diff --git a/src/main/ssh/ssh-relay-endpoints.test.ts b/src/main/ssh/ssh-relay-endpoints.test.ts
new file mode 100644
index 00000000000..5b001497ecf
--- /dev/null
+++ b/src/main/ssh/ssh-relay-endpoints.test.ts
@@ -0,0 +1,46 @@
+import { describe, expect, it } from 'vitest'
+import { relayEndpointForHost } from './ssh-relay-endpoints'
+import { getRemoteHostPlatform } from './ssh-remote-platform'
+
+describe('ssh-relay-endpoints', () => {
+  describe('relayEndpointForHost', () => {
+    it('returns the full path for a posix host if length <= 107', () => {
+      const hostPlatform = getRemoteHostPlatform('linux-x64')
+      const remoteDir = '/home/user/.orca-remote/relay'
+      const sockName = 'relay.sock'
+      const result = relayEndpointForHost(hostPlatform, remoteDir, sockName)
+      expect(result).toBe('/home/user/.orca-remote/relay/relay.sock')
+    })
+
+    it('hashes the path and uses parent dir if length > 107 and parent dir fits', () => {
+      const hostPlatform = getRemoteHostPlatform('linux-x64')
+      // parent dir is 79 bytes. 79 + 30 (relay-v1.0.0/relay-12345.sock) = 109 > 107
+      const remoteDir =
+        '/home/a-seventy-nine-byte-long-path-up-to-here-that-fits-nicely-X/.orca-remote/relay-v1.0.0'
+      const sockName = 'relay-12345.sock'
+      const result = relayEndpointForHost(hostPlatform, remoteDir, sockName)
+      expect(result).toMatch(
+        /^\/home\/a-seventy-nine-byte-long-path-up-to-here-that-fits-nicely-X\/\.orca-remote\/[a-f0-9]{12}\.sock$/
+      )
+      expect(Buffer.byteLength(result, 'utf8')).toBeLessThanOrEqual(107)
+    })
+
+    it('falls back to /tmp if even the parent dir hashed path is too long (> 107)', () => {
+      const hostPlatform = getRemoteHostPlatform('linux-x64')
+      const remoteDir =
+        '/home/extremely-long-user-name-that-is-so-long-it-completely-fills-the-entire-buffer-by-itself-and-leaves-no-room-for-parent-dir/.orca-remote/relay-v1.0.0'
+      const sockName = 'relay.sock'
+      const result = relayEndpointForHost(hostPlatform, remoteDir, sockName)
+      expect(result).toMatch(/^\/tmp\/orca-[a-f0-9]{12}\.sock$/)
+      expect(Buffer.byteLength(result, 'utf8')).toBeLessThanOrEqual(107)
+    })
+
+    it('returns windows named pipe format for windows host', () => {
+      const hostPlatform = getRemoteHostPlatform('win32-x64')
+      const remoteDir = 'C:/Users/user/.orca-remote/relay'
+      const sockName = 'relay.sock'
+      const result = relayEndpointForHost(hostPlatform, remoteDir, sockName)
+      expect(result.startsWith('\\\\.\\pipe\\orca-relay-')).toBe(true)
+    })
+  })
+})
diff --git a/src/main/ssh/ssh-relay-endpoints.ts b/src/main/ssh/ssh-relay-endpoints.ts
index bcf1f86aae9..5fb0c32ce4f 100644
--- a/src/main/ssh/ssh-relay-endpoints.ts
+++ b/src/main/ssh/ssh-relay-endpoints.ts
@@ -14,7 +14,19 @@ export function relayEndpointForHost(
   sockName: string
 ): string {
   if (!isWindowsRemoteHost(hostPlatform)) {
-    return joinRemotePath(hostPlatform, remoteDir, sockName)
+    const fullPath = joinRemotePath(hostPlatform, remoteDir, sockName)
+    if (Buffer.byteLength(fullPath, 'utf8') > 107) {
+      const parentDir = remoteDir.includes('/relay-')
+        ? remoteDir.substring(0, remoteDir.lastIndexOf('/'))
+        : remoteDir
+      const hash = createHash('sha256').update(fullPath).digest('hex').slice(0, 12)
+      const shortened = joinRemotePath(hostPlatform, parentDir, `${hash}.sock`)
+      if (Buffer.byteLength(shortened, 'utf8') <= 107) {
+        return shortened
+      }
+      return `/tmp/orca-${hash}.sock`
+    }
+    return fullPath
   }
   const endpointHash = createHash('sha256')
     .update(`${remoteDir}\0${sockName}`)