diff --git a/burr/core/action.py b/burr/core/action.py
index b2e7c16d3..df15b7f0d 100644
--- a/burr/core/action.py
+++ b/burr/core/action.py
@@ -423,26 +423,105 @@ def run(self, state: State, **run_kwargs) -> dict:
     def reads(self) -> list[str]:
         return self._keys
 
+    _OPERATORS = {
+        "eq": ("==", lambda a, b: a == b),
+        "ne": ("!=", lambda a, b: a != b),
+        "lt": ("<", lambda a, b: a < b),
+        "lte": ("<=", lambda a, b: a <= b),
+        "gt": (">", lambda a, b: a > b),
+        "gte": (">=", lambda a, b: a >= b),
+        "in": ("in", lambda a, b: a in b),
+        "notin": ("not in", lambda a, b: a not in b),
+        "contains": ("contains", lambda a, b: b in a),
+        "is": ("is", lambda a, b: a is b),
+        "isnot": ("is not", lambda a, b: a is not b),
+    }
+
+    @classmethod
+    def _parse_kwarg(cls, kwarg_key: str, value):
+        """Parse a kwarg key into (state_key, operator_symbol, comparison_func, explicit).
+
+        Supports Django-style lookups: ``key__gte=10`` parses as key >= 10.
+        Plain ``key=value`` defaults to equality (implicit).
+
+        Returns a tuple of (state_key, symbol, func, explicit) where explicit
+        indicates whether an operator suffix was present.
+        """
+        for suffix, (symbol, func) in cls._OPERATORS.items():
+            dunder = f"__{suffix}"
+            if kwarg_key.endswith(dunder):
+                state_key = kwarg_key[: -len(dunder)]
+                if not state_key:
+                    raise ValueError(
+                        f"Invalid when() key: '{kwarg_key}' — " f"no state key before '__{suffix}'"
+                    )
+                return state_key, symbol, func, True
+        return kwarg_key, "=", lambda a, b: a == b, False
+
     @classmethod
     def when(cls, **kwargs):
-        """Returns a condition that checks if the given keys are in the
-        state and equal to the given values.
+        """Returns a condition that checks state values using optional operators.
 
         You can also refer to this as ``from burr.core import when`` in the API.
 
-        :param kwargs: Keyword arguments of keys and values to check -- will be an AND condition
-        :return: A condition that checks if the given keys are in the state and equal to the given values
+        Basic equality (unchanged from original)::
+
+            when(foo="bar")            # state["foo"] == "bar"
+            when(foo="bar", baz="qux") # state["foo"] == "bar" AND state["baz"] == "qux"
+
+        Comparison operators via ``__`` suffix::
+
+            when(age__gt=18)           # state["age"] > 18
+            when(age__gte=18)          # state["age"] >= 18
+            when(age__lt=18)           # state["age"] < 18
+            when(age__lte=18)          # state["age"] <= 18
+            when(age__ne=0)            # state["age"] != 0
+            when(age__eq=18)           # state["age"] == 18  (explicit)
+
+        Membership operators::
+
+            when(status__in=["a", "b"])     # state["status"] in ["a", "b"]
+            when(status__notin=["x", "y"])  # state["status"] not in ["x", "y"]
+            when(tags__contains="python")   # "python" in state["tags"]
+
+        Identity operators::
+
+            when(value__is=None)            # state["value"] is None
+            when(value__isnot=None)         # state["value"] is not None
+
+        Multiple conditions are ANDed together::
+
+            when(age__gte=18, status="active")  # age >= 18 AND status == "active"
+
+        :param kwargs: Keyword arguments with optional ``__operator`` suffixes
+        :return: A condition that checks all specified constraints (AND)
         """
-        keys = list(kwargs.keys())
+        parsed = []
+        for kwarg_key, value in kwargs.items():
+            state_key, symbol, func, explicit = cls._parse_kwarg(kwarg_key, value)
+            parsed.append((state_key, symbol, func, value, explicit))
+
+        state_keys = list(dict.fromkeys(p[0] for p in parsed))
 
         def condition_func(state: State) -> bool:
-            for key, value in kwargs.items():
-                if state.get(key) != value:
+            for state_key, _symbol, func, value, _explicit in parsed:
+                if not func(state.get(state_key), value):
                     return False
             return True
 
-        name = f"{', '.join(f'{key}={value}' for key, value in sorted(kwargs.items()))}"
-        return Condition(keys, condition_func, name=name)
+        name_parts = []
+        for state_key, symbol, _func, value, explicit in sorted(parsed, key=lambda p: p[0]):
+            if not explicit:
+                # Backward-compatible format: key=value (no repr, no spaces)
+                name_parts.append(f"{state_key}={value}")
+            elif symbol.isalnum() or " " in symbol:
+                # Word operators like "in", "not in", "contains"
+                name_parts.append(f"{state_key} {symbol} {value!r}")
+            else:
+                # Symbol operators like >=, !=, etc.
+                name_parts.append(f"{state_key}{symbol}{value!r}")
+        name = ", ".join(name_parts)
+        return Condition(state_keys, condition_func, name=name)
 
     def __repr__(self):
         return f"condition: {self._name}"
diff --git a/docs/concepts/transitions.rst b/docs/concepts/transitions.rst
index a3338395f..479ee881a 100644
--- a/docs/concepts/transitions.rst
+++ b/docs/concepts/transitions.rst
@@ -54,6 +54,40 @@ Conditions have a few APIs, but the most common are the three convenience functi
     )
 
 
+``when()`` also supports comparison operators via Django-style ``__`` suffixes:
+
+.. code-block:: python
+
+    from burr.core import when
+    with_transitions(
+        ("check", "adult", when(age__gte=18)),       # age >= 18
+        ("check", "child", when(age__lt=18)),         # age < 18
+        ("check", "valid", when(score__gt=0, score__lte=100)),  # 0 < score <= 100
+        ("check", "active", when(status__in=["active", "pending"])),  # membership
+        ("check", "tagged", when(tags__contains="python")),  # collection contains value
+        ("check", "clean", when(status__notin=["banned", "suspended"])),  # not in
+        ("check", "changed", when(status__ne="initial")),  # not equal
+        ("check", "missing", when(value__is=None)),  # identity check
+        ("check", "present", when(value__isnot=None)),  # not-identity check
+    )
+
+Available operators:
+
+- ``key=value`` — exact equality (default, unchanged)
+- ``key__eq=value`` — explicit equality
+- ``key__ne=value`` — not equal
+- ``key__gt=value`` — greater than
+- ``key__gte=value`` — greater than or equal
+- ``key__lt=value`` — less than
+- ``key__lte=value`` — less than or equal
+- ``key__in=[values]`` — value is in the given collection
+- ``key__notin=[values]`` — value is not in the given collection
+- ``key__contains=value`` — collection/string in state contains the value
+- ``key__is=value`` — identity check (``is``), useful for ``None``/``True``/``False``
+- ``key__isnot=value`` — negated identity check (``is not``)
+
+Multiple keyword arguments are ANDed together. For more complex expressions, use ``expr()``.
+
 Conditions are evaluated in the order they are specified, and the first one that evaluates to True will be the transition that is selected
 when determining which action to run next. If no condition evaluates to ``True``, the application execution will stop early.
 
diff --git a/tests/core/test_action.py b/tests/core/test_action.py
index 83fecf3b3..f65a06831 100644
--- a/tests/core/test_action.py
+++ b/tests/core/test_action.py
@@ -126,6 +126,171 @@ def test_condition_when_complex():
     assert cond.run(State({"foo": "baz", "baz": "corge"})) == {Condition.KEY: False}
 
 
+# --- when() operator tests ---
+
+
+@pytest.mark.parametrize(
+    "kwargs,state_dict,expected",
+    [
+        # __eq (explicit equality)
+        ({"age__eq": 18}, {"age": 18}, True),
+        ({"age__eq": 18}, {"age": 19}, False),
+        # __ne (not equal)
+        ({"age__ne": 0}, {"age": 5}, True),
+        ({"age__ne": 0}, {"age": 0}, False),
+        # __gt (greater than)
+        ({"age__gt": 18}, {"age": 19}, True),
+        ({"age__gt": 18}, {"age": 18}, False),
+        ({"age__gt": 18}, {"age": 17}, False),
+        # __gte (greater than or equal)
+        ({"age__gte": 18}, {"age": 19}, True),
+        ({"age__gte": 18}, {"age": 18}, True),
+        ({"age__gte": 18}, {"age": 17}, False),
+        # __lt (less than)
+        ({"age__lt": 18}, {"age": 17}, True),
+        ({"age__lt": 18}, {"age": 18}, False),
+        ({"age__lt": 18}, {"age": 19}, False),
+        # __lte (less than or equal)
+        ({"age__lte": 18}, {"age": 17}, True),
+        ({"age__lte": 18}, {"age": 18}, True),
+        ({"age__lte": 18}, {"age": 19}, False),
+        # __in (membership)
+        ({"status__in": ["active", "pending"]}, {"status": "active"}, True),
+        ({"status__in": ["active", "pending"]}, {"status": "pending"}, True),
+        ({"status__in": ["active", "pending"]}, {"status": "banned"}, False),
+        # __notin (not in)
+        ({"status__notin": ["banned", "suspended"]}, {"status": "active"}, True),
+        ({"status__notin": ["banned", "suspended"]}, {"status": "banned"}, False),
+        # __contains (collection contains value)
+        ({"tags__contains": "python"}, {"tags": ["python", "java"]}, True),
+        ({"tags__contains": "go"}, {"tags": ["python", "java"]}, False),
+        ({"text__contains": "hello"}, {"text": "say hello world"}, True),
+        ({"text__contains": "goodbye"}, {"text": "say hello world"}, False),
+        # __is (identity)
+        ({"value__is": None}, {"value": None}, True),
+        ({"value__is": None}, {"value": 0}, False),
+        ({"value__is": True}, {"value": True}, True),
+        ({"value__is": True}, {"value": 1}, False),
+        # __isnot (not identity)
+        ({"value__isnot": None}, {"value": "hello"}, True),
+        ({"value__isnot": None}, {"value": None}, False),
+    ],
+    ids=[
+        "eq-match",
+        "eq-no-match",
+        "ne-different",
+        "ne-same",
+        "gt-above",
+        "gt-equal",
+        "gt-below",
+        "gte-above",
+        "gte-equal",
+        "gte-below",
+        "lt-below",
+        "lt-equal",
+        "lt-above",
+        "lte-below",
+        "lte-equal",
+        "lte-above",
+        "in-first",
+        "in-second",
+        "in-missing",
+        "notin-absent",
+        "notin-present",
+        "contains-list-match",
+        "contains-list-no-match",
+        "contains-str-match",
+        "contains-str-no-match",
+        "is-none-match",
+        "is-none-no-match",
+        "is-true-match",
+        "is-true-not-identical",
+        "isnot-not-none",
+        "isnot-is-none",
+    ],
+)
+def test_condition_when_operators(kwargs, state_dict, expected):
+    cond = Condition.when(**kwargs)
+    assert cond.run(State(state_dict)) == {Condition.KEY: expected}
+
+
+@pytest.mark.parametrize(
+    "kwargs,expected_reads",
+    [
+        ({"age__gte": 18}, ["age"]),
+        ({"status__in": ["a"]}, ["status"]),
+        ({"tags__contains": "x"}, ["tags"]),
+        ({"age__gte": 18, "status": "active"}, ["age", "status"]),
+        # same key with different operators
+        ({"age__gte": 10, "age__lt": 20}, ["age"]),
+    ],
+    ids=["gte", "in", "contains", "mixed", "same-key-two-ops"],
+)
+def test_condition_when_operators_reads(kwargs, expected_reads):
+    cond = Condition.when(**kwargs)
+    assert sorted(cond.reads) == sorted(expected_reads)
+
+
+@pytest.mark.parametrize(
+    "kwargs,expected_name",
+    [
+        ({"age__gte": 18}, "age>=18"),
+        ({"age__lt": 5}, "age<5"),
+        ({"age__ne": 0}, "age!=0"),
+        ({"status__in": ["a", "b"]}, "status in ['a', 'b']"),
+        ({"status__notin": ["x"]}, "status not in ['x']"),
+        ({"tags__contains": "py"}, "tags contains 'py'"),
+        ({"value__is": None}, "value is None"),
+        ({"value__isnot": None}, "value is not None"),
+        # plain equality still uses old format
+        ({"foo": "bar"}, "foo=bar"),
+        ({"foo": "bar", "baz": "qux"}, "baz=qux, foo=bar"),
+    ],
+    ids=["gte", "lt", "ne", "in", "notin", "contains", "is", "isnot", "plain-eq", "plain-multi"],
+)
+def test_condition_when_operators_name(kwargs, expected_name):
+    cond = Condition.when(**kwargs)
+    assert cond.name == expected_name
+
+
+def test_condition_when_operators_combined():
+    """Test multiple operators ANDed together."""
+    cond = Condition.when(age__gte=18, status="active", score__lt=100)
+    assert cond.run(State({"age": 20, "status": "active", "score": 50})) == {Condition.KEY: True}
+    assert cond.run(State({"age": 17, "status": "active", "score": 50})) == {Condition.KEY: False}
+    assert cond.run(State({"age": 20, "status": "inactive", "score": 50})) == {Condition.KEY: False}
+    assert cond.run(State({"age": 20, "status": "active", "score": 100})) == {Condition.KEY: False}
+
+
+def test_condition_when_operators_with_invert():
+    """Ensure operator-based conditions work with ~ (invert)."""
+    cond = ~Condition.when(age__gte=18)
+    assert cond.run(State({"age": 17})) == {Condition.KEY: True}
+    assert cond.run(State({"age": 18})) == {Condition.KEY: False}
+
+
+def test_condition_when_operators_with_or():
+    """Ensure operator-based conditions work with | (or)."""
+    cond = Condition.when(age__lt=13) | Condition.when(age__gte=65)
+    assert cond.run(State({"age": 10})) == {Condition.KEY: True}
+    assert cond.run(State({"age": 70})) == {Condition.KEY: True}
+    assert cond.run(State({"age": 30})) == {Condition.KEY: False}
+
+
+def test_condition_when_operators_with_and():
+    """Ensure operator-based conditions work with & (and)."""
+    cond = Condition.when(age__gte=18) & Condition.when(age__lt=65)
+    assert cond.run(State({"age": 30})) == {Condition.KEY: True}
+    assert cond.run(State({"age": 17})) == {Condition.KEY: False}
+    assert cond.run(State({"age": 65})) == {Condition.KEY: False}
+
+
+def test_condition_when_invalid_key():
+    """Empty state key before operator suffix should raise."""
+    with pytest.raises(ValueError, match="no state key"):
+        Condition.when(__gte=18)
+
+
 def test_condition_default():
     cond = default
     assert cond.name == "default"