diff --git a/pipenv/utils/internet.py b/pipenv/utils/internet.py
index 96448afa..af04baa5 100644
--- a/pipenv/utils/internet.py
+++ b/pipenv/utils/internet.py
@@ -1,21 +1,18 @@
 import re
 from urllib.parse import urlparse
 
+from pipenv.patched.pip._vendor import requests
+from pipenv.patched.pip._vendor.requests.adapters import HTTPAdapter
 from pipenv.patched.pip._vendor.urllib3 import util as urllib3_util
 
-requests_session = None  # type: ignore
 
-
-def _get_requests_session(max_retries=1):
+def _get_requests_session(max_retries=1, verify_ssl=True):
     """Load requests lazily."""
-    global requests_session
-    if requests_session is not None:
-        return requests_session
-    from pipenv.patched.pip._vendor import requests
-
     requests_session = requests.Session()
-    adapter = requests.adapters.HTTPAdapter(max_retries=max_retries)
-    requests_session.mount("https://pypi.org/pypi", adapter)
+    adapter = HTTPAdapter(max_retries=max_retries)
+    requests_session.mount("https://", adapter)
+    if verify_ssl is False:
+        requests_session.verify = False
     return requests_session
 
 
@@ -46,6 +43,7 @@ def create_mirror_source(url, name):
 def download_file(url, filename, max_retries=1):
     """Downloads file from url to a path with filename"""
     r = _get_requests_session(max_retries).get(url, stream=True)
+    r.close()
     if not r.ok:
         raise OSError("Unable to download file")
 
@@ -117,6 +115,7 @@ def proper_case(package_name):
     r = _get_requests_session().get(
         f"https://pypi.org/pypi/{package_name}/json", timeout=0.3, stream=True
     )
+    r.close()
     if not r.ok:
         raise OSError(f"Unable to find package {package_name} in PyPI repository.")
 
diff --git a/pipenv/utils/resolver.py b/pipenv/utils/resolver.py
index 5cc689b3..4a209d50 100644
--- a/pipenv/utils/resolver.py
+++ b/pipenv/utils/resolver.py
@@ -180,6 +180,7 @@ class Resolver:
         self._pip_command = None
         self._retry_attempts = 0
         self._hash_cache = None
+        self._sessions = {}
 
     def __repr__(self):
         return (
@@ -594,7 +595,7 @@ class Resolver:
                 session=self.session,
             )
             # It would be nice if `shims.get_package_finder` took an
-            # `ignore_compatibility` parameter, but that's some vendorered code
+            # `ignore_compatibility` parameter, but that's some vendored code
             # we'd rather avoid touching.
             index_lookup = self.prepare_index_lookup()
             ignore_compatibility_finder._ignore_compatibility = True
@@ -744,9 +745,19 @@ class Resolver:
             cleaned_checksums.add(checksum)
         return cleaned_checksums
 
-    def _get_hashes_from_pypi(self, ireq):
+    def _get_requests_session_for_source(self, source):
+        if self._sessions.get(source["name"]):
+            session = self._sessions[source["name"]]
+        else:
+            session = _get_requests_session(
+                self.project.s.PIPENV_MAX_RETRIES, source.get("verify_ssl", True)
+            )
+            self._sessions[source["name"]] = session
+        return session
+
+    def _get_hashes_from_pypi(self, ireq, source):
         pkg_url = f"https://pypi.org/pypi/{ireq.name}/json"
-        session = _get_requests_session(self.project.s.PIPENV_MAX_RETRIES)
+        session = self._get_requests_session_for_source(source)
         try:
             collected_hashes = set()
             # Grab the hashes from the new warehouse API.
@@ -776,7 +787,7 @@ class Resolver:
 
     def _get_hashes_from_remote_index_urls(self, ireq, source):
         pkg_url = f"{source['url']}/{ireq.name}/"
-        session = _get_requests_session(self.project.s.PIPENV_MAX_RETRIES)
+        session = self._get_requests_session_for_source(source)
         try:
             collected_hashes = set()
             # Grab the hashes from the new warehouse API.
@@ -828,7 +839,7 @@ class Resolver:
         source = sources[0] if len(sources) else None
         if source:
             if is_pypi_url(source["url"]):
-                hashes = self._get_hashes_from_pypi(ireq)
+                hashes = self._get_hashes_from_pypi(ireq, source)
                 if hashes:
                     return hashes
             else: