diff --git a/prost-build/src/config.rs b/prost-build/src/config.rs
index af57497f1..a696e404b 100644
--- a/prost-build/src/config.rs
+++ b/prost-build/src/config.rs
@@ -826,8 +826,8 @@ impl Config {
             self.write_includes(
                 modules.keys().collect(),
                 &mut file,
-                0,
                 if target_is_env { None } else { Some(&target) },
+                &file_names,
             )?;
             file.flush()?;
         }
@@ -955,67 +955,58 @@ impl Config {
         self.compile_fds(file_descriptor_set)
     }
 
-    fn write_includes(
+    pub(crate) fn write_includes(
         &self,
-        mut entries: Vec<&Module>,
-        outfile: &mut fs::File,
-        depth: usize,
+        mut modules: Vec<&Module>,
+        outfile: &mut impl Write,
         basepath: Option<&PathBuf>,
-    ) -> Result<usize> {
-        let mut written = 0;
-        entries.sort();
-
-        while !entries.is_empty() {
-            let modident = entries[0].part(depth);
-            let matching: Vec<&Module> = entries
-                .iter()
-                .filter(|&v| v.part(depth) == modident)
-                .copied()
-                .collect();
-            {
-                // Will NLL sort this mess out?
-                let _temp = entries
-                    .drain(..)
-                    .filter(|&v| v.part(depth) != modident)
-                    .collect();
-                entries = _temp;
+        file_names: &HashMap<Module, String>,
+    ) -> Result<()> {
+        modules.sort();
+
+        let mut stack = Vec::new();
+
+        for module in modules {
+            while !module.starts_with(&stack) {
+                stack.pop();
+                self.write_line(outfile, stack.len(), "}")?;
             }
-            self.write_line(outfile, depth, &format!("pub mod {} {{", modident))?;
-            let subwritten = self.write_includes(
-                matching
-                    .iter()
-                    .filter(|v| v.len() > depth + 1)
-                    .copied()
-                    .collect(),
-                outfile,
-                depth + 1,
-                basepath,
-            )?;
-            written += subwritten;
-            if subwritten != matching.len() {
-                let modname = matching[0].to_partial_file_name(..=depth);
-                if basepath.is_some() {
-                    self.write_line(
-                        outfile,
-                        depth + 1,
-                        &format!("include!(\"{}.rs\");", modname),
-                    )?;
-                } else {
-                    self.write_line(
-                        outfile,
-                        depth + 1,
-                        &format!("include!(concat!(env!(\"OUT_DIR\"), \"/{}.rs\"));", modname),
-                    )?;
-                }
-                written += 1;
+            while stack.len() < module.len() {
+                self.write_line(
+                    outfile,
+                    stack.len(),
+                    &format!("pub mod {} {{", module.part(stack.len())),
+                )?;
+                stack.push(module.part(stack.len()).to_owned());
             }
 
+            let file_name = file_names
+                .get(module)
+                .expect("every module should have a filename");
+
+            if basepath.is_some() {
+                self.write_line(
+                    outfile,
+                    stack.len(),
+                    &format!("include!(\"{}\");", file_name),
+                )?;
+            } else {
+                self.write_line(
+                    outfile,
+                    stack.len(),
+                    &format!("include!(concat!(env!(\"OUT_DIR\"), \"/{}\"));", file_name),
+                )?;
+            }
+        }
+
+        for depth in (0..stack.len()).rev() {
             self.write_line(outfile, depth, "}")?;
         }
-        Ok(written)
+
+        Ok(())
     }
 
-    fn write_line(&self, outfile: &mut fs::File, depth: usize, line: &str) -> Result<()> {
+    fn write_line(&self, outfile: &mut impl Write, depth: usize, line: &str) -> Result<()> {
         outfile.write_all(format!("{}{}\n", ("    ").to_owned().repeat(depth), line).as_bytes())
     }
 
diff --git a/prost-build/src/fixtures/write_includes/_.includes.rs b/prost-build/src/fixtures/write_includes/_.includes.rs
new file mode 100644
index 000000000..99b555635
--- /dev/null
+++ b/prost-build/src/fixtures/write_includes/_.includes.rs
@@ -0,0 +1,23 @@
+include!(concat!(env!("OUT_DIR"), "/_.default.rs"));
+pub mod bar {
+    include!(concat!(env!("OUT_DIR"), "/bar.rs"));
+}
+pub mod foo {
+    include!(concat!(env!("OUT_DIR"), "/foo.rs"));
+    pub mod bar {
+        include!(concat!(env!("OUT_DIR"), "/foo.bar.rs"));
+        pub mod a {
+            pub mod b {
+                pub mod c {
+                    include!(concat!(env!("OUT_DIR"), "/foo.bar.a.b.c.rs"));
+                }
+            }
+        }
+        pub mod baz {
+            include!(concat!(env!("OUT_DIR"), "/foo.bar.baz.rs"));
+        }
+        pub mod qux {
+            include!(concat!(env!("OUT_DIR"), "/foo.bar.qux.rs"));
+        }
+    }
+}
diff --git a/prost-build/src/lib.rs b/prost-build/src/lib.rs
index a3c62d60b..304f82e4b 100644
--- a/prost-build/src/lib.rs
+++ b/prost-build/src/lib.rs
@@ -530,4 +530,32 @@ mod tests {
         f.read_to_string(&mut content).unwrap();
         content
     }
+
+    #[test]
+    fn write_includes() {
+        let modules = [
+            Module::from_protobuf_package_name("foo.bar.baz"),
+            Module::from_protobuf_package_name(""),
+            Module::from_protobuf_package_name("foo.bar"),
+            Module::from_protobuf_package_name("bar"),
+            Module::from_protobuf_package_name("foo"),
+            Module::from_protobuf_package_name("foo.bar.qux"),
+            Module::from_protobuf_package_name("foo.bar.a.b.c"),
+        ];
+
+        let file_names = modules
+            .iter()
+            .map(|m| (m.clone(), m.to_file_name_or("_.default")))
+            .collect();
+
+        let mut buf = Vec::new();
+        Config::new()
+            .default_package_filename("_.default")
+            .write_includes(modules.iter().collect(), &mut buf, None, &file_names)
+            .unwrap();
+        let expected =
+            read_all_content("src/fixtures/write_includes/_.includes.rs").replace("\r\n", "\n");
+        let actual = String::from_utf8(buf).unwrap();
+        assert_eq!(expected, actual);
+    }
 }
diff --git a/prost-build/src/module.rs b/prost-build/src/module.rs
index 21cab1163..02715c16e 100644
--- a/prost-build/src/module.rs
+++ b/prost-build/src/module.rs
@@ -1,5 +1,4 @@
 use std::fmt;
-use std::ops::RangeToInclusive;
 
 use crate::ident::to_snake;
 
@@ -40,6 +39,15 @@ impl Module {
         self.components.iter().map(|s| s.as_str())
     }
 
+    #[must_use]
+    #[inline(always)]
+    pub(crate) fn starts_with(&self, needle: &[String]) -> bool
+    where
+        String: PartialEq,
+    {
+        self.components.starts_with(needle)
+    }
+
     /// Format the module path into a filename for generated Rust code.
     ///
     /// If the module path is empty, `default` is used to provide the root of the filename.
@@ -65,10 +73,6 @@ impl Module {
         self.components.is_empty()
     }
 
-    pub(crate) fn to_partial_file_name(&self, range: RangeToInclusive<usize>) -> String {
-        self.components[range].join(".")
-    }
-
     pub(crate) fn part(&self, idx: usize) -> &str {
         self.components[idx].as_str()
     }
diff --git a/tests/src/build.rs b/tests/src/build.rs
index 7b2c0bc5e..0403d2603 100644
--- a/tests/src/build.rs
+++ b/tests/src/build.rs
@@ -178,6 +178,7 @@ fn main() {
     no_root_packages_config
         .out_dir(&no_root_packages)
         .default_package_filename("__.default")
+        .include_file("__.include.rs")
         .compile_protos(
             &[src.join("no_root_packages/widget_factory.proto")],
             &[src.join("no_root_packages")],
diff --git a/tests/src/no_root_packages/mod.rs b/tests/src/no_root_packages/mod.rs
index 2025eb983..7ef3b4c4e 100644
--- a/tests/src/no_root_packages/mod.rs
+++ b/tests/src/no_root_packages/mod.rs
@@ -16,6 +16,10 @@ pub mod widget {
     }
 }
 
+pub mod generated_include {
+    include!(concat!(env!("OUT_DIR"), "/no_root_packages/__.include.rs"));
+}
+
 #[test]
 fn test() {
     use prost::Message;
@@ -44,3 +48,32 @@ fn test() {
     widget_factory.gizmo_inner = Some(gizmo::gizmo::Inner {});
     assert_eq!(14, widget_factory.encoded_len());
 }
+
+#[test]
+fn generated_include() {
+    use prost::Message;
+
+    let mut widget_factory = generated_include::widget::factory::WidgetFactory::default();
+    assert_eq!(0, widget_factory.encoded_len());
+
+    widget_factory.inner = Some(generated_include::widget::factory::widget_factory::Inner {});
+    assert_eq!(2, widget_factory.encoded_len());
+
+    widget_factory.root = Some(generated_include::Root {});
+    assert_eq!(4, widget_factory.encoded_len());
+
+    widget_factory.root_inner = Some(generated_include::root::Inner {});
+    assert_eq!(6, widget_factory.encoded_len());
+
+    widget_factory.widget = Some(generated_include::widget::Widget {});
+    assert_eq!(8, widget_factory.encoded_len());
+
+    widget_factory.widget_inner = Some(generated_include::widget::widget::Inner {});
+    assert_eq!(10, widget_factory.encoded_len());
+
+    widget_factory.gizmo = Some(generated_include::gizmo::Gizmo {});
+    assert_eq!(12, widget_factory.encoded_len());
+
+    widget_factory.gizmo_inner = Some(generated_include::gizmo::gizmo::Inner {});
+    assert_eq!(14, widget_factory.encoded_len());
+}