diff --git a/news/6185.bugfix.rst b/news/6185.bugfix.rst
new file mode 100644
index 0000000000..bc0bd085e0
--- /dev/null
+++ b/news/6185.bugfix.rst
@@ -0,0 +1 @@
+Fixed ``pipenv uninstall --all`` failing when the virtual environment no longer exists.
diff --git a/pipenv/environment.py b/pipenv/environment.py
index d75243894a..a93817303d 100644
--- a/pipenv/environment.py
+++ b/pipenv/environment.py
@@ -19,6 +19,7 @@
 from pipenv.patched.pip._vendor.packaging.specifiers import SpecifierSet
 from pipenv.patched.pip._vendor.packaging.utils import canonicalize_name
 from pipenv.patched.pip._vendor.packaging.version import parse as parse_version
+from pipenv.patched.pip._vendor.typing_extensions import Iterable
 from pipenv.utils import console
 from pipenv.utils.fileutils import normalize_path, temp_path
 from pipenv.utils.funktools import chunked, unnest
@@ -72,8 +73,9 @@ def __init__(
             pipfile = project.parsed_pipfile
         self.pipfile = pipfile
         self.extra_dists = []
-        prefix = prefix if prefix else sys.prefix
-        self.prefix = Path(prefix)
+        if self.is_venv and prefix is not None and not Path(prefix).exists():
+            return
+        self.prefix = Path(prefix if prefix else sys.prefix)
         self._base_paths = {}
         if self.is_venv:
             self._base_paths = self.get_paths()
@@ -96,11 +98,14 @@ def safe_import(self, name: str) -> ModuleType:
         return module
 
     @cached_property
-    def python_version(self) -> str:
-        with self.activated():
-            sysconfig = self.safe_import("sysconfig")
-            py_version = sysconfig.get_python_version()
-            return py_version
+    def python_version(self) -> str | None:
+        with self.activated() as active:
+            if active:
+                sysconfig = self.safe_import("sysconfig")
+                py_version = sysconfig.get_python_version()
+                return py_version
+            else:
+                return None
 
     @property
     def python_info(self) -> dict[str, str]:
@@ -703,9 +708,10 @@ def reverse_dependencies(self):
                 }
         return rdeps
 
-    def get_working_set(self):
+    def get_working_set(self) -> Iterable:
         """Retrieve the working set of installed packages for the environment."""
-
+        if not hasattr(self, "sys_path"):
+            return []
         return importlib_metadata.distributions(path=self.sys_path)
 
     def is_installed(self, pkgname):
@@ -781,6 +787,16 @@ def activated(self):
         to `os.environ["PATH"]` to ensure that calls to `~Environment.run()` use the
         environment's path preferentially.
         """
+
+        # Fail if the virtualenv is needed but cannot be found
+        if self.is_venv and (
+            hasattr(self, "prefix")
+            and not self.prefix.exists()
+            or not hasattr(self, "prefix")
+        ):
+            yield False
+            return
+
         original_path = sys.path
         original_prefix = sys.prefix
         prefix = self.prefix.as_posix()
@@ -806,7 +822,7 @@ def activated(self):
             sys.path = self.sys_path
             sys.prefix = self.sys_prefix
             try:
-                yield
+                yield True
             finally:
                 sys.path = original_path
                 sys.prefix = original_prefix
diff --git a/pipenv/routines/uninstall.py b/pipenv/routines/uninstall.py
index 81b3d0f4ff..7939ccbd35 100644
--- a/pipenv/routines/uninstall.py
+++ b/pipenv/routines/uninstall.py
@@ -3,7 +3,9 @@
 
 from pipenv import exceptions
 from pipenv.patched.pip._internal.build_env import get_runnable_pip
+from pipenv.project import Project
 from pipenv.routines.lock import do_lock
+from pipenv.utils import console
 from pipenv.utils.dependencies import (
     expansive_install_req_from_line,
     get_lockfile_section_using_pipfile_category,
@@ -18,10 +20,13 @@
 from pipenv.vendor.importlib_metadata.compat.py39 import normalized_name
 
 
-def _uninstall_from_environment(project, package, system=False):
+def _uninstall_from_environment(project: Project, package, system=False):
     # Execute the uninstall command for the package
-    click.secho(f"Uninstalling {package}...", fg="green", bold=True)
-    with project.environment.activated():
+    with project.environment.activated() as is_active:
+        if not is_active:
+            return False
+
+        console.print(f"Uninstalling {package}...", style="bold green")
         cmd = [
             project_python(project, system=system),
             get_runnable_pip(),
@@ -38,7 +43,7 @@ def _uninstall_from_environment(project, package, system=False):
 
 
 def do_uninstall(
-    project,
+    project: Project,
     packages=None,
     editable_packages=None,
     python=False,
diff --git a/tests/integration/test_uninstall.py b/tests/integration/test_uninstall.py
index e78f90dc23..04c338bd90 100644
--- a/tests/integration/test_uninstall.py
+++ b/tests/integration/test_uninstall.py
@@ -336,3 +336,23 @@ def test_category_not_sorted_without_directive(pipenv_instance_private_pypi):
             "colorama",
             "atomicwrites",
         ]
+
+
+@pytest.mark.uninstall
+def test_uninstall_without_venv(pipenv_instance_private_pypi):
+    with pipenv_instance_private_pypi() as p:
+        with open(p.pipfile_path, "w") as f:
+            contents = """
+[packages]
+colorama = "*"
+atomicwrites = "*"
+            """.strip()
+            f.write(contents)
+
+        c = p.pipenv("install")
+        assert c.returncode == 0
+
+        c = p.pipenv("uninstall --all")
+        assert c.returncode == 0
+        # uninstall --all shold not remove packages from Pipfile
+        assert list(p.pipfile["packages"].keys()) == ["colorama", "atomicwrites"]