diff --git a/crates/lib/src/lints.rs b/crates/lib/src/lints.rs
index e997f0ca2..46c8efc6d 100644
--- a/crates/lib/src/lints.rs
+++ b/crates/lib/src/lints.rs
@@ -345,7 +345,9 @@ fn lint_inner<'skip>(
         let name = lint.name;
         let r = match r {
             Ok(r) => r,
-            Err(e) => anyhow::bail!("Unexpected runtime error running lint {name}: {e}"),
+            Err(e) => {
+                return Err(e.context(format!("Unexpected runtime error running lint {name}")));
+            }
         };
 
         if let Err(e) = r {
@@ -1586,4 +1588,55 @@ mod tests {
         );
         Ok(())
     }
+
+    #[test]
+    fn test_runtime_deps_escape() -> Result<()> {
+        let root = &fixture()?;
+        root.create_dir("usr")?;
+        // Same shape as /usr/local -> ../../var/usrlocal, on the directory
+        // runtime dependency lookup actually searches.
+        root.symlink_contents("../../var/usrbin", "usr/bin")?;
+
+        let config = &LintExecutionConfig::default();
+        let mut out = Vec::new();
+        let err = lint_inner(
+            root,
+            RootType::Alternative,
+            config,
+            LINTS
+                .iter()
+                .filter(|lint| lint.name != "runtime-deps")
+                .map(|lint| lint.name),
+            &mut out,
+        )
+        .expect_err("lookup failure must remain a runtime error");
+
+        let bin = resolved_runtime_bins()
+            .into_iter()
+            .next()
+            .expect("runtime dependency");
+        let attempted = format!("usr/bin/{bin}");
+        assert_eq!(
+            err.to_string(),
+            "Unexpected runtime error running lint runtime-deps"
+        );
+        assert!(
+            err.chain()
+                .any(|source| source.to_string().contains(&attempted)),
+            "{err:?}"
+        );
+        assert!(
+            err.chain().any(|source| {
+                source
+                    .downcast_ref::<std::io::Error>()
+                    .is_some_and(|io_err| {
+                        io_err
+                            .to_string()
+                            .contains("a path led outside of the filesystem")
+                    })
+            }),
+            "{err:?}"
+        );
+        Ok(())
+    }
 }
diff --git a/crates/lib/src/utils.rs b/crates/lib/src/utils.rs
index 544415e0f..fd0d613b7 100644
--- a/crates/lib/src/utils.rs
+++ b/crates/lib/src/utils.rs
@@ -93,7 +93,10 @@ fn executable_candidates(name: &str) -> Vec<PathBuf> {
 pub fn have_executable_in_root(root: &Dir, name: &str) -> Result<bool> {
     for candidate in executable_candidates(name) {
         let candidate = candidate.strip_prefix("/").unwrap_or(&candidate);
-        if root.try_exists(candidate)? {
+        if root
+            .try_exists(candidate)
+            .with_context(|| format!("checking whether {} exists", candidate.display()))?
+        {
             return Ok(true);
         }
     }
@@ -368,6 +371,61 @@ mod tests {
         root.write("usr/bin/podman", "")?;
         assert!(have_executable_in_root(&root, "podman")?);
         assert!(!have_executable_in_root(&root, "missing")?);
+
+        // An absolute name replaces each PATH entry via PathBuf::push, so the
+        // candidate is independent of the process PATH.
+        const PROBE: &str = "/usr/local/bin/probe";
+        let cases = [
+            ("present", Some(true)),
+            ("absent", Some(false)),
+            ("escapes", None),
+            ("contained-symlink", Some(true)),
+        ];
+        for (label, expected) in cases {
+            let root = cap_std_ext::cap_tempfile::tempdir(cap_std::ambient_authority())?;
+            match label {
+                "present" => {
+                    root.create_dir_all("usr/local/bin")?;
+                    root.write("usr/local/bin/probe", "")?;
+                }
+                "absent" => {}
+                "escapes" => {
+                    root.create_dir("usr")?;
+                    root.symlink_contents("../../var/usrlocal", "usr/local")?;
+                }
+                "contained-symlink" => {
+                    root.create_dir_all("var/usrlocal/bin")?;
+                    root.write("var/usrlocal/bin/probe", "")?;
+                    root.create_dir("usr")?;
+                    root.symlink_contents("../var/usrlocal", "usr/local")?;
+                }
+                _ => unreachable!("{label}"),
+            }
+            let found = have_executable_in_root(&root, PROBE);
+            match expected {
+                Some(expected) => assert_eq!(found?, expected, "{label}"),
+                None => {
+                    let err = found.expect_err(label);
+                    assert!(
+                        err.chain()
+                            .any(|source| source.to_string().contains("usr/local/bin/probe")),
+                        "{label}: {err:?}"
+                    );
+                    assert!(
+                        err.chain().any(|source| {
+                            source
+                                .downcast_ref::<std::io::Error>()
+                                .is_some_and(|io_err| {
+                                    io_err
+                                        .to_string()
+                                        .contains("a path led outside of the filesystem")
+                                })
+                        }),
+                        "{label}: {err:?}"
+                    );
+                }
+            }
+        }
         Ok(())
     }
 }