diff --git a/crates/nu-engine/src/compile/operator.rs b/crates/nu-engine/src/compile/operator.rs
index 6e127c8d5b..2a913f8836 100644
--- a/crates/nu-engine/src/compile/operator.rs
+++ b/crates/nu-engine/src/compile/operator.rs
@@ -70,6 +70,8 @@ pub(crate) fn compile_binary_op(
                     Boolean::Xor => unreachable!(),
                 };
 
+                // Before match against lhs_reg, it's important to collect it first to get a concrete value if there is a subexpression.
+                builder.push(Instruction::Collect { src_dst: lhs_reg }.into_spanned(lhs.span))?;
                 // Short-circuit to return `lhs_reg`. `match` op does not consume `lhs_reg`.
                 let short_circuit_label = builder.label(None);
                 builder.r#match(
diff --git a/tests/shell/pipeline/commands/external.rs b/tests/shell/pipeline/commands/external.rs
index e5c6915565..c0cf8e1adb 100644
--- a/tests/shell/pipeline/commands/external.rs
+++ b/tests/shell/pipeline/commands/external.rs
@@ -717,3 +717,11 @@ fn external_error_with_backtrace() {
         assert_eq!(chained_error_cnt.len(), 0);
     });
 }
+
+#[test]
+fn sub_external_expression_with_and_op_should_raise_proper_error() {
+    let actual = nu!("(nu --testbin cococo false) and true");
+    assert!(actual
+        .err
+        .contains("The 'and' operator does not work on values of type 'string'"))
+}