diff --git a/apps/desktop/src/app/chat/sidebar/index.tsx b/apps/desktop/src/app/chat/sidebar/index.tsx
index 53fb9688e..4d7385747 100644
--- a/apps/desktop/src/app/chat/sidebar/index.tsx
+++ b/apps/desktop/src/app/chat/sidebar/index.tsx
@@ -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 }
 ]
@@ -189,24 +195,45 @@ 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])
 
   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 +263,10 @@ 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) => {
@@ -536,7 +566,7 @@ 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 2f6d8deb8..debcdd8cd 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 ba513a2cf..58a7dd0e5 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/hermes.ts b/apps/desktop/src/hermes.ts
index 3e06027fc..6e41f3828 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 000000000..d9d2befb7
--- /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 6cd26f6b9..cf2372f3d 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 550b66deb..0fbad5f25 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 92d4119cf..4a3e20a6e 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 8dd39fa1f..d994797e4 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