diff --git a/python/pdstools/pega_io/File.py b/python/pdstools/pega_io/File.py
index 0b042767..977ddcfe 100644
--- a/python/pdstools/pega_io/File.py
+++ b/python/pdstools/pega_io/File.py
@@ -105,7 +105,14 @@ def read_ds_export(
 
         except ImportError:
             warnings.warn(
-                "Unable to import `requests`, so not able to check for remote files. If you're trying to read in a file from the internet (or, for instance, using the built-in cdh_sample method), try installing the 'requests' package (`uv pip install requests`)"
+                "Unable to import `requests`, so not able to check for remote files. If you're trying to read in a file from the internet (or, for instance, using the built-in cdh_sample method), try installing the 'requests' package (`uv pip install requests`)",
+                ImportWarning,
+            )
+
+        except (urllib.error.URLError, requests.exceptions.SSLError):
+            warnings.warn(
+                "There was an error making a HTTP request call. This is likely due to your certificates not being installed correctly. Please follow these instructions: https://stackoverflow.com/a/70495761",
+                RuntimeWarning,
             )
 
         except Exception as e:
diff --git a/python/pdstools/utils/datasets.py b/python/pdstools/utils/datasets.py
index 6ae56247..cc96f3b4 100644
--- a/python/pdstools/utils/datasets.py
+++ b/python/pdstools/utils/datasets.py
@@ -1,3 +1,4 @@
+import warnings
 from typing import Optional
 
 from ..adm.ADMDatamart import ADMDatamart
@@ -22,18 +23,30 @@ def cdh_sample(query: Optional[QUERY] = None) -> ADMDatamart:
     path = "https://raw.githubusercontent.com/pegasystems/pega-datascientist-tools/master/data"
     models = "Data-Decision-ADM-ModelSnapshot_pyModelSnapshots_20210526T131808_GMT.zip"
     predictors = "Data-Decision-ADM-PredictorBinningSnapshot_pyADMPredictorSnapshots_20210526T133622_GMT.zip"
-    return ADMDatamart.from_ds_export(
-        model_filename=models,
-        predictor_filename=predictors,
-        base_path=path,
-        query=query,
-    )
+    with warnings.catch_warnings(record=True) as w:
+        try:
+            return ADMDatamart.from_ds_export(
+                model_filename=models,
+                predictor_filename=predictors,
+                base_path=path,
+                query=query,
+            )
+        except Exception as e:
+            raise RuntimeError(
+                f"Error importing CDH Sample. Warnings: {w}, exceptions: {e}"
+            )
 
 
 def sample_trees():
-    return ADMTrees(
-        "https://raw.githubusercontent.com/pegasystems/pega-datascientist-tools/master/data/agb/_974a7f9c-66a6-4f00-bf3e-3acf5f188b1d.txt"
-    )
+    with warnings.catch_warnings(record=True) as w:
+        try:
+            return ADMTrees(
+                "https://raw.githubusercontent.com/pegasystems/pega-datascientist-tools/master/data/agb/_974a7f9c-66a6-4f00-bf3e-3acf5f188b1d.txt"
+            )
+        except Exception as e:
+            raise RuntimeError(
+                f"Error importing the Sample Trees dataset. Warnings: {w}, exceptions: {e}"
+            )
 
 
 def sample_value_finder(threshold: Optional[float] = None) -> ValueFinder:
@@ -51,9 +64,15 @@ def sample_value_finder(threshold: Optional[float] = None) -> ValueFinder:
     ValueFinder
         The Value Finder class populated with the Value Finder simulation data
     """
-    return ValueFinder.from_ds_export(
-        base_path="https://raw.githubusercontent.com/pegasystems/pega-datascientist-tools/master/data",
-        filename="Data-Insights_pyValueFinder_20210824T112615_GMT.zip",
-        n_customers=10000,
-        threshold=threshold,
-    )
+    with warnings.catch_warnings(record=True) as w:
+        try:
+            return ValueFinder.from_ds_export(
+                base_path="https://raw.githubusercontent.com/pegasystems/pega-datascientist-tools/master/data",
+                filename="Data-Insights_pyValueFinder_20210824T112615_GMT.zip",
+                n_customers=10000,
+                threshold=threshold,
+            )
+        except Exception as e:
+            raise RuntimeError(
+                f"Error importing the Value Finder dataset. Warnings: {w}, exceptions: {e}"
+            )