diff --git a/src/specify_cli/workflows/expressions.py b/src/specify_cli/workflows/expressions.py
index 2dc474a140..e2cd9ce215 100644
--- a/src/specify_cli/workflows/expressions.py
+++ b/src/specify_cli/workflows/expressions.py
@@ -578,6 +578,40 @@ def _is_wrapped_in_parens(text: str) -> bool:
     return False
 
 
+def _collapse_whitespace(text: str) -> str:
+    """Strip *text* and turn each run of whitespace outside a quoted string into
+    one space.
+
+    The operator scans below match word operators by their surrounding spaces
+    (``" or "``, ``" not in "``, ``expr.startswith("not ")``), so an operator
+    next to a newline or tab was never found. A condition wrapped across lines
+    in YAML keeps those newlines -- a ``|`` block scalar keeps every one, and a
+    ``>`` folded scalar keeps the break before a more-indented continuation
+    line -- so ``{{ inputs.a or\\n   inputs.b }}`` was resolved as one dot path,
+    came back ``None``, and read false with no error. Jinja2 treats any
+    whitespace between tokens alike; so does this, while quoted operands keep
+    their text exactly.
+    """
+    out: list[str] = []
+    quote: str | None = None
+    pending_space = False
+    for ch in text.strip():
+        if quote is not None:
+            out.append(ch)
+            if ch == quote:
+                quote = None
+        elif ch.isspace():
+            pending_space = True
+        else:
+            if pending_space:
+                out.append(" ")
+                pending_space = False
+            if ch in ("'", '"'):
+                quote = ch
+            out.append(ch)
+    return "".join(out)
+
+
 def _evaluate_simple_expression(expr: str, namespace: dict[str, Any]) -> Any:
     """Evaluate a simple expression against the namespace.
 
@@ -589,7 +623,7 @@ def _evaluate_simple_expression(expr: str, namespace: dict[str, Any]) -> Any:
     - Pipe filters: ``| default('...')``, ``| join(', ')``, ``| contains('...')``, ``| from_json``, ``| map('...')``
     - String and numeric literals
     """
-    expr = expr.strip()
+    expr = _collapse_whitespace(expr)
 
     # String literal — only when the WHOLE expression is one quoted string,
     # i.e. the opening quote's matching close is the final character. Checking
diff --git a/tests/test_workflows.py b/tests/test_workflows.py
index acfdaa0b3b..25c2a79eb1 100644
--- a/tests/test_workflows.py
+++ b/tests/test_workflows.py
@@ -1030,6 +1030,64 @@ def test_parenthesised_grouping(self):
         assert evaluate_expression("{{ 'a(b' }}", ctx) == "a(b"
         assert evaluate_expression("{{ ('(') }}", ctx) == "("
 
+    @pytest.mark.parametrize(
+        ("expression", "expected"),
+        [
+            ("{{ inputs.b or\n  inputs.a }}", True),
+            ("{{ inputs.a and\n  inputs.c }}", True),
+            ("{{ inputs.b\nor inputs.a }}", True),
+            ("{{ inputs.a\tand inputs.c }}", True),
+            ("{{ not\n  inputs.b }}", True),
+            ("{{ 'x' in\n  inputs.tags }}", True),
+            ("{{ 'z' not\n  in inputs.tags }}", True),
+            ("{{ 'z' not in\n  inputs.tags }}", True),
+            ("{{ (inputs.b or\r\n  inputs.a) and inputs.c }}", True),
+        ],
+    )
+    def test_operators_separated_by_any_whitespace(self, expression, expected):
+        """Word operators are found across newlines and tabs, as in Jinja2.
+
+        The operator scans match ``" or "`` and friends by their spaces, so an
+        operator next to a line break was never split on: the whole expression
+        was looked up as one dot path and came back ``None`` -- a false
+        condition with no error.
+        """
+        from specify_cli.workflows.expressions import evaluate_expression
+        from specify_cli.workflows.base import StepContext
+
+        ctx = StepContext(
+            inputs={"a": True, "b": False, "c": True, "mode": "fast", "tags": ["x", "y"]}
+        )
+        assert evaluate_expression(expression, ctx) is expected
+
+    def test_condition_wrapped_across_lines_in_yaml(self):
+        """A long condition broken after its operator keeps the line break in
+        YAML (the continuation line is more indented, so ``>`` does not fold
+        it), and still has to evaluate as written."""
+        from specify_cli.workflows.expressions import evaluate_condition
+        from specify_cli.workflows.base import StepContext
+
+        step = yaml.safe_load(
+            "condition: >-\n"
+            "  {{ inputs.skip_review or\n"
+            "     inputs.scope == 'docs' }}\n"
+        )
+        assert "\n" in step["condition"]
+
+        ctx = StepContext(inputs={"skip_review": False, "scope": "docs"})
+        assert evaluate_condition(step["condition"], ctx) is True
+
+    def test_whitespace_inside_quoted_operand_is_kept(self):
+        """Collapsing whitespace between tokens leaves string literals alone."""
+        from specify_cli.workflows.expressions import evaluate_expression
+        from specify_cli.workflows.base import StepContext
+
+        ctx = StepContext(inputs={"title": "two  spaces", "text": "tab\there"})
+        assert evaluate_expression("{{ inputs.title == 'two  spaces' }}", ctx) is True
+        assert evaluate_expression("{{ inputs.title == 'two spaces' }}", ctx) is False
+        assert evaluate_expression("{{ inputs.text\n  == 'tab\there' }}", ctx) is True
+        assert evaluate_expression("{{ 'a  or  b' }}", ctx) == "a  or  b"
+
     def test_list_indexing(self):
         from specify_cli.workflows.expressions import evaluate_expression
         from specify_cli.workflows.base import StepContext
diff --git a/tests/unit/test_condition_expression_block.py b/tests/unit/test_condition_expression_block.py
index f13a830526..591d7d11a4 100644
--- a/tests/unit/test_condition_expression_block.py
+++ b/tests/unit/test_condition_expression_block.py
@@ -560,10 +560,6 @@ def test_incomplete_operand_covers_every_operator_the_evaluator_splits_on():
     ("inputs.a === inputs.b", "is not a name the evaluator can resolve"),
     ("bogus == 'x'", "is not one of the namespace roots"),
     ("inputs.payload | from_json()", "the evaluator rejects it"),
-    # `_find_top_level` matches " and " with literal spaces, so a newline before
-    # the keyword is not an operator: the wrapped form evaluates False where the
-    # same expression with a space evaluates True.
-    ("inputs.x == 1\nand inputs.name == 'abc'", "is not a name the evaluator can resolve"),
 ]
 
 
@@ -578,6 +574,25 @@ def test_gates_inspect_every_position_not_just_the_first(step_cls, condition, ex
     assert expected in errors[0]
 
 
+@pytest.mark.parametrize("step_cls", STEP_CLASSES)
+def test_a_condition_wrapped_across_lines_gets_a_paste_ready_correction(step_cls):
+    """A line break before ``and`` no longer hides the operator.
+
+    The evaluator used to match " and " with literal spaces, so the wrapped form
+    of this condition read False where the one-line form read True, and the gate
+    had to withhold the correction. It now splits on any whitespace, so wrapping
+    repairs the condition and the correction is offered.
+    """
+    condition = "inputs.x == 1\nand inputs.name == 'abc'"
+    config = {"id": "s1", "condition": condition, "then": [], "steps": []}
+    errors = [e for e in step_cls().validate(config) if "'condition'" in e]
+
+    assert len(errors) == 1
+    assert "Wrap the expression" in errors[0]
+    ctx = StepContext(inputs={"x": 1, "name": "abc"})
+    assert evaluate_condition("{{ " + condition + " }}", ctx) is True
+
+
 @pytest.mark.parametrize(
     "text,unbalanced",
     [