diff --git a/docs/changelog.rst b/docs/changelog.rst
index 93af3bbee..2502605e5 100644
--- a/docs/changelog.rst
+++ b/docs/changelog.rst
@@ -35,6 +35,11 @@ mouse anywhere in the current command to move the cursor there. See
 Detailed list of changes
 -------------------------------------
 
+0.26.1 [future]
+~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
+
+- ssh kitten: Fix executable permission missing from kitty bootstrap script (:iss:`5438`)
+
 0.26.0 [2022-08-29]
 ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
 
diff --git a/kitty_tests/check_build.py b/kitty_tests/check_build.py
index f1ed3a6c1..87a2edd16 100644
--- a/kitty_tests/check_build.py
+++ b/kitty_tests/check_build.py
@@ -3,6 +3,7 @@
 
 
 import os
+import stat
 import sys
 import unittest
 from functools import partial
@@ -58,7 +59,15 @@ class TestBuild(BaseTest):
         self.assertTrue(os.path.isdir(terminfo_dir), f'Terminfo dir: {terminfo_dir}')
         self.assertTrue(os.path.exists(logo_png_file), f'Logo file: {logo_png_file}')
         self.assertTrue(os.path.exists(zsh), f'Shell integration: {zsh}')
-        self.assertTrue(os.access(os.path.join(shell_integration_dir, 'ssh', 'askpass.py'), os.X_OK))
+
+        def is_executable(x):
+            mode = os.stat(x).st_mode
+            q = stat.S_IXUSR | stat.S_IXGRP | stat.S_IXOTH
+            return mode & q == q
+
+        for x in ('kitty', 'askpass.py'):
+            x = os.path.join(shell_integration_dir, 'ssh', x)
+            self.assertTrue(is_executable(x), f'{x} is not executable')
         if getattr(sys, 'frozen', False):
             self.assertTrue(os.path.isdir(local_docs()), f'Local docs: {local_docs()}')
 
@@ -76,8 +85,8 @@ class TestBuild(BaseTest):
         del pygments
 
     def test_docs_url(self):
-        from kitty.utils import docs_url
         from kitty.constants import website_url
+        from kitty.utils import docs_url
 
         def run_tests(p, base, suffix='.html'):
             def t(x, e):
diff --git a/setup.py b/setup.py
index 8da6a7032..08571c8d2 100755
--- a/setup.py
+++ b/setup.py
@@ -1363,10 +1363,19 @@ def package(args: Options, bundle_type: str) -> None:
             f.seek(0), f.truncate(), f.write(raw)
 
     compile_python(libdir)
+
+    def should_be_executable(path: str) -> bool:
+        if path.endswith('.so'):
+            return True
+        q = path.split(os.sep)[-2:]
+        if len(q) == 2 and q[0] == 'ssh' and q[1] in ('askpass.py', 'kitty'):
+            return True
+        return False
+
     for root, dirs, files in os.walk(libdir):
         for f_ in files:
             path = os.path.join(root, f_)
-            os.chmod(path, 0o755 if f_.endswith('.so') or os.path.basename(f_) == 'askpass.py' else 0o644)
+            os.chmod(path, 0o755 if should_be_executable(path) else 0o644)
     if not is_macos:
         create_linux_bundle_gunk(ddir, args.libdir_name)