diff --git a/src/specify_cli/workflows/expressions.py b/src/specify_cli/workflows/expressions.py
index b7ed17e801..b3e1de8016 100644
--- a/src/specify_cli/workflows/expressions.py
+++ b/src/specify_cli/workflows/expressions.py
@@ -383,9 +383,25 @@ def evaluate_expression(template: str, context: Any) -> Any:
 
     namespace = _build_namespace(context)
 
-    # Single expression: return typed value
-    match = _EXPR_PATTERN.fullmatch(template.strip())
-    if match:
+    # Single expression: return typed value (preserving type).
+    #
+    # The fast path must fire only when the whole template is one ``{{ ... }}``
+    # block. ``fullmatch`` cannot decide this: the pattern's non-greedy body
+    # ``(.+?)`` is defeated by ``fullmatch``, so ``"{{ a }} {{ b }}"`` still
+    # matches with the body expanded to ``"a }} {{ b"`` -- garbage that fails
+    # resolution and returns ``None``, bypassing the ``sub()`` interpolation
+    # path that handles each expression correctly (issue #3208).
+    #
+    # Anchor a single match at the start instead and require it to consume the
+    # entire stripped string. The non-greedy body then stops at the first
+    # ``}}``: a genuine two-block template leaves a trailing ``}}`` and fails the
+    # span check, while a lone expression -- even one with a literal ``{{`` in a
+    # string argument such as ``{{ inputs.text | contains('{{') }}`` -- matches
+    # to the end and keeps its typed return value. (Counting ``{{`` would
+    # misclassify that expression as multi-block and coerce it to ``str``.)
+    stripped = template.strip()
+    match = _EXPR_PATTERN.match(stripped)
+    if match and match.end() == len(stripped):
         return _evaluate_simple_expression(match.group(1).strip(), namespace)
 
     # Multi-expression: string interpolation
diff --git a/tests/test_workflows.py b/tests/test_workflows.py
index 988730d783..8e6393b963 100644
--- a/tests/test_workflows.py
+++ b/tests/test_workflows.py
@@ -226,6 +226,40 @@ def test_string_interpolation(self):
         result = evaluate_expression("Feature: {{ inputs.name }} done", ctx)
         assert result == "Feature: login done"
 
+    def test_multi_expression_no_surrounding_text(self):
+        """Two expressions with no surrounding literal text must interpolate each,
+        not collapse to None via the fullmatch fast path (#3208)."""
+        from specify_cli.workflows.expressions import evaluate_expression
+        from specify_cli.workflows.base import StepContext
+
+        ctx = StepContext(inputs={"issue": "23"}, run_id="47c5eb4b")
+        result = evaluate_expression(
+            "{{ context.run_id }} {{ inputs.issue }}", ctx
+        )
+        assert result == "47c5eb4b 23"
+
+    def test_multi_expression_adjacent_no_separator(self):
+        """Back-to-back expressions with no separator still interpolate (#3208)."""
+        from specify_cli.workflows.expressions import evaluate_expression
+        from specify_cli.workflows.base import StepContext
+
+        ctx = StepContext(inputs={"a": "foo", "b": "bar"})
+        result = evaluate_expression("{{ inputs.a }}{{ inputs.b }}", ctx)
+        assert result == "foobar"
+
+    def test_single_expression_with_literal_braces_preserves_type(self):
+        """A lone expression whose string argument contains a literal ``{{`` or ``}}``
+        must still take the typed fast path and return a bool, not a string
+        (the fix for #3208 must not coerce it to ``\"True\"``)."""
+        from specify_cli.workflows.expressions import evaluate_expression
+        from specify_cli.workflows.base import StepContext
+
+        ctx = StepContext(inputs={"text": "uses {{ jinja }} syntax"})
+        assert evaluate_expression("{{ inputs.text | contains('{{') }}", ctx) is True
+
+        ctx = StepContext(inputs={"text": "uses }} syntax"})
+        assert evaluate_expression("{{ inputs.text | contains('}}') }}", ctx) is True
+
     def test_comparison_equals(self):
         from specify_cli.workflows.expressions import evaluate_expression
         from specify_cli.workflows.base import StepContext