diff --git a/libs/preprocessor/src/processor/mod.rs b/libs/preprocessor/src/processor/mod.rs
index c07319a0..92c50654 100644
--- a/libs/preprocessor/src/processor/mod.rs
+++ b/libs/preprocessor/src/processor/mod.rs
@@ -138,7 +138,12 @@ impl Processor {
                 }
                 (Symbol::Directive, false) => {
                     let token = stream.next().expect("peeked above");
-                    if in_macro.is_some() && stream.peek().map_or(false, |t| t.symbol().is_word()) {
+                    if in_macro.is_some()
+                        && stream.peek().map_or(false, |t| t.symbol().is_word())
+                        // check if the # token is from another file, or defined before the callsite, ie not in the root arguments
+                        && (token.position().path() != callsite.unwrap().path()
+                            || token.position().start().0 < callsite.unwrap().start().0)
+                    {
                         self.output(
                             Token::new(Symbol::DoubleQuote, token.position().clone()),
                             buffer,
diff --git a/libs/preprocessor/tests/bootstrap.rs b/libs/preprocessor/tests/bootstrap.rs
index 9d79f88c..f87bec05 100644
--- a/libs/preprocessor/tests/bootstrap.rs
+++ b/libs/preprocessor/tests/bootstrap.rs
@@ -41,34 +41,35 @@ bootstrap!(cba_is_admin);
 bootstrap!(cba_multiline);
 bootstrap!(comment_edgecase);
 bootstrap!(define_builtin);
-bootstrap!(define_function);
 bootstrap!(define_function_empty);
 bootstrap!(define_function_multiline);
+bootstrap!(define_function);
 bootstrap!(define_inside_else);
 bootstrap!(define_multi);
-bootstrap!(define_nested);
 bootstrap!(define_nested_nested);
+bootstrap!(define_nested);
 bootstrap!(define_single);
 bootstrap!(define_undef);
 bootstrap!(define_use_define);
 bootstrap!(define_with_dash);
+bootstrap!(hashtag_outside_macro);
 bootstrap!(if_nested);
 bootstrap!(if_operators);
 bootstrap!(if_pass);
 bootstrap!(if_read);
 bootstrap!(if_value);
 bootstrap!(ignore_quoted);
-bootstrap!(include);
 bootstrap!(include_empty);
+bootstrap!(include);
 bootstrap!(join_digit);
 bootstrap!(join_ignore);
 bootstrap!(name_collision);
 bootstrap!(procedural_texture);
-bootstrap!(quote);
 bootstrap!(quote_recursive);
+bootstrap!(quote);
 bootstrap!(redefine_external);
 bootstrap!(self_recursion);
-bootstrap!(sqf);
 bootstrap!(sqf_select);
+bootstrap!(sqf);
 bootstrap!(strings);
 bootstrap!(utf);
diff --git a/libs/preprocessor/tests/bootstrap/hashtag_outside_macro/expected.hpp b/libs/preprocessor/tests/bootstrap/hashtag_outside_macro/expected.hpp
new file mode 100644
index 00000000..136bbb63
--- /dev/null
+++ b/libs/preprocessor/tests/bootstrap/hashtag_outside_macro/expected.hpp
@@ -0,0 +1,2 @@
+
+"#structural"
diff --git a/libs/preprocessor/tests/bootstrap/hashtag_outside_macro/source.hpp b/libs/preprocessor/tests/bootstrap/hashtag_outside_macro/source.hpp
new file mode 100644
index 00000000..fdfb1314
--- /dev/null
+++ b/libs/preprocessor/tests/bootstrap/hashtag_outside_macro/source.hpp
@@ -0,0 +1,3 @@
+#define QOUTE(s) #s
+
+QOUTE(#structural)