diff --git a/src/specify_cli/workflows/expressions.py b/src/specify_cli/workflows/expressions.py
index a38cd6cb68..38a29890ae 100644
--- a/src/specify_cli/workflows/expressions.py
+++ b/src/specify_cli/workflows/expressions.py
@@ -671,8 +671,20 @@ def evaluate_condition(condition: str, context: Any) -> bool:
     result = evaluate_expression(condition, context)
     # Treat plain "false"/"true" strings as booleans so that
     # condition: "false" (without {{ }}) behaves as expected.
+    #
+    # Strip before matching: the string a condition resolves to is most often
+    # captured command output, and a ``shell`` step stores ``proc.stdout``
+    # verbatim, so ``run: echo false`` resolves to ``"false\n"``. Without the
+    # strip that trailing newline matches neither branch and falls through to
+    # ``bool("false\n")`` -> True, silently taking an ``if`` step's ``then``
+    # branch (and keeping a ``while``/``do-while`` looping) on a step that
+    # printed "false". A workflow cannot strip it itself -- the registered
+    # filters are default/join/map/contains/from_json, there is no ``trim``.
+    # ``InitStep._resolve_bool`` and the catalog readers already strip before
+    # matching boolean text. ``bool(result)`` below still sees the raw string,
+    # so no non-boolean text changes truthiness.
     if isinstance(result, str):
-        lower = result.lower()
+        lower = result.strip().lower()
         if lower == "false":
             return False
         if lower == "true":
diff --git a/tests/test_workflows.py b/tests/test_workflows.py
index 57536081ea..295803d4b5 100644
--- a/tests/test_workflows.py
+++ b/tests/test_workflows.py
@@ -783,6 +783,39 @@ def test_condition_evaluation(self):
         assert evaluate_condition("{{ inputs.ready }}", ctx) is True
         assert evaluate_condition("{{ inputs.missing }}", ctx) is False
 
+    def test_condition_strips_captured_command_output(self):
+        """A condition resolving to captured stdout must honour "false".
+
+        A ``shell`` step stores ``proc.stdout`` verbatim, so ``run: echo false``
+        resolves to ``"false\\n"``. Without stripping, the trailing newline
+        matched neither the "false" nor the "true" branch and fell through to
+        ``bool("false\\n")`` -> True, so an ``if`` step took its ``then`` branch
+        on a step that printed "false". There is no ``trim`` filter, so a
+        workflow author cannot strip it themselves.
+        """
+        from specify_cli.workflows.expressions import evaluate_condition
+        from specify_cli.workflows.base import StepContext
+
+        ctx = StepContext(steps={"check": {"output": {"stdout": "false\n"}}})
+        assert evaluate_condition("{{ steps.check.output.stdout }}", ctx) is False
+
+        for raw in ("false\n", "false\r\n", " false", "false ", "FALSE\n"):
+            assert evaluate_condition(raw, StepContext()) is False, raw
+        for raw in ("true\n", " true ", "TRUE\r\n"):
+            assert evaluate_condition(raw, StepContext()) is True, raw
+
+    def test_condition_whitespace_only_string_stays_truthy(self):
+        """Stripping must not turn a whitespace-only string into False.
+
+        Only the "false"/"true" special case is stripped; everything else still
+        falls through to ``bool(result)`` on the raw string.
+        """
+        from specify_cli.workflows.expressions import evaluate_condition
+        from specify_cli.workflows.base import StepContext
+
+        assert evaluate_condition("   ", StepContext()) is True
+        assert evaluate_condition("falsey", StepContext()) is True
+
     def test_non_string_passthrough(self):
         from specify_cli.workflows.expressions import evaluate_expression
         from specify_cli.workflows.base import StepContext