diff --git a/src/main/ai-vault/session-scanner-cursor-local-bounds.test.ts b/src/main/ai-vault/session-scanner-cursor-local-bounds.test.ts
index 21bbe468adf..0303bd1727a 100644
--- a/src/main/ai-vault/session-scanner-cursor-local-bounds.test.ts
+++ b/src/main/ai-vault/session-scanner-cursor-local-bounds.test.ts
@@ -264,6 +264,28 @@ describe('local Cursor sidecar discovery bounds', () => {
     ).rejects.toThrow('cursor_sidecar_scan_cancelled')
   })
 
+  it('honors cancellation that lands while resolving a missing chats root', async () => {
+    const root = await mkdtemp(join(tmpdir(), 'orca-cursor-cancel-missing-'))
+    tempRoots.push(root)
+    let checks = 0
+    const signal = {
+      get aborted() {
+        checks += 1
+        return checks > 1
+      }
+    } as AbortSignal
+
+    await expect(
+      discoverLocalCursorSidecarsBounded({
+        chatsDir: join(root, 'missing-chats'),
+        scopePaths: [],
+        issues: [],
+        signal
+      })
+    ).rejects.toThrow('cursor_sidecar_scan_cancelled')
+    expect(checks).toBe(2)
+  })
+
   it('rejects on second-phase cancellation instead of resolving with an issue', async () => {
     const root = await mkdtemp(join(tmpdir(), 'orca-cursor-cancel-2nd-'))
     tempRoots.push(root)
@@ -276,7 +298,7 @@ describe('local Cursor sidecar discovery bounds', () => {
     const signal = {
       get aborted() {
         checks += 1
-        // First check (post-realpath) passes; later enumeration-phase checks abort.
+        // The pre-realpath check passes; the post-realpath check observes cancellation.
         return checks > 1
       }
     } as AbortSignal
diff --git a/src/relay/cursor-sidecar-scan.test.ts b/src/relay/cursor-sidecar-scan.test.ts
index 7641e5d9d7a..6de8ebeef8c 100644
--- a/src/relay/cursor-sidecar-scan.test.ts
+++ b/src/relay/cursor-sidecar-scan.test.ts
@@ -12,7 +12,7 @@ import { cursorBucketForCwd } from '../main/ai-vault/session-scanner-cursor-path
 
 const roots: string[] = []
 const context = { clientId: 1, isStale: () => false }
-const CHECKS_BEFORE_FIRST_VERIFIED_READ = 8
+const CHECKS_BEFORE_FIRST_VERIFIED_READ = 9
 
 async function createRoot(): Promise<string> {
   const root = await mkdtemp(join(tmpdir(), 'orca-cursor-scan-'))
@@ -89,6 +89,48 @@ describe('scanCursorSidecars', () => {
     })
   })
 
+  it('shares bounded session capacity across exact scope buckets', async () => {
+    const root = await createRoot()
+    const chatsRoot = join(root, 'chats')
+    const scopes = [join(root, 'a-workspace'), join(root, 'z-workspace')]
+    await Promise.all(scopes.map((scope) => mkdir(scope)))
+    const firstBucket = cursorBucketForCwd(scopes[0], process.platform)
+    await Promise.all([
+      addSession(chatsRoot, firstBucket, 'first-a'),
+      addSession(chatsRoot, firstBucket, 'first-b'),
+      addSession(chatsRoot, cursorBucketForCwd(scopes[1], process.platform), 'second')
+    ])
+    const request = defaultCursorSidecarScanRequest(chatsRoot, scopes, process.platform)
+    request.maxSessionDirs = 2
+
+    const result = await scanCursorSidecars(request, context)
+
+    expect(result.sidecars.map((sidecar) => sidecar.sessionId).sort()).toEqual([
+      'first-a',
+      'second'
+    ])
+    expect(result.truncated.sessionDirs).toBe(true)
+  })
+
+  it('keeps exact scope sessions within the requested cap', async () => {
+    const root = await createRoot()
+    const chatsRoot = join(root, 'chats')
+    const scope = join(root, 'workspace')
+    await mkdir(scope)
+    const bucket = cursorBucketForCwd(scope, process.platform)
+    await Promise.all([
+      addSession(chatsRoot, bucket, 'first-scoped'),
+      addSession(chatsRoot, bucket, 'second-scoped')
+    ])
+    const request = defaultCursorSidecarScanRequest(chatsRoot, [scope], process.platform)
+    request.maxSessionDirs = 1
+
+    const result = await scanCursorSidecars(request, context)
+
+    expect(result.sidecars).toHaveLength(1)
+    expect(result.truncated.sessionDirs).toBe(true)
+  })
+
   it.skipIf(process.platform === 'win32')(
     'keeps missing files silent and rejects symlinked sidecars',
     async () => {
diff --git a/src/shared/cursor-sidecar-scan-cancellation.ts b/src/shared/cursor-sidecar-scan-cancellation.ts
new file mode 100644
index 00000000000..906cef1675a
--- /dev/null
+++ b/src/shared/cursor-sidecar-scan-cancellation.ts
@@ -0,0 +1,19 @@
+export type CursorSidecarScanCancellation = {
+  throwIfCancelled: () => void
+}
+
+export function isCursorSidecarScanCancelledError(error: unknown): boolean {
+  return error instanceof Error && error.message === 'cursor_sidecar_scan_cancelled'
+}
+
+export function cursorSidecarScanCancellationFromSignal(
+  signal?: AbortSignal
+): CursorSidecarScanCancellation {
+  return {
+    throwIfCancelled: () => {
+      if (signal?.aborted) {
+        throw new Error('cursor_sidecar_scan_cancelled')
+      }
+    }
+  }
+}
diff --git a/src/shared/cursor-sidecar-scan-directory.test.ts b/src/shared/cursor-sidecar-scan-directory.test.ts
index 02fad24c122..6d332ec4eb3 100644
--- a/src/shared/cursor-sidecar-scan-directory.test.ts
+++ b/src/shared/cursor-sidecar-scan-directory.test.ts
@@ -1,5 +1,5 @@
 import type { Dirent } from 'node:fs'
-import { mkdir, mkdtemp, readdir, rm, writeFile } from 'node:fs/promises'
+import { mkdir, mkdtemp, rm, writeFile } from 'node:fs/promises'
 import { tmpdir } from 'node:os'
 import { join } from 'node:path'
 import { afterEach, describe, expect, it, vi } from 'vitest'
@@ -85,22 +85,14 @@ describe('cursor sidecar directory examination bounds', () => {
     expect(onDirentCount).toBe(budget)
   })
 
-  it('hard-bounds the readdir fallback without retaining an unbounded listing', async () => {
+  it('fails bounded when directory streaming is unsupported', async () => {
     const root = await tempDir('orca-cursor-dir-fallback-')
     const budget = 16
-    const names = await fillDirectory(root, budget + 8)
+    await fillDirectory(root, budget + 8)
 
-    let readdirCalls = 0
-    let observedListingLength = 0
     setStreamDirectoryIoForTests({
       opendir: async () => {
         throw unsupportedDirectoryStreamError()
-      },
-      readdirWithFileTypes: async (dirPath) => {
-        readdirCalls += 1
-        const entries = await readdir(dirPath, { withFileTypes: true })
-        observedListingLength = entries.length
-        return entries
       }
     })
 
@@ -113,13 +105,8 @@ describe('cursor sidecar directory examination bounds', () => {
       { maxEntriesExamined: budget }
     )
 
-    expect(readdirCalls).toBe(1)
-    expect(result.entriesExamined).toBe(budget)
-    expect(result.examinationTruncated).toBe(true)
-    expect(visited).toHaveLength(budget)
-    expect(observedListingLength).toBe(names.length)
-    // After return, the eager listing must not remain as a retained examination set.
-    expect(visited.every((name) => names.includes(name))).toBe(true)
+    expect(result).toEqual({ entriesExamined: 0, examinationTruncated: true })
+    expect(visited).toEqual([])
   })
 
   it('propagates cancellation from onDirent during examination', async () => {
@@ -140,29 +127,6 @@ describe('cursor sidecar directory examination bounds', () => {
     expect(seen).toBe(10)
   })
 
-  it('propagates cancellation on the readdir fallback path', async () => {
-    const root = await tempDir('orca-cursor-dir-cancel-fallback-')
-    await fillDirectory(root, 40)
-    setStreamDirectoryIoForTests({
-      opendir: async () => {
-        throw unsupportedDirectoryStreamError()
-      }
-    })
-    let seen = 0
-    await expect(
-      streamDirectoryNames(root, () => undefined, {
-        maxEntriesExamined: 40,
-        onDirent: () => {
-          seen += 1
-          if (seen >= 5) {
-            throw new Error('cursor_sidecar_scan_cancelled')
-          }
-        }
-      })
-    ).rejects.toThrow('cursor_sidecar_scan_cancelled')
-    expect(seen).toBe(5)
-  })
-
   it('keeps listLexicographic examination-truncated when the walk hits the budget with more left', async () => {
     const root = await tempDir('orca-cursor-dir-list-trunc-')
     await fillDirectory(root, 20, 'z')
@@ -226,7 +190,7 @@ describe('cursor sidecar directory examination bounds', () => {
     expect(listed.names).toHaveLength(64)
   }, 60_000)
 
-  it('fallback path never visits more than the examination budget on a 10k store', async () => {
+  it('unsupported streaming does not traverse a 10k store', async () => {
     const root = await tempDir('orca-cursor-dir-10k-fallback-')
     await fillDirectory(root, 10_000)
     setStreamDirectoryIoForTests({
@@ -243,9 +207,8 @@ describe('cursor sidecar directory examination bounds', () => {
       },
       { maxEntriesExamined: budget }
     )
-    expect(visits).toBe(budget)
-    expect(result.entriesExamined).toBe(budget)
-    expect(result.examinationTruncated).toBe(true)
+    expect(visits).toBe(0)
+    expect(result).toEqual({ entriesExamined: 0, examinationTruncated: true })
   }, 60_000)
 
   it('retainLexicographic keeps only the first `limit` names in order', () => {
@@ -257,6 +220,32 @@ describe('cursor sidecar directory examination bounds', () => {
     expect(selected).toEqual(['a', 'b', 'm'])
   })
 
+  it('bounds comparisons for reverse-ordered retained names', () => {
+    const originalLocaleCompare = String.prototype.localeCompare
+    let comparisons = 0
+    const localeCompare = vi.spyOn(String.prototype, 'localeCompare').mockImplementation(function (
+      this: string,
+      value: string
+    ) {
+      comparisons += 1
+      return originalLocaleCompare.call(this, value)
+    })
+    const selected: string[] = []
+
+    try {
+      for (let index = 255; index >= 0; index -= 1) {
+        retainLexicographic(selected, String(index).padStart(3, '0'), 64)
+      }
+    } finally {
+      localeCompare.mockRestore()
+    }
+
+    expect(comparisons).toBeLessThan(2_500)
+    expect(selected).toEqual(
+      Array.from({ length: 64 }, (_, index) => String(index).padStart(3, '0'))
+    )
+  })
+
   it('treats a zero examination budget as already truncated', async () => {
     const root = await tempDir('orca-cursor-dir-zero-')
     await fillDirectory(root, 3)
diff --git a/src/shared/cursor-sidecar-scan-directory.ts b/src/shared/cursor-sidecar-scan-directory.ts
index 8b91c4bed14..09dcb733262 100644
--- a/src/shared/cursor-sidecar-scan-directory.ts
+++ b/src/shared/cursor-sidecar-scan-directory.ts
@@ -1,5 +1,5 @@
 import type { Dir, Dirent } from 'node:fs'
-import { opendir, readdir, realpath } from 'node:fs/promises'
+import { opendir, realpath } from 'node:fs/promises'
 import { posix, win32 } from 'node:path'
 
 /** Per-directory dirent examination budget; keeps cold scans hard-bounded. */
@@ -18,12 +18,18 @@ export function retainLexicographic(selected: string[], name: string, limit: num
   if (name.localeCompare(last) >= 0) {
     return true
   }
-  let index = limit - 1
-  while (index > 0 && name.localeCompare(selected[index - 1]) < 0) {
-    selected[index] = selected[index - 1]
-    index -= 1
+  let low = 0
+  let high = limit
+  while (low < high) {
+    const middle = Math.floor((low + high) / 2)
+    if (name.localeCompare(selected[middle]) < 0) {
+      high = middle
+    } else {
+      low = middle + 1
+    }
   }
-  selected[index] = name
+  selected.splice(low, 0, name)
+  selected.pop()
   return true
 }
 
@@ -36,22 +42,18 @@ export type StreamDirectoryNamesOptions = {
 
 type StreamDirectoryIo = {
   opendir: (path: string) => ReturnType<typeof opendir>
-  readdirWithFileTypes: (path: string) => Promise<Dirent[]>
 }
 
 const defaultStreamDirectoryIo: StreamDirectoryIo = {
-  opendir,
-  readdirWithFileTypes: (path) => readdir(path, { withFileTypes: true })
+  opendir
 }
 let streamDirectoryIo: StreamDirectoryIo = defaultStreamDirectoryIo
 
-/** Test isolation for opendir vs readdir-fallback paths. */
+/** Test isolation for streamed and unsupported directory paths. */
 export function setStreamDirectoryIoForTests(next?: Partial<StreamDirectoryIo>): void {
   streamDirectoryIo = next
     ? {
-        opendir: next.opendir ?? defaultStreamDirectoryIo.opendir,
-        readdirWithFileTypes:
-          next.readdirWithFileTypes ?? defaultStreamDirectoryIo.readdirWithFileTypes
+        opendir: next.opendir ?? defaultStreamDirectoryIo.opendir
       }
     : defaultStreamDirectoryIo
 }
@@ -82,12 +84,12 @@ export async function streamDirectoryNames(
       await directory.close().catch(() => undefined)
     }
   } catch (error) {
-    // Fallback keeps remote-wire hosts that only expose readdir working.
     if (!isUnsupportedDirectoryStream(error)) {
       throw error
     }
+    // readdir is eager and cannot preserve this function's memory/IO bound.
+    return { entriesExamined: 0, examinationTruncated: true }
   }
-  return examineReaddirFallback(dirPath, visit, options, maxEntries)
 }
 
 /**
@@ -198,33 +200,6 @@ async function examineDirectoryStream(
   return { entriesExamined, examinationTruncated }
 }
 
-async function examineReaddirFallback(
-  dirPath: string,
-  visit: (name: string, entry: Dirent) => void,
-  options: StreamDirectoryNamesOptions,
-  maxEntries: number
-): Promise<{ entriesExamined: number; examinationTruncated: boolean }> {
-  // Why: readdir eagerly allocates the full listing. Shrink immediately to the
-  // examination window so adversarial directories cannot keep an unbounded
-  // Dirent array alive past the budget (peak alloc is platform-limited).
-  const entries = await streamDirectoryIo.readdirWithFileTypes(dirPath)
-  let entriesExamined = 0
-  try {
-    const examinationTruncated = entries.length > maxEntries
-    if (examinationTruncated) {
-      entries.length = maxEntries
-    }
-    for (const entry of entries) {
-      entriesExamined += 1
-      options.onDirent?.()
-      visit(entry.name, entry)
-    }
-    return { entriesExamined, examinationTruncated }
-  } finally {
-    entries.length = 0
-  }
-}
-
 function isUnsupportedDirectoryStream(error: unknown): boolean {
   const code = (error as NodeJS.ErrnoException | null)?.code
   return code === 'ERR_FEATURE_UNAVAILABLE_ON_PLATFORM' || code === 'ENOTSUP'
diff --git a/src/shared/cursor-sidecar-scan-discovery.ts b/src/shared/cursor-sidecar-scan-discovery.ts
index 25e98caeaff..73bec4e896a 100644
--- a/src/shared/cursor-sidecar-scan-discovery.ts
+++ b/src/shared/cursor-sidecar-scan-discovery.ts
@@ -2,16 +2,34 @@ import { createHash } from 'node:crypto'
 import type { Stats } from 'node:fs'
 import { lstat, realpath } from 'node:fs/promises'
 import { join } from 'node:path'
-import type { CursorSidecarScanRequest, CursorSidecarScanResponse } from './cursor-sidecar-scan'
+import {
+  CURSOR_REMOTE_MAX_SESSION_DIRS,
+  type CursorSidecarScanRequest,
+  type CursorSidecarScanResponse
+} from './cursor-sidecar-scan'
+import {
+  isCursorSidecarScanCancelledError,
+  type CursorSidecarScanCancellation
+} from './cursor-sidecar-scan-cancellation'
 import {
   CURSOR_DIR_MAX_ENTRIES_EXAMINED,
   listLexicographicDirectoryNames,
-  resolveTargetScopePathVariants,
-  safeBasename
+  resolveTargetScopePathVariants
 } from './cursor-sidecar-scan-directory'
+import {
+  CURSOR_SIDECAR_SCAN_CONCURRENCY,
+  retainCursorSidecarSessions,
+  type CursorSidecarScanBucket as Bucket,
+  type CursorSidecarScanSession
+} from './cursor-sidecar-scan-session-retention'
+
+export {
+  cursorSidecarScanCancellationFromSignal,
+  isCursorSidecarScanCancelledError,
+  type CursorSidecarScanCancellation
+} from './cursor-sidecar-scan-cancellation'
 
 const BUCKET_PATTERN = /^[0-9a-f]{32}$/u
-const BUCKET_READ_CONCURRENCY = 8
 /** Check cancellation every N dirents during cold directory walks. */
 const CANCEL_CHECK_EVERY_DIRENTS = 64
 
@@ -23,11 +41,6 @@ export type CursorSidecarScanCaps = {
   aggregateBytes: number
 }
 
-export type CursorSidecarScanCancellation = {
-  throwIfCancelled: () => void
-}
-
-type Bucket = { name: string; path: string; scopeCwd: string | null }
 type ScanArgs = {
   caps: CursorSidecarScanCaps
   response: CursorSidecarScanResponse
@@ -42,22 +55,6 @@ export type CursorSidecarScanCandidate = Bucket & {
   store: Stats
 }
 
-export function isCursorSidecarScanCancelledError(error: unknown): boolean {
-  return error instanceof Error && error.message === 'cursor_sidecar_scan_cancelled'
-}
-
-export function cursorSidecarScanCancellationFromSignal(
-  signal?: AbortSignal
-): CursorSidecarScanCancellation {
-  return {
-    throwIfCancelled: () => {
-      if (signal?.aborted) {
-        throw new Error('cursor_sidecar_scan_cancelled')
-      }
-    }
-  }
-}
-
 export async function discoverCursorSidecarCandidates(args: {
   request: CursorSidecarScanRequest
   caps: CursorSidecarScanCaps
@@ -71,10 +68,12 @@ export async function discoverCursorSidecarCandidates(args: {
   const pathPlatform = args.pathPlatform ?? process.platform
   const chatsRoot = args.request.chatsRoot
   let rootRealPath: string
+  args.cancellation.throwIfCancelled()
   try {
     rootRealPath = await realpath(chatsRoot)
   } catch (error) {
     rethrowCancel(error)
+    args.cancellation.throwIfCancelled()
     if (!isMissing(error)) {
       addIssue(args.response, chatsRoot, error)
     }
@@ -85,7 +84,12 @@ export async function discoverCursorSidecarCandidates(args: {
 
   const direct = await scopeBuckets(args.request, chatsRoot, pathPlatform, args)
   const enumerated = await enumeratedBuckets(chatsRoot, direct, args)
-  const sessions = await retainSessions([...direct.values(), ...enumerated], args)
+  const sessions = await retainCursorSidecarSessions({
+    buckets: [...direct.values(), ...enumerated],
+    sessionLimit: args.caps.sessions,
+    response: args.response,
+    cancellation: args.cancellation
+  })
   return { rootRealPath, candidates: await eligibleCandidates(sessions, args) }
 }
 
@@ -155,86 +159,16 @@ async function enumeratedBuckets(
   }
 }
 
-async function retainSessions(
-  buckets: readonly Bucket[],
-  args: ScanArgs
-): Promise<(Bucket & { sessionId: string })[]> {
-  const retained: (Bucket & { sessionId: string })[] = []
-  for (
-    let index = 0;
-    index < buckets.length && retained.length < args.caps.sessions;
-    index += BUCKET_READ_CONCURRENCY
-  ) {
-    args.cancellation.throwIfCancelled()
-    const batch = buckets.slice(index, index + BUCKET_READ_CONCURRENCY)
-    const listings = await Promise.all(
-      batch.map((bucket) => listBucketSessions(bucket, args, retained.length))
-    )
-    args.cancellation.throwIfCancelled()
-    for (let listingIndex = 0; listingIndex < listings.length; listingIndex += 1) {
-      const { bucket, names, truncated } = listings[listingIndex]
-      if (retained.length >= args.caps.sessions) {
-        if (
-          listings.slice(listingIndex).some((listing) => listing.truncated || listing.names.length)
-        ) {
-          args.response.truncated.sessionDirs = true
-        }
-        break
-      }
-      const capacity = args.caps.sessions - retained.length
-      retained.push(...names.slice(0, capacity).map((sessionId) => ({ ...bucket, sessionId })))
-      if (truncated || names.length > capacity) {
-        args.response.truncated.sessionDirs = true
-      }
-    }
-    if (retained.length >= args.caps.sessions && index + batch.length < buckets.length) {
-      args.response.truncated.sessionDirs = true
-    }
-  }
-  return retained
-}
-
-async function listBucketSessions(
-  bucket: Bucket,
-  args: ScanArgs,
-  retainedCount: number
-): Promise<{ bucket: Bucket; names: string[]; truncated: boolean }> {
-  try {
-    if (bucket.scopeCwd) {
-      args.response.counters.fileLstat++
-      const stats = await lstat(bucket.path)
-      if (!stats.isDirectory() || stats.isSymbolicLink()) {
-        return { bucket, names: [], truncated: false }
-      }
-    }
-    args.response.counters.bucketReaddir++
-    const listed = await listLexicographicDirectoryNames({
-      dirPath: bucket.path,
-      limit: Math.max(0, args.caps.sessions - retainedCount),
-      maxEntriesExamined: CURSOR_DIR_MAX_ENTRIES_EXAMINED,
-      accept: (name, entry) => entry.isDirectory() && !entry.isSymbolicLink() && safeBasename(name),
-      onDirent: createDirentCancelChecker(args.cancellation)
-    })
-    return { bucket, names: listed.names, truncated: listed.truncated }
-  } catch (error) {
-    rethrowCancel(error)
-    if (!isMissing(error)) {
-      addIssue(args.response, bucket.path, error)
-    }
-    return { bucket, names: [], truncated: false }
-  }
-}
-
 async function eligibleCandidates(
-  sessions: readonly (Bucket & { sessionId: string })[],
+  sessions: readonly CursorSidecarScanSession[],
   args: ScanArgs
 ): Promise<CursorSidecarScanCandidate[]> {
   // Collect every eligible candidate first, then apply newest-first retention
   // before the aggregate byte budget (stable lexical ties).
   const eligible: CursorSidecarScanCandidate[] = []
-  for (let index = 0; index < sessions.length; index += BUCKET_READ_CONCURRENCY) {
+  for (let index = 0; index < sessions.length; index += CURSOR_SIDECAR_SCAN_CONCURRENCY) {
     args.cancellation.throwIfCancelled()
-    const batch = sessions.slice(index, index + BUCKET_READ_CONCURRENCY)
+    const batch = sessions.slice(index, index + CURSOR_SIDECAR_SCAN_CONCURRENCY)
     const results = await Promise.all(batch.map((session) => inspectSession(session, args)))
     args.cancellation.throwIfCancelled()
     for (const result of results) {
@@ -247,7 +181,7 @@ async function eligibleCandidates(
 }
 
 async function inspectSession(
-  session: Bucket & { sessionId: string },
+  session: CursorSidecarScanSession,
   args: ScanArgs
 ): Promise<CursorSidecarScanCandidate | null> {
   const sessionDir = join(session.path, session.sessionId)
@@ -287,9 +221,25 @@ function retainByNewestThenAggregate(
         Math.max(left.meta.mtimeMs, left.store.mtimeMs) ||
       `${left.name}\0${left.sessionId}`.localeCompare(`${right.name}\0${right.sessionId}`)
   )
+  const representatives = new Set<CursorSidecarScanCandidate>()
+  const representedBuckets = new Set<string>()
+  for (const candidate of ranked) {
+    if (candidate.scopeCwd && !representedBuckets.has(candidate.name)) {
+      representedBuckets.add(candidate.name)
+      representatives.add(candidate)
+    }
+  }
+  const prioritized = [
+    ...representatives,
+    ...ranked.filter((candidate) => !representatives.has(candidate))
+  ]
   const retained: CursorSidecarScanCandidate[] = []
   let aggregateBytes = 0
-  for (const candidate of ranked) {
+  for (const candidate of prioritized) {
+    if (retained.length >= CURSOR_REMOTE_MAX_SESSION_DIRS) {
+      args.response.truncated.sessionDirs = true
+      break
+    }
     if (aggregateBytes + candidate.meta.size > args.caps.aggregateBytes) {
       args.response.truncated.sidecarBytes = true
       break
diff --git a/src/shared/cursor-sidecar-scan-session-retention.ts b/src/shared/cursor-sidecar-scan-session-retention.ts
new file mode 100644
index 00000000000..ad0832cac48
--- /dev/null
+++ b/src/shared/cursor-sidecar-scan-session-retention.ts
@@ -0,0 +1,203 @@
+import { lstat } from 'node:fs/promises'
+import type { CursorSidecarScanResponse } from './cursor-sidecar-scan'
+import {
+  isCursorSidecarScanCancelledError,
+  type CursorSidecarScanCancellation
+} from './cursor-sidecar-scan-cancellation'
+import {
+  CURSOR_DIR_MAX_ENTRIES_EXAMINED,
+  listLexicographicDirectoryNames,
+  safeBasename
+} from './cursor-sidecar-scan-directory'
+
+export const CURSOR_SIDECAR_SCAN_CONCURRENCY = 8
+const CANCEL_CHECK_EVERY_DIRENTS = 64
+
+export type CursorSidecarScanBucket = { name: string; path: string; scopeCwd: string | null }
+export type CursorSidecarScanSession = CursorSidecarScanBucket & { sessionId: string }
+
+type RetentionArgs = {
+  buckets: readonly CursorSidecarScanBucket[]
+  sessionLimit: number
+  response: CursorSidecarScanResponse
+  cancellation: CursorSidecarScanCancellation
+}
+
+export async function retainCursorSidecarSessions(
+  args: RetentionArgs
+): Promise<CursorSidecarScanSession[]> {
+  const retained: CursorSidecarScanSession[] = []
+  const scopedBuckets = args.buckets.filter((bucket) => bucket.scopeCwd !== null)
+  const unscopedBuckets = args.buckets.filter((bucket) => bucket.scopeCwd === null)
+  const scopedBucketLimit = scopedBuckets.length
+    ? Math.max(1, Math.floor(CURSOR_DIR_MAX_ENTRIES_EXAMINED / scopedBuckets.length))
+    : 0
+  const scopedListings = await listBucketSessionsBatched(scopedBuckets, args, scopedBucketLimit)
+  retainScopedSessionListings(scopedListings, retained, args)
+  if (retained.length >= args.sessionLimit) {
+    if (unscopedBuckets.length) {
+      args.response.truncated.sessionDirs = true
+    }
+    return retained
+  }
+  await retainUnscopedSessions(unscopedBuckets, retained, args)
+  return retained
+}
+
+async function listBucketSessionsBatched(
+  buckets: readonly CursorSidecarScanBucket[],
+  args: RetentionArgs,
+  limit: number
+): Promise<BucketSessionListing[]> {
+  const listings: BucketSessionListing[] = []
+  for (let index = 0; index < buckets.length; index += CURSOR_SIDECAR_SCAN_CONCURRENCY) {
+    args.cancellation.throwIfCancelled()
+    const batch = buckets.slice(index, index + CURSOR_SIDECAR_SCAN_CONCURRENCY)
+    listings.push(
+      ...(await Promise.all(batch.map((bucket) => listBucketSessions(bucket, args, limit, limit))))
+    )
+    args.cancellation.throwIfCancelled()
+  }
+  return listings
+}
+
+function retainScopedSessionListings(
+  listings: readonly BucketSessionListing[],
+  retained: CursorSidecarScanSession[],
+  args: RetentionArgs
+): void {
+  let depth = 0
+  while (retained.length < args.sessionLimit) {
+    let found = false
+    for (const { bucket, names } of listings) {
+      const sessionId = names[depth]
+      if (sessionId === undefined) {
+        continue
+      }
+      found = true
+      retained.push({ ...bucket, sessionId })
+      if (retained.length >= args.sessionLimit) {
+        break
+      }
+    }
+    if (!found) {
+      break
+    }
+    depth += 1
+  }
+  const listedCount = listings.reduce((total, listing) => total + listing.names.length, 0)
+  if (listings.some((listing) => listing.truncated) || listedCount > retained.length) {
+    args.response.truncated.sessionDirs = true
+  }
+}
+
+async function retainUnscopedSessions(
+  buckets: readonly CursorSidecarScanBucket[],
+  retained: CursorSidecarScanSession[],
+  args: RetentionArgs
+): Promise<void> {
+  for (let index = 0; index < buckets.length; index += CURSOR_SIDECAR_SCAN_CONCURRENCY) {
+    args.cancellation.throwIfCancelled()
+    const batch = buckets.slice(index, index + CURSOR_SIDECAR_SCAN_CONCURRENCY)
+    const listings = await Promise.all(
+      batch.map((bucket) =>
+        listBucketSessions(
+          bucket,
+          args,
+          args.sessionLimit - retained.length,
+          CURSOR_DIR_MAX_ENTRIES_EXAMINED
+        )
+      )
+    )
+    args.cancellation.throwIfCancelled()
+    retainUnscopedSessionListings(listings, retained, args)
+    if (retained.length >= args.sessionLimit && index + batch.length < buckets.length) {
+      args.response.truncated.sessionDirs = true
+      break
+    }
+  }
+}
+
+function retainUnscopedSessionListings(
+  listings: readonly BucketSessionListing[],
+  retained: CursorSidecarScanSession[],
+  args: RetentionArgs
+): void {
+  for (let index = 0; index < listings.length; index += 1) {
+    const { bucket, names, truncated } = listings[index]
+    if (retained.length >= args.sessionLimit) {
+      if (listings.slice(index).some((listing) => listing.truncated || listing.names.length)) {
+        args.response.truncated.sessionDirs = true
+      }
+      break
+    }
+    const capacity = args.sessionLimit - retained.length
+    const selected = names.slice(0, capacity)
+    retained.push(...selected.map((sessionId) => ({ ...bucket, sessionId })))
+    if (truncated || names.length > capacity) {
+      args.response.truncated.sessionDirs = true
+    }
+  }
+}
+
+type BucketSessionListing = {
+  bucket: CursorSidecarScanBucket
+  names: string[]
+  truncated: boolean
+}
+
+async function listBucketSessions(
+  bucket: CursorSidecarScanBucket,
+  args: RetentionArgs,
+  limit: number,
+  maxEntriesExamined: number
+): Promise<BucketSessionListing> {
+  try {
+    if (bucket.scopeCwd) {
+      args.response.counters.fileLstat++
+      const stats = await lstat(bucket.path)
+      if (!stats.isDirectory() || stats.isSymbolicLink()) {
+        return { bucket, names: [], truncated: false }
+      }
+    }
+    args.response.counters.bucketReaddir++
+    const listed = await listLexicographicDirectoryNames({
+      dirPath: bucket.path,
+      limit: Math.max(0, limit),
+      maxEntriesExamined,
+      accept: (name, entry) => entry.isDirectory() && !entry.isSymbolicLink() && safeBasename(name),
+      onDirent: createDirentCancelChecker(args.cancellation)
+    })
+    return { bucket, names: listed.names, truncated: listed.truncated }
+  } catch (error) {
+    if (isCursorSidecarScanCancelledError(error)) {
+      throw error
+    }
+    if (!isMissing(error)) {
+      addIssue(args.response, bucket.path, error)
+    }
+    return { bucket, names: [], truncated: false }
+  }
+}
+
+function createDirentCancelChecker(cancellation: CursorSidecarScanCancellation): () => void {
+  let seen = 0
+  return () => {
+    seen += 1
+    if (seen % CANCEL_CHECK_EVERY_DIRENTS === 0) {
+      cancellation.throwIfCancelled()
+    }
+  }
+}
+
+function addIssue(response: CursorSidecarScanResponse, path: string, error: unknown): void {
+  response.issues.push({
+    path,
+    message: error instanceof Error ? error.message.slice(0, 1_024) : 'Cursor scan failed.'
+  })
+}
+
+function isMissing(error: unknown): boolean {
+  const code = (error as NodeJS.ErrnoException | null)?.code
+  return code === 'ENOENT' || code === 'ENOTDIR'
+}