diff --git a/cli/src/lib.rs b/cli/src/lib.rs
index 4bb7309..fa9ea70 100644
--- a/cli/src/lib.rs
+++ b/cli/src/lib.rs
@@ -406,6 +406,94 @@ pub fn run_session(command: SessionCommand, options: &Options) -> Result<ExitCod
     }
 }
 
+/// Strip the Windows verbatim-device prefix (`\\?\`, including `\\?\UNC\`)
+/// that `canonicalize` adds, so vanished paths still match canonicalized
+/// parents. Wide-char math keeps non-UTF8 paths intact.
+#[cfg(windows)]
+const VERBATIM_PREFIX: &[u16] = &[0x5C, 0x5C, 0x3F, 0x5C]; // `\\?\`
+#[cfg(windows)]
+const UNC_PREFIX: &[u16] = &[0x5C, 0x5C, 0x3F, 0x5C, 0x55, 0x4E, 0x43, 0x5C]; // `\\?\UNC\`
+
+#[cfg(windows)]
+fn strip_verbatim_prefix(path: &std::path::Path) -> std::path::PathBuf {
+    use std::os::windows::ffi::{OsStrExt, OsStringExt};
+    let wide: Vec<u16> = path.as_os_str().encode_wide().collect();
+    if let Some(rest) = wide.strip_prefix(UNC_PREFIX) {
+        // `\\?\UNC\server\share` ⟺ `\\server\share`.
+        let mut full = vec![0x5C, 0x5C];
+        full.extend_from_slice(rest);
+        std::ffi::OsString::from_wide(&full).into()
+    } else if let Some(rest) = wide.strip_prefix(VERBATIM_PREFIX) {
+        std::ffi::OsString::from_wide(rest).into()
+    } else {
+        path.to_path_buf()
+    }
+}
+
+#[cfg(not(windows))]
+fn strip_verbatim_prefix(path: &std::path::Path) -> std::path::PathBuf {
+    path.to_path_buf()
+}
+
+/// Component-wise `starts_with` that folds case on Windows, where `C:\Users`
+/// and `c:\users` are the same directory. Non-Windows keeps the exact
+/// `Path::starts_with`.
+fn path_starts_with(child: &std::path::Path, parent: &std::path::Path) -> bool {
+    #[cfg(windows)]
+    {
+        let mut child_comps = child.components();
+        let mut parent_comps = parent.components();
+        loop {
+            match (parent_comps.next(), child_comps.next()) {
+                (None, _) => return true,
+                (Some(_), None) => return false,
+                (Some(p), Some(c)) => {
+                    // Unicode lowercase approximates the filesystem's own
+                    // case folding; ASCII-only would miss e.g. `é` vs `É`.
+                    if p.as_os_str().to_string_lossy().to_lowercase()
+                        != c.as_os_str().to_string_lossy().to_lowercase()
+                    {
+                        return false;
+                    }
+                }
+            }
+        }
+    }
+    #[cfg(not(windows))]
+    {
+        child.starts_with(parent)
+    }
+}
+
+/// Canonicalize the longest existing prefix of `path`, re-appending the
+/// vanished tail verbatim, so the parent still resolves symlinks, junctions,
+/// or 8.3 short names the raw spelling would mismatch.
+fn canonicalize_lenient(path: &std::path::Path) -> std::path::PathBuf {
+    use std::path::Component;
+    let mut tail: Vec<std::ffi::OsString> = Vec::new();
+    let mut current = path;
+    loop {
+        if let Ok(base) = current.canonicalize() {
+            let mut out = strip_verbatim_prefix(&base);
+            for component in tail.iter().rev() {
+                out.push(component);
+            }
+            return out;
+        }
+        let mut components = current.components();
+        match components.next_back() {
+            // Empty path, or only a prefix/root remains: nothing resolvable.
+            None | Some(Component::Prefix(_) | Component::RootDir) => {
+                return strip_verbatim_prefix(path);
+            }
+            Some(last) => {
+                tail.push(last.as_os_str().to_os_string());
+                current = components.as_path();
+            }
+        }
+    }
+}
+
 /// True when a session's recorded `cwd` is `dir` or anywhere under it, so a
 /// monorepo session started in `repo/packages/foo` shows up when listing
 /// `repo`. The check is component-wise (`/foo/barbaz` is not under
@@ -415,8 +503,10 @@ pub fn run_session(command: SessionCommand, options: &Options) -> Result<ExitCod
 /// vanished directories compare as plain components.
 #[must_use]
 pub fn under_dir(session_cwd: &str, dir: &std::path::Path) -> bool {
-    let canon = |p: &std::path::Path| p.canonicalize().unwrap_or_else(|_| p.to_path_buf());
-    canon(std::path::Path::new(session_cwd)).starts_with(canon(dir))
+    path_starts_with(
+        &canonicalize_lenient(std::path::Path::new(session_cwd)),
+        &canonicalize_lenient(dir),
+    )
 }
 
 /// The `--from`/`--cwd` session filters shared by `list` and `query`.
@@ -693,6 +783,46 @@ mod filter_tests {
             Some(repo)
         ));
     }
+
+    #[test]
+    fn strip_verbatim_prefix_leaves_plain_paths_alone() {
+        let p = std::path::Path::new("some/relative/dir");
+        assert_eq!(super::strip_verbatim_prefix(p), p.to_path_buf());
+    }
+
+    #[cfg(windows)]
+    #[test]
+    fn strip_verbatim_prefix_strips_device_and_unc_forms() {
+        assert_eq!(
+            super::strip_verbatim_prefix(std::path::Path::new(r"\\?\C:\some\repo")),
+            std::path::PathBuf::from(r"C:\some\repo")
+        );
+        assert_eq!(
+            super::strip_verbatim_prefix(std::path::Path::new(r"\\?\UNC\server\share")),
+            std::path::PathBuf::from(r"\\server\share")
+        );
+    }
+
+    // Drive-letter paths only parse where `\` separates components.
+    // The tempdir case is the reported scenario: live `dir`, vanished child.
+    #[cfg(windows)]
+    #[test]
+    fn cwd_filter_matches_vanished_child_of_live_dir() {
+        let dir = tempfile::tempdir().unwrap();
+        let gone = dir.path().join("packages").join("foo");
+        assert!(super::under_dir(gone.to_str().unwrap(), dir.path()));
+    }
+
+    #[cfg(windows)]
+    #[test]
+    fn cwd_filter_handles_windows_verbatim_prefixes_and_casing() {
+        let dir = std::path::Path::new(r"C:\some\repo");
+        assert!(super::under_dir(r"C:\some\repo\packages\foo", dir));
+        assert!(super::under_dir(r"c:\Some\Repo\packages\foo", dir));
+        assert!(super::under_dir(r"C:/some/repo/packages/foo", dir));
+        assert!(!super::under_dir(r"C:\some\repo2", dir));
+        assert!(!super::under_dir(r"C:\other\repo", dir));
+    }
 }
 
 #[cfg(test)]