diff --git a/news/5380.bugfix b/news/5380.bugfix
new file mode 100644
index 000000000..7e4d20256
--- /dev/null
+++ b/news/5380.bugfix
@@ -0,0 +1 @@
+Raise user friendly errors on network failures
diff --git a/src/pip/_internal/network/utils.py b/src/pip/_internal/network/utils.py
index 134848ae5..3c8e9ab83 100644
--- a/src/pip/_internal/network/utils.py
+++ b/src/pip/_internal/network/utils.py
@@ -1,6 +1,7 @@
 from typing import Dict, Generator
 
 from pip._vendor.requests.models import CONTENT_CHUNK_SIZE, Response
+from pip._vendor.urllib3.exceptions import NewConnectionError, ReadTimeoutError
 
 from pip._internal.exceptions import NetworkConnectionError
 
@@ -94,3 +95,8 @@ def response_chunks(
             if not chunk:
                 break
             yield chunk
+    except (NewConnectionError, ReadTimeoutError) as exc:
+        raise NetworkConnectionError(
+            "Failed to get address for host! Check your network connectivity "
+            "and DNS settings.\nDetails: {}".format(exc)
+        )