diff --git a/apps/staged/src/lib/features/projects/ProjectSection.svelte b/apps/staged/src/lib/features/projects/ProjectSection.svelte
index 48727c9e..fcea01cd 100644
--- a/apps/staged/src/lib/features/projects/ProjectSection.svelte
+++ b/apps/staged/src/lib/features/projects/ProjectSection.svelte
@@ -663,6 +663,7 @@
   )}
   <SessionModal
     sessionId={openSessionId}
+    repoDir={branches.find((b) => b.worktreePath)?.worktreePath ?? null}
     projectId={project.id}
     noteInfo={noteForSession
       ? { id: noteForSession.id, title: noteForSession.title, content: noteForSession.content }
diff --git a/apps/staged/src/lib/features/sessions/SessionLauncher.svelte b/apps/staged/src/lib/features/sessions/SessionLauncher.svelte
index bc0466c3..af7928b1 100644
--- a/apps/staged/src/lib/features/sessions/SessionLauncher.svelte
+++ b/apps/staged/src/lib/features/sessions/SessionLauncher.svelte
@@ -238,7 +238,11 @@
 
 <!-- Open SessionModals — one per open session, stacked -->
 {#each [...openModals] as modalSessionId (modalSessionId)}
-  <SessionModal sessionId={modalSessionId} onClose={() => closeModal(modalSessionId)} />
+  <SessionModal
+    sessionId={modalSessionId}
+    repoDir={null}
+    onClose={() => closeModal(modalSessionId)}
+  />
 {/each}
 
 <style>
diff --git a/apps/staged/src/lib/features/sessions/sessionModalHelpers.ts b/apps/staged/src/lib/features/sessions/sessionModalHelpers.ts
index 6503274e..86c58336 100644
--- a/apps/staged/src/lib/features/sessions/sessionModalHelpers.ts
+++ b/apps/staged/src/lib/features/sessions/sessionModalHelpers.ts
@@ -30,11 +30,27 @@ export function parseToolCall(content: string): ParsedToolCall | null {
 /**
  * Replace absolute paths that fall within `repoDir` with relative paths.
  * If repoDir is empty/null, returns the text unchanged.
+ *
+ * When the exact `repoDir` prefix isn't found in the text, ancestor directories
+ * are tried (up to 3 levels). This handles the common case where the session's
+ * working directory includes a repo subpath (e.g. `worktree_root/apps/staged`)
+ * but tool call paths reference the worktree root directly.
  */
 export function makePathsRelative(text: string, repoDir: string | null | undefined): string {
   if (!repoDir) return text;
-  const prefix = repoDir.endsWith('/') ? repoDir : repoDir + '/';
-  return text.replaceAll(prefix, '');
+
+  let dir = repoDir;
+  for (let i = 0; i < 4; i++) {
+    const prefix = dir.endsWith('/') ? dir : dir + '/';
+    if (text.includes(prefix)) {
+      return text.replaceAll(prefix, '');
+    }
+    const parentEnd = dir.lastIndexOf('/');
+    if (parentEnd <= 0) break;
+    dir = dir.slice(0, parentEnd);
+  }
+
+  return text;
 }
 
 const TOOL_VERBS: Record<string, [past: string, present: string]> = {