diff --git a/kitty/boss.py b/kitty/boss.py
index 3c0bf2420..5b58ca87f 100644
--- a/kitty/boss.py
+++ b/kitty/boss.py
@@ -15,7 +15,8 @@ from .cli import create_opts, parse_args
 from .config import (
     MINIMUM_FONT_SIZE, initial_window_size, prepare_config_file_for_editing
 )
-from .constants import appname, editor, set_boss, config_dir
+from .config_utils import to_cmdline
+from .constants import appname, config_dir, editor, set_boss
 from .fast_data_types import (
     ChildMonitor, create_os_window, current_os_window, destroy_global_data,
     destroy_sprite_map, get_clipboard_string, glfw_post_empty_event,
@@ -562,6 +563,8 @@ class Boss:
 
     def open_url(self, url, program=None):
         if url:
+            if isinstance(program, str):
+                program = to_cmdline(program)
             open_url(url, program or self.opts.open_url_with)
 
     def open_url_lines(self, lines, program=None):
diff --git a/kitty/config.py b/kitty/config.py
index 0261ad6eb..b56e4e25f 100644
--- a/kitty/config.py
+++ b/kitty/config.py
@@ -6,7 +6,6 @@ import ast
 import json
 import os
 import re
-import shlex
 import sys
 import tempfile
 from collections import namedtuple
@@ -15,7 +14,7 @@ from contextlib import contextmanager
 from . import fast_data_types as defines
 from .config_utils import (
     init_config, load_config as _load_config, merge_dicts, parse_config_base,
-    positive_float, positive_int, to_bool, to_color, unit_float
+    positive_float, positive_int, to_bool, to_cmdline, to_color, unit_float
 )
 from .constants import cache_dir, defconf
 from .fast_data_types import CURSOR_BEAM, CURSOR_BLOCK, CURSOR_UNDERLINE
@@ -119,7 +118,7 @@ def parse_key_action(action):
     elif func == 'set_font_size':
         args = (float(rest),)
     elif func in shlex_actions:
-        args = shlex.split(rest)
+        args = to_cmdline(rest)
     return KeyAction(func, args)
 
 
@@ -292,7 +291,8 @@ type_map = {
     'adjust_line_height': adjust_line_height,
     'adjust_column_width': adjust_line_height,
     'scrollback_lines': positive_int,
-    'scrollback_pager': shlex.split,
+    'scrollback_pager': to_cmdline,
+    'open_url_with': to_cmdline,
     'font_size': to_font_size,
     'font_size_delta': positive_float,
     'focus_follows_mouse': to_bool,
diff --git a/kitty/config_utils.py b/kitty/config_utils.py
index 1d5f13aa2..688f89fc8 100644
--- a/kitty/config_utils.py
+++ b/kitty/config_utils.py
@@ -4,6 +4,7 @@
 
 import os
 import re
+import shlex
 
 from .rgb import to_color as as_color
 from .utils import log_error
@@ -31,6 +32,12 @@ def to_bool(x):
     return x.lower() in 'y yes true'.split()
 
 
+def to_cmdline(x):
+    ans = shlex.split(x)
+    ans[0] = os.path.expandvars(os.path.expanduser(ans[0]))
+    return ans
+
+
 def parse_line(line, type_map, special_handling, ans, all_keys, base_path_for_includes):
     line = line.strip()
     if not line or line.startswith('#'):
diff --git a/kitty/utils.py b/kitty/utils.py
index c7a14e18b..f47a4eb8d 100644
--- a/kitty/utils.py
+++ b/kitty/utils.py
@@ -8,7 +8,6 @@ import fcntl
 import math
 import os
 import re
-import shlex
 import socket
 import string
 import subprocess
@@ -111,10 +110,11 @@ def base64_encode(
 
 
 def command_for_open(program='default'):
-    if program == 'default':
+    if isinstance(program, str):
+        from .config_utils import to_cmdline
+        program = to_cmdline(program)
+    if program == ['default']:
         cmd = ['open'] if is_macos else ['xdg-open']
-    else:
-        cmd = shlex.split(program)
     return cmd