diff --git a/news/5539.vendor.rst b/news/5539.vendor.rst
new file mode 100644
index 00000000..1ca7573d
--- /dev/null
+++ b/news/5539.vendor.rst
@@ -0,0 +1 @@
+Bump plette version to 0.4.4
diff --git a/pipenv/vendor/plette/__init__.py b/pipenv/vendor/plette/__init__.py
index 6e842ee4..7734698d 100644
--- a/pipenv/vendor/plette/__init__.py
+++ b/pipenv/vendor/plette/__init__.py
@@ -3,7 +3,7 @@ __all__ = [
     "Lockfile", "Pipfile",
 ]
 
-__version__ = '0.4.2'
+__version__ = '0.4.4'
 
 from .lockfiles import Lockfile
 from .pipfiles import Pipfile
diff --git a/pipenv/vendor/plette/__main__.py b/pipenv/vendor/plette/__main__.py
new file mode 100644
index 00000000..e5798bae
--- /dev/null
+++ b/pipenv/vendor/plette/__main__.py
@@ -0,0 +1,24 @@
+"""
+A simple entry point which can be use to test Pipfiles
+
+e.g.
+
+python -m plette -f examples/Pipfile.valid.list 
+python -m plette -f examples/Pipfile.valid.editable
+# throws exception
+python -m plette -f examples/Pipfile.invalid.list  
+
+"""
+from pipenv.vendor.plette import Pipfile
+
+import argparse
+
+parser = argparse.ArgumentParser()
+parser.add_argument("-f", "--file", help="Input file")
+
+args = parser.parse_args()
+
+dest = args.file
+
+with open(dest) as f:
+    pipfile = Pipfile.load(f)
diff --git a/pipenv/vendor/plette/models/__init__.py b/pipenv/vendor/plette/models/__init__.py
index 42b8c49f..20c28993 100644
--- a/pipenv/vendor/plette/models/__init__.py
+++ b/pipenv/vendor/plette/models/__init__.py
@@ -16,5 +16,11 @@ from .scripts import Script
 from .sources import Source
 
 from .sections import (
-    Meta, Requires, PackageCollection, ScriptCollection, SourceCollection,
+    Meta,
+    Requires,
+    PackageCollection,
+    Pipenv,
+    PipfileSection,
+    ScriptCollection,
+    SourceCollection,
 )
diff --git a/pipenv/vendor/plette/models/packages.py b/pipenv/vendor/plette/models/packages.py
index 93b35c3a..8b0ebe4f 100644
--- a/pipenv/vendor/plette/models/packages.py
+++ b/pipenv/vendor/plette/models/packages.py
@@ -21,7 +21,9 @@ class Package(DataView):
     def validate(cls, data):
         # HACK: Make this validatable for Cerberus. See comments in validation
         # side for more information.
-        return super(Package, cls).validate({"__package__": data})
+        super(Package, cls).validate({"__package__": data})
+        if isinstance(data, dict):
+            PackageSpecfiers.validate({"__specifiers__": data})
 
     def __getattr__(self, key):
         if isinstance(self._data, str):
@@ -41,3 +43,16 @@ class Package(DataView):
             self._data = value
         else:
             self._data[key] = value
+
+class PackageSpecfiers(DataView):
+    # TODO: one could add here more validation for path editable
+    # and more stuff which is currently allowed and undocumented
+    __SCHEMA__ = {
+        "__specifiers__": {
+            "type": "dict",
+            "schema":{
+                "version": {"type": "string"},
+                "extras": {"type": "list"},
+                }
+            }
+        }
diff --git a/pipenv/vendor/plette/models/sections.py b/pipenv/vendor/plette/models/sections.py
index 2600bb1f..acaaa4dd 100644
--- a/pipenv/vendor/plette/models/sections.py
+++ b/pipenv/vendor/plette/models/sections.py
@@ -50,6 +50,16 @@ META_SECTIONS = {
     "sources": SourceCollection,
 }
 
+class PipfileSection(DataView):
+
+    """
+    Dummy pipfile validator that needs to be completed in a future PR
+    Hint: many pipfile features are undocumented in  pipenv/project.py
+    """
+
+    @classmethod
+    def validate(cls, data):
+        pass
 
 class Meta(DataView):
     """Representation of the `_meta` section in a Pipfile.lock."""
@@ -119,3 +129,11 @@ class Meta(DataView):
     @sources.setter
     def sources(self, value):
         self["sources"] = value
+
+
+class Pipenv(DataView):
+    """Represent the [pipenv] section in Pipfile"""
+
+    __SCHEMA__ = {
+        "allow_prereleases": {"type": "boolean", "required": False},
+    }
diff --git a/pipenv/vendor/plette/pipfiles.py b/pipenv/vendor/plette/pipfiles.py
index 85260fba..0113ebee 100644
--- a/pipenv/vendor/plette/pipfiles.py
+++ b/pipenv/vendor/plette/pipfiles.py
@@ -4,7 +4,7 @@ import json
 import pipenv.vendor.tomlkit as tomlkit
 
 from .models import (
-    DataView, Hash, Requires,
+    DataView, Hash, Requires, PipfileSection, Pipenv,
     PackageCollection, ScriptCollection, SourceCollection,
 )
 
@@ -15,6 +15,8 @@ PIPFILE_SECTIONS = {
     "dev-packages": PackageCollection,
     "requires": Requires,
     "scripts": ScriptCollection,
+    "pipfile":  PipfileSection,
+    "pipenv": Pipenv
 }
 
 DEFAULT_SOURCE_TOML = """\
@@ -24,7 +26,6 @@ url = "https://pypi.org/simple"
 verify_ssl = true
 """
 
-
 class Pipfile(DataView):
     """Representation of a Pipfile.
     """
@@ -42,6 +43,11 @@ class Pipfile(DataView):
                 continue
             klass.validate(data[key])
 
+        package_categories = set(data.keys()) - set(PIPFILE_SECTIONS.keys())        
+
+        for category in package_categories:
+            PackageCollection.validate(data[category])
+
     @classmethod
     def load(cls, f, encoding=None):
         content = f.read()
diff --git a/pipenv/vendor/vendor.txt b/pipenv/vendor/vendor.txt
index c3b58032..37494fad 100644
--- a/pipenv/vendor/vendor.txt
+++ b/pipenv/vendor/vendor.txt
@@ -7,7 +7,7 @@ dparse==0.6.2
 markupsafe==2.0.1
 pexpect==4.8.0
 pipdeptree==2.3.1
-plette[validation]==0.4.2
+plette[validation]==0.4.4
 ptyprocess==0.7.0
 pyparsing==3.0.9
 python-dotenv==0.19.0