diff --git a/poetry.lock b/poetry.lock
index abded65a..1adc405a 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -42,111 +42,98 @@ files = [
 
 [[package]]
 name = "aiohttp"
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+version = "3.9.0"
 description = "Async http client/server framework (asyncio)"
 optional = false
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+python-versions = ">=3.8"
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 [package.dependencies]
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 multidict = ">=4.5,<7.0"
 yarl = ">=1.0,<2.0"
 
 [package.extras]
-speedups = ["Brotli", "aiodns", "cchardet"]
+speedups = ["Brotli", "aiodns", "brotlicffi"]
 
 [[package]]
 name = "aiosignal"
@@ -273,17 +260,6 @@ six = ">=1.12.0"
 [package.extras]
 test = ["astroid", "pytest"]
 
-[[package]]
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-
 [[package]]
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 version = "3.41.2"
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 name = "langchain"
-version = "0.0.327"
+version = "0.0.329"
 description = "Building applications with LLMs through composability"
 optional = false
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 ]
 
 [package.dependencies]
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 [[package]]
 name = "pyarrow"
-version = "13.0.0"
+version = "14.0.1"
 description = "Python library for Apache Arrow"
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+    {file = "scipy-1.10.0-cp38-cp38-win_amd64.whl", hash = "sha256:9b878c671655864af59c108c20e4da1e796154bd78c0ed6bb02bc41c84625686"},
+    {file = "scipy-1.10.0-cp39-cp39-macosx_10_15_x86_64.whl", hash = "sha256:3afcbddb4488ac950ce1147e7580178b333a29cd43524c689b2e3543a080a2c8"},
+    {file = "scipy-1.10.0-cp39-cp39-macosx_12_0_arm64.whl", hash = "sha256:6e4497e5142f325a5423ff5fda2fff5b5d953da028637ff7c704378c8c284ea7"},
+    {file = "scipy-1.10.0-cp39-cp39-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:441cab2166607c82e6d7a8683779cb89ba0f475b983c7e4ab88f3668e268c143"},
+    {file = "scipy-1.10.0-cp39-cp39-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:0490dc499fe23e4be35b8b6dd1e60a4a34f0c4adb30ac671e6332446b3cbbb5a"},
+    {file = "scipy-1.10.0-cp39-cp39-win_amd64.whl", hash = "sha256:954ff69d2d1bf666b794c1d7216e0a746c9d9289096a64ab3355a17c7c59db54"},
+    {file = "scipy-1.10.0.tar.gz", hash = "sha256:c8b3cbc636a87a89b770c6afc999baa6bcbb01691b5ccbbc1b1791c7c0a07540"},
 ]
 
 [package.dependencies]
-numpy = ">=1.18.5,<1.26.0"
+numpy = ">=1.19.5,<1.27.0"
 
 [package.extras]
-dev = ["flake8", "mypy", "pycodestyle", "typing_extensions"]
-doc = ["matplotlib (>2)", "numpydoc", "pydata-sphinx-theme (==0.9.0)", "sphinx (!=4.1.0)", "sphinx-panels (>=0.5.2)", "sphinx-tabs"]
-test = ["asv", "gmpy2", "mpmath", "pytest", "pytest-cov", "pytest-xdist", "scikit-umfpack", "threadpoolctl"]
+dev = ["click", "doit (>=0.36.0)", "flake8", "mypy", "pycodestyle", "pydevtool", "rich-click", "typing_extensions"]
+doc = ["matplotlib (>2)", "numpydoc", "pydata-sphinx-theme (==0.9.0)", "sphinx (!=4.1.0)", "sphinx-design (>=0.2.0)"]
+test = ["asv", "gmpy2", "mpmath", "pooch", "pytest", "pytest-cov", "pytest-timeout", "pytest-xdist", "scikit-umfpack", "threadpoolctl"]
 
 [[package]]
 name = "semantic-version"
@@ -4624,17 +4607,17 @@ files = [
 
 [[package]]
 name = "urllib3"
-version = "1.26.16"
+version = "1.26.18"
 description = "HTTP library with thread-safe connection pooling, file post, and more."
 optional = false
 python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*, !=3.5.*"
 files = [
-    {file = "urllib3-1.26.16-py2.py3-none-any.whl", hash = "sha256:8d36afa7616d8ab714608411b4a3b13e58f463aee519024578e062e141dce20f"},
-    {file = "urllib3-1.26.16.tar.gz", hash = "sha256:8f135f6502756bde6b2a9b28989df5fbe87c9970cecaa69041edcce7f0589b14"},
+    {file = "urllib3-1.26.18-py2.py3-none-any.whl", hash = "sha256:34b97092d7e0a3a8cf7cd10e386f401b3737364026c45e622aa02903dffe0f07"},
+    {file = "urllib3-1.26.18.tar.gz", hash = "sha256:f8ecc1bba5667413457c529ab955bf8c67b45db799d159066261719e328580a0"},
 ]
 
 [package.extras]
-brotli = ["brotli (>=1.0.9)", "brotlicffi (>=0.8.0)", "brotlipy (>=0.6.0)"]
+brotli = ["brotli (==1.0.9)", "brotli (>=1.0.9)", "brotlicffi (>=0.8.0)", "brotlipy (>=0.6.0)"]
 secure = ["certifi", "cryptography (>=1.3.4)", "idna (>=2.0.0)", "ipaddress", "pyOpenSSL (>=0.14)", "urllib3-secure-extra"]
 socks = ["PySocks (>=1.5.6,!=1.5.7,<2.0)"]
 
@@ -5051,4 +5034,4 @@ llama-index-notebooks = ["bitsandbytes", "gradio", "httpx", "ipykernel", "nbconv
 [metadata]
 lock-version = "2.0"
 python-versions = ">=3.11,<3.12"
-content-hash = "777883c38ebc6f2bb1722a8d527439cd2d202b1d58813dc19121709c677ae9ad"
+content-hash = "600637acf96d7886432c8fef9a73e07db9c55ddab3dfe03e046f77e92728faf2"
diff --git a/pyproject.toml b/pyproject.toml
index c1d10119..36057571 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -26,7 +26,7 @@ gitpython = "^3.1.36"
 gradio = { version="^3.34.0", optional=true }
 httpx = { version="^0.25.0", optional=true }
 ipykernel = { version="^6.23.2", optional=true }
-langchain = "^0.0.327"
+langchain = "^0.0.329"
 llama-cpp-python = "^0.2.11"
 llama-index = "^0.8.57"
 llama-hub = "^0.0.42"
diff --git a/reginald/slack_bot/bot.py b/reginald/slack_bot/bot.py
index ed8e3898..7594cb8a 100644
--- a/reginald/slack_bot/bot.py
+++ b/reginald/slack_bot/bot.py
@@ -382,50 +382,94 @@ async def _process_request(
         # start processing the message
         logging.info(f"Processing message '{message}' from user '{user_id}'.")
 
+        # remove clock as we're about to process the message
         await client.web_client.reactions_remove(
             name="clock2",
             channel=event["channel"],
             timestamp=event["ts"],
         )
 
-        # if this is a direct message to Reginald...
-        if event_type == "message" and event_subtype is None:
-            await self.react(client, event["channel"], event["ts"])
-            model_response = await asyncio.get_running_loop().run_in_executor(
-                None,
-                lambda: requests.get(
-                    f"{self.api_url}/direct_message",
-                    json={"message": message, "user_id": user_id},
-                ),
-            )
-
-        # if @Reginald is mentioned in a channel
-        elif event_type == "app_mention":
-            await self.react(client, event["channel"], event["ts"])
-            model_response = await asyncio.get_running_loop().run_in_executor(
-                None,
-                lambda: requests.get(
-                    f"{self.api_url}/channel_mention",
-                    json={"message": message, "user_id": user_id},
-                ),
-            )
+        try:
+            # try to get a response from the model api
+            # if this is a direct message to Reginald...
+            if event_type == "message" and event_subtype is None:
+                await self.react(client, event["channel"], event["ts"])
+                model_response = await asyncio.get_running_loop().run_in_executor(
+                    None,
+                    lambda: requests.get(
+                        f"{self.api_url}/direct_message",
+                        json={"message": message, "user_id": user_id},
+                    ),
+                )
 
-        # otherwise
-        else:
-            logging.info(f"Received unexpected event of type '{event['type']}'.")
-            return
+            # if @Reginald is mentioned in a channel
+            elif event_type == "app_mention":
+                await self.react(client, event["channel"], event["ts"])
+                model_response = await asyncio.get_running_loop().run_in_executor(
+                    None,
+                    lambda: requests.get(
+                        f"{self.api_url}/channel_mention",
+                        json={"message": message, "user_id": user_id},
+                    ),
+                )
 
-        if model_response.status_code != 200:
-            raise ValueError("Unable to get response.")
-        model_response = model_response.json()
+            # otherwise
+            else:
+                logging.info(f"Received unexpected event of type '{event['type']}'.")
+                return
+
+            model_response.raise_for_status()
+            model_response = model_response.json()
+        except requests.exceptions.ConnectTimeout:
+            # if the model api times out, return a out of office message
+            logging.info("Model API timed out.")
+            # add a error flag to the response so we send an error message
+            model_response = {
+                "message": "Reginald is out of office",
+                "user_id": user_id,
+                "error": True,
+                "timeout": True,
+            }
+        except Exception as err:
+            logging.error(
+                f"Something went wrong in processing a Slack request.\n{str(err)}"
+            )
+            # add a error flag to the response so we send an error message
+            model_response = {
+                "message": f"while processing your request, something went wrong: {type(err).__name__} - {err}",
+                "user_id": user_id,
+                "error": True,
+                "timeout": False,
+            }
 
         # add a reply as required
         if model_response and model_response["message"]:
-            logging.info(f"Posting reply {model_response['message']}.")
-            await client.web_client.chat_postMessage(
-                channel=event["channel"],
-                text=f"<@{user_id}>, you asked me: '{message}'.\n{model_response['message']}",
-            )
+            logging.info(f"Posting reply: {model_response['message']}.")
+            if model_response.get("error"):
+                if model_response["timeout"]:
+                    # react with a sleeping emoji if timeout
+                    await client.web_client.reactions_add(
+                        name="sleeping",
+                        channel=event["channel"],
+                        timestamp=event["ts"],
+                    )
+                else:
+                    # react with a general error emoji
+                    await client.web_client.reactions_add(
+                        name="x",
+                        channel=event["channel"],
+                        timestamp=event["ts"],
+                    )
+                # if timeout, we send an out of office message
+                await client.web_client.chat_postMessage(
+                    channel=event["channel"],
+                    text=f"<@{user_id}>, {model_response['message']}.",
+                )
+            else:
+                await client.web_client.chat_postMessage(
+                    channel=event["channel"],
+                    text=f"<@{user_id}>, you asked me: '{message}'.\n{model_response['message']}",
+                )
         else:
             logging.info("No reply was generated.")
 
diff --git a/reginald/slack_bot/setup_bot.py b/reginald/slack_bot/setup_bot.py
index 17d5f3cb..51df3df7 100755
--- a/reginald/slack_bot/setup_bot.py
+++ b/reginald/slack_bot/setup_bot.py
@@ -118,13 +118,19 @@ async def main():
     parser.add_argument(
         "--api-url",
         "-a",
-        help="Select the API URL for the model",
+        help=(
+            "Select the API URL for the model. If not set, "
+            "must be set as the REGINALD_API_URL environment variable"
+        ),
         default=os.environ.get("REGINALD_API_URL"),
     )
     parser.add_argument(
         "--emoji",
         "-e",
-        help="Select the emoji for the model",
+        help=(
+            "Select the emoji for the model. By default, looks for the REGINALD_EMOJI "
+            "environment variable or uses the rocket emoji"
+        ),
         default=os.environ.get("REGINALD_EMOJI") or "rocket",
     )
     args = parser.parse_args()