diff --git a/docs/source/whats_new.rst b/docs/source/whats_new.rst
index ddb65ea94..549a803e7 100644
--- a/docs/source/whats_new.rst
+++ b/docs/source/whats_new.rst
@@ -21,6 +21,7 @@ Enhancements
 ~~~~~~~~~~~~
 - Introduce a new logo for the MOABB library (:gh:`858` by `Pierre Guetschel`_ and community)
 - Better verbosity control for initialization of the library (:gh:`850` by `Bruno Aristimunha`_)
+- Improved error messages for dataset compatibility checks in evaluations - now provides specific reasons when datasets are incompatible (e.g., "dataset has only 1 session(s), but CrossSessionEvaluation requires at least 2 sessions") by `Bruno Aristimunha`_
 - Ability to join rows from the tables of MOABB predictive performance scores and detailed CodeCarbon compute profiling metrics by the column `codecarbon_task_name` in MOABB results and the column `task_name` in CodeCarbon results (:gh:`866` by `Ethan Davis`_).
 - Adding two c-VEP datasets: :class:`moabb.datasets.MartinezCagigal2023Checker` and :class:`moabb.datasets.MartinezCagigal2023Pary` by `Victor Martinez-Cagigal`_
 - Allow custom paradigms to have multiple scores for evaluations (:gh:`948` by `Ethan Davis`_)
diff --git a/moabb/evaluations/base.py b/moabb/evaluations/base.py
index 2ade65574..04ad0e1c1 100644
--- a/moabb/evaluations/base.py
+++ b/moabb/evaluations/base.py
@@ -168,8 +168,11 @@ def __init__(
                 )
                 rm.append(dataset)
             elif not valid_for_eval:
+                # Get specific reason for incompatibility
+                eval_type = self.__class__.__name__
+                reason = self._get_incompatibility_reason(dataset)
                 log.warning(
-                    f"{dataset} not compatible with evaluation. "
+                    f"{dataset} not compatible with {eval_type}: {reason}. "
                     "Removing this dataset from the list."
                 )
                 rm.append(dataset)
@@ -324,6 +327,25 @@ def is_valid(self, dataset):
             The dataset to verify.
         """
 
+    def _get_incompatibility_reason(self, dataset):
+        """Get a human-readable reason why dataset is incompatible.
+
+        This method should be overridden by subclasses to provide
+        specific incompatibility reasons.
+
+        Parameters
+        ----------
+        dataset : dataset instance
+            The dataset to check.
+
+        Returns
+        -------
+        str
+            A human-readable reason for incompatibility.
+
+        """
+        return "requirements not met"
+
     def _grid_search(self, param_grid, name, grid_clf, inner_cv):
         extra_params = {}
         if param_grid is not None:
diff --git a/moabb/evaluations/evaluations.py b/moabb/evaluations/evaluations.py
index 9f7c53188..8d667f8d6 100644
--- a/moabb/evaluations/evaluations.py
+++ b/moabb/evaluations/evaluations.py
@@ -525,7 +525,10 @@ def evaluate(
         self, dataset, pipelines, param_grid, process_pipeline, postprocess_pipeline=None
     ):
         if not self.is_valid(dataset):
-            raise AssertionError("Dataset is not appropriate for evaluation")
+            reason = self._get_incompatibility_reason(dataset)
+            raise AssertionError(
+                f"Dataset '{dataset.code}' is not appropriate for {self.__class__.__name__}: {reason}"
+            )
             # Progressbar at subject level
         for subject in tqdm(dataset.subject_list, desc=f"{dataset.code}-CrossSession"):
             # check if we already have result for this subject/pipeline
@@ -638,6 +641,16 @@ def evaluate(
     def is_valid(self, dataset):
         return dataset.n_sessions > 1
 
+    def _get_incompatibility_reason(self, dataset):
+        """Get specific reason for dataset incompatibility."""
+        n_sessions = dataset.n_sessions
+        if n_sessions <= 1:
+            return (
+                f"dataset has only {n_sessions} session(s), "
+                f"but {self.__class__.__name__} requires at least 2 sessions"
+            )
+        return "requirements not met"
+
 
 class CrossSubjectEvaluation(BaseEvaluation):
     """Cross-subject evaluation performance.
@@ -692,7 +705,10 @@ def evaluate(
         self, dataset, pipelines, param_grid, process_pipeline, postprocess_pipeline=None
     ):
         if not self.is_valid(dataset):
-            raise AssertionError("Dataset is not appropriate for evaluation")
+            reason = self._get_incompatibility_reason(dataset)
+            raise AssertionError(
+                f"Dataset '{dataset.code}' is not appropriate for {self.__class__.__name__}: {reason}"
+            )
         # this is a bit awkward, but we need to check if at least one pipe
         # have to be run before loading the data. If at least one pipeline
         # need to be run, we have to load all the data.
@@ -828,3 +844,13 @@ def evaluate(
 
     def is_valid(self, dataset):
         return len(dataset.subject_list) > 1
+
+    def _get_incompatibility_reason(self, dataset):
+        """Get specific reason for dataset incompatibility."""
+        n_subjects = len(dataset.subject_list)
+        if n_subjects <= 1:
+            return (
+                f"dataset has only {n_subjects} subject(s), "
+                f"but {self.__class__.__name__} requires at least 2 subjects"
+            )
+        return "requirements not met"
diff --git a/moabb/evaluations/splitters.py b/moabb/evaluations/splitters.py
index 2f35bb63d..760594a36 100644
--- a/moabb/evaluations/splitters.py
+++ b/moabb/evaluations/splitters.py
@@ -359,7 +359,7 @@ def split(self, y, metadata):
 
             if len(sessions) <= 1:
                 log.info(
-                    f"Skipping subject {subject}: Only one session available"
+                    f"Skipping subject {subject}: Only one session available. "
                     f"Cross-session evaluation requires at least two sessions."
                 )
                 continue  # Skip subjects with only one session
diff --git a/moabb/tests/test_evaluations.py b/moabb/tests/test_evaluations.py
index 6beb73edb..1901a36dc 100644
--- a/moabb/tests/test_evaluations.py
+++ b/moabb/tests/test_evaluations.py
@@ -382,6 +382,17 @@ def test_compatible_dataset(self):
         ds = FakeDataset(["left_hand", "right_hand"], n_sessions=2)
         assert self.eval.is_valid(dataset=ds)
 
+    def test_incompatibility_error_message(self):
+        """Test that incompatibility error message is clear and informative."""
+        ds = FakeDataset(["left_hand", "right_hand"], n_sessions=1)
+        # Test that the error message includes the dataset code and reason
+        with pytest.raises(AssertionError) as exc_info:
+            list(self.eval.evaluate(ds, pipelines, None, None))
+        error_msg = str(exc_info.value)
+        assert "CrossSessionEvaluation" in error_msg
+        assert "1 session" in error_msg
+        assert "requires at least 2 sessions" in error_msg
+
 
 class UtilEvaluation:
     def test_save_model_cv(self):
diff --git a/moabb/tests/test_verbose.py b/moabb/tests/test_verbose.py
index aae29cbaf..2d7151f01 100644
--- a/moabb/tests/test_verbose.py
+++ b/moabb/tests/test_verbose.py
@@ -19,8 +19,9 @@ def test_verbose_warning(caplog):
         with caplog.at_level(logging.WARNING):
             CrossSessionEvaluation(paradigm=paradigm, datasets=[dataset])
 
-    # Check if warning was logged
-    assert "not compatible with evaluation" in caplog.text
+    # Check if warning was logged with specific incompatibility reason
+    assert "not compatible with CrossSessionEvaluation" in caplog.text
+    assert "requires at least 2 sessions" in caplog.text
 
 
 def test_verbose_error_suppression(caplog):
@@ -35,7 +36,7 @@ def test_verbose_error_suppression(caplog):
             CrossSessionEvaluation(paradigm=paradigm, datasets=[dataset], verbose="ERROR")
 
     # Check if warning was suppressed
-    assert "not compatible with evaluation" not in caplog.text
+    assert "not compatible with CrossSessionEvaluation" not in caplog.text
 
 
 def test_verbose_false_warning(caplog):
@@ -50,5 +51,6 @@ def test_verbose_false_warning(caplog):
         ):  # Set to INFO to see if behavior is consistent
             CrossSessionEvaluation(paradigm=paradigm, datasets=[dataset], verbose=False)
 
-    # Check if warning was logged (since verbose=False -> WARNING)
-    assert "not compatible with evaluation" in caplog.text
+    # Check if warning was logged (since verbose=False -> WARNING) with new specific message
+    assert "not compatible with CrossSessionEvaluation" in caplog.text
+    assert "requires at least 2 sessions" in caplog.text