diff --git a/src/poetry/installation/wheel_installer.py b/src/poetry/installation/wheel_installer.py
index 27a867f85bc..468bc915065 100644
--- a/src/poetry/installation/wheel_installer.py
+++ b/src/poetry/installation/wheel_installer.py
@@ -95,7 +95,7 @@ def install(self, wheel: Path) -> None:
             except _WheelFileValidationError as e:
                 self.invalid_wheels[wheel] = e.issues
 
-            scheme_dict = self._env.paths.copy()
+            scheme_dict = self._env.installer_scheme_dict.copy()
             scheme_dict["headers"] = str(
                 Path(scheme_dict["include"]) / source.distribution
             )
diff --git a/src/poetry/utils/env/base_env.py b/src/poetry/utils/env/base_env.py
index 5f4d558a5f0..9e40c5eff77 100644
--- a/src/poetry/utils/env/base_env.py
+++ b/src/poetry/utils/env/base_env.py
@@ -17,6 +17,7 @@
 from poetry.utils.env.exceptions import EnvCommandError
 from poetry.utils.env.site_packages import SitePackages
 from poetry.utils.helpers import get_real_windows_path
+from poetry.utils.helpers import is_dir_writable
 
 
 if TYPE_CHECKING:
@@ -55,6 +56,7 @@ def __init__(self, path: Path, base: Path | None = None) -> None:
         self._marker_env: dict[str, Any] | None = None
         self._site_packages: SitePackages | None = None
         self._paths: dict[str, str] | None = None
+        self._installer_scheme_dict: dict[str, str] | None = None
         self._supported_tags: list[Tag] | None = None
         self._purelib: Path | None = None
         self._platlib: Path | None = None
@@ -242,6 +244,41 @@ def paths(self) -> dict[str, str]:
 
         return self._paths
 
+    @property
+    def installer_scheme_dict(self) -> dict[str, str]:
+        """
+        This property exists to allow cases where system environment paths are not writable and
+        user site is enabled. This enables us to ensure packages (wheels) are correctly installed
+        into directories where the current user can write to.
+        """
+        if self._installer_scheme_dict is None:
+            paths = self.paths.copy()
+
+            if not self.is_venv() and paths.get("userbase"):
+                overrides: dict[str, str] = {}
+                base_path = os.path.commonpath([paths["include"], paths["purelib"]])
+
+                for key in [
+                    "include",
+                    "purelib",
+                    "platlib",
+                    "stdlib",
+                    "platinclude",
+                    "scripts",
+                    "data",
+                ]:
+                    if not is_dir_writable(path=Path(paths[key]), create=True):
+                        overrides[key] = paths[key].replace(
+                            base_path, paths["userbase"]
+                        )
+
+                for k, v in overrides.items():
+                    paths[k] = v
+
+            self._installer_scheme_dict = paths
+
+        return self._installer_scheme_dict
+
     @property
     def supported_tags(self) -> list[Tag]:
         if self._supported_tags is None:
@@ -312,7 +349,9 @@ def run_pip(self, *args: str, **kwargs: Any) -> str:
     def run_python_script(self, content: str, **kwargs: Any) -> str:
         return self.run(
             self._executable,
-            "-I",
+            # if isolation is enabled for system env, user site would be
+            # incorrectly disabled
+            *(["-I"] if self.is_venv() else []),
             "-W",
             "ignore",
             "-c",