diff --git a/crates/typos-cli/src/file_type.rs b/crates/typos-cli/src/file_type.rs
index afaff6f..c5787b6 100644
--- a/crates/typos-cli/src/file_type.rs
+++ b/crates/typos-cli/src/file_type.rs
@@ -107,9 +107,15 @@ impl Types {
     }
 
     pub fn file_matched(&self, path: &std::path::Path) -> Option<&str> {
-        let file_name = path.file_name()?.to_str()?.trim_end_matches(".in");
+        let mut file_name = path.file_name()?.to_str()?;
         let mut matches = self.matches.get_or_default().borrow_mut();
-        self.set.matches_into(file_name, &mut *matches);
+        loop {
+            self.set.matches_into(file_name, &mut *matches);
+            if !matches.is_empty() || !file_name.ends_with(".in") {
+                break;
+            }
+            file_name = file_name.strip_suffix(".in")?;
+        }
         matches
             .last()
             .copied()
@@ -145,16 +151,22 @@ mod tests {
             ("js", &["*.js"]),
             ("json", &["*.json"]),
             ("lock", &["package-lock.json", "*.lock"]),
+            ("js-in", &["*.js.in"]),
         ]
     }
+    fn in_types() -> &'static [(&'static str, &'static [&'static str])] {
+        &[("html", &["*.html", "*.htm"]), ("in-canary", &["*.in"])]
+    }
 
     matched!(basic_match, types(), "leftpad.js", "js");
     matched!(multi_def_1, types(), "index.html", "html");
     matched!(multi_def_2, types(), "index.htm", "html");
     matched!(no_match, types(), "leftpad.ada", None);
     matched!(more_specific, types(), "package-lock.json", "lock");
-    matched!(trailing_in, types(), "index.html.in", "html");
-    matched!(trailing_in_in, types(), "index.html.in.in", "html");
+    matched!(basic_in, types(), "index.html.in", "html");
+    matched!(basic_in_in, types(), "index.html.in.in", "html");
+    matched!(ext_plus_in, types(), "foo.js.in", "js-in");
+    matched!(toplevel_in, in_types(), "index.html.in", "in-canary");
 
     macro_rules! sort {
         ($name:ident, $actual:expr, $expected:expr) => {