diff --git a/redbot/cogs/downloader/downloader.py b/redbot/cogs/downloader/downloader.py
index 29a9d126e87..267d5e8d1c7 100644
--- a/redbot/cogs/downloader/downloader.py
+++ b/redbot/cogs/downloader/downloader.py
@@ -566,6 +566,20 @@ async def _repo_add(
             await ctx.send(
                 _("The repo name you provided is already in use. Please choose another name.")
             )
+        except errors.AuthenticationError as err:
+            await ctx.send(
+                _(
+                    "Failed to authenticate or repository does not exist."
+                    " See logs for more information."
+                )
+            )
+            log.exception(
+                "Something went wrong whilst cloning %s (to revision: %s)",
+                repo_url,
+                branch,
+                exc_info=err,
+            )
+
         except errors.CloningError as err:
             await ctx.send(
                 _(
diff --git a/redbot/cogs/downloader/errors.py b/redbot/cogs/downloader/errors.py
index ee0c6ab2ebe..412885b97c1 100644
--- a/redbot/cogs/downloader/errors.py
+++ b/redbot/cogs/downloader/errors.py
@@ -13,6 +13,7 @@
     "CopyingError",
     "ExistingGitRepo",
     "MissingGitRepo",
+    "AuthenticationError",
     "CloningError",
     "CurrentHashError",
     "HardResetError",
@@ -79,6 +80,15 @@ class MissingGitRepo(DownloaderException):
     pass
 
 
+class AuthenticationError(GitException):
+    """
+    Thrown when git failed to authenticate with
+    the server
+    """
+
+    pass
+
+
 class CloningError(GitException):
     """
     Thrown when git clone returns a non zero exit code.
diff --git a/redbot/cogs/downloader/repo_manager.py b/redbot/cogs/downloader/repo_manager.py
index e0e404d1593..8d9b3fa06cc 100644
--- a/redbot/cogs/downloader/repo_manager.py
+++ b/redbot/cogs/downloader/repo_manager.py
@@ -188,6 +188,17 @@ def _existing_git_repo(self) -> Tuple[bool, Path]:
         git_path = self.folder_path / ".git"
         return git_path.exists(), git_path
 
+    def _parse_git_error(self, git_command: str, stderr: str) -> errors.GitException:
+        stderr = stderr.lower()
+        # Expected to catch:
+        #   Could not read from remote repository
+        #   could not read X for 'URL': terminal prompts disabled
+        #   Authentication failed
+        if "could not read" in stderr or "authentication failed" in stderr:
+            return errors.AuthenticationError("Failed to Authenticate", git_command)
+
+        return errors.CloningError("Error when running git clone.", git_command)
+
     async def is_ancestor(self, maybe_ancestor_rev: str, descendant_rev: str) -> bool:
         """
         Check if the first is an ancestor of the second.
@@ -548,13 +559,20 @@ async def _run(
         """
         env = os.environ.copy()
         env["GIT_TERMINAL_PROMPT"] = "0"
+        env["GIT_TRACE"] = "0"
+        # make sure we never enter an askpass routine
+        # https://github.com/git/git/blob/1424303/prompt.c#L56
         env.pop("GIT_ASKPASS", None)
+        env.pop("SSH_ASKPASS", None)
         # attempt to force all output to plain ascii english
         # some methods that parse output may expect it
         # according to gettext manual both variables have to be set:
         # https://www.gnu.org/software/gettext/manual/gettext.html#Locale-Environment-Variables
         env["LC_ALL"] = "C"
         env["LANGUAGE"] = "C"
+        # Make sure git does not consider us smart
+        # https://github.com/git/git/blob/a7312d1a2/editor.c#L11-L15
+        env["TERM"] = "dumb"
         kwargs["env"] = env
         async with self._repo_lock:
             p: CompletedProcess = await asyncio.get_running_loop().run_in_executor(
@@ -659,7 +677,7 @@ async def clone(self) -> Tuple[Installable, ...]:
         if p.returncode:
             # Try cleaning up folder
             shutil.rmtree(str(self.folder_path), ignore_errors=True)
-            raise errors.CloningError("Error when running git clone.", git_command)
+            raise self._parse_git_error(git_command, p.stderr.decode(**DECODE_PARAMS))
 
         if self.branch is None:
             self.branch = await self.current_branch()