diff --git a/changelog.d/20230508_072605_michael.hanke_cerror.md b/changelog.d/20230508_072605_michael.hanke_cerror.md
new file mode 100644
index 0000000..3301441
--- /dev/null
+++ b/changelog.d/20230508_072605_michael.hanke_cerror.md
@@ -0,0 +1,15 @@
+### 💫 Enhancements and new features
+
+- `Constraint` implementations now raise `ConstraintError` consistently
+  on a violation. This now makes it possible to distinguish properly
+  handled violations from improper implementation of such checks.
+  Moreover, `raise_for()` is now used consistently, providing
+  uniform, structured information on such violations.
+  `ConstraintError` is derived from `ValueError` (the exception
+  that was previously (mostly) raised. Therefore, client-code should
+  continue to work without modification, unless a specific wording
+  of an exception message is relied upon. In few cases, an implicit
+  `TypeError` (e.g., `EnsureIterableof`) has been replaced by an
+  explicit `ConstraintError`, and client code needs to be adjusted.
+  The underlying exception continues to be available via
+  `ConstraintError.caused_by`. (by @mih)
diff --git a/datalad_next/constraints/__init__.py b/datalad_next/constraints/__init__.py
index d910e28..05442fd 100644
--- a/datalad_next/constraints/__init__.py
+++ b/datalad_next/constraints/__init__.py
@@ -1,5 +1,38 @@
 """Data validation, coercion, and parameter documentation
 
+This module provides a set of uniform classes to validate and document
+particular aspects of inputs. In a nutshell, each of these
+:class:`~datalad_next.constraints.base.Constraint` class:
+
+- focuses on a specific aspect, such as data type coercion,
+  or checking particular input properties
+- is instantiated with a set of parameters to customize
+  such an instance for a particular task
+- performs its task by receiving an input via its ``__call__()``
+  method
+- provides default auto-documentation that can be customized
+  by wrapping an instance in
+  :class:`~datalad_next.constraints.compound.WithDescription`
+
+Individual ``Constraint`` instances can be combined with logical AND
+(:class:`~datalad_next.constraints.base.AllOf`) and OR
+(:class:`~datalad_next.constraints.base.AnyOf`) operations to form arbitrarily
+complex constructs.
+
+On (validation/coercion) error, instances raise
+:class:`~datalad_next.constraints.exceptions.ConstraintError`) via their
+``raise_for()`` method. This approach to error reporting helps to communicate
+standard (yet customizable) error messages, aids structured error reporting,
+and is capable of communication the underlying causes of an error in full
+detail without the need to generate long textual descriptions.
+
+:class:`~datalad_next.constraints.parameter.EnsureCommandParameterization` is a
+particular variant of a ``Constraint`` that is capable of validating a complete
+parameterization of a command (or function), for each parameter individually,
+and for arbitrary combinations of parameters. It puts a particular emphasis on
+structured error reporting.
+
+
 .. currentmodule:: datalad_next.constraints
 .. autosummary::
    :toctree: generated
diff --git a/datalad_next/constraints/basic.py b/datalad_next/constraints/basic.py
index 186b4f8..0d9c56b 100644
--- a/datalad_next/constraints/basic.py
+++ b/datalad_next/constraints/basic.py
@@ -43,7 +43,11 @@ class EnsureValue(Constraint):
         if value == self._target_value:
             return value
         else:
-            raise ValueError(f"value must be {self._target_value!r}")
+            self.raise_for(
+                value,
+                "must be {target_value!r}",
+                target_value=self._target_value,
+            )
 
     def short_description(self):
         return f'{self._target_value!r}'
@@ -120,9 +124,7 @@ class EnsureBool(Constraint):
                 return False
             elif value in ('1', 'yes', 'on', 'enable', 'true'):
                 return True
-        raise ValueError(
-            "value '{}' must be convertible to boolean".format(
-                value))
+        self.raise_for(value, "must be convertible to boolean")
 
     def long_description(self):
         return 'value must be convertible to type bool'
@@ -162,14 +164,17 @@ class EnsureStr(Constraint):
             # do not perform a blind conversion ala str(), as almost
             # anything can be converted and the result is most likely
             # unintended
-            raise ValueError("%s is not a string" % repr(value))
+            self.raise_for(value, "must be a string")
         if len(value) < self._min_len:
-            raise ValueError("%r is shorter than of minimal length %d"
-                             % (value, self._min_len))
+            self.raise_for(value, "must have minimum length {len}",
+                                 len=self._min_len)
         if self._match:
             if not self._match.match(value):
-                raise ValueError(
-                    f'{value} does not match {self._match.pattern}')
+                self.raise_for(
+                    value,
+                    'does not match {pattern}',
+                    pattern=self._match.pattern,
+                )
         return value
 
     def long_description(self):
@@ -203,8 +208,11 @@ class EnsureStrPrefix(EnsureStr):
     def __call__(self, value):
         super().__call__(value)
         if not value.startswith(self._prefix):
-            raise ValueError("%r does not start with '%s'"
-                             % (value, self._prefix))
+            self.raise_for(
+                value,
+                "does not start with {prefix!r}",
+                prefix=self._prefix,
+            )
         return value
 
     def long_description(self):
@@ -226,7 +234,7 @@ class EnsureCallable(Constraint):
         if hasattr(value, '__call__'):
             return value
         else:
-            raise ValueError("value must be a callable")
+            self.raise_for(value, "must be a callable")
 
     def short_description(self):
         return 'callable'
@@ -285,7 +293,7 @@ class EnsureKeyChoice(EnsureChoice):
 
     def __call__(self, value):
         if self._key not in value:
-            raise ValueError("value not dict-like")
+            self.raise_for(value, "must be dict-like")
         super(EnsureKeyChoice, self).__call__(value[self._key])
         return value
 
@@ -382,7 +390,7 @@ class EnsurePath(Constraint):
         ref:
           If set, defines a reference Path any given path is compared to. The
           comparison operation is given by `ref_is`.
-        ref_is: {'parent-or-identical'}
+        ref_is: {'parent-or-same-as', 'parent-of'}
           Comparison operation to perform when `ref` is given.
         dsarg: DatasetParameter, optional
           If given, incoming paths are resolved in the following fashion:
@@ -399,6 +407,8 @@ class EnsurePath(Constraint):
         self._ref = ref
         self._ref_is = ref_is
         self._dsarg = dsarg
+        assert self._ref_is in ('parent-or-same-as', 'parent-of'), \
+            'Unrecognized `ref_is` operation label'
 
     def __call__(self, value):
         # turn it into the target type to make everything below
@@ -410,9 +420,9 @@ class EnsurePath(Constraint):
         if self._is_format is not None:
             is_abs = path.is_absolute()
             if self._is_format == 'absolute' and not is_abs:
-                raise ValueError(f'{path} is not an absolute path')
+                self.raise_for(path, 'is not an absolute path')
             elif self._is_format == 'relative' and is_abs:
-                raise ValueError(f'{path} is not a relative path')
+                self.raise_for(path, 'is not a relative path')
 
         # resolve relative paths against a dataset, if given
         if self._dsarg:
@@ -430,24 +440,30 @@ class EnsurePath(Constraint):
                 pass
         if self._lexists is not None:
             if self._lexists and mode is None:
-                raise ValueError(f'{path} does not exist')
+                self.raise_for(path, 'does not exist')
             elif not self._lexists and mode is not None:
-                raise ValueError(f'{path} does (already) exist')
+                self.raise_for(path, 'does (already) exist')
         if self._is_mode is not None:
             if not self._is_mode(mode):
-                raise ValueError(f'{path} does not match desired mode')
+                self.raise_for(path, 'does not match desired mode')
         if self._ref:
             ok = True
             if self._ref_is == 'parent-or-same-as':
                 ok = (path == self._ref or self._ref in path.parents)
             elif self._ref_is == 'parent-of':
                 ok = self._ref in path.parents
-            else:
-                raise ValueError('Unknown `ref_is` operation label')
+            else:  # pragma: nocover
+                # this code cannot be reached with normal usage.
+                # it is prevented by an assertion in __init__()
+                raise RuntimeError('Unknown `ref_is` operation label')
 
             if not ok:
-                raise ValueError(
-                    f'{self._ref} is not {self._ref_is} {path}')
+                self.raise_for(
+                    path,
+                    '{ref} is not {ref_is} {path}',
+                    ref=self._ref,
+                    ref_is=self._ref_is,
+                )
         return path
 
     def for_dataset(self, dataset: DatasetParameter) -> Constraint:
diff --git a/datalad_next/constraints/compound.py b/datalad_next/constraints/compound.py
index 2b2b2ae..99fe8d6 100644
--- a/datalad_next/constraints/compound.py
+++ b/datalad_next/constraints/compound.py
@@ -73,21 +73,32 @@ class EnsureIterableOf(Constraint):
         return self._item_constraint
 
     def __call__(self, value):
-        iter = self._iter_type(
-            self._item_constraint(i) for i in value
-        )
+        try:
+            iter = self._iter_type(
+                self._item_constraint(i) for i in value
+            )
+        except TypeError as e:
+            self.raise_for(
+                value,
+                "cannot coerce to target (item) type",
+                __caused_by__=e,
+            )
         if self._min_len is not None or self._max_len is not None:
             # only do this if necessary, generators will not support
             # __len__, for example
             iter_len = len(iter)
             if self._min_len is not None and iter_len < self._min_len:
-                raise ValueError(
-                    f'Length-{iter_len} iterable is shorter than '
-                    f'required minimum length {self._min_len}')
+                self.raise_for(
+                    iter,
+                    'must have minimum length {len}',
+                    len=self._min_len,
+                )
             if self._max_len is not None and iter_len > self._max_len:
-                raise ValueError(
-                    f'Length-{iter_len} iterable is longer than '
-                    f'required maximum length {self._max_len}')
+                self.raise_for(
+                    iter,
+                    'must not exceed maximum length {len}',
+                    len=self._max_len,
+                )
         return iter
 
     def short_description(self):
diff --git a/datalad_next/constraints/dataset.py b/datalad_next/constraints/dataset.py
index 7d4bb38..1b9752b 100644
--- a/datalad_next/constraints/dataset.py
+++ b/datalad_next/constraints/dataset.py
@@ -70,21 +70,20 @@ class EnsureDataset(Constraint):
         # anticipate what require_dataset() could handle and fail if we got
         # something else
         elif not isinstance(value, (str, PurePath, type(None))):
-            raise TypeError(f"Cannot create Dataset from {type(value)}")
+            self.raise_for(
+                value, "cannot create Dataset from {type}", type=type(value)
+            )
         else:
             ds = self._require_dataset(value)
         assert ds
         if self._installed is not None:
             is_installed = ds.is_installed()
             if self._installed is False and is_installed:
-                raise ValueError(f'{ds} already exists locally')
+                self.raise_for(ds, 'already exists locally')
             if self._installed and not is_installed:
-                # for uniformity with require_dataset() below, use
-                # this custom exception
-                raise NoDatasetFound(f'{ds} is not installed')
+                self.raise_for(ds, 'not installed')
         if self._require_id and not ds.id:
-            raise NoDatasetFound(f'{ds} does not have a valid '
-                                 f'datalad-id')
+            self.raise_for(ds, 'does not have a valid datalad-id')
         return DatasetParameter(value, ds)
 
     def short_description(self) -> str:
diff --git a/datalad_next/constraints/exceptions.py b/datalad_next/constraints/exceptions.py
index b7022fa..a3e4d9a 100644
--- a/datalad_next/constraints/exceptions.py
+++ b/datalad_next/constraints/exceptions.py
@@ -100,8 +100,16 @@ class ConstraintError(ValueError):
         return self.args[1]
 
     @property
-    def caused_by(self):
-        return self.context.get('__caused_by__', None)
+    def caused_by(self) -> Tuple[Exception] | None:
+        """Returns a tuple of any underlying exceptions that caused a violation
+        """
+        cb = self.context.get('__caused_by__', None)
+        if cb is None:
+            return
+        elif isinstance(cb, Exception):
+            return (cb,)
+        else:
+            return tuple(cb)
 
     @property
     def value(self):
diff --git a/datalad_next/constraints/git.py b/datalad_next/constraints/git.py
index 31c773e..ead342b 100644
--- a/datalad_next/constraints/git.py
+++ b/datalad_next/constraints/git.py
@@ -35,7 +35,7 @@ class EnsureGitRefName(Constraint):
     def __call__(self, value: str) -> str:
         if not value:
             # simple, do here
-            raise ValueError('refname must not be empty')
+            self.raise_for(value, 'refname must not be empty')
 
         from datalad.runner import GitRunner, StdOutCapture
         from datalad_next.exceptions import CommandError
@@ -54,7 +54,11 @@ class EnsureGitRefName(Constraint):
         try:
             out = runner.run(cmd, protocol=StdOutCapture)
         except CommandError as e:
-            raise ValueError(f'{value} is not a valid refname') from e
+            self.raise_for(
+                value,
+                'is not a valid refname',
+                __caused_by__=e,
+            )
 
         if self._normalize:
             return out['stdout'].strip()

diff --git a/datalad_next/constraints/tests/test_basic.py b/datalad_next/constraints/tests/test_basic.py
index f189783..2748a15 100644
--- a/datalad_next/constraints/tests/test_basic.py
+++ b/datalad_next/constraints/tests/test_basic.py
@@ -298,9 +298,8 @@ def test_EnsurePath(tmp_path):
     with pytest.raises(ValueError):
         assert c(target)
     assert c.short_description() == f'path that is parent-of {target}'
-    c = EnsurePath(ref=target, ref_is='stupid')
-    with pytest.raises(ValueError):
-        c('doesnotmatter')
+    with pytest.raises(AssertionError):
+        c = EnsurePath(ref=target, ref_is='stupid')
 
 
 def test_EnsurePath_fordataset(existing_dataset):
diff --git a/datalad_next/constraints/tests/test_compound.py b/datalad_next/constraints/tests/test_compound.py
index 486b79b..59907d2 100644
--- a/datalad_next/constraints/tests/test_compound.py
+++ b/datalad_next/constraints/tests/test_compound.py
@@ -64,7 +64,7 @@ def test_EnsureIterableOf():
     with pytest.raises(ValueError):
         # invalid specification min>max
         EnsureIterableOf(list, bool, min_len=1, max_len=0)
-    with pytest.raises(TypeError):
+    with pytest.raises(ValueError):
         # item_constraint fails
         EnsureIterableOf(list, dict)([5.6, 3.2])
     with pytest.raises(ValueError):
diff --git a/datalad_next/constraints/tests/test_special_purpose.py b/datalad_next/constraints/tests/test_special_purpose.py
index 5d35fa5..167c6b2 100644
--- a/datalad_next/constraints/tests/test_special_purpose.py
+++ b/datalad_next/constraints/tests/test_special_purpose.py
@@ -85,7 +85,7 @@ def test_EnsureParameterConstraint():
         Parameter(nargs=2),
         (None, None))
     assert c({'some': [3, 4]}) == dict(some=[3, 4])
-    with pytest.raises(TypeError):
+    with pytest.raises(ValueError):
         c({'some': 3})
     with pytest.raises(ValueError):
         c({'some': [3, 4, 5]})
@@ -119,9 +119,9 @@ def test_EnsureParameterConstraint():
     with pytest.raises(ValueError):
         c({'some': [[3, 2], [1]]})
     # no iterable
-    with pytest.raises(TypeError):
+    with pytest.raises(ValueError):
         c({'some': [3, [1, 2]]})
-    with pytest.raises(TypeError):
+    with pytest.raises(ValueError):
         c({'some': 3})
     # overwrite an item constraint and nargs
     c = EnsureParameterConstraint.from_parameter(
@@ -297,7 +297,7 @@ def test_EnsureURL_match():
 
 
 def test_EnsureDataset(tmp_path):
-    with pytest.raises(TypeError):
+    with pytest.raises(ValueError):
         # will not return a Dataset from sensless input
         EnsureDataset()(5)
     # by default the installation state is not checked
@@ -367,5 +367,5 @@ def test_EnsureDataset(tmp_path):
     # bring it back later in case future tests need it
     id = ds.config.get('datalad.dataset.id')
     ds.config.unset('datalad.dataset.id', scope='branch')
-    with pytest.raises(NoDatasetFound):
+    with pytest.raises(ValueError):
         EnsureDataset(require_id=True)(tmp_path)

Double-check use of `raise_for()` in any `Constraint` implementation
This is necessary for compatibility with the auto-generation of (structured) error messages in command parameter validation, and helps "harness code" to distinguish between a `ValueError` occurring due to an improper validator implementation vs a detected validation error. A dedicated exception makes this trivially accessible.
datalad_next/constraints/tests/test_basic.py::test_EnsurePath datalad_next/constraints/tests/test_compound.py::test_EnsureIterableOf datalad_next/constraints/tests/test_special_purpose.py::test_EnsureParameterConstraint
datalad_next/constraints/tests/test_basic.py::test_noconstraint datalad_next/constraints/tests/test_basic.py::test_int datalad_next/constraints/tests/test_basic.py::test_float datalad_next/constraints/tests/test_basic.py::test_bool datalad_next/constraints/tests/test_basic.py::test_str datalad_next/constraints/tests/test_basic.py::test_str_min_len datalad_next/constraints/tests/test_basic.py::test_EnsureStr_match datalad_next/constraints/tests/test_basic.py::test_EnsureStrPrefix datalad_next/constraints/tests/test_basic.py::test_EnsureValue datalad_next/constraints/tests/test_basic.py::test_none datalad_next/constraints/tests/test_basic.py::test_callable datalad_next/constraints/tests/test_basic.py::test_choice datalad_next/constraints/tests/test_basic.py::test_keychoice datalad_next/constraints/tests/test_basic.py::test_range datalad_next/constraints/tests/test_basic.py::test_type_str datalad_next/constraints/tests/test_compound.py::test_EnsureTupleOf datalad_next/constraints/tests/test_compound.py::test_EnsureListOf datalad_next/constraints/tests/test_compound.py::test_EnsureMapping datalad_next/constraints/tests/test_compound.py::test_EnsureGeneratorFromFileLike datalad_next/constraints/tests/test_compound.py::test_ConstraintWithPassthrough datalad_next/constraints/tests/test_compound.py::test_WithDescription datalad_next/constraints/tests/test_special_purpose.py::test_EnsureGitRefName datalad_next/constraints/tests/test_special_purpose.py::test_EnsureParameterConstraint_passthrough datalad_next/constraints/tests/test_special_purpose.py::test_EnsureJSONLines datalad_next/constraints/tests/test_special_purpose.py::test_EnsureURL datalad_next/constraints/tests/test_special_purpose.py::test_EnsureURL_match