diff --git a/crates/spfs-vfs/src/winfsp/mount.rs b/crates/spfs-vfs/src/winfsp/mount.rs
index e992f6e995..3e8809c748 100644
--- a/crates/spfs-vfs/src/winfsp/mount.rs
+++ b/crates/spfs-vfs/src/winfsp/mount.rs
@@ -171,12 +171,10 @@ impl Mount {
             return None;
         };
 
-        const TRIM_START: &[char] = &['/', '.'];
         const TRIM_END: &[char] = &['/'];
         let path = str_path.replace('\\', "/");
-        let path = path
-            .trim_start_matches(TRIM_START)
-            .trim_end_matches(TRIM_END);
+        let path =
+            spfs::tracking::Manifest::trim_leading_slash(path.as_str()).trim_end_matches(TRIM_END);
         let mut entry = self
             .inodes
             .get(&ROOT_INODE)
diff --git a/crates/spfs/src/tracking/manifest.rs b/crates/spfs/src/tracking/manifest.rs
index dfbefc26b2..ba390f74e7 100644
--- a/crates/spfs/src/tracking/manifest.rs
+++ b/crates/spfs/src/tracking/manifest.rs
@@ -115,12 +115,8 @@ impl<T> Manifest<T> {
 
     /// Get an entry in this manifest given its filepath.
     pub fn get_path<P: AsRef<str>>(&self, path: P) -> Option<&Entry<T>> {
-        const TRIM_START: &[char] = &['/', '.'];
         const TRIM_END: &[char] = &['/'];
-        let path = path
-            .as_ref()
-            .trim_start_matches(TRIM_START)
-            .trim_end_matches(TRIM_END);
+        let path = Self::trim_leading_slash(path.as_ref()).trim_end_matches(TRIM_END);
         let mut entry = &self.root;
         if path.is_empty() {
             return Some(entry);
@@ -228,8 +224,7 @@ where
     /// file mode, but can and should be replaced by a new entry in the
     /// case where this is not desired.
     pub fn mkdirs<P: AsRef<str>>(&mut self, path: P) -> MkResult<&mut Entry<T>> {
-        const TRIM_PAT: &[char] = &['/', '.'];
-        let path = path.as_ref().trim_start_matches(TRIM_PAT);
+        let path = Self::trim_leading_slash(path.as_ref());
         if path.is_empty() {
             return Err(MkError::AlreadyExists(path.into()));
         }
@@ -262,15 +257,31 @@ where
 }
 
 impl<T> Manifest<T> {
+    /// Remove any leading '/' or elements at the front of the path that are
+    /// redundant, like "/./".
+    #[inline]
+    pub fn trim_leading_slash(path: &str) -> &str {
+        match *path.as_bytes() {
+            [b'.', b'/', ref rest @ ..] => {
+                // Safety: we know that the rest of the path is valid utf-8
+                Self::trim_leading_slash(unsafe { std::str::from_utf8_unchecked(rest) })
+            }
+            [b'/', ref rest @ ..] => {
+                // Safety: we know that the rest of the path is valid utf-8
+                Self::trim_leading_slash(unsafe { std::str::from_utf8_unchecked(rest) })
+            }
+            _ => path,
+        }
+    }
+
     pub fn mknod<P: AsRef<str>>(
         &mut self,
         path: P,
         new_entry: Entry<T>,
     ) -> MkResult<&mut Entry<T>> {
         use relative_path::Component;
-        const TRIM_PAT: &[char] = &['/', '.'];
 
-        let path = path.as_ref().trim_start_matches(TRIM_PAT);
+        let path = Self::trim_leading_slash(path.as_ref());
         if path.is_empty() {
             return Err(MkError::AlreadyExists(path.into()));
         }
diff --git a/crates/spk-cli/cmd-build/src/cmd_build_test/mod.rs b/crates/spk-cli/cmd-build/src/cmd_build_test/mod.rs
index c7020245dd..129f7342e9 100644
--- a/crates/spk-cli/cmd-build/src/cmd_build_test/mod.rs
+++ b/crates/spk-cli/cmd-build/src/cmd_build_test/mod.rs
@@ -653,3 +653,78 @@ build:
         .await
         .unwrap();
 }
+
+/// A package may contain files/directories with a leading dot
+#[rstest]
+#[tokio::test]
+async fn test_dot_files_are_collected(tmpdir: tempfile::TempDir) {
+    let rt = spfs_runtime().await;
+
+    build_package!(
+        tmpdir,
+        "dot.spk.yaml",
+        br#"
+api: v0/package
+pkg: dot/1.0.0
+build:
+  script:
+    - touch /spfs/no_dot
+    - touch /spfs/.dot
+    - mkdir /spfs/dot
+    - touch /spfs/dot/.dot
+    - mkdir /spfs/.dot2
+    - touch /spfs/.dot2/dot
+    - touch /spfs/.dot2/.dot
+    - ln -s .dot2 /spfs/.dot3
+"#,
+    );
+
+    let build = rt
+        .tmprepo
+        .list_package_builds(&version_ident!("dot/1.0.0"))
+        .await
+        .unwrap()
+        .into_iter()
+        .find(|b| !b.is_source())
+        .unwrap();
+
+    let digest = *rt
+        .tmprepo
+        .read_components(&build)
+        .await
+        .unwrap()
+        .get(&Component::Run)
+        .unwrap();
+
+    let spk_storage::RepositoryHandle::SPFS(repo) = &*rt.tmprepo else {
+        panic!("Expected SPFS repo");
+    };
+
+    let layer = repo.read_layer(digest).await.unwrap();
+
+    let manifest = repo
+        .read_manifest(
+            *layer
+                .manifest()
+                .expect("Layer should have a manifest in this test"),
+        )
+        .await
+        .unwrap()
+        .to_tracking_manifest();
+
+    for path in &[
+        "/no_dot",
+        "/.dot",
+        "/dot/.dot",
+        "/.dot2",
+        "/.dot2/dot",
+        "/.dot2/.dot",
+        "/.dot3",
+    ] {
+        let entry = manifest.get_path(path);
+        assert!(
+            entry.is_some(),
+            "should capture file/directory with leading dot: {path}"
+        );
+    }
+}