diff --git a/HISTORY.md b/HISTORY.md
index 0b0521c9ca..f712a84fb3 100644
--- a/HISTORY.md
+++ b/HISTORY.md
@@ -6,6 +6,11 @@ dev
 
 - \[Short description of non-trivial change.\]
 
+**Bugfixes**
+
+- Fixed urllib3 exception leak, wrapping `urllib3.exceptions.SSLError` with
+  `requests.exceptions.SSLError` for `content` and `iter_content`.
+
 2.27.1 (2022-01-05)
 -------------------
 
diff --git a/requests/models.py b/requests/models.py
index dfbea854f9..f65afa858f 100644
--- a/requests/models.py
+++ b/requests/models.py
@@ -19,7 +19,12 @@
 from urllib3.filepost import encode_multipart_formdata
 from urllib3.util import parse_url
 from urllib3.exceptions import (
-    DecodeError, ReadTimeoutError, ProtocolError, LocationParseError)
+    DecodeError,
+    LocationParseError,
+    ProtocolError,
+    ReadTimeoutError,
+    SSLError,
+)
 
 from io import UnsupportedOperation
 from .hooks import default_hooks
@@ -32,6 +37,7 @@
     ContentDecodingError, ConnectionError, StreamConsumedError,
     InvalidJSONError)
 from .exceptions import JSONDecodeError as RequestsJSONDecodeError
+from .exceptions import SSLError as RequestsSSLError
 from ._internal_utils import to_native_string, unicode_is_ascii
 from .utils import (
     guess_filename, get_auth_from_url, requote_uri,
@@ -765,6 +771,8 @@ def generate():
                     raise ContentDecodingError(e)
                 except ReadTimeoutError as e:
                     raise ConnectionError(e)
+                except SSLError as e:
+                    raise RequestsSSLError(e)
             else:
                 # Standard file-like object.
                 while True:
diff --git a/tests/test_requests.py b/tests/test_requests.py
index 328da4bd43..074c372a82 100644
--- a/tests/test_requests.py
+++ b/tests/test_requests.py
@@ -14,6 +14,7 @@
 import io
 import requests
 import pytest
+import urllib3
 from requests.adapters import HTTPAdapter
 from requests.auth import HTTPDigestAuth, _basic_auth_str
 from requests.compat import (
@@ -22,9 +23,25 @@
 from requests.cookies import (
     cookiejar_from_dict, morsel_to_cookie)
 from requests.exceptions import (
-    ConnectionError, ConnectTimeout, InvalidSchema, InvalidURL,
-    MissingSchema, ReadTimeout, Timeout, RetryError, RequestException, TooManyRedirects,
-    ProxyError, InvalidHeader, UnrewindableBodyError, SSLError, InvalidProxyURL, InvalidJSONError)
+    ChunkedEncodingError,
+    ConnectionError,
+    ConnectTimeout,
+    ContentDecodingError,
+    InvalidHeader,
+    InvalidJSONError,
+    InvalidProxyURL,
+    InvalidSchema,
+    InvalidURL,
+    MissingSchema,
+    ProxyError,
+    ReadTimeout,
+    RequestException,
+    RetryError,
+    Timeout,
+    TooManyRedirects,
+    UnrewindableBodyError,
+)
+from requests.exceptions import SSLError as RequestsSSLError
 from requests.models import PreparedRequest
 from requests.structures import CaseInsensitiveDict
 from requests.sessions import SessionRedirectMixin
@@ -910,7 +927,7 @@ def test_certificate_failure(self, httpbin_secure):
         """
         When underlying SSL problems occur, an SSLError is raised.
         """
-        with pytest.raises(SSLError):
+        with pytest.raises(RequestsSSLError):
             # Our local httpbin does not have a trusted CA, so this call will
             # fail if we use our default trust bundle.
             requests.get(httpbin_secure('status', '200'))
@@ -1320,6 +1337,26 @@ def test_response_chunk_size_type(self):
         with pytest.raises(TypeError):
             chunks = r.iter_content("1024")
 
+    @pytest.mark.parametrize(
+        'exception, args, expected', (
+            (urllib3.exceptions.ProtocolError, tuple(), ChunkedEncodingError),
+            (urllib3.exceptions.DecodeError, tuple(), ContentDecodingError),
+            (urllib3.exceptions.ReadTimeoutError, (None, '', ''), ConnectionError),
+            (urllib3.exceptions.SSLError, tuple(), RequestsSSLError),
+        )
+    )
+    def test_iter_content_wraps_exceptions(
+        self, httpbin, mocker, exception, args, expected
+    ):
+        r = requests.Response()
+        r.raw = mocker.Mock()
+        # ReadTimeoutError can't be initialized by mock
+        # so we'll manually create the instance with args
+        r.raw.stream.side_effect = exception(*args)
+
+        with pytest.raises(expected):
+            next(r.iter_content(1024))
+
     def test_request_and_response_are_pickleable(self, httpbin):
         r = requests.get(httpbin('get'))