diff --git a/src/comet_llm/experiment_api/comet_api_client.py b/src/comet_llm/experiment_api/comet_api_client.py
index 62f28ce70..511abd8da 100644
--- a/src/comet_llm/experiment_api/comet_api_client.py
+++ b/src/comet_llm/experiment_api/comet_api_client.py
@@ -99,7 +99,6 @@ def log_experiment_tags(
             json={"experimentKey": experiment_key, "addedTags": tags},
         )
 
-    @request_exception_wrapper.wrap
     def _request(self, method: str, path: str, *args, **kwargs) -> ResponseContent:  # type: ignore
         url = urllib.parse.urljoin(self._comet_url, path)
         response = requests.request(method, url, headers=self._headers, *args, **kwargs)
diff --git a/src/comet_llm/experiment_api/experiment_api.py b/src/comet_llm/experiment_api/experiment_api.py
index 5ed06e359..ca0115d58 100644
--- a/src/comet_llm/experiment_api/experiment_api.py
+++ b/src/comet_llm/experiment_api/experiment_api.py
@@ -14,10 +14,11 @@
 
 from typing import IO, Any, List, Optional
 
-from . import comet_api_client
+from . import comet_api_client, request_exception_wrapper
 
 
 class ExperimentAPI:
+    @request_exception_wrapper.wrap(check_on_prem=True)
     def __init__(
         self,
         api_key: str,
@@ -46,18 +47,22 @@ def _initialize_links(self, link: str) -> None:
         self._link = link
         self._project_link = link[: link.rfind("/")]
 
+    @request_exception_wrapper.wrap(check_on_prem=True)
     def log_asset_with_io(self, name: str, file: IO, asset_type: str) -> None:
         self._client.log_experiment_asset_with_io(
             self._experiment_key, name=name, file=file, asset_type=asset_type
         )
 
+    @request_exception_wrapper.wrap()
     def log_parameter(self, name: str, value: Any) -> None:
         self._client.log_experiment_parameter(
             self._experiment_key, name=name, value=value
         )
 
+    @request_exception_wrapper.wrap()
     def log_metric(self, name: str, value: Any) -> None:
         self._client.log_experiment_metric(self._experiment_key, name=name, value=value)
 
+    @request_exception_wrapper.wrap()
     def log_tags(self, tags: List[str]) -> None:
         self._client.log_experiment_tags(self._experiment_key, tags=tags)
diff --git a/src/comet_llm/experiment_api/request_exception_wrapper.py b/src/comet_llm/experiment_api/request_exception_wrapper.py
index 665e0b561..f41325e5e 100644
--- a/src/comet_llm/experiment_api/request_exception_wrapper.py
+++ b/src/comet_llm/experiment_api/request_exception_wrapper.py
@@ -14,19 +14,40 @@
 
 
 import functools
-from typing import Any, Callable
+import urllib.parse
+from typing import Any, Callable, List
 
 import requests  # type: ignore
 
-from .. import exceptions
+from .. import config, exceptions
 
 
-def wrap(func: Callable) -> Callable:
-    @functools.wraps(func)
-    def wrapper(*args, **kwargs) -> Any:  # type: ignore
-        try:
-            return func(*args, **kwargs)
-        except requests.RequestException as exception:
-            raise exceptions.CometLLMException() from exception
+def wrap(check_on_prem: bool = False) -> Callable:
+    def inner_wrap(func: Callable) -> Callable:
+        @functools.wraps(func)
+        def wrapper(*args, **kwargs) -> Any:  # type: ignore
+            try:
+                return func(*args, **kwargs)
+            except requests.RequestException as exception:
+                exception_args: List[Any] = []
 
-    return wrapper
+                if check_on_prem:
+                    comet_url = config.comet_url()
+                    if _is_on_prem(comet_url):
+                        exception_args.append(
+                            f"Failed to send prompt to your Comet installation at "
+                            f"{comet_url}. Check that your Comet "
+                            f"installation is up-to-date and check the traceback for more details."
+                        )
+
+                raise exceptions.CometLLMException(*exception_args) from exception
+
+        return wrapper
+
+    return inner_wrap
+
+
+def _is_on_prem(url: str) -> bool:
+    parsed = urllib.parse.urlparse(url)
+    root = f"{parsed.scheme}://{parsed.hostname}/"
+    return root != "https://www.comet.com/"
diff --git a/tests/unit/experiment_api/test_request_exception_wrapper.py b/tests/unit/experiment_api/test_request_exception_wrapper.py
index d5ff10b91..ac2849594 100644
--- a/tests/unit/experiment_api/test_request_exception_wrapper.py
+++ b/tests/unit/experiment_api/test_request_exception_wrapper.py
@@ -1,20 +1,26 @@
 import pytest
 import requests
+from testix import *
 
 from comet_llm import exceptions
 from comet_llm.experiment_api import request_exception_wrapper
 
 
-def test_reraiser_no_exceptions():
-    @request_exception_wrapper.wrap
+@pytest.fixture(autouse=True)
+def mock_imports(patch_module):
+    patch_module(request_exception_wrapper, "config")
+
+
+def test_wrap_no_exceptions():
+    @request_exception_wrapper.wrap()
     def f():
         return "return-value"
 
     assert f() == "return-value"
 
 
-def test_reraiser__request_exception_caught__comet_exception_raised():
-    @request_exception_wrapper.wrap
+def test_wrap__request_exception_caught__comet_exception_raised():
+    @request_exception_wrapper.wrap()
     def f():
         raise requests.RequestException
 
@@ -22,10 +28,25 @@ def f():
         f()
 
 
-def test_reraiser__generic_exception_not_caught():
-    @request_exception_wrapper.wrap
+def test_wrap__on_prem_check_enabled__request_exception_caught__on_prem_detected__comet_exception_raised_with_additional_message():
+    @request_exception_wrapper.wrap(check_on_prem=True)
     def f():
-        raise Exception
+        raise requests.RequestException
+
+    with Scenario() as s:
+        s.config.comet_url() >> "https://not.comet.cloud/ddf/"
+        with pytest.raises(exceptions.CometLLMException):
+            f()
+
+
+def test_wrap__on_prem_check_enabled__request_exception_caught__on_prem_not_detected__comet_exception_raised_without_additional_message():
+    @request_exception_wrapper.wrap(check_on_prem=True)
+    def f():
+        raise requests.RequestException
+
+    COMET_CLOUD_URL = "https://www.comet.com/clientlib/"
 
-    with pytest.raises(Exception):
-        f()
\ No newline at end of file
+    with Scenario() as s:
+        s.config.comet_url() >> COMET_CLOUD_URL
+        with pytest.raises(exceptions.CometLLMException):
+            f()
\ No newline at end of file