diff --git a/src/main/ipc/ssh-browse.test.ts b/src/main/ipc/ssh-browse.test.ts
index 5c3775bb168..1c11332efb5 100644
--- a/src/main/ipc/ssh-browse.test.ts
+++ b/src/main/ipc/ssh-browse.test.ts
@@ -70,7 +70,7 @@ describe('registerSshBrowseHandler', () => {
       ]
     })
     expect(exec).toHaveBeenCalledWith(
-      expect.stringContaining('\ncd "$HOME" && pwd && command ls -1Ap\n')
+      expect.stringContaining('\ncd "$HOME" && pwd && entries=$(command ls -1A) && ')
     )
     expect(channel.listenerCount('data')).toBe(0)
     expect(channel.listenerCount('exit')).toBe(0)
@@ -160,7 +160,7 @@ describe('registerSshBrowseHandler', () => {
       entries: []
     })
     expect(exec).toHaveBeenCalledWith(
-      expect.stringContaining("\ncd '/tmp/it'\\''s here' && pwd && command ls -1Ap\n")
+      expect.stringContaining("\ncd '/tmp/it'\\''s here' && pwd && entries=$(command ls -1A) && ")
     )
   })
 
@@ -203,7 +203,7 @@ describe('registerSshBrowseHandler', () => {
     expect(exec).toHaveBeenCalledTimes(2)
     expect(exec).toHaveBeenNthCalledWith(
       1,
-      expect.stringContaining("\ncd 'C:/Users/alice' && pwd && command ls -1Ap\n")
+      expect.stringContaining("\ncd 'C:/Users/alice' && pwd && entries=$(command ls -1A) && ")
     )
     expect(exec.mock.calls[1]?.[0]).toMatch(/^powershell\.exe /)
     expect(exec.mock.calls[1]?.[1]).toEqual({ wrapCommand: false })
diff --git a/src/main/runtime/runtime-server-environment-commands.test.ts b/src/main/runtime/runtime-server-environment-commands.test.ts
new file mode 100644
index 00000000000..ee1fdf9b4c5
--- /dev/null
+++ b/src/main/runtime/runtime-server-environment-commands.test.ts
@@ -0,0 +1,56 @@
+import { mkdir, mkdtemp, rm, symlink, writeFile } from 'node:fs/promises'
+import { tmpdir } from 'node:os'
+import { join } from 'node:path'
+import { afterEach, beforeEach, describe, expect, it } from 'vitest'
+import { RuntimeServerEnvironmentCommands } from './runtime-server-environment-commands'
+
+const dirLinkType = process.platform === 'win32' ? 'junction' : 'dir'
+
+describe('RuntimeServerEnvironmentCommands.browseDirectory', () => {
+  let root: string
+
+  beforeEach(async () => {
+    root = await mkdtemp(join(tmpdir(), 'orca-server-browse-symlink-'))
+  })
+
+  afterEach(async () => {
+    await rm(root, { recursive: true, force: true })
+  })
+
+  it.skipIf(process.platform === 'win32')(
+    'lists a symlinked directory as a directory and keeps broken links and loops as files',
+    async () => {
+      await mkdir(join(root, 'real-dir'))
+      await writeFile(join(root, 'real-file.txt'), 'x\n')
+      await symlink(join(root, 'real-dir'), join(root, 'linked-dir'), dirLinkType)
+      await symlink(join(root, 'real-file.txt'), join(root, 'linked-file'))
+      await symlink(join(root, 'missing-target'), join(root, 'broken-link'))
+      await symlink(join(root, 'loop-b'), join(root, 'loop-a'))
+      await symlink(join(root, 'loop-a'), join(root, 'loop-b'))
+
+      const result = await new RuntimeServerEnvironmentCommands().browseDirectory(root)
+
+      expect(result.entries).toEqual([
+        { name: 'linked-dir', isDirectory: true, isSymlink: true },
+        { name: 'real-dir', isDirectory: true, isSymlink: false },
+        { name: 'broken-link', isDirectory: false, isSymlink: true },
+        { name: 'linked-file', isDirectory: false, isSymlink: true },
+        { name: 'loop-a', isDirectory: false, isSymlink: true },
+        { name: 'loop-b', isDirectory: false, isSymlink: true },
+        { name: 'real-file.txt', isDirectory: false, isSymlink: false }
+      ])
+    }
+  )
+
+  it('navigates into a symlinked directory', async () => {
+    await mkdir(join(root, 'real-dir', 'project'), { recursive: true })
+    await symlink(join(root, 'real-dir'), join(root, 'linked-dir'), dirLinkType)
+
+    const result = await new RuntimeServerEnvironmentCommands().browseDirectory(
+      join(root, 'linked-dir')
+    )
+
+    expect(result.resolvedPath).toBe(join(root, 'linked-dir'))
+    expect(result.entries).toEqual([{ name: 'project', isDirectory: true, isSymlink: false }])
+  })
+})
diff --git a/src/main/runtime/runtime-server-environment-commands.ts b/src/main/runtime/runtime-server-environment-commands.ts
index 7671481b1e5..aa74845167e 100644
--- a/src/main/runtime/runtime-server-environment-commands.ts
+++ b/src/main/runtime/runtime-server-environment-commands.ts
@@ -1,6 +1,7 @@
 import { readdir, stat } from 'node:fs/promises'
 import { homedir } from 'node:os'
-import { isAbsolute, resolve } from 'node:path'
+import type { Dirent } from 'node:fs'
+import { isAbsolute, join, resolve } from 'node:path'
 import type { DirEntry, FilesystemPathFlavor } from '../../shared/filesystem-entry-types'
 import { sortDirEntries } from '../../shared/file-name-sort'
 import { probeGitAvailability } from '../git/git-availability'
@@ -24,6 +25,21 @@ function resolveServerBrowsePath(pathValue: string): string {
   return resolve(homedir(), trimmed)
 }
 
+// Why: Dirent.isDirectory() is false for a symlink, so a linked folder would be unreachable; follow it, and treat broken links or loops (ENOENT/ELOOP) as files.
+async function isBrowseEntryDirectory(dirPath: string, entry: Dirent): Promise<boolean> {
+  if (entry.isDirectory()) {
+    return true
+  }
+  if (!entry.isSymbolicLink()) {
+    return false
+  }
+  try {
+    return (await stat(join(dirPath, entry.name))).isDirectory()
+  } catch {
+    return false
+  }
+}
+
 export class RuntimeServerEnvironmentCommands {
   async browseDirectory(pathValue: string): Promise<{
     resolvedPath: string
@@ -39,13 +55,15 @@ export class RuntimeServerEnvironmentCommands {
       throw new Error(`${dirPath} is not a directory`)
     }
     const entries = await readdir(dirPath, { withFileTypes: true })
-    const mapped = entries
-      .filter((entry) => entry.name !== '.' && entry.name !== '..')
-      .map((entry) => ({
-        name: entry.name,
-        isDirectory: entry.isDirectory(),
-        isSymlink: entry.isSymbolicLink()
-      }))
+    const mapped = await Promise.all(
+      entries
+        .filter((entry) => entry.name !== '.' && entry.name !== '..')
+        .map(async (entry) => ({
+          name: entry.name,
+          isDirectory: await isBrowseEntryDirectory(dirPath, entry),
+          isSymlink: entry.isSymbolicLink()
+        }))
+    )
     sortDirEntries(mapped)
     return {
       resolvedPath: dirPath,
diff --git a/src/main/ssh/ssh-remote-directory-browse.test.ts b/src/main/ssh/ssh-remote-directory-browse.test.ts
new file mode 100644
index 00000000000..5b9f31dfc4d
--- /dev/null
+++ b/src/main/ssh/ssh-remote-directory-browse.test.ts
@@ -0,0 +1,98 @@
+import { spawn } from 'node:child_process'
+import { EventEmitter } from 'node:events'
+import { chmod, mkdir, mkdtemp, rm, symlink, writeFile } from 'node:fs/promises'
+import { tmpdir } from 'node:os'
+import { join } from 'node:path'
+import { afterEach, beforeEach, describe, expect, it } from 'vitest'
+import { browseSshDirectory } from './ssh-remote-directory-browse'
+
+// Runs the generated remote command in a real local `sh`, standing in for the SSH exec channel.
+function shellBackedManager(): Parameters<typeof browseSshDirectory>[0] {
+  const exec = async (command: string): Promise<EventEmitter & { stderr: EventEmitter }> => {
+    const child = spawn('/bin/sh', ['-c', command], { stdio: ['ignore', 'pipe', 'pipe'] })
+    const channel = Object.assign(new EventEmitter(), { stderr: new EventEmitter() })
+    child.stdout.on('data', (data: Buffer) => channel.emit('data', data))
+    child.stderr.on('data', (data: Buffer) => channel.stderr.emit('data', data))
+    child.on('close', (code) => {
+      channel.emit('exit', code)
+      channel.emit('close', code)
+    })
+    return channel
+  }
+  // oxlint-disable-next-line typescript/consistent-type-assertions -- SAFETY: browseSshDirectory only calls getConnection(id).exec(command).
+  return { getConnection: () => ({ exec }) } as never
+}
+
+describe.skipIf(process.platform === 'win32')('browseSshDirectory over a POSIX shell', () => {
+  let root: string
+
+  beforeEach(async () => {
+    root = await mkdtemp(join(tmpdir(), 'orca-ssh-browse-symlink-'))
+  })
+
+  afterEach(async () => {
+    await rm(root, { recursive: true, force: true })
+  })
+
+  it('marks a symlinked directory as a directory and keeps broken links and loops as files', async () => {
+    await mkdir(join(root, 'real-dir'))
+    await writeFile(join(root, 'real-file.txt'), 'x\n')
+    await writeFile(join(root, '.hidden'), 'x\n')
+    await writeFile(join(root, 'name with space'), 'x\n')
+    await symlink(join(root, 'real-dir'), join(root, 'linked-dir'))
+    await symlink(join(root, 'real-file.txt'), join(root, 'linked-file'))
+    await symlink(join(root, 'missing-target'), join(root, 'broken-link'))
+    await symlink(join(root, 'loop-b'), join(root, 'loop-a'))
+    await symlink(join(root, 'loop-a'), join(root, 'loop-b'))
+
+    const result = await browseSshDirectory(shellBackedManager(), 'ssh-1', root)
+
+    expect(result.pathFlavor).toBe('posix')
+    expect(result.entries).toEqual([
+      { name: 'linked-dir', isDirectory: true },
+      { name: 'real-dir', isDirectory: true },
+      { name: '.hidden', isDirectory: false },
+      { name: 'broken-link', isDirectory: false },
+      { name: 'linked-file', isDirectory: false },
+      { name: 'loop-a', isDirectory: false },
+      { name: 'loop-b', isDirectory: false },
+      { name: 'name with space', isDirectory: false },
+      { name: 'real-file.txt', isDirectory: false }
+    ])
+  })
+
+  it('navigates into a symlinked directory and lists an empty one as empty', async () => {
+    await mkdir(join(root, 'real-dir', 'project'), { recursive: true })
+    await mkdir(join(root, 'empty-real'))
+    await symlink(join(root, 'real-dir'), join(root, 'linked-dir'))
+    await symlink(join(root, 'empty-real'), join(root, 'linked-empty'))
+
+    const linked = await browseSshDirectory(shellBackedManager(), 'ssh-1', join(root, 'linked-dir'))
+    const empty = await browseSshDirectory(
+      shellBackedManager(),
+      'ssh-1',
+      join(root, 'linked-empty')
+    )
+
+    expect(linked.entries).toEqual([{ name: 'project', isDirectory: true }])
+    expect(empty.entries).toEqual([])
+  })
+
+  it('still fails instead of looking empty when the directory cannot be listed', async () => {
+    await expect(
+      browseSshDirectory(shellBackedManager(), 'ssh-1', join(root, 'missing'))
+    ).rejects.toThrow()
+    // Execute-only: `cd` and `pwd` succeed but `ls` cannot read it.
+    const unreadable = join(root, 'unreadable')
+    await mkdir(unreadable, { mode: 0o100 })
+    try {
+      if (process.getuid?.() !== 0) {
+        await expect(
+          browseSshDirectory(shellBackedManager(), 'ssh-1', unreadable)
+        ).rejects.toThrow()
+      }
+    } finally {
+      await chmod(unreadable, 0o700)
+    }
+  })
+})
diff --git a/src/main/ssh/ssh-remote-directory-browse.ts b/src/main/ssh/ssh-remote-directory-browse.ts
index 08e16ffe1a4..25f1699c216 100644
--- a/src/main/ssh/ssh-remote-directory-browse.ts
+++ b/src/main/ssh/ssh-remote-directory-browse.ts
@@ -62,14 +62,23 @@ export async function browseSshDirectory(
   }
 }
 
+const POSIX_LIST_WITH_DIR_MARKERS =
+  'entries=$(command ls -1A) && printf \'%s\\n\' "$entries" | while IFS= read -r f; do ' +
+  'if [ -d "$f" ]; then printf \'%s/\\n\' "$f"; else printf \'%s\\n\' "$f"; fi; done'
+
 type SshBrowseConnection = NonNullable<ReturnType<SshConnectionManager['getConnection']>>
 
 function browseWithPosixShell(
   conn: SshBrowseConnection,
   dirPath: string
 ): Promise<RemoteBrowseResult> {
-  // Why: `command ls` skips aliases; `&&` makes a failing ls exit non-zero (not look empty); -1Ap = one-per-line + trailing / on dirs.
-  return runBrowseCommand(conn, `cd ${shellEscape(dirPath)} && pwd && command ls -1Ap`, 'posix')
+  // Why: `command ls` skips aliases; capturing it keeps a failing ls exiting non-zero (not looking empty).
+  // The trailing / comes from `[ -d ]`, which follows symlinks (ls -p doesn't); broken links and loops test false.
+  return runBrowseCommand(
+    conn,
+    `cd ${shellEscape(dirPath)} && pwd && ${POSIX_LIST_WITH_DIR_MARKERS}`,
+    'posix'
+  )
 }
 
 function browseWithWindowsPowerShell(