diff --git a/changelog.d/1257.feature.md b/changelog.d/1257.feature.md
new file mode 100644
index 0000000000..ad6c9364d4
--- /dev/null
+++ b/changelog.d/1257.feature.md
@@ -0,0 +1,4 @@
+Revert platform-specific directories on MacOS and Windows
+
+They were leading to a lot of issues with Windows sandboxing
+and spaces in shebangs on MacOS.
diff --git a/docs/installation.md b/docs/installation.md
index c90e4aca4d..52225cf8f1 100644
--- a/docs/installation.md
+++ b/docs/installation.md
@@ -124,10 +124,14 @@ The default binary location for pipx-installed apps is `~/.local/bin`. This can
 variable `PIPX_BIN_DIR`. The default manual page location for pipx-installed apps is `~/.local/share/man`. This can be
 overridden with the environment variable `PIPX_MAN_DIR`.
 
-pipx's default virtual environment location is typically `~/.local/share/pipx` on Linux/Unix,
-`%USERPROFILE%\AppData\Local\pipx` on Windows and `~/Library/Application Support/pipx` on macOS, and for compatibility
-reasons, if `~/.local/pipx` exists, it will be used as the default location instead. This can be overridden with the
-`PIPX_HOME` environment variable.
+pipx's default virtual environment location is typically `~/.local/share/pipx` on Linux/Unix, `~/.local/pipx` on MacOS
+and `~\pipx` on Windows. For compatibility reasons, if `~/.local/pipx` on Linux, `%USERPROFILE%\AppData\Local\pipx` or
+`~\.local\pipx` on Windows or `~/Library/Application Support/pipx` on MacOS exists, it will be used as the default location instead.
+This can be overridden with the `PIPX_HOME` environment variable.
+
+In case one of these fallback locations exist, we recommend either manually moving the pipx files to the new default location
+(see the `Troubleshooting` section of the docs), or setting the `PIPX_HOME` environment variable (discarding files existing in
+the fallback location).
 
 As an example, you can install global apps accessible by all users on your system with the following command (on MacOS,
 Linux, and Windows WSL):
@@ -152,6 +156,9 @@ sudo PIPX_HOME=/opt/pipx PIPX_BIN_DIR=/usr/local/bin PIPX_MAN_DIR=/usr/local/sha
 >
 > `user_data_dir()`, `user_cache_dir()` and `user_log_dir()` resolve to appropriate platform-specific user data, cache and log directories.
 > See the [platformdirs documentation](https://platformdirs.readthedocs.io/en/latest/api.html#platforms) for details.
+>
+> This was reverted in 1.5.0 for Windows and MacOS. We heavily recommend not using these locations on Windows and MacOS anymore, due to
+> multiple incompatibilities discovered with these locations, documented [here](https://github.com/pypa/pipx/discussions/1247#discussion-6188916).
 
 ### Global installation
 
diff --git a/docs/troubleshooting.md b/docs/troubleshooting.md
index efef10cfbf..b4b6503bb8 100644
--- a/docs/troubleshooting.md
+++ b/docs/troubleshooting.md
@@ -143,6 +143,9 @@ data, cache, and log directories under it. To maintain compatibility with older
 this old `PIPX_HOME` path if it exists. For a map of old and new paths, see
 [Installation](installation.md#installation-options).
 
+In Pipx version 1.5.0, this was reverted for Windows and MacOS. It defaults again to `~/.local/pipx` on MacOS and to
+`~\pipx` on Windows.
+
 If you have a `pipx` version later than 1.2.0 and want to migrate from the old path to the new paths, you can move the
 `~/.local/pipx` directory to the new location (after removing cache, log, and trash directories which will get recreated
 automatically) and then reinstall all packages. For example, on Linux systems, `PIPX_HOME` moves from `~/.local/pipx` to
@@ -153,3 +156,5 @@ rm -rf ~/.local/pipx/{.cache,logs,trash}
 mkdir -p ~/.local/share && mv ~/.local/pipx ~/.local/share/
 pipx reinstall-all
 ```
+
+For moving the paths back after 1.5.0, you can perform the same steps, switching the paths around.
diff --git a/src/pipx/constants.py b/src/pipx/constants.py
index fa7a54d8b8..eec4f98dc8 100644
--- a/src/pipx/constants.py
+++ b/src/pipx/constants.py
@@ -1,5 +1,5 @@
 import os
-import sys
+import platform
 import sysconfig
 from textwrap import dedent
 from typing import NewType
@@ -26,7 +26,15 @@
 
 
 def is_windows() -> bool:
-    return sys.platform == "win32"
+    return platform.system() == "Windows"
+
+
+def is_macos() -> bool:
+    return platform.system() == "Darwin"
+
+
+def is_linux() -> bool:
+    return platform.system() == "Linux"
 
 
 def is_mingw() -> bool:
@@ -34,6 +42,8 @@ def is_mingw() -> bool:
 
 
 WINDOWS: bool = is_windows()
+MACOS: bool = is_macos()
+LINUX: bool = is_linux()
 MINGW: bool = is_mingw()
 
 completion_instructions = dedent(
diff --git a/src/pipx/paths.py b/src/pipx/paths.py
index 7f790003a0..cbb9c38289 100644
--- a/src/pipx/paths.py
+++ b/src/pipx/paths.py
@@ -1,11 +1,24 @@
+import logging
 import os
 from pathlib import Path
-from typing import Optional, Union
+from typing import List, Optional, Union
 
 from platformdirs import user_cache_path, user_data_path, user_log_path
 
-DEFAULT_PIPX_HOME = user_data_path("pipx")
-FALLBACK_PIPX_HOME = Path.home() / ".local/pipx"
+from pipx.constants import LINUX, WINDOWS
+from pipx.emojis import hazard
+from pipx.util import pipx_wrap
+
+if LINUX:
+    DEFAULT_PIPX_HOME = user_data_path("pipx")
+    FALLBACK_PIPX_HOMES = [Path.home() / ".local/pipx"]
+elif WINDOWS:
+    DEFAULT_PIPX_HOME = Path.home() / "pipx"
+    FALLBACK_PIPX_HOMES = [Path.home() / ".local/pipx", user_data_path("pipx")]
+else:
+    DEFAULT_PIPX_HOME = Path.home() / ".local/pipx"
+    FALLBACK_PIPX_HOMES = [user_data_path("pipx")]
+
 DEFAULT_PIPX_BIN_DIR = Path.home() / ".local/bin"
 DEFAULT_PIPX_MAN_DIR = Path.home() / ".local/share/man"
 DEFAULT_PIPX_GLOBAL_HOME = "/opt/pipx"
@@ -13,6 +26,9 @@
 DEFAULT_PIPX_GLOBAL_MAN_DIR = "/usr/local/share/man"
 
 
+logger = logging.getLogger(__name__)
+
+
 def get_expanded_environ(env_name: str) -> Optional[Path]:
     val = os.environ.get(env_name)
     if val is not None:
@@ -25,8 +41,9 @@ class _PathContext:
     _base_bin: Optional[Union[Path, str]] = get_expanded_environ("PIPX_BIN_DIR")
     _base_man: Optional[Union[Path, str]] = get_expanded_environ("PIPX_MAN_DIR")
     _base_shared_libs: Optional[Union[Path, str]] = get_expanded_environ("PIPX_SHARED_LIBS")
-    _fallback_home: Path = Path.home() / ".local/pipx"
-    _home_exists: bool = _base_home is not None or _fallback_home.exists()
+    _fallback_homes: List[Path] = FALLBACK_PIPX_HOMES
+    _fallback_home: Optional[Path] = next(iter([fallback for fallback in _fallback_homes if fallback.exists()]), None)
+    _home_exists: bool = _base_home is not None or any(fallback.exists() for fallback in _fallback_homes)
     log_file: Optional[Path] = None
 
     @property
@@ -35,7 +52,7 @@ def venvs(self) -> Path:
 
     @property
     def logs(self) -> Path:
-        if self._home_exists:
+        if self._home_exists or not LINUX:
             return self.home / "logs"
         return user_log_path("pipx")
 
@@ -47,7 +64,7 @@ def trash(self) -> Path:
 
     @property
     def venv_cache(self) -> Path:
-        if self._home_exists:
+        if self._home_exists or not LINUX:
             return self.home / ".cache"
         return user_cache_path("pipx")
 
@@ -63,7 +80,7 @@ def man_dir(self) -> Path:
     def home(self) -> Path:
         if self._base_home:
             home = Path(self._base_home)
-        elif self._fallback_home.exists():
+        elif self._fallback_home:
             home = self._fallback_home
         else:
             home = Path(DEFAULT_PIPX_HOME)
@@ -77,17 +94,45 @@ def make_local(self) -> None:
         self._base_home = get_expanded_environ("PIPX_HOME")
         self._base_bin = get_expanded_environ("PIPX_BIN_DIR")
         self._base_man = get_expanded_environ("PIPX_MAN_DIR")
-        self._home_exists = self._base_home is not None or self._fallback_home.exists()
+        self._home_exists = self._base_home is not None or any(fallback.exists() for fallback in self._fallback_homes)
 
     def make_global(self) -> None:
         self._base_home = get_expanded_environ("PIPX_GLOBAL_HOME") or DEFAULT_PIPX_GLOBAL_HOME
         self._base_bin = get_expanded_environ("PIPX_GLOBAL_BIN_DIR") or DEFAULT_PIPX_GLOBAL_BIN_DIR
         self._base_man = get_expanded_environ("PIPX_GLOBAL_MAN_DIR") or DEFAULT_PIPX_GLOBAL_MAN_DIR
-        self._home_exists = self._base_home is not None or self._fallback_home.exists()
+        self._home_exists = self._base_home is not None or any(fallback.exists() for fallback in self._fallback_homes)
 
     @property
     def standalone_python_cachedir(self) -> Path:
         return self.home / "py"
 
+    def log_warnings(self):
+        if " " in str(self.home):
+            logger.warning(
+                pipx_wrap(
+                    (
+                        f"{hazard} Found a space in the home path. We heavily discourage this, due to "
+                        "multiple incompatibilities. Please check our docs for more information on this, "
+                        "as well as some pointers on how to migrate to a different home path."
+                    ),
+                    subsequent_indent=" " * 4,
+                )
+            )
+
+        fallback_home_exists = self._fallback_home is not None and self._fallback_home.exists()
+        specific_home_exists = self.home != self._fallback_home
+        if fallback_home_exists and specific_home_exists:
+            logger.info(
+                pipx_wrap(
+                    (
+                        f"Both a specific pipx home folder ({self.home}) and the fallback "
+                        f"pipx home folder ({self._fallback_home}) exist. If you are done migrating from the"
+                        "fallback to the new location, it is safe to delete the fallback location."
+                    ),
+                    subsequent_indent=" " * 4,
+                )
+            )
+
 
 ctx = _PathContext()
+ctx.log_warnings()