diff --git a/src/web/routes/session-routes.ts b/src/web/routes/session-routes.ts
index 03949776..e3a1c447 100644
--- a/src/web/routes/session-routes.ts
+++ b/src/web/routes/session-routes.ts
@@ -2551,7 +2551,12 @@ export function registerSessionRoutes(
       for (let end = maxLook - 1; end >= idx; end--) {
         const candidates: string[] = [];
         if (end === idx) {
-          candidates.push(segments[idx]);
+          // Skip an EMPTY segment: `isDir(current + '/' + '')` stats `current + '/'`,
+          // which always succeeds, so the empty candidate would match unconditionally
+          // and swallow the doubled dash that is the whole signature of a dotdir. It
+          // then resolves "/home/x/.sib" to "/home/x//sib" whenever a non-dot sibling
+          // exists, and shadows the dotdir branch below in every other case.
+          if (segments[idx] !== '') candidates.push(segments[idx]);
         } else {
           candidates.push(segments.slice(idx, end + 1).join('-'));
           candidates.push(segments.slice(idx, end + 1).join('_'));
@@ -2600,7 +2605,10 @@ export function registerSessionRoutes(
       for (let end = i; end < maxLook; end++) {
         const candidates: string[] = [];
         if (end === i) {
-          candidates.push(segments[i]);
+          // Same empty-segment skip as tryDecode above. This loop is shortest-match
+          // first, so without it the empty candidate matches on the very first try
+          // and sets `matched`, leaving the dotdir branch below permanently dead.
+          if (segments[i] !== '') candidates.push(segments[i]);
         } else {
           candidates.push(segments.slice(i, end + 1).join('_'));
           candidates.push(segments.slice(i, end + 1).join('-'));
@@ -2636,8 +2644,21 @@ export function registerSessionRoutes(
         }
       }
       if (!matched) {
-        current = current + '/' + segments[i];
-        i++;
+        if (segments[i] === '') {
+          // Nothing on disk matched (the usual reason this fallback runs at all is
+          // that the directory was deleted). An empty segment still means the
+          // encoder ate a literal '.', so guess the dotdir form rather than
+          // appending a bare '/' and emitting a "//" path.
+          if (i + 1 < segments.length) {
+            current = current + '/.' + segments[i + 1];
+            i += 2;
+          } else {
+            i++;
+          }
+        } else {
+          current = current + '/' + segments[i];
+          i++;
+        }
       }
     }
     const finalExists = await fs
diff --git a/test/routes/session-routes.test.ts b/test/routes/session-routes.test.ts
index 14b57c51..6d1a02cc 100644
--- a/test/routes/session-routes.test.ts
+++ b/test/routes/session-routes.test.ts
@@ -1321,6 +1321,35 @@ describe('session-routes', () => {
       expect(row.workingDir).toBe(realDir);
       expect(row.workingDir).not.toBe(home);
     });
+
+    it('prefers the dotdir over a same-named non-dot sibling, and never emits a "//" path', async () => {
+      // A doubled dash also lets the decoder read the empty split segment as a
+      // directory NAME. `isDir(current + '/' + '')` stats `current + '/'`, which
+      // always succeeds, so `~/.sib` + `~/sib` both existing used to resolve to
+      // "/home/x//sib": the wrong directory, spelled with a double slash that
+      // then fails every string comparison against session.workingDir. The empty
+      // candidate is never a real path component, so it is skipped outright,
+      // which is also what lets the dotdir branch below it run at all.
+      const home = process.env.HOME as string;
+      const dotDir = join(home, '.sib');
+      await mkdir(dotDir, { recursive: true });
+      await mkdir(join(home, 'sib'), { recursive: true });
+
+      const projectKey = dotDir.replace(/\//g, '-').replace(/\./g, '-');
+      const projDir = join(home, '.claude', 'projects', projectKey);
+      await mkdir(projDir, { recursive: true });
+
+      const sessionId = '22222222-2222-2222-2222-222222222222';
+      const line = JSON.stringify({ type: 'user', message: { role: 'user', content: 'hello world' } }) + '\n';
+      await writeFile(join(projDir, `${sessionId}.jsonl`), line + '#'.repeat(4200 - line.length));
+
+      const res = await harness.app.inject({ method: 'GET', url: `/api/history/sessions?projectKey=${projectKey}` });
+      expect(res.statusCode).toBe(200);
+      const row = JSON.parse(res.body).data.sessions.find((s: { sessionId: string }) => s.sessionId === sessionId);
+      expect(row).toBeDefined();
+      expect(row.workingDir).toBe(dotDir);
+      expect(row.workingDir).not.toContain('//');
+    });
   });
 
   // ========== POST /api/sessions (with resumeSessionId) ==========