diff --git a/.jules/sentinel.md b/.jules/sentinel.md
new file mode 100644
index 00000000..9f076026
--- /dev/null
+++ b/.jules/sentinel.md
@@ -0,0 +1,4 @@
+## 2024-05-30 - Path Traversal in Manual Path Normalization
+**Vulnerability:** Path traversal vulnerability in TypeScript module resolution where manual `../` (ParentDir) handling in `typescript.rs` popped components indiscriminately, even after exhausting the base path.
+**Learning:** When falling back to manual path normalisation via `.components()` because a file doesn't exist yet (canonicalize fails), naively popping components on `Component::ParentDir` allows malicious inputs like `../../` to escape the root directory context or resolve to arbitrary files, completely bypassing intended base path restrictions.
+**Prevention:** Always preserve `ParentDir` components when the component list is empty or already ends in `ParentDir`. Never pop `RootDir` or `Prefix` components, effectively treating the root as an absolute boundary that `..` cannot traverse above.
diff --git a/crates/flow/src/incremental/extractors/typescript.rs b/crates/flow/src/incremental/extractors/typescript.rs
index 1bdda4ef..227229d5 100644
--- a/crates/flow/src/incremental/extractors/typescript.rs
+++ b/crates/flow/src/incremental/extractors/typescript.rs
@@ -808,7 +808,16 @@ impl TypeScriptDependencyExtractor {
                 for component in resolved.components() {
                     match component {
                         std::path::Component::ParentDir => {
-                            components.pop();
+                            if components.is_empty() || components.last() == Some(&std::path::Component::ParentDir) {
+                                components.push(std::path::Component::ParentDir);
+                            } else if let Some(last) = components.last() {
+                                match last {
+                                    std::path::Component::RootDir | std::path::Component::Prefix(_) => {
+                                        // Cannot go above root/prefix, ignore
+                                    }
+                                    _ => { components.pop(); }
+                                }
+                            }
                         }
                         std::path::Component::CurDir => {}
                         _ => components.push(component),