diff --git a/server/coding-cli/providers/claude.ts b/server/coding-cli/providers/claude.ts
index 157aee3e..96d76f3b 100644
--- a/server/coding-cli/providers/claude.ts
+++ b/server/coding-cli/providers/claude.ts
@@ -7,7 +7,7 @@ import { getClaudeHome } from '../../claude-home.js'
 import type { CodingCliProvider } from '../provider.js'
 import { normalizeFirstUserMessage, type NormalizedEvent, type ParsedSessionMeta, type TokenSummary } from '../types.js'
 import { parseClaudeEvent, isMessageEvent, isResultEvent, isToolResultContent, isToolUseContent, isTextContent } from '../../claude-stream-types.js'
-import { looksLikePath, isSystemContext, extractFromIdeContext, resolveGitCheckoutRoot } from '../utils.js'
+import { looksLikePath, isSystemContext, extractFromIdeContext, resolveGitRepoRoot } from '../utils.js'
 
 export type JsonlMeta = {
   sessionId?: string
@@ -579,7 +579,7 @@ export const claudeProvider: CodingCliProvider = {
 
   async resolveProjectPath(_filePath: string, meta: ParsedSessionMeta): Promise<string> {
     if (!meta.cwd) return 'unknown'
-    return resolveGitCheckoutRoot(meta.cwd)
+    return resolveGitRepoRoot(meta.cwd)
   },
 
   extractSessionId(filePath: string): string {
diff --git a/server/coding-cli/session-indexer.ts b/server/coding-cli/session-indexer.ts
index 981a25e3..c83be728 100644
--- a/server/coding-cli/session-indexer.ts
+++ b/server/coding-cli/session-indexer.ts
@@ -9,6 +9,7 @@ import { configStore, SessionOverride } from '../config-store.js'
 import type { CodingCliProvider } from './provider.js'
 import { makeSessionKey, type CodingCliSession, type CodingCliProviderName, type ProjectGroup } from './types.js'
 import { sanitizeCodexTaskEventsForTruncatedSnippet } from './providers/codex.js'
+import { resolveGitCheckoutRoot } from './utils.js'
 import { diffProjects } from '../sessions-sync/diff.js'
 import type { SessionMetadataStore, SessionMetadataEntry } from '../session-metadata-store.js'
 
@@ -530,10 +531,14 @@ export class CodingCliSessionIndexer {
           ? (meta.lastActivityAt ?? previous?.lastActivityAt ?? createdAt ?? 0)
           : (meta.lastActivityAt ?? createdAt ?? 0))
 
+    const checkoutRoot = meta.cwd ? await resolveGitCheckoutRoot(meta.cwd) : undefined
+    const checkoutPath = checkoutRoot && checkoutRoot !== projectPath ? checkoutRoot : undefined
+
     const baseSession: CodingCliSession = {
       provider: provider.name,
       sessionId,
       projectPath,
+      ...(checkoutPath ? { checkoutPath } : {}),
       lastActivityAt,
       createdAt,
       messageCount: meta.messageCount,
diff --git a/server/coding-cli/types.ts b/server/coding-cli/types.ts
index 7f586708..4435b293 100644
--- a/server/coding-cli/types.ts
+++ b/server/coding-cli/types.ts
@@ -166,6 +166,7 @@ export interface CodingCliSession {
   provider: CodingCliProviderName
   sessionId: string
   projectPath: string
+  checkoutPath?: string
   lastActivityAt: number
   createdAt?: number
   archived?: boolean
diff --git a/server/session-directory/projection.ts b/server/session-directory/projection.ts
index 0ae24d81..b8ec7d81 100644
--- a/server/session-directory/projection.ts
+++ b/server/session-directory/projection.ts
@@ -15,6 +15,7 @@ function comparableItemsEqual(a: SessionDirectoryComparableItem, b: SessionDirec
     a.provider === b.provider &&
     a.sessionId === b.sessionId &&
     a.projectPath === b.projectPath &&
+    a.checkoutPath === b.checkoutPath &&
     a.title === b.title &&
     a.summary === b.summary &&
     a.lastActivityAt === b.lastActivityAt &&
@@ -33,6 +34,7 @@ export function toSessionDirectoryComparableItem(session: CodingCliSession): Ses
     provider: session.provider,
     sessionId: session.sessionId,
     projectPath: session.projectPath,
+    checkoutPath: session.checkoutPath,
     title: session.title,
     summary: session.summary,
     lastActivityAt: session.lastActivityAt,
diff --git a/shared/read-models.ts b/shared/read-models.ts
index b4b9c7f6..e58322aa 100644
--- a/shared/read-models.ts
+++ b/shared/read-models.ts
@@ -41,6 +41,7 @@ export const SessionDirectoryItemSchema = z.object({
   sessionId: z.string().min(1),
   provider: z.string().min(1),
   projectPath: z.string().min(1),
+  checkoutPath: z.string().optional(),
   title: z.string().optional(),
   summary: z.string().optional(),
   snippet: z.string().optional(),
diff --git a/shared/settings.ts b/shared/settings.ts
index bd0b49a6..40dfd917 100644
--- a/shared/settings.ts
+++ b/shared/settings.ts
@@ -21,6 +21,7 @@ const TAB_ATTENTION_STYLE_VALUES = ['highlight', 'pulse', 'darken', 'none'] as c
 const ATTENTION_DISMISS_VALUES = ['click', 'type'] as const
 const SESSION_OPEN_MODE_VALUES = ['tab', 'split'] as const
 const SIDEBAR_SORT_MODE_VALUES = ['recency', 'recency-pinned', 'activity', 'project'] as const
+const WORKTREE_GROUPING_VALUES = ['repo', 'worktree'] as const
 export const CODEX_SANDBOX_VALUES = ['read-only', 'workspace-write', 'danger-full-access'] as const
 export const CLAUDE_PERMISSION_MODE_VALUES = ['default', 'plan', 'acceptEdits', 'bypassPermissions'] as const
 const EXTERNAL_EDITOR_VALUES = ['auto', 'cursor', 'code', 'custom'] as const
@@ -50,6 +51,7 @@ const TERMINAL_LOCAL_KEYS = [
 const PANES_LOCAL_KEYS = ['snapThreshold', 'iconsOnTabs', 'tabAttentionStyle', 'attentionDismiss', 'sessionOpenMode'] as const
 const SIDEBAR_LOCAL_KEYS = [
   'sortMode',
+  'worktreeGrouping',
   'showProjectBadges',
   'showSubagents',
   'ignoreCodexSubagents',
@@ -68,6 +70,7 @@ export type TabAttentionStyle = (typeof TAB_ATTENTION_STYLE_VALUES)[number]
 export type AttentionDismiss = (typeof ATTENTION_DISMISS_VALUES)[number]
 export type SessionOpenMode = (typeof SESSION_OPEN_MODE_VALUES)[number]
 export type SidebarSortMode = (typeof SIDEBAR_SORT_MODE_VALUES)[number]
+export type WorktreeGrouping = (typeof WORKTREE_GROUPING_VALUES)[number]
 export type CodexSandboxMode = (typeof CODEX_SANDBOX_VALUES)[number]
 export type ClaudePermissionMode = (typeof CLAUDE_PERMISSION_MODE_VALUES)[number]
 export type ExternalEditor = (typeof EXTERNAL_EDITOR_VALUES)[number]
@@ -168,6 +171,7 @@ export type LocalSettings = {
   }
   sidebar: {
     sortMode: SidebarSortMode
+    worktreeGrouping: WorktreeGrouping
     showProjectBadges: boolean
     showSubagents: boolean
     ignoreCodexSubagents: boolean
@@ -257,6 +261,10 @@ function mergeRecordOfObjects<T extends Record<string, unknown>>(
   return merged
 }
 
+function normalizeWorktreeGrouping(value: unknown): WorktreeGrouping {
+  return WORKTREE_GROUPING_VALUES.includes(value as WorktreeGrouping) ? (value as WorktreeGrouping) : 'repo'
+}
+
 function normalizeLocalSortMode(mode: unknown): SidebarSortMode {
   if (mode === 'hybrid') {
     return 'activity'
@@ -423,6 +431,9 @@ function normalizeExtractedLocalSeed(patch: Record<string, unknown>): LocalSetti
     if (hasOwn(patch.sidebar, 'sortMode')) {
       sidebar.sortMode = normalizeLocalSortMode(patch.sidebar.sortMode)
     }
+    if (hasOwn(patch.sidebar, 'worktreeGrouping')) {
+      sidebar.worktreeGrouping = normalizeWorktreeGrouping(patch.sidebar.worktreeGrouping)
+    }
     if (typeof patch.sidebar.showProjectBadges === 'boolean') {
       sidebar.showProjectBadges = patch.sidebar.showProjectBadges as boolean
     }
@@ -675,6 +686,7 @@ export const defaultLocalSettings: LocalSettings = {
   },
   sidebar: {
     sortMode: 'activity',
+    worktreeGrouping: 'repo',
     showProjectBadges: true,
     showSubagents: false,
     ignoreCodexSubagents: true,
@@ -964,6 +976,7 @@ export function resolveLocalSettings(patch?: LocalSettingsPatch): LocalSettings
     sidebar: {
       ...mergeDefined(defaultLocalSettings.sidebar, patch?.sidebar),
       sortMode: normalizeLocalSortMode(patch?.sidebar?.sortMode),
+      worktreeGrouping: normalizeWorktreeGrouping(patch?.sidebar?.worktreeGrouping),
     },
     notifications: mergeDefined(defaultLocalSettings.notifications, patch?.notifications),
   }
@@ -998,6 +1011,9 @@ export function mergeLocalSettings(base: LocalSettingsPatch | undefined, patch:
   if (hasOwn(sidebar, 'sortMode')) {
     sidebar.sortMode = normalizeLocalSortMode(sidebar.sortMode)
   }
+  if (hasOwn(sidebar, 'worktreeGrouping')) {
+    sidebar.worktreeGrouping = normalizeWorktreeGrouping(sidebar.worktreeGrouping)
+  }
   if (Object.keys(sidebar).length > 0) {
     next.sidebar = sidebar as LocalSettingsPatch['sidebar']
   }
diff --git a/src/components/settings/WorkspaceSettings.tsx b/src/components/settings/WorkspaceSettings.tsx
index 0ecce170..87b5da79 100644
--- a/src/components/settings/WorkspaceSettings.tsx
+++ b/src/components/settings/WorkspaceSettings.tsx
@@ -4,6 +4,7 @@ import { useState, useEffect, useRef } from 'react'
 import { KEYBOARD_SHORTCUTS } from '@/lib/keyboard-shortcuts'
 import type {
   SidebarSortMode,
+  WorktreeGrouping,
   SessionOpenMode,
   TabAttentionStyle,
   AttentionDismiss,
@@ -59,6 +60,20 @@ export default function WorkspaceSettings({
           </select>
         </SettingsRow>
 
+        <SettingsRow label="Worktree grouping">
+          <select
+            value={settings.sidebar?.worktreeGrouping || 'repo'}
+            onChange={(e) => {
+              const v = e.target.value as WorktreeGrouping
+              applyLocalSetting({ sidebar: { worktreeGrouping: v } })
+            }}
+            className="h-10 w-full px-3 text-sm bg-muted border-0 rounded-md focus:outline-none focus:ring-1 focus:ring-border md:h-8 md:w-auto"
+          >
+            <option value="repo">Repository</option>
+            <option value="worktree">Worktree</option>
+          </select>
+        </SettingsRow>
+
         <SettingsRow label="Show project badges">
           <Toggle
             checked={settings.sidebar?.showProjectBadges ?? true}
diff --git a/src/lib/api.ts b/src/lib/api.ts
index 6f42c68a..ed5393d6 100644
--- a/src/lib/api.ts
+++ b/src/lib/api.ts
@@ -275,6 +275,7 @@ export type SearchResult = {
   sessionId: string
   provider: CodingCliProviderName
   projectPath: string
+  checkoutPath?: string
   title?: string
   summary?: string
   sessionType?: string
@@ -329,6 +330,7 @@ function groupDirectoryItemsAsProjects(items: ReadModelSessionDirectoryItem[]) {
       provider: item.provider,
       sessionId: item.sessionId,
       projectPath: item.projectPath,
+      ...(item.checkoutPath ? { checkoutPath: item.checkoutPath } : {}),
       lastActivityAt: item.lastActivityAt,
       createdAt: item.createdAt,
       archived: item.archived,
diff --git a/src/store/selectors/sidebarSelectors.ts b/src/store/selectors/sidebarSelectors.ts
index 612b356c..fb20f710 100644
--- a/src/store/selectors/sidebarSelectors.ts
+++ b/src/store/selectors/sidebarSelectors.ts
@@ -1,6 +1,6 @@
 import { createSelector } from '@reduxjs/toolkit'
 import type { RootState } from '../store'
-import type { BackgroundTerminal, CodingCliProviderName } from '../types'
+import type { BackgroundTerminal, CodingCliProviderName, WorktreeGrouping } from '../types'
 import { isValidClaudeSessionId } from '@/lib/claude-session-id'
 import { collectSessionRefsFromNode, collectSessionRefsFromTabs } from '@/lib/session-utils'
 import { getAgentChatProviderConfig } from '@/lib/agent-chat-utils'
@@ -44,6 +44,7 @@ const selectSessionActivityForSort = (state: RootState) => {
   if (sortMode !== 'activity') return EMPTY_ACTIVITY
   return state.sessionActivity?.sessions || EMPTY_ACTIVITY
 }
+const selectWorktreeGrouping = (state: RootState): WorktreeGrouping => state.settings.settings.sidebar?.worktreeGrouping || 'repo'
 const selectShowSubagents = (state: RootState) => state.settings.settings.sidebar?.showSubagents ?? false
 const selectIgnoreCodexSubagents = (state: RootState) => state.settings.settings.sidebar?.ignoreCodexSubagents ?? true
 const selectShowNoninteractiveSessions = (state: RootState) => state.settings.settings.sidebar?.showNoninteractiveSessions ?? false
@@ -64,7 +65,8 @@ export function buildSessionItems(
   tabs: RootState['tabs']['tabs'],
   panes: RootState['panes'],
   terminals: BackgroundTerminal[],
-  sessionActivity: Record<string, number>
+  sessionActivity: Record<string, number>,
+  worktreeGrouping: WorktreeGrouping = 'repo',
 ): SidebarSessionItem[] {
   const items: SidebarSessionItem[] = []
   const runningSessionMap = new Map<string, { terminalId: string; createdAt: number; allTerminalIds: string[] }>()
@@ -103,6 +105,9 @@ export function buildSessionItems(
       const tabInfo = tabSessionMap.get(key)
       const ratchetedActivity = sessionActivity[key]
       const hasTitle = !!session.title
+      const effectivePath = worktreeGrouping === 'worktree'
+        ? (session.checkoutPath || project.projectPath)
+        : project.projectPath
       items.push({
         id: `session-${provider}-${session.sessionId}`,
         sessionId: session.sessionId,
@@ -110,8 +115,8 @@ export function buildSessionItems(
         sessionType: session.sessionType || provider,
         title: session.title || session.sessionId.slice(0, 8),
         hasTitle,
-        subtitle: getProjectName(project.projectPath),
-        projectPath: project.projectPath,
+        subtitle: getProjectName(effectivePath),
+        projectPath: effectivePath,
         projectColor: project.color,
         archived: session.archived,
         timestamp: session.lastActivityAt,
@@ -414,6 +419,7 @@ export const makeSelectSortedSessionItems = () =>
       selectPanes,
       selectSessionActivityForSort,
       selectSortMode,
+      selectWorktreeGrouping,
       selectShowSubagents,
       selectIgnoreCodexSubagents,
       selectShowNoninteractiveSessions,
@@ -431,6 +437,7 @@ export const makeSelectSortedSessionItems = () =>
       panes,
       sessionActivity,
       sortMode,
+      worktreeGrouping,
       showSubagents,
       ignoreCodexSubagents,
       showNoninteractiveSessions,
@@ -442,7 +449,7 @@ export const makeSelectSortedSessionItems = () =>
       terminals,
       filter
     ) => {
-      const items = buildSessionItems(projects, tabs, panes, terminals, sessionActivity)
+      const items = buildSessionItems(projects, tabs, panes, terminals, sessionActivity, worktreeGrouping)
       const visible = filterSessionItemsByVisibility(items, {
         showSubagents,
         ignoreCodexSubagents,
diff --git a/src/store/sessionsThunks.ts b/src/store/sessionsThunks.ts
index 101be949..b1194e78 100644
--- a/src/store/sessionsThunks.ts
+++ b/src/store/sessionsThunks.ts
@@ -68,6 +68,7 @@ function searchResultsToProjects(results: Awaited<ReturnType<typeof searchSessio
       provider: result.provider,
       sessionId: result.sessionId,
       projectPath: result.projectPath,
+      ...(result.checkoutPath ? { checkoutPath: result.checkoutPath } : {}),
       lastActivityAt: result.lastActivityAt,
       createdAt: result.createdAt,
       archived: result.archived,
diff --git a/src/store/types.ts b/src/store/types.ts
index 7737c914..e3016bca 100644
--- a/src/store/types.ts
+++ b/src/store/types.ts
@@ -18,6 +18,7 @@ import type {
   TerminalRendererMode,
   TerminalTheme,
   TabAttentionStyle,
+  WorktreeGrouping,
 } from '@shared/settings'
 import type { CodingCliProviderName, TokenSummary } from '@shared/ws-protocol'
 export type { CodingCliProviderName }
@@ -81,6 +82,7 @@ export interface CodingCliSession {
   sessionType?: string
   sessionId: string
   projectPath: string
+  checkoutPath?: string
   createdAt?: number
   lastActivityAt: number
   messageCount?: number
@@ -134,6 +136,7 @@ export type {
   TabAttentionStyle,
   TerminalRendererMode,
   TerminalTheme,
+  WorktreeGrouping,
 }
 
 export type AppSettings = ResolvedSettings
diff --git a/test/unit/client/store/selectors/sidebarSelectors.test.ts b/test/unit/client/store/selectors/sidebarSelectors.test.ts
index ce89860b..b287709f 100644
--- a/test/unit/client/store/selectors/sidebarSelectors.test.ts
+++ b/test/unit/client/store/selectors/sidebarSelectors.test.ts
@@ -465,6 +465,70 @@ describe('sidebarSelectors', () => {
     })
   })
 
+  describe('worktree grouping', () => {
+    const emptyTabs: [] = []
+    const emptyPanes = { layouts: {} } as any
+    const emptyTerminals: [] = []
+    const emptyActivity: Record<string, number> = {}
+
+    function makeProject(sessions: Partial<CodingCliSession>[], projectPath = '/test/repo', color?: string): ProjectGroup {
+      return {
+        projectPath,
+        color,
+        sessions: sessions.map((s) => ({
+          provider: 'claude' as const,
+          sessionId: 'sess-1',
+          projectPath,
+          lastActivityAt: 1000,
+          ...s,
+        })),
+      }
+    }
+
+    it('uses projectPath for subtitle in repo mode (default)', () => {
+      const projects = [
+        makeProject([
+          { sessionId: 'wt-1', checkoutPath: '/test/repo/.worktrees/feature-a' },
+          { sessionId: 'wt-2' },
+        ], '/test/repo'),
+      ]
+
+      const items = buildSessionItems(projects, emptyTabs, emptyPanes, emptyTerminals, emptyActivity)
+
+      expect(items[0].subtitle).toBe('repo')
+      expect(items[0].projectPath).toBe('/test/repo')
+      expect(items[1].subtitle).toBe('repo')
+      expect(items[1].projectPath).toBe('/test/repo')
+    })
+
+    it('uses checkoutPath for subtitle in worktree mode', () => {
+      const projects = [
+        makeProject([
+          { sessionId: 'wt-1', checkoutPath: '/test/repo/.worktrees/feature-a' },
+          { sessionId: 'wt-2' },
+        ], '/test/repo'),
+      ]
+
+      const items = buildSessionItems(projects, emptyTabs, emptyPanes, emptyTerminals, emptyActivity, 'worktree')
+
+      expect(items[0].subtitle).toBe('feature-a')
+      expect(items[0].projectPath).toBe('/test/repo/.worktrees/feature-a')
+      expect(items[1].subtitle).toBe('repo')
+      expect(items[1].projectPath).toBe('/test/repo')
+    })
+
+    it('falls back to projectPath when session has no checkoutPath in worktree mode', () => {
+      const projects = [
+        makeProject([{ sessionId: 'no-wt' }], '/test/repo'),
+      ]
+
+      const items = buildSessionItems(projects, emptyTabs, emptyPanes, emptyTerminals, emptyActivity, 'worktree')
+
+      expect(items[0].subtitle).toBe('repo')
+      expect(items[0].projectPath).toBe('/test/repo')
+    })
+  })
+
   describe('makeSelectSortedSessionItems', () => {
     it('uses the applied title query to keep only matching fallback rows and rejects ancestor-only matches', () => {
       const matchingFallback = createFallbackTab('tab-match', 'fallback-match', 'Matching Fallback', '/tmp/local/trycycle')