diff --git a/apps/desktop/electron/bootstrap-runner.cjs b/apps/desktop/electron/bootstrap-runner.cjs
index 9e427d147d5..51f24090b02 100644
--- a/apps/desktop/electron/bootstrap-runner.cjs
+++ b/apps/desktop/electron/bootstrap-runner.cjs
@@ -482,6 +482,18 @@ async function runBootstrap(opts) {
     writeMarker // callback to write the bootstrap-complete marker; main.cjs provides
   } = opts
 
+  // Bail before spawning anything if the user already cancelled — otherwise an
+  // already-aborted signal would still fetch the manifest (a spawn) before the
+  // in-loop abort check fires.
+  if (abortSignal && abortSignal.aborted) {
+    if (typeof onEvent === 'function') {
+      try {
+        onEvent({ type: 'failed', error: 'bootstrap cancelled by user' })
+      } catch {}
+    }
+    return { ok: false, cancelled: true }
+  }
+
   const runLog = openRunLog(logRoot || path.join(hermesHome, 'logs'))
 
   // Tee every event to the runLog AND the caller's onEvent. This gives us a
diff --git a/apps/desktop/electron/bootstrap-runner.test.cjs b/apps/desktop/electron/bootstrap-runner.test.cjs
new file mode 100644
index 00000000000..f105c735564
--- /dev/null
+++ b/apps/desktop/electron/bootstrap-runner.test.cjs
@@ -0,0 +1,27 @@
+const assert = require('node:assert/strict')
+const test = require('node:test')
+
+const { runBootstrap } = require('./bootstrap-runner.cjs')
+
+test('runBootstrap bails immediately when the signal is already aborted', async () => {
+  const controller = new AbortController()
+  controller.abort()
+
+  const events = []
+  const result = await runBootstrap({
+    installStamp: null,
+    activeRoot: '/tmp/hermes-runner-test',
+    sourceRepoRoot: null,
+    hermesHome: '/tmp/hermes-runner-test',
+    logRoot: '/tmp/hermes-runner-test',
+    onEvent: ev => events.push(ev),
+    abortSignal: controller.signal
+  })
+
+  // Cancelled before any install script is spawned.
+  assert.deepEqual(result, { ok: false, cancelled: true })
+  assert.ok(
+    events.some(ev => ev.type === 'failed' && /cancelled/i.test(ev.error)),
+    'should emit a cancelled failure event'
+  )
+})
diff --git a/apps/desktop/electron/main.cjs b/apps/desktop/electron/main.cjs
index b07e53ee030..bd94e69a5f1 100644
--- a/apps/desktop/electron/main.cjs
+++ b/apps/desktop/electron/main.cjs
@@ -435,6 +435,9 @@ let connectionPromise = null
 // instead of re-running install.ps1 in a hot loop. Cleared explicitly by
 // the renderer's "Reload and retry" path or by quitting the app.
 let bootstrapFailure = null
+// Active first-launch install, so the renderer's Cancel button (and app quit)
+// can abort the in-flight install.sh/ps1 instead of leaving it running.
+let bootstrapAbortController = null
 let connectionConfigCache = null
 const hermesLog = []
 const previewWatchers = new Map()
@@ -1740,12 +1743,15 @@ async function ensureRuntime(backend) {
       })
     } catch {}
 
+    bootstrapAbortController = new AbortController()
+
     const bootstrapResult = await runBootstrap({
       installStamp: backend.installStamp,
       activeRoot: backend.activeRoot,
       sourceRepoRoot: SOURCE_REPO_ROOT,
       hermesHome: HERMES_HOME,
       logRoot: path.join(HERMES_HOME, 'logs'),
+      abortSignal: bootstrapAbortController.signal,
       onEvent: ev => {
         // Tee every bootstrap event to (a) the desktop log for forensics
         // and (b) the renderer for live progress UI. Either may be absent;
@@ -1761,6 +1767,16 @@ async function ensureRuntime(backend) {
       writeMarker: writeBootstrapMarker
     })
 
+    bootstrapAbortController = null
+
+    if (bootstrapResult.cancelled) {
+      const cancelledError = new Error('Hermes install was cancelled.')
+      cancelledError.isBootstrapFailure = true
+      cancelledError.bootstrapCancelled = true
+      bootstrapFailure = cancelledError
+      throw cancelledError
+    }
+
     if (!bootstrapResult.ok) {
       const bootstrapError = new Error(
         `Hermes bootstrap failed${bootstrapResult.failedStage ? ` at stage '${bootstrapResult.failedStage}'` : ''}: ` +
@@ -3256,6 +3272,18 @@ ipcMain.handle('hermes:bootstrap:repair', async () => {
   resetHermesConnection()
   return { ok: true }
 })
+ipcMain.handle('hermes:bootstrap:cancel', async () => {
+  // Renderer's Cancel button during first-launch install. Abort the running
+  // install script (SIGTERM via the runner's abortSignal). runBootstrap
+  // resolves with { cancelled: true }, which surfaces the recovery overlay.
+  if (bootstrapAbortController) {
+    try {
+      bootstrapAbortController.abort()
+    } catch {}
+    return { ok: true, cancelled: true }
+  }
+  return { ok: false, cancelled: false }
+})
 ipcMain.handle('hermes:boot-progress:get', async () => bootProgressState)
 ipcMain.handle('hermes:bootstrap:get', async () => getBootstrapState())
 ipcMain.handle('hermes:connection-config:get', async () => sanitizeDesktopConnectionConfig())
@@ -3726,6 +3754,13 @@ app.whenReady().then(() => {
 })
 
 app.on('before-quit', () => {
+  // Quitting mid-install should stop the installer, not orphan it.
+  if (bootstrapAbortController) {
+    try {
+      bootstrapAbortController.abort()
+    } catch {}
+  }
+
   if (desktopLogFlushTimer) {
     clearTimeout(desktopLogFlushTimer)
     desktopLogFlushTimer = null
diff --git a/apps/desktop/electron/preload.cjs b/apps/desktop/electron/preload.cjs
index eb0fc1fdf2e..fcdf789ae3e 100644
--- a/apps/desktop/electron/preload.cjs
+++ b/apps/desktop/electron/preload.cjs
@@ -91,6 +91,7 @@ contextBridge.exposeInMainWorld('hermesDesktop', {
   getBootstrapState: () => ipcRenderer.invoke('hermes:bootstrap:get'),
   resetBootstrap: () => ipcRenderer.invoke('hermes:bootstrap:reset'),
   repairBootstrap: () => ipcRenderer.invoke('hermes:bootstrap:repair'),
+  cancelBootstrap: () => ipcRenderer.invoke('hermes:bootstrap:cancel'),
   onBootstrapEvent: callback => {
     const listener = (_event, payload) => callback(payload)
     ipcRenderer.on('hermes:bootstrap:event', listener)
diff --git a/apps/desktop/package.json b/apps/desktop/package.json
index 7056ec73601..a9a0db7e21b 100644
--- a/apps/desktop/package.json
+++ b/apps/desktop/package.json
@@ -32,7 +32,7 @@
     "test:desktop:nsis": "node scripts/test-desktop.mjs nsis",
     "test:desktop:existing": "node scripts/test-desktop.mjs existing",
     "test:desktop:fresh": "node scripts/test-desktop.mjs fresh",
-    "test:desktop:platforms": "node --test electron/bootstrap-platform.test.cjs electron/hardening.test.cjs electron/backend-probes.test.cjs",
+    "test:desktop:platforms": "node --test electron/bootstrap-platform.test.cjs electron/hardening.test.cjs electron/backend-probes.test.cjs electron/bootstrap-runner.test.cjs",
     "type-check": "tsc -b",
     "lint": "eslint src/ electron/",
     "lint:fix": "eslint src/ electron/ --fix",
diff --git a/apps/desktop/src/app/chat/sidebar/index.tsx b/apps/desktop/src/app/chat/sidebar/index.tsx
index 53fb9688e3e..351a57c0ded 100644
--- a/apps/desktop/src/app/chat/sidebar/index.tsx
+++ b/apps/desktop/src/app/chat/sidebar/index.tsx
@@ -17,7 +17,7 @@ import {
 import { CSS } from '@dnd-kit/utilities'
 import { useStore } from '@nanostores/react'
 import type * as React from 'react'
-import { useMemo, useState } from 'react'
+import { useEffect, useMemo, useState } from 'react'
 
 import { Button } from '@/components/ui/button'
 import { Codicon } from '@/components/ui/codicon'
@@ -33,7 +33,7 @@ import {
   SidebarMenuItem
 } from '@/components/ui/sidebar'
 import { Skeleton } from '@/components/ui/skeleton'
-import type { SessionInfo } from '@/hermes'
+import { searchSessions, type SessionInfo, type SessionSearchResult } from '@/hermes'
 import { cn } from '@/lib/utils'
 import {
   $pinnedSessionIds,
@@ -54,7 +54,8 @@ import {
   $sessions,
   $sessionsLoading,
   $sessionsTotal,
-  $workingSessionIds
+  $workingSessionIds,
+  sessionPinId
 } from '@/store/session'
 
 import { type AppView, ARTIFACTS_ROUTE, MESSAGING_ROUTE, SKILLS_ROUTE } from '../../routes'
@@ -73,7 +74,12 @@ const SIDEBAR_NAV: SidebarNavItem[] = [
     icon: props => <Codicon name="robot" {...props} />,
     action: 'new-session'
   },
-  { id: 'skills', label: 'Skills & Tools', icon: props => <Codicon name="symbol-misc" {...props} />, route: SKILLS_ROUTE },
+  {
+    id: 'skills',
+    label: 'Skills & Tools',
+    icon: props => <Codicon name="symbol-misc" {...props} />,
+    route: SKILLS_ROUTE
+  },
   { id: 'messaging', label: 'Messaging', icon: props => <Codicon name="comment" {...props} />, route: MESSAGING_ROUTE },
   { id: 'artifacts', label: 'Artifacts', icon: props => <Codicon name="files" {...props} />, route: ARTIFACTS_ROUTE }
 ]
@@ -120,6 +126,31 @@ const baseName = (path: string) =>
     .filter(Boolean)
     .pop()
 
+// FTS results cover sessions that aren't in the loaded page; synthesize a
+// minimal SessionInfo so they render in the same row component (resume works
+// by id; the snippet stands in for the preview).
+function searchResultToSession(result: SessionSearchResult): SessionInfo {
+  const ts = result.session_started ?? Date.now() / 1000
+
+  return {
+    archived: false,
+    cwd: null,
+    ended_at: null,
+    id: result.session_id,
+    input_tokens: 0,
+    is_active: false,
+    last_active: ts,
+    message_count: 0,
+    model: result.model ?? null,
+    output_tokens: 0,
+    preview: result.snippet?.trim() || null,
+    source: result.source ?? null,
+    started_at: ts,
+    title: null,
+    tool_call_count: 0
+  }
+}
+
 function workspaceGroupsFor(sessions: SessionInfo[]): SidebarSessionGroup[] {
   const groups = new Map<string, SidebarSessionGroup>()
 
@@ -133,6 +164,14 @@ function workspaceGroupsFor(sessions: SessionInfo[]): SidebarSessionGroup[] {
     groups.set(id, group)
   }
 
+  // Groups keep recency order (Map insertion = first-seen in the recency-sorted
+  // input, so an active project floats up), but rows *within* a group sort by
+  // creation time so they don't reshuffle every time a message lands — keeps
+  // muscle memory intact.
+  for (const group of groups.values()) {
+    group.sessions.sort((a, b) => b.started_at - a.started_at)
+  }
+
   return [...groups.values()]
 }
 
@@ -179,6 +218,9 @@ export function ChatSidebar({
   const workingSessionIds = useStore($workingSessionIds)
   const [agentOrderIds, setAgentOrderIds] = useState<string[]>([])
   const [workspaceOrderIds, setWorkspaceOrderIds] = useState<string[]>([])
+  const [searchQuery, setSearchQuery] = useState('')
+  const [serverMatches, setServerMatches] = useState<SessionSearchResult[]>([])
+  const trimmedQuery = searchQuery.trim()
 
   const activeSidebarSessionId = currentView === 'chat' ? selectedSessionId : null
 
@@ -189,24 +231,99 @@ export function ChatSidebar({
 
   const sortedSessions = useMemo(() => [...sessions].sort((a, b) => sessionTime(b) - sessionTime(a)), [sessions])
 
-  const sessionsById = useMemo(() => new Map(sessions.map(s => [s.id, s])), [sessions])
   const workingSessionIdSet = useMemo(() => new Set(workingSessionIds), [workingSessionIds])
 
-  const visiblePinnedIds = useMemo(
-    () => pinnedSessionIds.filter(id => sessionsById.has(id)),
-    [pinnedSessionIds, sessionsById]
-  )
+  // Index sessions by both their live id and their lineage-root id so a pin
+  // stored as the pre-compression root resolves to the live continuation tip.
+  const sessionByAnyId = useMemo(() => {
+    const map = new Map<string, SessionInfo>()
 
-  const visiblePinnedIdSet = useMemo(() => new Set(visiblePinnedIds), [visiblePinnedIds])
+    for (const s of sessions) {
+      map.set(s.id, s)
 
-  const pinnedSessions = useMemo(
-    () => visiblePinnedIds.map(id => sessionsById.get(id)!).filter(Boolean),
-    [visiblePinnedIds, sessionsById]
-  )
+      if (s._lineage_root_id && !map.has(s._lineage_root_id)) {
+        map.set(s._lineage_root_id, s)
+      }
+    }
+
+    return map
+  }, [sessions])
+
+  const pinnedSessions = useMemo(() => {
+    const seen = new Set<string>()
+    const out: SessionInfo[] = []
+
+    for (const pinId of pinnedSessionIds) {
+      const session = sessionByAnyId.get(pinId)
+
+      if (session && !seen.has(session.id)) {
+        seen.add(session.id)
+        out.push(session)
+      }
+    }
+
+    return out
+  }, [pinnedSessionIds, sessionByAnyId])
+
+  const pinnedRealIdSet = useMemo(() => new Set(pinnedSessions.map(s => s.id)), [pinnedSessions])
+
+  // Full-text search across *all* sessions (not just the loaded page) so 699
+  // sessions stay findable. Debounced; loaded sessions are matched instantly
+  // client-side and merged ahead of the server hits.
+  useEffect(() => {
+    if (!trimmedQuery) {
+      setServerMatches([])
+
+      return
+    }
+
+    let cancelled = false
+
+    const id = window.setTimeout(() => {
+      void searchSessions(trimmedQuery)
+        .then(res => {
+          if (!cancelled) {
+            setServerMatches(res.results)
+          }
+        })
+        .catch(() => undefined)
+    }, 200)
+
+    return () => {
+      cancelled = true
+      window.clearTimeout(id)
+    }
+  }, [trimmedQuery])
+
+  const searchResults = useMemo(() => {
+    if (!trimmedQuery) {
+      return []
+    }
+
+    const needle = trimmedQuery.toLowerCase()
+    const out = new Map<string, SessionInfo>()
+
+    for (const s of sortedSessions) {
+      if (`${s.title ?? ''} ${s.preview ?? ''} ${s.cwd ?? ''}`.toLowerCase().includes(needle)) {
+        out.set(s.id, s)
+      }
+    }
+
+    for (const match of serverMatches) {
+      if (out.has(match.session_id)) {
+        continue
+      }
+
+      const loaded = sessionByAnyId.get(match.session_id)
+      out.set(match.session_id, loaded ?? searchResultToSession(match))
+    }
+
+    return [...out.values()]
+  }, [trimmedQuery, sortedSessions, serverMatches, sessionByAnyId])
 
   const unpinnedAgentSessions = useMemo(
-    () => sortedSessions.filter(s => !visiblePinnedIdSet.has(s.id)),
-    [sortedSessions, visiblePinnedIdSet]
+    () => sortedSessions.filter(s => !pinnedRealIdSet.has(s.id)),
+    [sortedSessions, pinnedRealIdSet]
   )
 
   const agentSessions = useMemo(
@@ -236,7 +353,10 @@ export function ChatSidebar({
       return
     }
 
-    reorderPinnedSession(String(active.id), newIndex)
+    // Sortable ids are live session ids; the pinned store is keyed by durable
+    // (lineage-root) ids, so translate before reordering.
+    const dragged = sessionByAnyId.get(String(active.id))
+    reorderPinnedSession(dragged ? sessionPinId(dragged) : String(active.id), newIndex)
   }
 
   const handleAgentDragEnd = ({ active, over }: DragEndEvent) => {
@@ -331,6 +451,56 @@ export function ChatSidebar({
         </SidebarGroup>
 
         {sidebarOpen && showSessionSections && (
+          <div className="shrink-0 pb-1 pt-1">
+            <div className="flex items-center gap-1.5 rounded-md border border-transparent bg-transparent px-2 transition-colors focus-within:border-(--ui-stroke-tertiary)">
+              <Codicon className="shrink-0 text-(--ui-text-tertiary)" name="search" size="0.75rem" />
+              <input
+                aria-label="Search sessions"
+                className="h-6 min-w-0 flex-1 bg-transparent text-[0.8125rem] text-foreground placeholder:text-(--ui-text-tertiary) focus:outline-none"
+                onChange={event => setSearchQuery(event.target.value)}
+                placeholder="Search sessions…"
+                type="text"
+                value={searchQuery}
+              />
+              {searchQuery && (
+                <button
+                  aria-label="Clear search"
+                  className="grid size-4 shrink-0 cursor-pointer place-items-center rounded-sm text-(--ui-text-tertiary) hover:bg-(--ui-control-active-background) hover:text-foreground"
+                  onClick={() => setSearchQuery('')}
+                  type="button"
+                >
+                  <Codicon name="close" size="0.75rem" />
+                </button>
+              )}
+            </div>
+          </div>
+        )}
+
+        {sidebarOpen && showSessionSections && trimmedQuery && (
+          <SidebarSessionsSection
+            activeSessionId={activeSidebarSessionId}
+            contentClassName="flex min-h-0 flex-1 flex-col gap-px overflow-y-auto overscroll-contain pb-1.75"
+            emptyState={
+              <div className="grid min-h-24 place-items-center rounded-lg px-2 text-center text-xs text-(--ui-text-tertiary)">
+                No sessions match “{trimmedQuery}”.
+              </div>
+            }
+            label="Results"
+            labelMeta={String(searchResults.length)}
+            onArchiveSession={onArchiveSession}
+            onDeleteSession={onDeleteSession}
+            onResumeSession={onResumeSession}
+            onToggle={() => undefined}
+            onTogglePin={pinSession}
+            open
+            pinned={false}
+            rootClassName="min-h-0 flex-1 p-0"
+            sessions={searchResults}
+            workingSessionIdSet={workingSessionIdSet}
+          />
+        )}
+
+        {sidebarOpen && showSessionSections && !trimmedQuery && (
           <SidebarSessionsSection
             activeSessionId={activeSidebarSessionId}
             contentClassName="flex min-h-10 shrink-0 flex-col gap-px rounded-lg pb-2 pt-1"
@@ -352,7 +522,7 @@ export function ChatSidebar({
           />
         )}
 
-        {sidebarOpen && showSessionSections && (
+        {sidebarOpen && showSessionSections && !trimmedQuery && (
           <SidebarSessionsSection
             activeSessionId={activeSidebarSessionId}
             contentClassName="flex min-h-0 flex-1 flex-col gap-px overflow-y-auto overscroll-contain pb-1.75"
@@ -536,7 +706,7 @@ function SidebarSessionsSection({
       isWorking: workingSessionIdSet.has(session.id),
       onArchive: () => onArchiveSession(session.id),
       onDelete: () => onDeleteSession(session.id),
-      onPin: () => onTogglePin(session.id),
+      onPin: () => onTogglePin(sessionPinId(session)),
       onResume: () => onResumeSession(session.id),
       session
     }
diff --git a/apps/desktop/src/app/chat/sidebar/virtual-session-list.tsx b/apps/desktop/src/app/chat/sidebar/virtual-session-list.tsx
index 2f6d8deb8cd..debcdd8cd82 100644
--- a/apps/desktop/src/app/chat/sidebar/virtual-session-list.tsx
+++ b/apps/desktop/src/app/chat/sidebar/virtual-session-list.tsx
@@ -5,6 +5,7 @@ import { type FC, useCallback, useMemo, useRef } from 'react'
 
 import type { SessionInfo } from '@/hermes'
 import { cn } from '@/lib/utils'
+import { sessionPinId } from '@/store/session'
 
 import { SidebarSessionRow } from './session-row'
 
@@ -77,7 +78,7 @@ export const VirtualSessionList: FC<VirtualSessionListProps> = ({
       isWorking: workingSessionIdSet.has(session.id),
       onArchive: () => onArchiveSession(session.id),
       onDelete: () => onDeleteSession(session.id),
-      onPin: () => onTogglePin(session.id),
+      onPin: () => onTogglePin(sessionPinId(session)),
       onResume: () => onResumeSession(session.id)
     }
 
diff --git a/apps/desktop/src/app/desktop-controller.tsx b/apps/desktop/src/app/desktop-controller.tsx
index 6ede12a197a..22bd7eedbe9 100644
--- a/apps/desktop/src/app/desktop-controller.tsx
+++ b/apps/desktop/src/app/desktop-controller.tsx
@@ -32,6 +32,8 @@ import {
   $freshDraftReady,
   $gatewayState,
   $selectedStoredSessionId,
+  $sessions,
+  sessionPinId,
   setAwaitingResponse,
   setBusy,
   setCurrentBranch,
@@ -224,10 +226,14 @@ export function DesktopController() {
       return
     }
 
-    if ($pinnedSessionIds.get().includes(sessionId)) {
-      unpinSession(sessionId)
+    // Pin on the durable lineage-root id so the pin survives auto-compression.
+    const session = $sessions.get().find(s => s.id === sessionId || s._lineage_root_id === sessionId)
+    const pinId = session ? sessionPinId(session) : sessionId
+
+    if ($pinnedSessionIds.get().includes(pinId)) {
+      unpinSession(pinId)
     } else {
-      pinSession(sessionId)
+      pinSession(pinId)
     }
   }, [])
 
diff --git a/apps/desktop/src/components/desktop-install-overlay.tsx b/apps/desktop/src/components/desktop-install-overlay.tsx
index 1864c6840ca..2ddac1b41b1 100644
--- a/apps/desktop/src/components/desktop-install-overlay.tsx
+++ b/apps/desktop/src/components/desktop-install-overlay.tsx
@@ -62,9 +62,7 @@ function formatStageName(name: string): string {
   if (name.length <= 3) return name
   return name
     .split('-')
-    .map((word, i) =>
-      i === 0 ? word.charAt(0).toUpperCase() + word.slice(1) : word
-    )
+    .map((word, i) => (i === 0 ? word.charAt(0).toUpperCase() + word.slice(1) : word))
     .join(' ')
 }
 
@@ -116,17 +114,10 @@ function StageRow({ descriptor, result, isCurrent, now }: StageRowProps) {
         state === 'failed' && 'bg-destructive/10'
       )}
     >
-      <div className="flex h-5 w-5 flex-shrink-0 items-center justify-center">
-        {icon}
-      </div>
+      <div className="flex h-5 w-5 flex-shrink-0 items-center justify-center">{icon}</div>
       <div className="min-w-0 flex-1">
         <div className="flex items-baseline justify-between gap-2">
-          <span
-            className={cn(
-              'truncate text-sm font-medium',
-              state === 'pending' && 'text-muted-foreground'
-            )}
-          >
+          <span className={cn('truncate text-sm font-medium', state === 'pending' && 'text-muted-foreground')}>
             {formatStageName(descriptor.name)}
           </span>
           <span className="flex-shrink-0 text-xs tabular-nums text-muted-foreground">
@@ -135,9 +126,7 @@ function StageRow({ descriptor, result, isCurrent, now }: StageRowProps) {
             {state === 'failed' ? STATE_LABEL[state] : null}
           </span>
         </div>
-        {reason && state !== 'pending' && (
-          <p className="mt-0.5 truncate text-xs text-muted-foreground">{reason}</p>
-        )}
+        {reason && state !== 'pending' && <p className="mt-0.5 truncate text-xs text-muted-foreground">{reason}</p>}
       </div>
     </li>
   )
@@ -180,7 +169,7 @@ function applyEvent(state: DesktopBootstrapState, ev: DesktopBootstrapEvent): De
           durationMs: ev.durationMs ?? null,
           // Stamp the start time on the running transition so the UI can show
           // a live elapsed timer; preserve it across repeated running events.
-          startedAt: ev.state === 'running' ? prev?.startedAt ?? Date.now() : prev?.startedAt ?? null,
+          startedAt: ev.state === 'running' ? (prev?.startedAt ?? Date.now()) : (prev?.startedAt ?? null),
           json: ev.json ?? null,
           error: ev.error ?? null
         }
@@ -217,6 +206,7 @@ export function DesktopInstallOverlay({ enabled = true }: DesktopInstallOverlayP
   const [state, setState] = useState<DesktopBootstrapState>(EMPTY_STATE)
   const [logOpen, setLogOpen] = useState(false)
   const [copied, setCopied] = useState(false)
+  const [cancelling, setCancelling] = useState(false)
   const [now, setNow] = useState(() => Date.now())
   const logEndRef = useRef<HTMLDivElement | null>(null)
 
@@ -293,8 +283,8 @@ export function DesktopInstallOverlay({ enabled = true }: DesktopInstallOverlayP
         <div className="w-full max-w-xl rounded-xl border bg-card p-8 shadow-xl">
           <h2 className="text-2xl font-semibold tracking-tight">Hermes needs a one-time install</h2>
           <p className="mt-2 text-sm text-muted-foreground">
-            Automated first-launch install isn{'\u2019'}t available on {platformLabel} yet. Open Terminal and
-            run the command below, then relaunch this app. Subsequent launches will skip this step.
+            Automated first-launch install isn{'\u2019'}t available on {platformLabel} yet. Open Terminal and run the
+            command below, then relaunch this app. Subsequent launches will skip this step.
           </p>
 
           <div className="mt-4">
@@ -328,11 +318,7 @@ export function DesktopInstallOverlay({ enabled = true }: DesktopInstallOverlayP
             <span className="text-xs text-muted-foreground">
               Will install to <code className="rounded bg-muted/50 px-1 py-0.5 font-mono">{ups.activeRoot}</code>
             </span>
-            <Button
-              variant="default"
-              size="sm"
-              onClick={() => window.location.reload()}
-            >
+            <Button variant="default" size="sm" onClick={() => window.location.reload()}>
               I{'\u2019'}ve run it -- retry
             </Button>
           </div>
@@ -382,10 +368,7 @@ export function DesktopInstallOverlay({ enabled = true }: DesktopInstallOverlayP
               </div>
               <div className="h-1.5 w-full overflow-hidden rounded-full bg-muted">
                 <div
-                  className={cn(
-                    'h-full transition-all duration-300',
-                    failed ? 'bg-destructive' : 'bg-primary'
-                  )}
+                  className={cn('h-full transition-all duration-300', failed ? 'bg-destructive' : 'bg-primary')}
                   style={{ width: `${progressPct}%` }}
                 />
               </div>
@@ -431,14 +414,18 @@ export function DesktopInstallOverlay({ enabled = true }: DesktopInstallOverlayP
             >
               {logOpen ? <ChevronDown className="h-3.5 w-3.5" /> : <ChevronRight className="h-3.5 w-3.5" />}
               <span>{logOpen ? 'Hide installer output' : 'Show installer output'}</span>
-              <span className="ml-1 tabular-nums">({state.log.length} line{state.log.length === 1 ? '' : 's'})</span>
+              <span className="ml-1 tabular-nums">
+                ({state.log.length} line{state.log.length === 1 ? '' : 's'})
+              </span>
             </button>
 
             {logOpen && (
-              <div className={cn(
-                'mt-2 overflow-auto rounded-md border bg-muted/30 p-2 font-mono text-[11px] leading-relaxed',
-                failed ? 'max-h-96' : 'max-h-64'
-              )}>
+              <div
+                className={cn(
+                  'mt-2 overflow-auto rounded-md border bg-muted/30 p-2 font-mono text-[11px] leading-relaxed',
+                  failed ? 'max-h-96' : 'max-h-64'
+                )}
+              >
                 {state.log.length === 0 ? (
                   <div className="text-muted-foreground">No output yet.</div>
                 ) : (
@@ -457,12 +444,38 @@ export function DesktopInstallOverlay({ enabled = true }: DesktopInstallOverlayP
           </div>
         </div>
 
+        {/* Active footer: let the user actually cancel a running install. */}
+        {state.active && !failed && (
+          <div className="flex-shrink-0 border-t bg-card p-4">
+            <div className="flex items-center justify-end">
+              <Button
+                disabled={cancelling}
+                onClick={async () => {
+                  setCancelling(true)
+
+                  try {
+                    await window.hermesDesktop?.cancelBootstrap?.()
+                  } catch {
+                    // ignore -- the failed/cancelled event will surface the result
+                  }
+                }}
+                size="sm"
+                variant="ghost"
+              >
+                {cancelling ? <Loader2 className="h-4 w-4 animate-spin" /> : null}
+                {cancelling ? 'Cancelling...' : 'Cancel install'}
+              </Button>
+            </div>
+          </div>
+        )}
+
         {/* Footer -- always visible, never scrolls; only renders on failure */}
         {failed && (
           <div className="flex-shrink-0 border-t bg-card p-4">
             <div className="flex items-center justify-between gap-2">
               <span className="text-xs text-muted-foreground">
-                Full transcript saved to <code className="rounded bg-muted/50 px-1 py-0.5 font-mono">%LOCALAPPDATA%\hermes\logs\</code>
+                Full transcript saved to{' '}
+                <code className="rounded bg-muted/50 px-1 py-0.5 font-mono">%LOCALAPPDATA%\hermes\logs\</code>
               </span>
               <div className="flex gap-2">
                 <Button
diff --git a/apps/desktop/src/global.d.ts b/apps/desktop/src/global.d.ts
index d278042e8b2..eed81556eb6 100644
--- a/apps/desktop/src/global.d.ts
+++ b/apps/desktop/src/global.d.ts
@@ -48,6 +48,7 @@ declare global {
       getBootstrapState: () => Promise<DesktopBootstrapState>
       resetBootstrap: () => Promise<{ ok: boolean }>
       repairBootstrap: () => Promise<{ ok: boolean }>
+      cancelBootstrap: () => Promise<{ ok: boolean; cancelled: boolean }>
       onBootstrapEvent: (callback: (payload: DesktopBootstrapEvent) => void) => () => void
       getVersion: () => Promise<DesktopVersionInfo>
       updates: {
@@ -194,12 +195,7 @@ export interface DesktopBootstrapStageDescriptor {
   needs_user_input?: boolean
 }
 
-export type DesktopBootstrapStageState =
-  | 'pending'
-  | 'running'
-  | 'succeeded'
-  | 'skipped'
-  | 'failed'
+export type DesktopBootstrapStageState = 'pending' | 'running' | 'succeeded' | 'skipped' | 'failed'
 
 export interface DesktopBootstrapStageResult {
   state: DesktopBootstrapStageState
@@ -248,7 +244,6 @@ export type DesktopBootstrapEvent =
       docsUrl: string
     }
 
-
 export interface HermesApiRequest {
   path: string
   method?: string
diff --git a/apps/desktop/src/hermes.ts b/apps/desktop/src/hermes.ts
index 3e06027fc07..6e41f382804 100644
--- a/apps/desktop/src/hermes.ts
+++ b/apps/desktop/src/hermes.ts
@@ -114,10 +114,11 @@ export class HermesGateway extends JsonRpcGatewayClient {
 export async function listSessions(
   limit = 40,
   minMessages = 0,
-  archived: 'exclude' | 'include' | 'only' = 'exclude'
+  archived: 'exclude' | 'include' | 'only' = 'exclude',
+  order: 'created' | 'recent' = 'recent'
 ): Promise<PaginatedSessions> {
   const result = await window.hermesDesktop.api<PaginatedSessions>({
-    path: `/api/sessions?limit=${limit}&offset=0&min_messages=${Math.max(0, minMessages)}&archived=${archived}`
+    path: `/api/sessions?limit=${limit}&offset=0&min_messages=${Math.max(0, minMessages)}&archived=${archived}&order=${order}`
   })
 
   return {
diff --git a/apps/desktop/src/store/session.test.ts b/apps/desktop/src/store/session.test.ts
new file mode 100644
index 00000000000..d9d2befb7e4
--- /dev/null
+++ b/apps/desktop/src/store/session.test.ts
@@ -0,0 +1,36 @@
+import { describe, expect, it } from 'vitest'
+
+import type { SessionInfo } from '@/types/hermes'
+
+import { sessionPinId } from './session'
+
+const session = (over: Partial<SessionInfo>): SessionInfo => ({
+  archived: false,
+  cwd: null,
+  ended_at: null,
+  id: 'live',
+  input_tokens: 0,
+  is_active: false,
+  last_active: 0,
+  message_count: 0,
+  model: null,
+  output_tokens: 0,
+  preview: null,
+  source: null,
+  started_at: 0,
+  title: null,
+  tool_call_count: 0,
+  ...over
+})
+
+describe('sessionPinId', () => {
+  it('uses the live id when there is no compression lineage', () => {
+    expect(sessionPinId(session({ id: 'abc' }))).toBe('abc')
+  })
+
+  it('uses the lineage root so a pin survives compression', () => {
+    // After auto-compression the entry surfaces under a fresh tip id but keeps
+    // the original root — pinning on the root keeps the pin stable.
+    expect(sessionPinId(session({ id: 'tip', _lineage_root_id: 'root' }))).toBe('root')
+  })
+})
diff --git a/apps/desktop/src/store/session.ts b/apps/desktop/src/store/session.ts
index 6cd26f6b95c..cf2372f3d04 100644
--- a/apps/desktop/src/store/session.ts
+++ b/apps/desktop/src/store/session.ts
@@ -16,6 +16,12 @@ function updateAtom<T>(store: AppAtom<T>, next: Updater<T>) {
   store.set(typeof next === 'function' ? (next as (current: T) => T)(store.get()) : next)
 }
 
+/** Durable id for pinning. Auto-compression rotates a conversation's session
+ *  id (root -> continuation tip), so pins keyed on the live id evaporate. The
+ *  lineage root is stable across every compression, so we pin on that. */
+export const sessionPinId = (session: Pick<SessionInfo, '_lineage_root_id' | 'id'>): string =>
+  session._lineage_root_id ?? session.id
+
 export const $connection = atom<HermesConnection | null>(null)
 export const $gatewayState = atom('idle')
 export const $sessions = atom<SessionInfo[]>([])
diff --git a/apps/desktop/src/types/hermes.ts b/apps/desktop/src/types/hermes.ts
index 550b66deb77..0fbad5f25a2 100644
--- a/apps/desktop/src/types/hermes.ts
+++ b/apps/desktop/src/types/hermes.ts
@@ -244,6 +244,10 @@ export interface SessionInfo {
   cwd?: null | string
   ended_at: null | number
   id: string
+  /** Original root id of a compression chain, when this entry is a projected
+   *  continuation tip. Stable across compressions — used as the durable id for
+   *  pins so a pinned conversation survives auto-compression. */
+  _lineage_root_id?: null | string
   input_tokens: number
   is_active: boolean
   last_active: number
diff --git a/hermes_cli/web_server.py b/hermes_cli/web_server.py
index 92d4119cf7d..4a3e20a6eaf 100644
--- a/hermes_cli/web_server.py
+++ b/hermes_cli/web_server.py
@@ -1363,6 +1363,7 @@ async def get_sessions(
     offset: int = 0,
     min_messages: int = 0,
     archived: str = "exclude",
+    order: str = "created",
 ):
     """List sessions.
 
@@ -1370,12 +1371,22 @@ async def get_sessions(
     ``exclude`` (default) hides them, ``only`` returns just the archived ones
     (used by the desktop "Archived sessions" settings panel), and ``include``
     returns both.
+
+    ``order`` controls pagination order: ``created`` (default, by original
+    start time) or ``recent`` (by latest activity across the compression
+    chain). ``recent`` keeps a long-running conversation on the first page
+    after it auto-compresses into a fresh continuation id.
     """
     if archived not in ("exclude", "only", "include"):
         raise HTTPException(
             status_code=400,
             detail="archived must be one of: exclude, only, include",
         )
+    if order not in ("created", "recent"):
+        raise HTTPException(
+            status_code=400,
+            detail="order must be one of: created, recent",
+        )
     try:
         from hermes_state import SessionDB
         db = SessionDB()
@@ -1389,6 +1400,7 @@ async def get_sessions(
                 min_message_count=min_message_count,
                 include_archived=include_archived,
                 archived_only=archived_only,
+                order_by_last_active=order == "recent",
             )
             total = db.session_count(
                 min_message_count=min_message_count,
diff --git a/tests/hermes_cli/test_web_server.py b/tests/hermes_cli/test_web_server.py
index 8dd39fa1f36..d994797e4e6 100644
--- a/tests/hermes_cli/test_web_server.py
+++ b/tests/hermes_cli/test_web_server.py
@@ -293,6 +293,49 @@ class TestWebServerEndpoints:
         resp = self.client.get("/api/sessions?archived=bogus")
         assert resp.status_code == 400
 
+    def test_get_sessions_rejects_unknown_order_value(self):
+        resp = self.client.get("/api/sessions?order=sideways")
+        assert resp.status_code == 400
+
+    def test_get_sessions_order_recent_surfaces_compression_tip(self):
+        """A long-running conversation that auto-compresses must stay on the
+        first page by recency, listed under its live continuation id."""
+        import time as _time
+
+        from hermes_state import SessionDB
+
+        db = SessionDB()
+        try:
+            old = _time.time() - 86_400
+            # Old conversation that later compresses into a fresh continuation.
+            # The continuation must start at/after the parent's ended_at to be
+            # recognised as a compression tip (not a sub-agent/branch).
+            db.create_session(session_id="root-old", source="cli")
+            db.append_message(session_id="root-old", role="user", content="kickoff")
+            db.end_session("root-old", "compression")
+            db._conn.execute(
+                "UPDATE sessions SET started_at = ?, ended_at = ? WHERE id = ?",
+                (old, old + 10, "root-old"),
+            )
+            db.create_session(session_id="tip-new", source="cli", parent_session_id="root-old")
+            db._conn.execute("UPDATE sessions SET started_at = ? WHERE id = ?", (old + 10, "tip-new"))
+            db.append_message(session_id="tip-new", role="user", content="continued just now")
+            # A brand-new unrelated session started after the root but before now.
+            db.create_session(session_id="mid", source="cli")
+            db._conn.execute("UPDATE sessions SET started_at = ? WHERE id = ?", (_time.time() - 3600, "mid"))
+            db.append_message(session_id="mid", role="user", content="hello")
+            db._conn.commit()
+        finally:
+            db.close()
+
+        rows = self.client.get("/api/sessions?order=recent&limit=5").json()["sessions"]
+        ids = [r["id"] for r in rows]
+        # The compressed conversation surfaces under its live tip id...
+        assert "tip-new" in ids
+        # ...carrying the durable lineage root so the desktop can match pins.
+        tip = next(r for r in rows if r["id"] == "tip-new")
+        assert tip.get("_lineage_root_id") == "root-old"
+
     def test_get_sessions_archived_is_boolean(self):
         from hermes_state import SessionDB
 
diff --git a/tests/test_tui_gateway_server.py b/tests/test_tui_gateway_server.py
index 4fc01772965..6c93dd629d3 100644
--- a/tests/test_tui_gateway_server.py
+++ b/tests/test_tui_gateway_server.py
@@ -933,8 +933,27 @@ def test_session_create_does_not_persist_empty_row(monkeypatch):
         server._sessions.pop(sid, None)
 
 
-def test_ensure_session_db_row_persists_with_cwd(monkeypatch, tmp_path):
-    """First prompt persists the row (INSERT OR IGNORE) capturing cwd up front."""
+def test_ensure_session_db_row_persists_explicit_cwd(monkeypatch, tmp_path):
+    """An explicitly chosen workspace is persisted as the session cwd."""
+    created = []
+
+    class _FakeDB:
+        def create_session(self, key, source=None, model=None, cwd=None):
+            created.append({"key": key, "source": source, "model": model, "cwd": cwd})
+
+    monkeypatch.setattr(server, "_get_db", lambda: _FakeDB())
+    monkeypatch.setattr(server, "_resolve_model", lambda: "test-model")
+
+    server._ensure_session_db_row({"session_key": "k1", "cwd": str(tmp_path), "explicit_cwd": True})
+
+    assert created == [
+        {"key": "k1", "source": "tui", "model": "test-model", "cwd": str(tmp_path)}
+    ]
+
+
+def test_ensure_session_db_row_defaults_to_no_workspace(monkeypatch, tmp_path):
+    """Without an explicit workspace, cwd is left null so the session groups
+    under "No workspace" rather than the gateway's launch directory."""
     created = []
 
     class _FakeDB:
@@ -946,9 +965,7 @@ def test_ensure_session_db_row_persists_with_cwd(monkeypatch, tmp_path):
 
     server._ensure_session_db_row({"session_key": "k1", "cwd": str(tmp_path)})
 
-    assert created == [
-        {"key": "k1", "source": "tui", "model": "test-model", "cwd": str(tmp_path)}
-    ]
+    assert created == [{"key": "k1", "source": "tui", "model": "test-model", "cwd": None}]
 
 
 def test_session_title_clears_pending_after_persist(monkeypatch):
diff --git a/tui_gateway/server.py b/tui_gateway/server.py
index 83963f80139..528e0b2b11f 100644
--- a/tui_gateway/server.py
+++ b/tui_gateway/server.py
@@ -708,8 +708,14 @@ def _ensure_session_db_row(session: dict) -> None:
     Called from prompt.submit so a row only exists once the user actually sends
     a message — abandoned drafts never leave an empty "Untitled" session behind.
     Uses INSERT OR IGNORE under the hood, so re-calls (and the AIAgent's own
-    lazy create) are no-ops. Captures cwd up front so workspace grouping works
-    without waiting for a separate cwd update.
+    lazy create) are no-ops.
+
+    Only an *explicitly chosen* workspace is persisted as the session's cwd.
+    The agent still runs in the auto-detected directory (session["cwd"]), but
+    we don't stamp that onto the row — otherwise every session the user never
+    picked a folder for gets grouped under whatever directory the desktop
+    happened to launch in (e.g. "desktop"). Leaving it null groups them under
+    "No workspace", which is the desired default.
     """
     key = session.get("session_key")
     if not key:
@@ -722,7 +728,7 @@ def _ensure_session_db_row(session: dict) -> None:
             key,
             source="tui",
             model=_resolve_model(),
-            cwd=_session_cwd(session),
+            cwd=_session_cwd(session) if session.get("explicit_cwd") else None,
         )
     except Exception:
         logger.debug("failed to persist desktop session row", exc_info=True)
@@ -733,6 +739,9 @@ def _set_session_cwd(session: dict, cwd: str) -> str:
     if not os.path.isdir(resolved):
         raise ValueError(f"working directory does not exist: {cwd}")
     session["cwd"] = resolved
+    # An explicit user choice — persist it as the workspace (and let a later
+    # lazy row creation persist it too, not the launch-dir fallback).
+    session["explicit_cwd"] = True
     _register_session_cwd(session)
     db = _get_db()
     if db is not None:
@@ -2746,6 +2755,15 @@ def _(rid, params: dict) -> dict:
     cols = int(params.get("cols", 80))
     history = _coerce_seed_history(params.get("messages"))
     title = str(params.get("title") or "").strip()
+    # Did the client pick a workspace, or are we falling back to the gateway's
+    # launch directory? Only an explicit choice is persisted as the session's
+    # workspace (see _ensure_session_db_row); otherwise it lands in "No
+    # workspace" instead of whatever folder the desktop launched in.
+    raw_cwd = str(params.get("cwd") or "").strip()
+    try:
+        explicit_cwd = bool(raw_cwd) and os.path.isdir(os.path.abspath(os.path.expanduser(raw_cwd)))
+    except Exception:
+        explicit_cwd = False
     _enable_gateway_prompts()
 
     ready = threading.Event()
@@ -2759,6 +2777,7 @@ def _(rid, params: dict) -> dict:
         "cols": cols,
         "created_at": now,
         "edit_snapshots": {},
+        "explicit_cwd": explicit_cwd,
         "history": history,
         "history_lock": threading.Lock(),
         "history_version": 0,