
+rm -f "$PYTEST_OUTPUT"
+echo
+
 # Check if uv.lock is in sync with pyproject.toml
 echo "🔒 Checking if uv.lock is up to date..."
 PRIMARY_EXTRAS=(--all-extras)
@@ -201,9 +262,15 @@ if $CHECKS_PASSED; then
 else
     echo -e "${RED}❌ Some checks failed${NC}"
     if [[ -z "$FIX_FLAG" ]]; then
+        # Show tips for each type of failure
         if $TYPECHECK_FAILED; then
             echo -e "💡 Tip: Type errors can't be auto-fixed by --fix. Re-run ${YELLOW}uv run pyright src${NC} to see full diagnostics."
-        else
+        fi
+        if $TESTS_FAILED; then
+            echo -e "💡 Tip: Test failures can't be auto-fixed by --fix. Re-run ${YELLOW}uv run pytest --nbval tests/unit${NC} to see full test output."
+        fi
+        # Show general fix tip if there are failures but not type/test specific ones
+        if ! $TYPECHECK_FAILED && ! $TESTS_FAILED; then
             echo -e "💡 Tip: Run ${YELLOW}./scripts/run_checks.sh --fix${NC} to automatically fix some issues"
         fi
     fi
diff --git a/src/art/local/backend.py b/src/art/local/backend.py
index 1129326e..957e088e 100644
--- a/src/art/local/backend.py
+++ b/src/art/local/backend.py
@@ -42,20 +42,20 @@
 from .. import dev
 from ..backend import Backend
 from ..model import Model, TrainableModel
+from ..preprocessing.pack import (
+    PackedTensors,
+    packed_tensors_from_tokenized_results,
+    packed_tensors_to_dir,
+    plot_packed_tensors,
+)
+from ..preprocessing.tokenize import tokenize_trajectory_groups
 from ..trajectories import Trajectory, TrajectoryGroup
 from ..types import Message, TrainConfig
 from ..utils import format_message, get_model_step
 from .checkpoints import (
     delete_checkpoints,
 )
-from .pack import (
-    PackedTensors,
-    packed_tensors_from_tokenized_results,
-    packed_tensors_to_dir,
-    plot_packed_tensors,
-)
 from .service import ModelService
-from .tokenize import tokenize_trajectory_groups
 
 
 class LocalBackend(Backend):
diff --git a/src/art/local/service.py b/src/art/local/service.py
index bcc7cb02..9aaf0e17 100644
--- a/src/art/local/service.py
+++ b/src/art/local/service.py
@@ -1,7 +1,7 @@
 from typing import AsyncIterator, Protocol, runtime_checkable
 
 from .. import dev, types
-from .pack import DiskPackedTensors
+from ..preprocessing.pack import DiskPackedTensors
 
 
 @runtime_checkable
diff --git a/src/art/preprocessing/__init__.py b/src/art/preprocessing/__init__.py
new file mode 100644
index 00000000..e69de29b
diff --git a/src/art/local/pack.py b/src/art/preprocessing/pack.py
similarity index 100%
rename from src/art/local/pack.py
rename to src/art/preprocessing/pack.py
diff --git a/src/art/local/tokenize.py b/src/art/preprocessing/tokenize.py
similarity index 75%
rename from src/art/local/tokenize.py
rename to src/art/preprocessing/tokenize.py
index 3bf355bb..e1500ba6 100644
--- a/src/art/local/tokenize.py
+++ b/src/art/preprocessing/tokenize.py
@@ -146,12 +146,18 @@ def tokenize_trajectory(
             tools=history.tools,  # type: ignore
         ),
     )
-    sentinal_token_id = max(
+    sentinal_start_token_id = max(
         set(range(cast(int, tokenizer.vocab_size))) - set(original_token_ids)
     )
-    sentinal_token = tokenizer.decode(sentinal_token_id)
-    result = cast(
-        dict,
+    sentinal_end_token_id = max(
+        set(range(cast(int, tokenizer.vocab_size)))
+        - set(original_token_ids)
+        - {sentinal_start_token_id}
+    )
+    sentinal_start_token = tokenizer.decode(sentinal_start_token_id)
+    sentinal_end_token = tokenizer.decode(sentinal_end_token_id)
+    token_ids = cast(
+        list[int],
         tokenizer.apply_chat_template(
             cast(
                 list[dict],
@@ -159,53 +165,54 @@ def tokenize_trajectory(
                     (
                         message_or_choice
                         if isinstance(message_or_choice, dict)
+                        and not message_or_choice["role"] == "assistant"
                         else {
                             "role": "assistant",
-                            "content": sentinal_token,
+                            "content": f"{sentinal_start_token}{message_or_choice.get('content', None) if isinstance(message_or_choice, dict) else message_or_choice.message.content or ''}{sentinal_end_token}",
                         }
                     )
                     for message_or_choice in messages_and_choices
                 ],
             ),
             tools=history.tools,  # type: ignore
-            return_dict=True,
-            return_assistant_token_mask=allow_training_without_logprobs,
         ),
     )
-    token_ids: list[int] = result["input_ids"]
-    assistant_mask: list[int] = (
-        result["attention_mask"]
-        if allow_training_without_logprobs
-        else [0] * len(token_ids)
-    )
+    assistant_mask: list[int] = [0] * len(token_ids)
     logprobs = [float("nan")] * len(token_ids)
     for message_or_choice in messages_and_choices:
-        if isinstance(message_or_choice, dict):
-            continue
-        choice = message_or_choice
-        assert choice.logprobs or allow_training_without_logprobs, (
-            "Chat completion choices must have logprobs"
-        )
-        if not choice.logprobs:
-            continue
-        token_logprobs = choice.logprobs.content or choice.logprobs.refusal or []
-        sentinal_index = token_ids.index(sentinal_token_id)
         if (
-            bytes(token_logprobs[0].bytes or []).decode("utf-8")
-            == "<think>"
-            == tokenizer.decode(token_ids[sentinal_index - 4])
+            isinstance(message_or_choice, dict)
+            and not message_or_choice["role"] == "assistant"
         ):
-            start = sentinal_index - 4
+            continue
+        start = token_ids.index(sentinal_start_token_id)
+        end = token_ids.index(sentinal_end_token_id) + 1
+        if isinstance(message_or_choice, dict):
+            token_ids[start:end] = token_ids[start + 1 : end - 1]
+            logprobs[start:end] = [float("nan")] * (end - start - 2)
+            assistant_mask[start:end] = [1] * (end - start - 2)
         else:
-            start = sentinal_index
-        end = sentinal_index + 1
-        token_ids[start:end] = (
-            int(token_logprob.token.split(":")[1]) for token_logprob in token_logprobs
-        )
-        logprobs[start:end] = (
-            token_logprob.logprob for token_logprob in token_logprobs
-        )
-        assistant_mask[start:end] = [1] * len(token_logprobs)
+            choice = message_or_choice
+            assert choice.logprobs or allow_training_without_logprobs, (
+                "Chat completion choices must have logprobs"
+            )
+            if not choice.logprobs:
+                continue
+            token_logprobs = choice.logprobs.content or choice.logprobs.refusal or []
+            if (
+                bytes(token_logprobs[0].bytes or []).decode("utf-8")
+                == "<think>"
+                == tokenizer.decode(token_ids[start - 4])
+            ):
+                start -= 4
+            token_ids[start:end] = (
+                int(token_logprob.token.split(":")[1])
+                for token_logprob in token_logprobs
+            )
+            logprobs[start:end] = (
+                token_logprob.logprob for token_logprob in token_logprobs
+            )
+            assistant_mask[start:end] = [1] * len(token_logprobs)
     return TokenizedResult(
         advantage=advantage,
         chat=chat,
diff --git a/src/art/torchtune/batch.py b/src/art/torchtune/batch.py
index 337a669d..b084b9fc 100644
--- a/src/art/torchtune/batch.py
+++ b/src/art/torchtune/batch.py
@@ -1,7 +1,7 @@
 from pydantic import BaseModel
 
 from .. import dev, types
-from ..local.pack import DiskPackedTensors
+from ..preprocessing.pack import DiskPackedTensors
 
 
 class Batch(BaseModel):
diff --git a/src/art/torchtune/recipe.py b/src/art/torchtune/recipe.py
index 48677cea..afaaec3d 100644
--- a/src/art/torchtune/recipe.py
+++ b/src/art/torchtune/recipe.py
@@ -47,7 +47,7 @@
 from tqdm import tqdm
 
 from .. import dev, types
-from ..local.pack import PackedTensors, packed_tensors_from_dir
+from ..preprocessing.pack import PackedTensors, packed_tensors_from_dir
 from .batch import Batch
 from .config import (
     CompileConfig,
diff --git a/src/art/torchtune/service.py b/src/art/torchtune/service.py
index 4abbd0d2..a22f954a 100644
--- a/src/art/torchtune/service.py
+++ b/src/art/torchtune/service.py
@@ -16,7 +16,7 @@
 from vllm.v1.engine.async_llm import AsyncLLM
 
 from .. import dev, types
-from ..local.pack import DiskPackedTensors
+from ..preprocessing.pack import DiskPackedTensors
 from ..vllm import get_llm, get_worker, openai_server_task, run_on_workers
 from .batch import Batch
 
diff --git a/src/art/unsloth/decoupled_service.py b/src/art/unsloth/decoupled_service.py
index 6fa42c28..428fbfb1 100644
--- a/src/art/unsloth/decoupled_service.py
+++ b/src/art/unsloth/decoupled_service.py
@@ -22,7 +22,11 @@
 
 from .. import dev, types
 from ..local.checkpoints import get_last_checkpoint_dir
-from ..local.pack import DiskPackedTensors, PackedTensors, packed_tensors_from_dir
+from ..preprocessing.pack import (
+    DiskPackedTensors,
+    PackedTensors,
+    packed_tensors_from_dir,
+)
 from ..utils.get_model_step import get_step_from_dir
 from ..utils.output_dirs import get_step_checkpoint_dir
 from ..vllm import get_llm, get_worker, openai_server_task, run_on_workers
diff --git a/src/art/unsloth/service.py b/src/art/unsloth/service.py
index efc04dcf..b47b8cfb 100644
--- a/src/art/unsloth/service.py
+++ b/src/art/unsloth/service.py
@@ -10,7 +10,11 @@
 
 from .. import dev, types
 from ..local.checkpoints import get_last_checkpoint_dir
-from ..local.pack import DiskPackedTensors, PackedTensors, packed_tensors_from_dir
+from ..preprocessing.pack import (
+    DiskPackedTensors,
+    PackedTensors,
+    packed_tensors_from_dir,
+)
 from .train import train
 
 if TYPE_CHECKING:
diff --git a/tests/unit/test_tokenize_trajectory_groups.ipynb b/tests/unit/test_tokenize_trajectory_groups.ipynb
new file mode 100644
index 00000000..ff715dba
--- /dev/null
+++ b/tests/unit/test_tokenize_trajectory_groups.ipynb
@@ -0,0 +1,111 @@
+{
+ "cells": [
+  {
+   "cell_type": "code",
+   "execution_count": 1,
+   "id": "93a238e4",
+   "metadata": {},
+   "outputs": [],
+   "source": [
+    "%load_ext autoreload\n",
+    "%autoreload 2"
+   ]
+  },
+  {
+   "cell_type": "code",
+   "execution_count": null,
+   "id": "84717d3b",
+   "metadata": {},
+   "outputs": [],
+   "source": [
+    "from IPython.display import clear_output\n",
+    "from openai.types.chat.chat_completion import Choice, ChoiceLogprobs\n",
+    "from openai.types.chat.chat_completion_message import ChatCompletionMessage\n",
+    "from openai.types.chat.chat_completion_token_logprob import ChatCompletionTokenLogprob\n",
+    "from transformers import AutoTokenizer\n",
+    "\n",
+    "import art\n",
+    "from art.preprocessing.tokenize import tokenize_trajectory_groups\n",
+    "\n",
+    "tokenizer = AutoTokenizer.from_pretrained(\"Qwen/Qwen2.5-7B-Instruct\")\n",
+    "clear_output()\n",
+    "\n",
+    "tokenized_results = list(\n",
+    "    tokenize_trajectory_groups(\n",
+    "        tokenizer,\n",
+    "        [\n",
+    "            art.TrajectoryGroup(\n",
+    "                [\n",
+    "                    art.Trajectory(\n",
+    "                        messages_and_choices=[\n",
+    "                            {\n",
+    "                                \"role\": \"user\",\n",
+    "                                \"content\": \"What is the capital of France?\",\n",
+    "                            },\n",
+    "                            {\"role\": \"assistant\", \"content\": \"London\"},\n",
+    "                        ],\n",
+    "                        reward=0.0,\n",
+    "                    ),\n",
+    "                    art.Trajectory(\n",
+    "                        messages_and_choices=[\n",
+    "                            {\n",
+    "                                \"role\": \"user\",\n",
+    "                                \"content\": \"What is the capital of France?\",\n",
+    "                            },\n",
+    "                            Choice(\n",
+    "                                finish_reason=\"stop\",\n",
+    "                                index=0,\n",
+    "                                logprobs=ChoiceLogprobs(\n",
+    "                                    content=[\n",
+    "                                        ChatCompletionTokenLogprob(\n",
+    "                                            token=\"token:59604\",\n",
+    "                                            bytes=[80, 97, 114, 105, 115],\n",
+    "                                            logprob=-0.01,\n",
+    "                                            top_logprobs=[],\n",
+    "                                        )\n",
+    "                                    ]\n",
+    "                                ),\n",
+    "                                message=ChatCompletionMessage(\n",
+    "                                    content=\"Paris\",\n",
+    "                                    role=\"assistant\",\n",
+    "                                ),\n",
+    "                            ),\n",
+    "                        ],\n",
+    "                        reward=1.0,\n",
+    "                    ),\n",
+    "                ]\n",
+    "            )\n",
+    "        ],\n",
+    "        allow_training_without_logprobs=True,\n",
+    "        scale_rewards=True,\n",
+    "    )\n",
+    ")\n",
+    "for result in tokenized_results:\n",
+    "    # set prompt_id to 0 to eliminate stochasticity\n",
+    "    result.prompt_id = 0\n",
+    "    display(result)"
+   ]
+  }
+ ],
+ "metadata": {
+  "kernelspec": {
+   "display_name": ".venv",
+   "language": "python",
+   "name": "python3"
+  },
+  "language_info": {
+   "codemirror_mode": {
+    "name": "ipython",
+    "version": 3
+   },
+   "file_extension": ".py",
+   "mimetype": "text/x-python",
+   "name": "python",
+   "nbconvert_exporter": "python",
+   "pygments_lexer": "ipython3",
+   "version": "3.10.13"
+  }
+ },
+ "nbformat": 4,
+ "nbformat_minor": 5
+}
diff --git a/uv.lock b/uv.lock
index e7ed93f1..c5b358c2 100644
--- a/uv.lock
+++ b/uv.lock
@@ -950,6 +950,91 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/87/68/7f46fb537958e87427d98a4074bcde4b67a70b04900cfc5ce29bc2f556c1/contourpy-1.3.2-pp311-pypy311_pp73-win_amd64.whl", hash = "sha256:8c5acb8dddb0752bf252e01a3035b21443158910ac16a3b0d20e7fed7d534ce5", size = 221791, upload-time = "2025-04-15T17:45:24.794Z" },
 ]
 
+[[package]]
+name = "coverage"
+version = "7.10.2"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/ee/76/17780846fc7aade1e66712e1e27dd28faa0a5d987a1f433610974959eaa8/coverage-7.10.2.tar.gz", hash = "sha256:5d6e6d84e6dd31a8ded64759626627247d676a23c1b892e1326f7c55c8d61055", size = 820754, upload-time = "2025-08-04T00:35:17.511Z" }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/d8/5f/5ce748ab3f142593698aff5f8a0cf020775aa4e24b9d8748b5a56b64d3f8/coverage-7.10.2-cp310-cp310-macosx_10_9_x86_64.whl", hash = "sha256:79f0283ab5e6499fd5fe382ca3d62afa40fb50ff227676a3125d18af70eabf65", size = 215003, upload-time = "2025-08-04T00:33:02.977Z" },
+    { url = "https://files.pythonhosted.org/packages/f4/ed/507088561217b000109552139802fa99c33c16ad19999c687b601b3790d0/coverage-7.10.2-cp310-cp310-macosx_11_0_arm64.whl", hash = "sha256:e4545e906f595ee8ab8e03e21be20d899bfc06647925bc5b224ad7e8c40e08b8", size = 215391, upload-time = "2025-08-04T00:33:05.645Z" },
+    { url = "https://files.pythonhosted.org/packages/79/1b/0f496259fe137c4c5e1e8eaff496fb95af88b71700f5e57725a4ddbe742b/coverage-7.10.2-cp310-cp310-manylinux1_i686.manylinux_2_28_i686.manylinux_2_5_i686.whl", hash = "sha256:ae385e1d58fbc6a9b1c315e5510ac52281e271478b45f92ca9b5ad42cf39643f", size = 242367, upload-time = "2025-08-04T00:33:07.189Z" },
+    { url = "https://files.pythonhosted.org/packages/b9/8e/5a8835fb0122a2e2a108bf3527931693c4625fdc4d953950a480b9625852/coverage-7.10.2-cp310-cp310-manylinux1_x86_64.manylinux_2_28_x86_64.manylinux_2_5_x86_64.whl", hash = "sha256:6f0cbe5f7dd19f3a32bac2251b95d51c3b89621ac88a2648096ce40f9a5aa1e7", size = 243627, upload-time = "2025-08-04T00:33:08.809Z" },
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